TY  - JOUR
AU  - Breberina, Luka
AU  - Nikolić, Milan
AU  - Stojanović, Srđan
AU  - Zlatović, Mario
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6502
AB  - The influences of π−π interactions in phycocyanin proteins and their
environmental preferences were analyzed. The observations indicate that the
majority of the aromatic residues in phycocyanin proteins are involved in π−π
interactions. Phenylalanine (Phe) and tyrosine (Tyr) residues were found to be
involved in π–π interactions much more frequently than tryptophan (Trp) or
histidine (His). Similarly, the Phe−Phe and Tyr−Tyr π–π interacting pair had
the highest frequency of occurrence. In addition to π-π interactions, the aromatic
residues also form π-networks in phycocyanins. The π–π interactions are
most favourable at the pair distance range of 5.5–7 Å, with a clear preference
for T-shaped ring arrangements. Using ab initio calculations, we observed that
most of the π−π interactions possess energy from 0 to −10 kJ mol-1. Stabilization
centres for these proteins showed that all residues found in π−π interactions
are important in locating one or more such centres. π−π interacting residues
are evolutionary conserved. The results obtained from this study will be
beneficial in further understanding the structural stability and eventual development
of protein engineering of phycocyanins.
AB  - Анализирани су утицаји π−π интеракција у протеинима фикоцијанинима и њихове
преференције ка окружењу. Запажања показују да је већина ароматичних остатака у
протеинима фикоцијанинима укључена у π−π интеракције. Утврђено је да су остаци фенилаланина (Phe) и тирозина (Tyr) много чешће укључени у π–π интеракције него триптофана (Trp) или хистидина (His). Слично томе, интерагујући π–π парови Phe−Phe и Tyr−Tyr имали су највећу учесталост појављивања. Додатно, ароматични остаци такође
стварају π-мреже у фикоцијанинима. π–π интеракције су најповољније у распону дистанци парова од 5,5–7 Å, с јасном склоношћу за распоред прстенова у облику слова Т. Користећи ab initio прорачуне, приметили смо да већина π−π интеракција има енергију у распону од 0 до −10 kJ mol-1. Стабилизациони центри ових протеина показали су да су сви остаци пронађени у π−π интеракцијама важни у лоцирању једног или више таквих центара. π−π интеракциони остаци су еволутивно конзервирани. Резултати добивени овом студијом биће од користи у даљем разумевању структурне стабилности и евентуалном развоју протеинског инжењеринга фикоцијанина.
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - On the importance of π–π interactions in structural stability of phycocyanins
T1  - О значају π−π интеракција у структурној стабилности фикоцијанина
VL  - 88
IS  - 5
SP  - 481
EP  - 494
DO  - 10.2298/JSC221201008B
ER  - 

@article{
author = "Breberina, Luka and Nikolić, Milan and Stojanović, Srđan and Zlatović, Mario",
year = "2023",
abstract = "The influences of π−π interactions in phycocyanin proteins and their
environmental preferences were analyzed. The observations indicate that the
majority of the aromatic residues in phycocyanin proteins are involved in π−π
interactions. Phenylalanine (Phe) and tyrosine (Tyr) residues were found to be
involved in π–π interactions much more frequently than tryptophan (Trp) or
histidine (His). Similarly, the Phe−Phe and Tyr−Tyr π–π interacting pair had
the highest frequency of occurrence. In addition to π-π interactions, the aromatic
residues also form π-networks in phycocyanins. The π–π interactions are
most favourable at the pair distance range of 5.5–7 Å, with a clear preference
for T-shaped ring arrangements. Using ab initio calculations, we observed that
most of the π−π interactions possess energy from 0 to −10 kJ mol-1. Stabilization
centres for these proteins showed that all residues found in π−π interactions
are important in locating one or more such centres. π−π interacting residues
are evolutionary conserved. The results obtained from this study will be
beneficial in further understanding the structural stability and eventual development
of protein engineering of phycocyanins., Анализирани су утицаји π−π интеракција у протеинима фикоцијанинима и њихове
преференције ка окружењу. Запажања показују да је већина ароматичних остатака у
протеинима фикоцијанинима укључена у π−π интеракције. Утврђено је да су остаци фенилаланина (Phe) и тирозина (Tyr) много чешће укључени у π–π интеракције него триптофана (Trp) или хистидина (His). Слично томе, интерагујући π–π парови Phe−Phe и Tyr−Tyr имали су највећу учесталост појављивања. Додатно, ароматични остаци такође
стварају π-мреже у фикоцијанинима. π–π интеракције су најповољније у распону дистанци парова од 5,5–7 Å, с јасном склоношћу за распоред прстенова у облику слова Т. Користећи ab initio прорачуне, приметили смо да већина π−π интеракција има енергију у распону од 0 до −10 kJ mol-1. Стабилизациони центри ових протеина показали су да су сви остаци пронађени у π−π интеракцијама важни у лоцирању једног или више таквих центара. π−π интеракциони остаци су еволутивно конзервирани. Резултати добивени овом студијом биће од користи у даљем разумевању структурне стабилности и евентуалном развоју протеинског инжењеринга фикоцијанина.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "On the importance of π–π interactions in structural stability of phycocyanins, О значају π−π интеракција у структурној стабилности фикоцијанина",
volume = "88",
number = "5",
pages = "481-494",
doi = "10.2298/JSC221201008B"
}

Breberina, L., Nikolić, M., Stojanović, S.,& Zlatović, M.. (2023). On the importance of π–π interactions in structural stability of phycocyanins. in Journal of the Serbian Chemical Society
Belgrade : Serbian Chemical Society., 88(5), 481-494.
https://doi.org/10.2298/JSC221201008B

Breberina L, Nikolić M, Stojanović S, Zlatović M. On the importance of π–π interactions in structural stability of phycocyanins. in Journal of the Serbian Chemical Society. 2023;88(5):481-494.
doi:10.2298/JSC221201008B .

Breberina, Luka, Nikolić, Milan, Stojanović, Srđan, Zlatović, Mario, "On the importance of π–π interactions in structural stability of phycocyanins" in Journal of the Serbian Chemical Society, 88, no. 5 (2023):481-494,
https://doi.org/10.2298/JSC221201008B . .

TY  - JOUR
AU  - Koračak, Ljiljana
AU  - Lupšić, Ema
AU  - Terzić-Jovanović, Nataša
AU  - Jovanović, Mirna
AU  - Novaković, Miroslav
AU  - Nedialkov, Paraskev
AU  - Trendafilova, Antoaneta
AU  - Zlatović, Mario
AU  - Pešić, Milica
AU  - Opsenica, Igor
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7172
AB  - The synthesis of 17 hybrid molecules, consisting of artesunate, a derivative of naturally occurring artemisinin, and synthetic 4-aryl-2-aminopyrimidines, is described. New compounds were designed to improve the parent compounds' cytotoxic properties, activity, and selectivity. The synthesized hybrid molecules (15a–f with ethylenediamine linker and 16a–k with piperazine linker), as well as their precursors – pyrimidine derivatives (13a–f and 14a–k), artemisinin, and artesunate, were tested on sensitive and multidrug-resistant (MDR) human non-small cell lung carcinoma (NSCLC) cells. All hybrid compounds with piperazine linker 16a–k were selective toward NSCLC cells and displayed IC50 values below 5 μM. Although they showed similar anticancer potency as artesunate, their selectivity against cancer cells was considerably improved. Importantly, 16h–k hybrid compounds were able to evade MDR phenotype, inhibit P-glycoprotein (P-gp) activity, and increase the sensitivity of MDR NSCLC cells to doxorubicin (DOX). The inhibition of P-gp activity induced by 16h–j was stronger than the one obtained with artesunate. Among these four hybrid compounds, 16k was the most potent anticancer agent with similar IC50 values of around 1.5 μM (for comparison – over 3.1 μM for artesunate) in sensitive and MDR NSCLC cells.
PB  - Royal Society of Chemistry
T2  - New Journal of Chemistry
T1  - Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells
VL  - 47
IS  - 14
SP  - 6844
EP  - 6855
DO  - 10.1039/D3NJ00427A
ER  - 

@article{
author = "Koračak, Ljiljana and Lupšić, Ema and Terzić-Jovanović, Nataša and Jovanović, Mirna and Novaković, Miroslav and Nedialkov, Paraskev and Trendafilova, Antoaneta and Zlatović, Mario and Pešić, Milica and Opsenica, Igor",
year = "2023",
abstract = "The synthesis of 17 hybrid molecules, consisting of artesunate, a derivative of naturally occurring artemisinin, and synthetic 4-aryl-2-aminopyrimidines, is described. New compounds were designed to improve the parent compounds' cytotoxic properties, activity, and selectivity. The synthesized hybrid molecules (15a–f with ethylenediamine linker and 16a–k with piperazine linker), as well as their precursors – pyrimidine derivatives (13a–f and 14a–k), artemisinin, and artesunate, were tested on sensitive and multidrug-resistant (MDR) human non-small cell lung carcinoma (NSCLC) cells. All hybrid compounds with piperazine linker 16a–k were selective toward NSCLC cells and displayed IC50 values below 5 μM. Although they showed similar anticancer potency as artesunate, their selectivity against cancer cells was considerably improved. Importantly, 16h–k hybrid compounds were able to evade MDR phenotype, inhibit P-glycoprotein (P-gp) activity, and increase the sensitivity of MDR NSCLC cells to doxorubicin (DOX). The inhibition of P-gp activity induced by 16h–j was stronger than the one obtained with artesunate. Among these four hybrid compounds, 16k was the most potent anticancer agent with similar IC50 values of around 1.5 μM (for comparison – over 3.1 μM for artesunate) in sensitive and MDR NSCLC cells.",
publisher = "Royal Society of Chemistry",
journal = "New Journal of Chemistry",
title = "Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells",
volume = "47",
number = "14",
pages = "6844-6855",
doi = "10.1039/D3NJ00427A"
}

Koračak, L., Lupšić, E., Terzić-Jovanović, N., Jovanović, M., Novaković, M., Nedialkov, P., Trendafilova, A., Zlatović, M., Pešić, M.,& Opsenica, I.. (2023). Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells. in New Journal of Chemistry
Royal Society of Chemistry., 47(14), 6844-6855.
https://doi.org/10.1039/D3NJ00427A

Koračak L, Lupšić E, Terzić-Jovanović N, Jovanović M, Novaković M, Nedialkov P, Trendafilova A, Zlatović M, Pešić M, Opsenica I. Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells. in New Journal of Chemistry. 2023;47(14):6844-6855.
doi:10.1039/D3NJ00427A .

Koračak, Ljiljana, Lupšić, Ema, Terzić-Jovanović, Nataša, Jovanović, Mirna, Novaković, Miroslav, Nedialkov, Paraskev, Trendafilova, Antoaneta, Zlatović, Mario, Pešić, Milica, Opsenica, Igor, "Novel artesunate–pyrimidine-based hybrids with anticancer potential against multidrug-resistant cancer cells" in New Journal of Chemistry, 47, no. 14 (2023):6844-6855,
https://doi.org/10.1039/D3NJ00427A . .

TY  - JOUR
AU  - Stojanović, Srđan
AU  - Zlatović, Mario
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6503
AB  - In the present work, the influences of π–π interactions in superoxide
dismutase (SOD) active centers were analyzed. The majority of the aromatic
residues are involved in π–π interactions. Predominant type of interacting pairs
is His–His and His–Trp pairs. In addition to π–π interactions, π residues also
form π-networks in SOD proteins. The π–π interactions are most favorable at
the pair distance range of 5–7 Å. We observed that most of the π–π interactions
shows stabilization energies in the range from −4.2 to −12.6 kJ mol-1, while the
metal assisted π–π interactions showed an energy in the range from −83.7 to
−334.7 kJ mol-1. Most of the π–π interacting residues were evolutionary conserved
and thus probably important in maintaining the structural stability of
proteins through these interactions. A high percentage of these residues could
be considered as stabilization centers, contributing to the net stability of SOD
proteins.
AB  - У овом раду анализирани су утицаји π–π интеракција у активним центрима супероксид-дисмутазе (SOD). Већина ароматичних остатака је укључена у π–π интеракције. 
Парови His–His и His–Trp су доминантни тип парова у интеракцији. Поред π–π интеракција, π остаци такође формирају π-мреже у SOD протеинима. π–π интерагујући парови
су најповољнији у опсегу дистанци од 5–7 Å. Приметили смо да већина π–π интеракција
има енергију у опсегу од −4,2 до −12,6 kJ mol-1, док су π–π интеракције уз асистенцију
метала показале енергију у опсегу −83,7 до −334,7 kJ mol-1. Већина π–π интерагујућих
остатака били су еволутивно конзервирани и могли би бити важни у одржавању структурне стабилности кроз ове интеракције. Висок проценат ових остатака може се сматрати стабилизационим центрима који доприносе нето стабилности SOD протеина.
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - π–π interactions in structural stability: Role in superoxide dismutases
T1  - Испитивање улоге катјон–π интеракција у активним центрима супероксид-дисмутаза
VL  - 88
IS  - 3
SP  - 223
EP  - 235
DO  - 10.2298/JSC220404052S
ER  - 

@article{
author = "Stojanović, Srđan and Zlatović, Mario",
year = "2023",
abstract = "In the present work, the influences of π–π interactions in superoxide
dismutase (SOD) active centers were analyzed. The majority of the aromatic
residues are involved in π–π interactions. Predominant type of interacting pairs
is His–His and His–Trp pairs. In addition to π–π interactions, π residues also
form π-networks in SOD proteins. The π–π interactions are most favorable at
the pair distance range of 5–7 Å. We observed that most of the π–π interactions
shows stabilization energies in the range from −4.2 to −12.6 kJ mol-1, while the
metal assisted π–π interactions showed an energy in the range from −83.7 to
−334.7 kJ mol-1. Most of the π–π interacting residues were evolutionary conserved
and thus probably important in maintaining the structural stability of
proteins through these interactions. A high percentage of these residues could
be considered as stabilization centers, contributing to the net stability of SOD
proteins., У овом раду анализирани су утицаји π–π интеракција у активним центрима супероксид-дисмутазе (SOD). Већина ароматичних остатака је укључена у π–π интеракције. 
Парови His–His и His–Trp су доминантни тип парова у интеракцији. Поред π–π интеракција, π остаци такође формирају π-мреже у SOD протеинима. π–π интерагујући парови
су најповољнији у опсегу дистанци од 5–7 Å. Приметили смо да већина π–π интеракција
има енергију у опсегу од −4,2 до −12,6 kJ mol-1, док су π–π интеракције уз асистенцију
метала показале енергију у опсегу −83,7 до −334,7 kJ mol-1. Већина π–π интерагујућих
остатака били су еволутивно конзервирани и могли би бити важни у одржавању структурне стабилности кроз ове интеракције. Висок проценат ових остатака може се сматрати стабилизационим центрима који доприносе нето стабилности SOD протеина.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "π–π interactions in structural stability: Role in superoxide dismutases, Испитивање улоге катјон–π интеракција у активним центрима супероксид-дисмутаза",
volume = "88",
number = "3",
pages = "223-235",
doi = "10.2298/JSC220404052S"
}

Stojanović, S.,& Zlatović, M.. (2023). π–π interactions in structural stability: Role in superoxide dismutases. in Journal of the Serbian Chemical Society
Belgrade : Serbian Chemical Society., 88(3), 223-235.
https://doi.org/10.2298/JSC220404052S

Stojanović S, Zlatović M. π–π interactions in structural stability: Role in superoxide dismutases. in Journal of the Serbian Chemical Society. 2023;88(3):223-235.
doi:10.2298/JSC220404052S .

Stojanović, Srđan, Zlatović, Mario, "π–π interactions in structural stability: Role in superoxide dismutases" in Journal of the Serbian Chemical Society, 88, no. 3 (2023):223-235,
https://doi.org/10.2298/JSC220404052S . .

TY  - JOUR
AU  - Breberina, Luka M.
AU  - Nikolić, Milan R.
AU  - Stojanović, Srđan
AU  - Zlatović, Mario
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5330
AB  - The influences of cation−π interactions in phycocyanin proteins and their environmental preferences were analyzed. The number of interactions formed by arginine showed to be higher than those formed by the lysine in the cationic group, while histidine is comparatively higher than phenylalanine and N-terminal residue in the π group. Arg−Tyr and Arg−Phe interacting pairs are predominant among the various pairs analyzed. Cation−π interactions are distance-dependent and can be realized above a wider area above the π ring. We analyzed the energy contribution resulting from cation−π interactions using ab initio calculations. The energy contribution resulting from the most frequent cation−π interactions was in the lower range of strong hydrogen bonds. The results showed that, while most of their interaction energies lay ranged from − 2 to − 8 kcal/mol, those energies could be up to −12− 12 kcal/mol. Stabilization centers for these proteins showed that all residues found in cation−π interactions are important in locating one or more of such centers. In the cation–π interacting residues, 54% of the amino acid residues involved in these interactions might be conserved in phycocyanins. From this study, we infer that cation−π forming residues play an important role in the stability of the multiply commercially used phycocyanin proteins and could help structural biologists and medicinal chemists to design better and safer drugs.
PB  - Elsevier
T2  - Computational Biology and Chemistry
T1  - Influence of cation−π interactions to the structural stability of phycocyanin proteins: A computational study
VL  - 100
IS  - 107752
DO  - 10.1016/j.compbiolchem.2022.107752
ER  - 

@article{
author = "Breberina, Luka M. and Nikolić, Milan R. and Stojanović, Srđan and Zlatović, Mario",
year = "2022",
abstract = "The influences of cation−π interactions in phycocyanin proteins and their environmental preferences were analyzed. The number of interactions formed by arginine showed to be higher than those formed by the lysine in the cationic group, while histidine is comparatively higher than phenylalanine and N-terminal residue in the π group. Arg−Tyr and Arg−Phe interacting pairs are predominant among the various pairs analyzed. Cation−π interactions are distance-dependent and can be realized above a wider area above the π ring. We analyzed the energy contribution resulting from cation−π interactions using ab initio calculations. The energy contribution resulting from the most frequent cation−π interactions was in the lower range of strong hydrogen bonds. The results showed that, while most of their interaction energies lay ranged from − 2 to − 8 kcal/mol, those energies could be up to −12− 12 kcal/mol. Stabilization centers for these proteins showed that all residues found in cation−π interactions are important in locating one or more of such centers. In the cation–π interacting residues, 54% of the amino acid residues involved in these interactions might be conserved in phycocyanins. From this study, we infer that cation−π forming residues play an important role in the stability of the multiply commercially used phycocyanin proteins and could help structural biologists and medicinal chemists to design better and safer drugs.",
publisher = "Elsevier",
journal = "Computational Biology and Chemistry",
title = "Influence of cation−π interactions to the structural stability of phycocyanin proteins: A computational study",
volume = "100",
number = "107752",
doi = "10.1016/j.compbiolchem.2022.107752"
}

Breberina, L. M., Nikolić, M. R., Stojanović, S.,& Zlatović, M.. (2022). Influence of cation−π interactions to the structural stability of phycocyanin proteins: A computational study. in Computational Biology and Chemistry
Elsevier., 100(107752).
https://doi.org/10.1016/j.compbiolchem.2022.107752

Breberina LM, Nikolić MR, Stojanović S, Zlatović M. Influence of cation−π interactions to the structural stability of phycocyanin proteins: A computational study. in Computational Biology and Chemistry. 2022;100(107752).
doi:10.1016/j.compbiolchem.2022.107752 .

Breberina, Luka M., Nikolić, Milan R., Stojanović, Srđan, Zlatović, Mario, "Influence of cation−π interactions to the structural stability of phycocyanin proteins: A computational study" in Computational Biology and Chemistry, 100, no. 107752 (2022),
https://doi.org/10.1016/j.compbiolchem.2022.107752 . .

TY  - JOUR
AU  - Stojanović, Srđan
AU  - Zlatović, Mario
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5013
AB  - In this study, we have analysed the influence of cation–π interactions on stability and properties of superoxide dismutase (SOD) active centres. The number of interactions formed by arginine is higher than by lysine in the cat­ionic group, while those formed by histidine are comparatively higher in the π group. The energy contribution resulting from most frequent cation–π interact­ions was in the lower range of strong hydrogen bonds. The cation–π interact­ions involving transition metal ions as cation have energy more negative than –418.4 kJ mol-1. The stabilization centres for these proteins showed that all the residues involved in cation–π interactions were important in locating one or more of such centres. The majority of the residues involved in cation–p inter­actions were evolutionarily conserved and might have a significant contribution towards the stability of SOD proteins. The results presented in this work can be very useful for understanding the contribution of cation–π interactions to the stability of SOD active centres.
AB  - У овој студији смо анализирали утицај катјон–π интеракција на стабилност и особине активних центара супероксид-дисмутазе (SOD). Број интеракција које формира аргинин је већи од лизина у групи катјона, док је хистидин сразмерно већи у π групи. Енергетски допринос који је резултат најчешћих катјон–π интеракција био је у доњемопсегу јаких водоничних веза. Катјон–π интеракције које укључују јоне прелазних метала као катјон имају енергију негативнију од –418,4 kJ mol-1. Стабилизациони центри ових протеина показали су да су сви остаци укључени у катјон–π интеракције важни у распоређивању једног или више таквих центара. Већина остатака који су укључени у катјон–π интеракције су еволуцијски конзервирани и могли би имати значајан допринос стабилности SOD протеина. Резултати представљени у овом раду могу бити веома корисни за разумевање доприноса катјон–π интеракција стабилности активних центара SOD.
PB  - Serbian Chemical Society
T2  - The Journal of the Serbian Chemical Society
T1  - Investigations on the role of cation–pi interactions in active centres of superoxide dismutase
T1  - Испитивање улоге катјон–π интеракција у активним центрима супероксид-дисмутаза
VL  - 87
IS  - 4
SP  - 465
EP  - 477
DO  - 10.2298/JSC220109013S
ER  - 

@article{
author = "Stojanović, Srđan and Zlatović, Mario",
year = "2022",
abstract = "In this study, we have analysed the influence of cation–π interactions on stability and properties of superoxide dismutase (SOD) active centres. The number of interactions formed by arginine is higher than by lysine in the cat­ionic group, while those formed by histidine are comparatively higher in the π group. The energy contribution resulting from most frequent cation–π interact­ions was in the lower range of strong hydrogen bonds. The cation–π interact­ions involving transition metal ions as cation have energy more negative than –418.4 kJ mol-1. The stabilization centres for these proteins showed that all the residues involved in cation–π interactions were important in locating one or more of such centres. The majority of the residues involved in cation–p inter­actions were evolutionarily conserved and might have a significant contribution towards the stability of SOD proteins. The results presented in this work can be very useful for understanding the contribution of cation–π interactions to the stability of SOD active centres., У овој студији смо анализирали утицај катјон–π интеракција на стабилност и особине активних центара супероксид-дисмутазе (SOD). Број интеракција које формира аргинин је већи од лизина у групи катјона, док је хистидин сразмерно већи у π групи. Енергетски допринос који је резултат најчешћих катјон–π интеракција био је у доњемопсегу јаких водоничних веза. Катјон–π интеракције које укључују јоне прелазних метала као катјон имају енергију негативнију од –418,4 kJ mol-1. Стабилизациони центри ових протеина показали су да су сви остаци укључени у катјон–π интеракције важни у распоређивању једног или више таквих центара. Већина остатака који су укључени у катјон–π интеракције су еволуцијски конзервирани и могли би имати значајан допринос стабилности SOD протеина. Резултати представљени у овом раду могу бити веома корисни за разумевање доприноса катјон–π интеракција стабилности активних центара SOD.",
publisher = "Serbian Chemical Society",
journal = "The Journal of the Serbian Chemical Society",
title = "Investigations on the role of cation–pi interactions in active centres of superoxide dismutase, Испитивање улоге катјон–π интеракција у активним центрима супероксид-дисмутаза",
volume = "87",
number = "4",
pages = "465-477",
doi = "10.2298/JSC220109013S"
}

Stojanović, S.,& Zlatović, M.. (2022). Investigations on the role of cation–pi interactions in active centres of superoxide dismutase. in The Journal of the Serbian Chemical Society
Serbian Chemical Society., 87(4), 465-477.
https://doi.org/10.2298/JSC220109013S

Stojanović S, Zlatović M. Investigations on the role of cation–pi interactions in active centres of superoxide dismutase. in The Journal of the Serbian Chemical Society. 2022;87(4):465-477.
doi:10.2298/JSC220109013S .

Stojanović, Srđan, Zlatović, Mario, "Investigations on the role of cation–pi interactions in active centres of superoxide dismutase" in The Journal of the Serbian Chemical Society, 87, no. 4 (2022):465-477,
https://doi.org/10.2298/JSC220109013S . .

TY  - JOUR
AU  - Komatović, Katarina
AU  - Matošević, Ana
AU  - Terzić-Jovanović, Nataša
AU  - Žunec, Suzana
AU  - Šegan, Sandra
AU  - Zlatović, Mario
AU  - Maraković, Nikola
AU  - Bosak, Anita
AU  - Opsenica, Dejan
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5232
AB  - Considering that acetylcholinesterase (AChE) inhibition is the most important mode of action expected of a potential drug used for the treatment of symptoms of Alzheimer’s disease (AD), our previous pilot study of 4-aminoquinolines as potential human cholinesterase inhibitors was extended to twenty-two new structurally distinct 4-aminoquinolines bearing an adamantane moiety. Inhibition studies revealed that all of the compounds were very potent inhibitors of AChE and butyrylcholinesterase (BChE), with inhibition constants (Ki) ranging between 0.075 and 25 µM. The tested compounds exhibited a modest selectivity between the two cholinesterases; the most selective for BChE was compound 14, which displayed a 10 times higher preference, while compound 19 was a 5.8 times more potent inhibitor of AChE. Most of the compounds were estimated to be able to cross the blood–brain barrier (BBB) by passive transport. Evaluation of druglikeness singled out fourteen compounds with possible oral route of administration. The tested compounds displayed modest but generally higher antioxidant activity than the structurally similar AD drug tacrine. Compound 19 showed the highest reducing power, comparable to those of standard antioxidants. Considering their simple structure, high inhibition of AChE and BChE, and ability to cross the BBB, 4-aminoquinoline-based adamantanes show promise as structural scaffolds for further design of novel central nervous system drugs. Among them, two compounds stand out: compound 5 as the most potent inhibitor of both cholinesterases with a Ki constant in low nano molar range and the potential to cross the BBB, and compound 8, which met all our requirements, including high cholinesterase inhibition, good oral bioavailability, and antioxidative effect. The QSAR model revealed that AChE and BChE inhibition was mainly influenced by the ring and topological descriptors MCD, Nnum, RP, and RSIpw3, which defined the shape, conformational flexibility, and surface properties of the molecules
PB  - MDPI
T2  - Pharmaceutics
T1  - 4-Aminoquinoline-Based Adamantanes as Potential Anticholinesterase Agents in Symptomatic Treatment of Alzheimer’s Disease
VL  - 14
IS  - 6
SP  - 1305
DO  - 10.3390/pharmaceutics14061305
ER  - 

@article{
author = "Komatović, Katarina and Matošević, Ana and Terzić-Jovanović, Nataša and Žunec, Suzana and Šegan, Sandra and Zlatović, Mario and Maraković, Nikola and Bosak, Anita and Opsenica, Dejan",
year = "2022",
abstract = "Considering that acetylcholinesterase (AChE) inhibition is the most important mode of action expected of a potential drug used for the treatment of symptoms of Alzheimer’s disease (AD), our previous pilot study of 4-aminoquinolines as potential human cholinesterase inhibitors was extended to twenty-two new structurally distinct 4-aminoquinolines bearing an adamantane moiety. Inhibition studies revealed that all of the compounds were very potent inhibitors of AChE and butyrylcholinesterase (BChE), with inhibition constants (Ki) ranging between 0.075 and 25 µM. The tested compounds exhibited a modest selectivity between the two cholinesterases; the most selective for BChE was compound 14, which displayed a 10 times higher preference, while compound 19 was a 5.8 times more potent inhibitor of AChE. Most of the compounds were estimated to be able to cross the blood–brain barrier (BBB) by passive transport. Evaluation of druglikeness singled out fourteen compounds with possible oral route of administration. The tested compounds displayed modest but generally higher antioxidant activity than the structurally similar AD drug tacrine. Compound 19 showed the highest reducing power, comparable to those of standard antioxidants. Considering their simple structure, high inhibition of AChE and BChE, and ability to cross the BBB, 4-aminoquinoline-based adamantanes show promise as structural scaffolds for further design of novel central nervous system drugs. Among them, two compounds stand out: compound 5 as the most potent inhibitor of both cholinesterases with a Ki constant in low nano molar range and the potential to cross the BBB, and compound 8, which met all our requirements, including high cholinesterase inhibition, good oral bioavailability, and antioxidative effect. The QSAR model revealed that AChE and BChE inhibition was mainly influenced by the ring and topological descriptors MCD, Nnum, RP, and RSIpw3, which defined the shape, conformational flexibility, and surface properties of the molecules",
publisher = "MDPI",
journal = "Pharmaceutics",
title = "4-Aminoquinoline-Based Adamantanes as Potential Anticholinesterase Agents in Symptomatic Treatment of Alzheimer’s Disease",
volume = "14",
number = "6",
pages = "1305",
doi = "10.3390/pharmaceutics14061305"
}

Komatović, K., Matošević, A., Terzić-Jovanović, N., Žunec, S., Šegan, S., Zlatović, M., Maraković, N., Bosak, A.,& Opsenica, D.. (2022). 4-Aminoquinoline-Based Adamantanes as Potential Anticholinesterase Agents in Symptomatic Treatment of Alzheimer’s Disease. in Pharmaceutics
MDPI., 14(6), 1305.
https://doi.org/10.3390/pharmaceutics14061305

Komatović K, Matošević A, Terzić-Jovanović N, Žunec S, Šegan S, Zlatović M, Maraković N, Bosak A, Opsenica D. 4-Aminoquinoline-Based Adamantanes as Potential Anticholinesterase Agents in Symptomatic Treatment of Alzheimer’s Disease. in Pharmaceutics. 2022;14(6):1305.
doi:10.3390/pharmaceutics14061305 .

Komatović, Katarina, Matošević, Ana, Terzić-Jovanović, Nataša, Žunec, Suzana, Šegan, Sandra, Zlatović, Mario, Maraković, Nikola, Bosak, Anita, Opsenica, Dejan, "4-Aminoquinoline-Based Adamantanes as Potential Anticholinesterase Agents in Symptomatic Treatment of Alzheimer’s Disease" in Pharmaceutics, 14, no. 6 (2022):1305,
https://doi.org/10.3390/pharmaceutics14061305 . .

TY  - JOUR
AU  - Stojanović, Srđan
AU  - Petrović, Zoran Z.
AU  - Zlatović, Mario
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4761
AB  - PaiIn this work, the influence of amide–π interactions on stability and properties of superoxide dismutase (SOD) active centres was analysed. In the data set of 43 proteins, 5017 amide–π interactions were observed, and every active centre formed averagely about 117 interactions. Most of the interactions belonged to the backbone of proteins. The analysis of the geometry of the amide–π interactions revealed two preferred structures, parallel-displaced and T-shaped structure. The aim of this study was to investigate the energy contribution resulting the from amide–π interactions, which were in the lower range of strong hydrogen bonds. The conservation patterns in the present study indicate that more than half of the residues involved in these interactions are evolutionarily conserved. The stabilization centres for these proteins showed that all residues involved in amide–π interactions were of use in locating one or more of such centres. The results presented in this work can be very useful for the understanding of contribution of amide–π interaction to the stability of SOD active centres.
AB  - У овом раду је анализиран утицај амид–π интеракција на стабилност и особине
активног центра супероксид-дисмутазe (SOD). Примећено је 5017 амид–π интеракција у
сету података од 43 протеина, где, просечно, сваки активни центар формира 117 интер-
акција. Већина интеракција је укључена у основни ланац протеина. Анализа геометрије
амид–π интеракција открива две приоритетне структуре, паралелно-измештен (parallel-
-displaced) и Т-облик (T-shaped) структуре. Ова студија има за циљ истраживање допри-
носа енергије амид–π интеракција чије јачине су у доњем рангу јаких водоничних веза.
Преглед конзервираности показује да је више од половине остатака укључених у ове
интеракције еволутивно конзервирано. Стабилизациони центри ових протеина показују
да су сви остаци који чине амид–_интеракције важни у распоређивању једног или више
таквих центара. Свеукупно, резултати у овом раду ће бити врло корисни за разумевање
доприноса амид–π интеракција када се анализира стабилност активних центара SOD.
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Amide–π interactions in active centres of superoxide dismutase
T1  - Amid-–π interakcije u aktivnom centru superoksid-dismutaza
VL  - 86
VL  - 9
SP  - 781
EP  - 793
DO  - 10.2298/JSC210321042S
ER  - 

@article{
author = "Stojanović, Srđan and Petrović, Zoran Z. and Zlatović, Mario",
year = "2021",
abstract = "PaiIn this work, the influence of amide–π interactions on stability and properties of superoxide dismutase (SOD) active centres was analysed. In the data set of 43 proteins, 5017 amide–π interactions were observed, and every active centre formed averagely about 117 interactions. Most of the interactions belonged to the backbone of proteins. The analysis of the geometry of the amide–π interactions revealed two preferred structures, parallel-displaced and T-shaped structure. The aim of this study was to investigate the energy contribution resulting the from amide–π interactions, which were in the lower range of strong hydrogen bonds. The conservation patterns in the present study indicate that more than half of the residues involved in these interactions are evolutionarily conserved. The stabilization centres for these proteins showed that all residues involved in amide–π interactions were of use in locating one or more of such centres. The results presented in this work can be very useful for the understanding of contribution of amide–π interaction to the stability of SOD active centres., У овом раду је анализиран утицај амид–π интеракција на стабилност и особине
активног центра супероксид-дисмутазe (SOD). Примећено је 5017 амид–π интеракција у
сету података од 43 протеина, где, просечно, сваки активни центар формира 117 интер-
акција. Већина интеракција је укључена у основни ланац протеина. Анализа геометрије
амид–π интеракција открива две приоритетне структуре, паралелно-измештен (parallel-
-displaced) и Т-облик (T-shaped) структуре. Ова студија има за циљ истраживање допри-
носа енергије амид–π интеракција чије јачине су у доњем рангу јаких водоничних веза.
Преглед конзервираности показује да је више од половине остатака укључених у ове
интеракције еволутивно конзервирано. Стабилизациони центри ових протеина показују
да су сви остаци који чине амид–_интеракције важни у распоређивању једног или више
таквих центара. Свеукупно, резултати у овом раду ће бити врло корисни за разумевање
доприноса амид–π интеракција када се анализира стабилност активних центара SOD.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Amide–π interactions in active centres of superoxide dismutase, Amid-–π interakcije u aktivnom centru superoksid-dismutaza",
volume = "86, 9",
pages = "781-793",
doi = "10.2298/JSC210321042S"
}

Stojanović, S., Petrović, Z. Z.,& Zlatović, M.. (2021). Amide–π interactions in active centres of superoxide dismutase. in Journal of the Serbian Chemical Society
Belgrade : Serbian Chemical Society., 86, 781-793.
https://doi.org/10.2298/JSC210321042S

Stojanović S, Petrović ZZ, Zlatović M. Amide–π interactions in active centres of superoxide dismutase. in Journal of the Serbian Chemical Society. 2021;86:781-793.
doi:10.2298/JSC210321042S .

Stojanović, Srđan, Petrović, Zoran Z., Zlatović, Mario, "Amide–π interactions in active centres of superoxide dismutase" in Journal of the Serbian Chemical Society, 86 (2021):781-793,
https://doi.org/10.2298/JSC210321042S . .

TY  - JOUR
AU  - Novaković, Miroslav
AU  - Simić, Stefan
AU  - Koračak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomić, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3867
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3441
AB  - Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.
PB  - Elsevier
T2  - Fitoterapia
T1  - Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives
VL  - 142
SP  - 104520
DO  - 10.1016/j.fitote.2020.104520
ER  - 

@article{
author = "Novaković, Miroslav and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomić, Tatjana and Asakawa, Yoshinori and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2020",
abstract = "Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.",
publisher = "Elsevier",
journal = "Fitoterapia",
title = "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives",
volume = "142",
pages = "104520",
doi = "10.1016/j.fitote.2020.104520"
}

Novaković, M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomić, T., Asakawa, Y., Nikodinović-Runić, J.,& Opsenica, I.. (2020). Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia
Elsevier., 142, 104520.
https://doi.org/10.1016/j.fitote.2020.104520

Novaković M, Simić S, Koračak L, Zlatović M, Ilić-Tomić T, Asakawa Y, Nikodinović-Runić J, Opsenica I. Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia. 2020;142:104520.
doi:10.1016/j.fitote.2020.104520 .

Novaković, Miroslav, Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomić, Tatjana, Asakawa, Yoshinori, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives" in Fitoterapia, 142 (2020):104520,
https://doi.org/10.1016/j.fitote.2020.104520 . .

TY  - JOUR
AU  - Novaković, Miroslav
AU  - Simić, Stefan
AU  - Koračak, Ljiljana
AU  - Zlatović, Mario
AU  - Ilić-Tomić, Tatjana
AU  - Asakawa, Yoshinori
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3449
AB  - Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.
PB  - Elsevier
T2  - Fitoterapia
T1  - Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives
VL  - 142
SP  - 104520
DO  - 10.1016/j.fitote.2020.104520
ER  - 

@article{
author = "Novaković, Miroslav and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomić, Tatjana and Asakawa, Yoshinori and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2020",
abstract = "Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.",
publisher = "Elsevier",
journal = "Fitoterapia",
title = "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives",
volume = "142",
pages = "104520",
doi = "10.1016/j.fitote.2020.104520"
}

Novaković, M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomić, T., Asakawa, Y., Nikodinović-Runić, J.,& Opsenica, I.. (2020). Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia
Elsevier., 142, 104520.
https://doi.org/10.1016/j.fitote.2020.104520

Novaković M, Simić S, Koračak L, Zlatović M, Ilić-Tomić T, Asakawa Y, Nikodinović-Runić J, Opsenica I. Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia. 2020;142:104520.
doi:10.1016/j.fitote.2020.104520 .

Novaković, Miroslav, Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomić, Tatjana, Asakawa, Yoshinori, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives" in Fitoterapia, 142 (2020):104520,
https://doi.org/10.1016/j.fitote.2020.104520 . .

TY  - JOUR
AU  - Zlatar, Matija
AU  - Vlahović, Filip
AU  - Mitić, Dragana
AU  - Zlatović, Mario
AU  - Gruden, Maja
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3857
AB  - In the present work, we examine the magnetic properties of 8 "end-to-end" thiocyanato, and 3 "end-to-end" cyanato double bridged Ni(II) binu­cle­ar complexes. Thiocyanato complexes are weakly ferromagnetic. Cyanato brid­ged complexes exhibit weak antiferromagnetic coupling. There­fore, it is a challenge for computational chemistry to calculate the exchange coupling constant in these systems accurately. 17 different Density Functional Approximations with different flavors are used to find the method of choice to study magnetic properties in binuclear Ni(II) complexes within the Broken-Symmetry approach. It is found that M06-2X and PWPB95 performed the best compared to experimental values for the entire set of examined complexes. Furthermore, the magneto-structural correlation rationalizes the results.
AB  - У овом раду, проучавана су магнетна својства 8 "end-to-end" тиоцијанато, и 3 "end-to-end" цијанато двоструко премошћених Ni(II) бинуклеарних комплекса. Tиоцијанато премошћени комплекси су слабо феромагнетни. Комплекси премошћени цијанато лигандима показују слабо антиферомагнетно купловање. Због тога је прецизно израчунавање константи купловања у овим системима изазов за рачунарску хемију. Константе купловања у овим системима су израчунате Broken-Symmetry приступом у оквиру Теорије функционала густине. 17 апроксимативних функционала густине су коришћени како би се пронашао најпоузданији ниво теорије за проучавање магнетних својстава бинуклеарних Ni(II) комплекса. Утврђено је да су M06-2X и PWPB95 показали најбоље слагање са експерименталним вредностима за цео скуп испитиваних комплекса. Напослетку, резултати су рационализовани магнетно-структурном корелацијом.
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Assessment of density functional approximations for calculation of exchange coupling constants in thiocyanato and cyanato double bridged binuclear Ni(II) complexes
T1  - Испитивање апроксимативних функционала густине за израчунавање константи купловања у двоструко премошћеним тиоцијанато и цијанато бинуклеарним Ni(II) kомплексима
VL  - 85
IS  - 12
SP  - 1577
EP  - 1590
DO  - 10.2298/JSC201106071Z
ER  - 

@article{
author = "Zlatar, Matija and Vlahović, Filip and Mitić, Dragana and Zlatović, Mario and Gruden, Maja",
year = "2020",
abstract = "In the present work, we examine the magnetic properties of 8 "end-to-end" thiocyanato, and 3 "end-to-end" cyanato double bridged Ni(II) binu­cle­ar complexes. Thiocyanato complexes are weakly ferromagnetic. Cyanato brid­ged complexes exhibit weak antiferromagnetic coupling. There­fore, it is a challenge for computational chemistry to calculate the exchange coupling constant in these systems accurately. 17 different Density Functional Approximations with different flavors are used to find the method of choice to study magnetic properties in binuclear Ni(II) complexes within the Broken-Symmetry approach. It is found that M06-2X and PWPB95 performed the best compared to experimental values for the entire set of examined complexes. Furthermore, the magneto-structural correlation rationalizes the results., У овом раду, проучавана су магнетна својства 8 "end-to-end" тиоцијанато, и 3 "end-to-end" цијанато двоструко премошћених Ni(II) бинуклеарних комплекса. Tиоцијанато премошћени комплекси су слабо феромагнетни. Комплекси премошћени цијанато лигандима показују слабо антиферомагнетно купловање. Због тога је прецизно израчунавање константи купловања у овим системима изазов за рачунарску хемију. Константе купловања у овим системима су израчунате Broken-Symmetry приступом у оквиру Теорије функционала густине. 17 апроксимативних функционала густине су коришћени како би се пронашао најпоузданији ниво теорије за проучавање магнетних својстава бинуклеарних Ni(II) комплекса. Утврђено је да су M06-2X и PWPB95 показали најбоље слагање са експерименталним вредностима за цео скуп испитиваних комплекса. Напослетку, резултати су рационализовани магнетно-структурном корелацијом.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Assessment of density functional approximations for calculation of exchange coupling constants in thiocyanato and cyanato double bridged binuclear Ni(II) complexes, Испитивање апроксимативних функционала густине за израчунавање константи купловања у двоструко премошћеним тиоцијанато и цијанато бинуклеарним Ni(II) kомплексима",
volume = "85",
number = "12",
pages = "1577-1590",
doi = "10.2298/JSC201106071Z"
}

Zlatar, M., Vlahović, F., Mitić, D., Zlatović, M.,& Gruden, M.. (2020). Assessment of density functional approximations for calculation of exchange coupling constants in thiocyanato and cyanato double bridged binuclear Ni(II) complexes. in Journal of the Serbian Chemical Society
Belgrade : Serbian Chemical Society., 85(12), 1577-1590.
https://doi.org/10.2298/JSC201106071Z

Zlatar M, Vlahović F, Mitić D, Zlatović M, Gruden M. Assessment of density functional approximations for calculation of exchange coupling constants in thiocyanato and cyanato double bridged binuclear Ni(II) complexes. in Journal of the Serbian Chemical Society. 2020;85(12):1577-1590.
doi:10.2298/JSC201106071Z .

Zlatar, Matija, Vlahović, Filip, Mitić, Dragana, Zlatović, Mario, Gruden, Maja, "Assessment of density functional approximations for calculation of exchange coupling constants in thiocyanato and cyanato double bridged binuclear Ni(II) complexes" in Journal of the Serbian Chemical Society, 85, no. 12 (2020):1577-1590,
https://doi.org/10.2298/JSC201106071Z . .

TY  - JOUR
AU  - Zlatar, Matija
AU  - Vlahović, Filip
AU  - Mitić, Dragana
AU  - Zlatović, Mario
AU  - Gruden, Maja
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4041
AB  - In the present work, we examine the magnetic properties of 8 “end-to-end” thiocyanato, and 3 “end-to-end” cyanato double bridged Ni(II) binuc­lear complexes. Thiocyanato complexes are weakly ferromagnetic. Cyanato brid­ged complexes exhibit weak antiferromagnetic coupling. There­fore, it is a chal­lenge for computational chemistry to calculate the exchange coupling constant in these systems accurately. 17 different density functional approxim­ations with different flavours are used to find the method of choice to study magnetic properties in binuclear Ni(II) complexes within the broken-symmetry approach. It is found that M06-2X and PWPB95 performed the best compared to the experimental values for the entire set of examined complexes. Further­more, the magneto-structural correlation rationalizes the results.
AB  - Проучавана су магнетна својства 8 „end-to-end“ тиоцијанато, и 3 „end-to-end“ цијанато двоструко премошћених Ni(II) бинуклеарних комплекса. Tиоцијанато премошћени комплекси су слабо феромагнетни. Комплекси премошћени цијанато лигандима показују слабо антиферомагнетно купловање. Због тога је прецизно израчунавање константи купловања у овим системима изазов за рачунарску хемију. Константе купловања у овим системима су израчунате Broken-Symmetry приступом у оквиру теорије функционала густине. Седамнаест апроксимативних функционала густине су коришћени како би се пронашао најпоузданији ниво теорије за проучавање магнетних својстава бинуклеарних Ni(II) комплекса. Утврђено је да су M06-2X и PWPB95 показали најбоље слагање са експерименталним вредностима за цео скуп испитиваних комплекса. Напослетку, резултати су рационализовани магнетно-структурном kорелацијом.
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Assessment of density functional approximations for calculation of exchange coupling constants in thiocyanato and cyanato double bridged binuclear Ni(II) complexes
T1  - Испитивање апроксимативних функционала густине за израчунавање константи купловања у двоструко премошћеним тиоцијанато и цијанато бинуклеарним Ni(II) kомплексима
VL  - 85
IS  - 12
SP  - 1577
EP  - 1590
DO  - 10.2298/JSC201106071Z
ER  - 

@article{
author = "Zlatar, Matija and Vlahović, Filip and Mitić, Dragana and Zlatović, Mario and Gruden, Maja",
year = "2020",
abstract = "In the present work, we examine the magnetic properties of 8 “end-to-end” thiocyanato, and 3 “end-to-end” cyanato double bridged Ni(II) binuc­lear complexes. Thiocyanato complexes are weakly ferromagnetic. Cyanato brid­ged complexes exhibit weak antiferromagnetic coupling. There­fore, it is a chal­lenge for computational chemistry to calculate the exchange coupling constant in these systems accurately. 17 different density functional approxim­ations with different flavours are used to find the method of choice to study magnetic properties in binuclear Ni(II) complexes within the broken-symmetry approach. It is found that M06-2X and PWPB95 performed the best compared to the experimental values for the entire set of examined complexes. Further­more, the magneto-structural correlation rationalizes the results., Проучавана су магнетна својства 8 „end-to-end“ тиоцијанато, и 3 „end-to-end“ цијанато двоструко премошћених Ni(II) бинуклеарних комплекса. Tиоцијанато премошћени комплекси су слабо феромагнетни. Комплекси премошћени цијанато лигандима показују слабо антиферомагнетно купловање. Због тога је прецизно израчунавање константи купловања у овим системима изазов за рачунарску хемију. Константе купловања у овим системима су израчунате Broken-Symmetry приступом у оквиру теорије функционала густине. Седамнаест апроксимативних функционала густине су коришћени како би се пронашао најпоузданији ниво теорије за проучавање магнетних својстава бинуклеарних Ni(II) комплекса. Утврђено је да су M06-2X и PWPB95 показали најбоље слагање са експерименталним вредностима за цео скуп испитиваних комплекса. Напослетку, резултати су рационализовани магнетно-структурном kорелацијом.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Assessment of density functional approximations for calculation of exchange coupling constants in thiocyanato and cyanato double bridged binuclear Ni(II) complexes, Испитивање апроксимативних функционала густине за израчунавање константи купловања у двоструко премошћеним тиоцијанато и цијанато бинуклеарним Ni(II) kомплексима",
volume = "85",
number = "12",
pages = "1577-1590",
doi = "10.2298/JSC201106071Z"
}

Zlatar, M., Vlahović, F., Mitić, D., Zlatović, M.,& Gruden, M.. (2020). Assessment of density functional approximations for calculation of exchange coupling constants in thiocyanato and cyanato double bridged binuclear Ni(II) complexes. in Journal of the Serbian Chemical Society
Belgrade : Serbian Chemical Society., 85(12), 1577-1590.
https://doi.org/10.2298/JSC201106071Z

Zlatar M, Vlahović F, Mitić D, Zlatović M, Gruden M. Assessment of density functional approximations for calculation of exchange coupling constants in thiocyanato and cyanato double bridged binuclear Ni(II) complexes. in Journal of the Serbian Chemical Society. 2020;85(12):1577-1590.
doi:10.2298/JSC201106071Z .

Zlatar, Matija, Vlahović, Filip, Mitić, Dragana, Zlatović, Mario, Gruden, Maja, "Assessment of density functional approximations for calculation of exchange coupling constants in thiocyanato and cyanato double bridged binuclear Ni(II) complexes" in Journal of the Serbian Chemical Society, 85, no. 12 (2020):1577-1590,
https://doi.org/10.2298/JSC201106071Z . .

TY  - JOUR
AU  - Sović, Irena
AU  - Cindrić, Maja
AU  - Perin, Nataša
AU  - Boček, Ida
AU  - Novaković, Irena
AU  - Damjanović, Ana
AU  - Stanojković, Tatjana
AU  - Zlatović, Mario
AU  - Hranjec, Marijana
AU  - Bertoša, Branimir
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3851
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3416
AB  - This paper discusses antioxidative and biological activities of 25 novel amidino substituted benzamides with a variety of heteroaromatic nuclei attached to the benzamide moiety and with a variable number of methoxy or hydroxy substituents. Targeted compounds, bearing either amidino or 2-imidazolinyl substituent, were obtained in the Pinner reaction from cyano precursors. 3D-QSAR models were generated to predict antioxidative activity of the 25 novel aromatic and heteroaromatic benzamide derivatives. The compounds were tested for antioxidative activity using in vitro spectrophotometric assays. Direct validation of 3D-QSAR approach for predicting activities of novel benzamide derivatives was carried out by comparing experimental and computationally predicted antioxidative activity. Experimentally determined activities for all novel compounds were found to be within a standard deviation of error of the models. Following this, structure–activity relationships among the synthesized compounds are discussed. Furthermore, antiproliferative activity in vitro against HeLa cells as well as antibacterial and antifungal activity was tested to confirm the other biological activities of the prepared compounds.
PB  - American Chemical Society (ACS)
T2  - Chemical Research in Toxicology
T1  - Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity.
VL  - 32
IS  - 9
SP  - 1880
EP  - 1892
DO  - 10.1021/acs.chemrestox.9b00256
ER  - 

@article{
author = "Sović, Irena and Cindrić, Maja and Perin, Nataša and Boček, Ida and Novaković, Irena and Damjanović, Ana and Stanojković, Tatjana and Zlatović, Mario and Hranjec, Marijana and Bertoša, Branimir",
year = "2019",
abstract = "This paper discusses antioxidative and biological activities of 25 novel amidino substituted benzamides with a variety of heteroaromatic nuclei attached to the benzamide moiety and with a variable number of methoxy or hydroxy substituents. Targeted compounds, bearing either amidino or 2-imidazolinyl substituent, were obtained in the Pinner reaction from cyano precursors. 3D-QSAR models were generated to predict antioxidative activity of the 25 novel aromatic and heteroaromatic benzamide derivatives. The compounds were tested for antioxidative activity using in vitro spectrophotometric assays. Direct validation of 3D-QSAR approach for predicting activities of novel benzamide derivatives was carried out by comparing experimental and computationally predicted antioxidative activity. Experimentally determined activities for all novel compounds were found to be within a standard deviation of error of the models. Following this, structure–activity relationships among the synthesized compounds are discussed. Furthermore, antiproliferative activity in vitro against HeLa cells as well as antibacterial and antifungal activity was tested to confirm the other biological activities of the prepared compounds.",
publisher = "American Chemical Society (ACS)",
journal = "Chemical Research in Toxicology",
title = "Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity.",
volume = "32",
number = "9",
pages = "1880-1892",
doi = "10.1021/acs.chemrestox.9b00256"
}

Sović, I., Cindrić, M., Perin, N., Boček, I., Novaković, I., Damjanović, A., Stanojković, T., Zlatović, M., Hranjec, M.,& Bertoša, B.. (2019). Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity.. in Chemical Research in Toxicology
American Chemical Society (ACS)., 32(9), 1880-1892.
https://doi.org/10.1021/acs.chemrestox.9b00256

Sović I, Cindrić M, Perin N, Boček I, Novaković I, Damjanović A, Stanojković T, Zlatović M, Hranjec M, Bertoša B. Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity.. in Chemical Research in Toxicology. 2019;32(9):1880-1892.
doi:10.1021/acs.chemrestox.9b00256 .

Sović, Irena, Cindrić, Maja, Perin, Nataša, Boček, Ida, Novaković, Irena, Damjanović, Ana, Stanojković, Tatjana, Zlatović, Mario, Hranjec, Marijana, Bertoša, Branimir, "Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity." in Chemical Research in Toxicology, 32, no. 9 (2019):1880-1892,
https://doi.org/10.1021/acs.chemrestox.9b00256 . .

TY  - JOUR
AU  - Sović, Irena
AU  - Cindrić, Maja
AU  - Perin, Nataša
AU  - Boček, Ida
AU  - Novaković, Irena
AU  - Damjanović, Ana
AU  - Stanojković, Tatjana
AU  - Zlatović, Mario
AU  - Hranjec, Marijana
AU  - Bertoša, Branimir
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3464
AB  - This paper discusses antioxidative and biological activities of 25 novel amidino substituted benzamides with a variety of heteroaromatic nuclei attached to the benzamide moiety and with a variable number of methoxy or hydroxy substituents. Targeted compounds, bearing either amidino or 2-imidazolinyl substituent, were obtained in the Pinner reaction from cyano precursors. 3D-QSAR models were generated to predict antioxidative activity of the 25 novel aromatic and heteroaromatic benzamide derivatives. The compounds were tested for antioxidative activity using in vitro spectrophotometric assays. Direct validation of 3D-QSAR approach for predicting activities of novel benzamide derivatives was carried out by comparing experimental and computationally predicted antioxidative activity. Experimentally determined activities for all novel compounds were found to be within a standard deviation of error of the models. Following this, structure–activity relationships among the synthesized compounds are discussed. Furthermore, antiproliferative activity in vitro against HeLa cells as well as antibacterial and antifungal activity was tested to confirm the other biological activities of the prepared compounds.
PB  - American Chemical Society (ACS)
T2  - Chemical Research in Toxicology
T1  - Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity.
VL  - 32
IS  - 9
SP  - 1880
EP  - 1892
DO  - 10.1021/acs.chemrestox.9b00256
ER  - 

@article{
author = "Sović, Irena and Cindrić, Maja and Perin, Nataša and Boček, Ida and Novaković, Irena and Damjanović, Ana and Stanojković, Tatjana and Zlatović, Mario and Hranjec, Marijana and Bertoša, Branimir",
year = "2019",
abstract = "This paper discusses antioxidative and biological activities of 25 novel amidino substituted benzamides with a variety of heteroaromatic nuclei attached to the benzamide moiety and with a variable number of methoxy or hydroxy substituents. Targeted compounds, bearing either amidino or 2-imidazolinyl substituent, were obtained in the Pinner reaction from cyano precursors. 3D-QSAR models were generated to predict antioxidative activity of the 25 novel aromatic and heteroaromatic benzamide derivatives. The compounds were tested for antioxidative activity using in vitro spectrophotometric assays. Direct validation of 3D-QSAR approach for predicting activities of novel benzamide derivatives was carried out by comparing experimental and computationally predicted antioxidative activity. Experimentally determined activities for all novel compounds were found to be within a standard deviation of error of the models. Following this, structure–activity relationships among the synthesized compounds are discussed. Furthermore, antiproliferative activity in vitro against HeLa cells as well as antibacterial and antifungal activity was tested to confirm the other biological activities of the prepared compounds.",
publisher = "American Chemical Society (ACS)",
journal = "Chemical Research in Toxicology",
title = "Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity.",
volume = "32",
number = "9",
pages = "1880-1892",
doi = "10.1021/acs.chemrestox.9b00256"
}

Sović, I., Cindrić, M., Perin, N., Boček, I., Novaković, I., Damjanović, A., Stanojković, T., Zlatović, M., Hranjec, M.,& Bertoša, B.. (2019). Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity.. in Chemical Research in Toxicology
American Chemical Society (ACS)., 32(9), 1880-1892.
https://doi.org/10.1021/acs.chemrestox.9b00256

Sović I, Cindrić M, Perin N, Boček I, Novaković I, Damjanović A, Stanojković T, Zlatović M, Hranjec M, Bertoša B. Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity.. in Chemical Research in Toxicology. 2019;32(9):1880-1892.
doi:10.1021/acs.chemrestox.9b00256 .

Sović, Irena, Cindrić, Maja, Perin, Nataša, Boček, Ida, Novaković, Irena, Damjanović, Ana, Stanojković, Tatjana, Zlatović, Mario, Hranjec, Marijana, Bertoša, Branimir, "Biological Potential of Novel Methoxy and Hydroxy Substituted Heteroaromatic Amides Designed as Promising Antioxidative Agents: Synthesis, 3D-QSAR Analysis, and Biological Activity." in Chemical Research in Toxicology, 32, no. 9 (2019):1880-1892,
https://doi.org/10.1021/acs.chemrestox.9b00256 . .

TY  - JOUR
AU  - Aleksic, Ivana
AU  - Jeremić, Jelena
AU  - Milivojevic, Dusan
AU  - Ilić-Tomić, Tatjana
AU  - Šegan, Sandra
AU  - Zlatović, Mario
AU  - Opsenica, Dejan
AU  - Senerovic, Lidija
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3198
AB  - Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.
PB  - American Chemical Society (ACS)
T2  - ACS Chemical Biology
T1  - N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa
VL  - 14
IS  - 12
SP  - 2800
EP  - 2809
DO  - 10.1021/acschembio.9b00682
ER  - 

@article{
author = "Aleksic, Ivana and Jeremić, Jelena and Milivojevic, Dusan and Ilić-Tomić, Tatjana and Šegan, Sandra and Zlatović, Mario and Opsenica, Dejan and Senerovic, Lidija",
year = "2019",
abstract = "Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.",
publisher = "American Chemical Society (ACS)",
journal = "ACS Chemical Biology",
title = "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa",
volume = "14",
number = "12",
pages = "2800-2809",
doi = "10.1021/acschembio.9b00682"
}

Aleksic, I., Jeremić, J., Milivojevic, D., Ilić-Tomić, T., Šegan, S., Zlatović, M., Opsenica, D.,& Senerovic, L.. (2019). N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology
American Chemical Society (ACS)., 14(12), 2800-2809.
https://doi.org/10.1021/acschembio.9b00682

Aleksic I, Jeremić J, Milivojevic D, Ilić-Tomić T, Šegan S, Zlatović M, Opsenica D, Senerovic L. N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology. 2019;14(12):2800-2809.
doi:10.1021/acschembio.9b00682 .

Aleksic, Ivana, Jeremić, Jelena, Milivojevic, Dusan, Ilić-Tomić, Tatjana, Šegan, Sandra, Zlatović, Mario, Opsenica, Dejan, Senerovic, Lidija, "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa" in ACS Chemical Biology, 14, no. 12 (2019):2800-2809,
https://doi.org/10.1021/acschembio.9b00682 . .

TY  - JOUR
AU  - Breberina, Luka
AU  - Zlatović, Mario
AU  - Nikolić, Milan
AU  - Stojanović, Srđan
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3233
AB  - Protein‐protein interactions are an important phenomenon in biological processes and functions. We used the manually curated non‐redundant dataset of 118 phycocyanin interfaces to gain additional insight into this phenomenon using a robust inter‐atomic non‐covalent interaction analyzing tool PPCheck. Our observations indicate that there is a relatively high composition of hydrophobic residues at the interfaces. Most of the interface residues are clustered at the middle of the range which we call “standard‐size” interfaces. Furthermore, the multiple interaction patterns founded in the present study indicate that more than half of the residues involved in these interactions participate in multiple and water‐bridged hydrogen bonds. Thus, hydrogen bonds contribute maximally towards the stability of protein‐protein complexes. The analysis shows that hydrogen bond energies contribute to about 88 % to the total energy and it also increases with interface size. Van der Waals (vdW) energy contributes to 9.3 %±1.7 % on average in these complexes. Moreover, there is about 1.9 %±1.5 % contribution by electrostatic energy. Nevertheless, the role by vdW and electrostatic energy could not be ignored in interface binding. Results show that the total binding energy is more for large phycocyanin interfaces. The normalized energy per residue was less than −16 kJ mol−1, while most of them have energy in the range from −6 to −14 kJ mol−1. The non‐covalent interacting residues in these proteins were found to be highly conserved. Obtained results might contribute to the understanding of structural stability of this class of evolutionary essential proteins with increased practical application and future designs of novel protein‐bioactive compound interactions.
PB  - Wiley
T2  - Molecular Informatics
T1  - Computational Analysis of Non‐covalent Interactions in Phycocyanin Subunit Interfaces
VL  - 38
IS  - 11-12
SP  - 1800145
DO  - 10.1002/minf.201800145
ER  - 

@article{
author = "Breberina, Luka and Zlatović, Mario and Nikolić, Milan and Stojanović, Srđan",
year = "2019",
abstract = "Protein‐protein interactions are an important phenomenon in biological processes and functions. We used the manually curated non‐redundant dataset of 118 phycocyanin interfaces to gain additional insight into this phenomenon using a robust inter‐atomic non‐covalent interaction analyzing tool PPCheck. Our observations indicate that there is a relatively high composition of hydrophobic residues at the interfaces. Most of the interface residues are clustered at the middle of the range which we call “standard‐size” interfaces. Furthermore, the multiple interaction patterns founded in the present study indicate that more than half of the residues involved in these interactions participate in multiple and water‐bridged hydrogen bonds. Thus, hydrogen bonds contribute maximally towards the stability of protein‐protein complexes. The analysis shows that hydrogen bond energies contribute to about 88 % to the total energy and it also increases with interface size. Van der Waals (vdW) energy contributes to 9.3 %±1.7 % on average in these complexes. Moreover, there is about 1.9 %±1.5 % contribution by electrostatic energy. Nevertheless, the role by vdW and electrostatic energy could not be ignored in interface binding. Results show that the total binding energy is more for large phycocyanin interfaces. The normalized energy per residue was less than −16 kJ mol−1, while most of them have energy in the range from −6 to −14 kJ mol−1. The non‐covalent interacting residues in these proteins were found to be highly conserved. Obtained results might contribute to the understanding of structural stability of this class of evolutionary essential proteins with increased practical application and future designs of novel protein‐bioactive compound interactions.",
publisher = "Wiley",
journal = "Molecular Informatics",
title = "Computational Analysis of Non‐covalent Interactions in Phycocyanin Subunit Interfaces",
volume = "38",
number = "11-12",
pages = "1800145",
doi = "10.1002/minf.201800145"
}

Breberina, L., Zlatović, M., Nikolić, M.,& Stojanović, S.. (2019). Computational Analysis of Non‐covalent Interactions in Phycocyanin Subunit Interfaces. in Molecular Informatics
Wiley., 38(11-12), 1800145.
https://doi.org/10.1002/minf.201800145

Breberina L, Zlatović M, Nikolić M, Stojanović S. Computational Analysis of Non‐covalent Interactions in Phycocyanin Subunit Interfaces. in Molecular Informatics. 2019;38(11-12):1800145.
doi:10.1002/minf.201800145 .

Breberina, Luka, Zlatović, Mario, Nikolić, Milan, Stojanović, Srđan, "Computational Analysis of Non‐covalent Interactions in Phycocyanin Subunit Interfaces" in Molecular Informatics, 38, no. 11-12 (2019):1800145,
https://doi.org/10.1002/minf.201800145 . .

TY  - JOUR
AU  - Aleksic, Ivana
AU  - Jeremić, Jelena
AU  - Milivojevic, Dusan
AU  - Ilić-Tomić, Tatjana
AU  - Šegan, Sandra
AU  - Zlatović, Mario
AU  - Opsenica, Dejan
AU  - Senerovic, Lidija
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3198
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3341
AB  - Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.
PB  - American Chemical Society (ACS)
T2  - ACS Chemical Biology
T1  - N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa
VL  - 14
IS  - 12
SP  - 2800
EP  - 2809
DO  - 10.1021/acschembio.9b00682
ER  - 

@article{
author = "Aleksic, Ivana and Jeremić, Jelena and Milivojevic, Dusan and Ilić-Tomić, Tatjana and Šegan, Sandra and Zlatović, Mario and Opsenica, Dejan and Senerovic, Lidija",
year = "2019",
abstract = "Pseudomonas aeruginosa is a leading cause of nosocomial infections that are becoming increasingly difficult to treat due to the occurrence of antibiotic resistant strains. Since P. aeruginosa virulence is controlled through quorum sensing, small molecule treatments inhibiting quorum sensing signaling pathways provide a promising therapeutic option. Consequently, we synthesized a series of N-octaneamino-4-aminoquinoline derivatives to optimize this chemotype’s antivirulence activity against P. aeruginosa via inhibition of pyocyanin production. The most potent derivative, which possesses a benzofuran substituent, provided effective inhibition of pyocyanin production (IC50 = 12 μM), biofilm formation (BFIC50 = 50 μM), and motility. Experimentally, the compound’s activity is achieved through competitive inhibition of PqsR, and structure–activity data were rationalized using molecular docking studies.",
publisher = "American Chemical Society (ACS)",
journal = "ACS Chemical Biology",
title = "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa",
volume = "14",
number = "12",
pages = "2800-2809",
doi = "10.1021/acschembio.9b00682"
}

Aleksic, I., Jeremić, J., Milivojevic, D., Ilić-Tomić, T., Šegan, S., Zlatović, M., Opsenica, D.,& Senerovic, L.. (2019). N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology
American Chemical Society (ACS)., 14(12), 2800-2809.
https://doi.org/10.1021/acschembio.9b00682

Aleksic I, Jeremić J, Milivojevic D, Ilić-Tomić T, Šegan S, Zlatović M, Opsenica D, Senerovic L. N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa. in ACS Chemical Biology. 2019;14(12):2800-2809.
doi:10.1021/acschembio.9b00682 .

Aleksic, Ivana, Jeremić, Jelena, Milivojevic, Dusan, Ilić-Tomić, Tatjana, Šegan, Sandra, Zlatović, Mario, Opsenica, Dejan, Senerovic, Lidija, "N-benzyl derivatives of long-chained 4-Amino-7-chloro-quionolines as inhibitors of pyocyanin production in Pseudomonas aeruginosa" in ACS Chemical Biology, 14, no. 12 (2019):2800-2809,
https://doi.org/10.1021/acschembio.9b00682 . .

TY  - JOUR
AU  - Marković, Olivera
AU  - Cvijetić, Ilija
AU  - Zlatović, Mario
AU  - Opsenica, Igor
AU  - Konstantinović, Jelena M.
AU  - Terzić-Jovanović, Nataša
AU  - Šolaja, Bogdan
AU  - Verbić, Tatjana
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2472
AB  - Interactions between eight in-house synthesized aminoquinolines, along with well-known chloroquine, and human serum albumin (HSA) have been studied by fluorescence spectroscopy. The synthesized aminoquinolines, despite being structurally diverse, were found to be very potent antimalarials. Fluorescence measurements indicate that three compounds having additional thiophene or benzothiophene substructure bind more strongly to HSA than other studied compounds. Competitive binding experiments indicate that these three compounds bind significantly stronger to warfarin compared to diazepam binding site. Fluorescence quenching at three temperatures (20, 25, and 37 degrees C) was analyzed using classical Stern-Volmer equation, and a static quenching mechanism was proposed. The enthalpy and entropy changes upon sulphur-containing compound-HSA interactions were calculated using Van't Hoff equation. Positive values of enthalpy and entropy changes indicate that non-specific, hydrophobic interactions are the main contributors to HSA-compound interaction. Molecular docking and calculated lipophilicity descriptors indicate the same, pointing out that the increased lipophilicity of sulphur-containing compounds might be a reason for their better binding to HSA. Obtained results might contribute to design of novel derivatives with improved-pharmacokinetic properties and drug efficacy.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
T1  - Human serum albumin binding of certain antimalarials
VL  - 192
SP  - 128
EP  - 139
DO  - 10.1016/j.saa.2017.10.061
ER  - 

@article{
author = "Marković, Olivera and Cvijetić, Ilija and Zlatović, Mario and Opsenica, Igor and Konstantinović, Jelena M. and Terzić-Jovanović, Nataša and Šolaja, Bogdan and Verbić, Tatjana",
year = "2018",
abstract = "Interactions between eight in-house synthesized aminoquinolines, along with well-known chloroquine, and human serum albumin (HSA) have been studied by fluorescence spectroscopy. The synthesized aminoquinolines, despite being structurally diverse, were found to be very potent antimalarials. Fluorescence measurements indicate that three compounds having additional thiophene or benzothiophene substructure bind more strongly to HSA than other studied compounds. Competitive binding experiments indicate that these three compounds bind significantly stronger to warfarin compared to diazepam binding site. Fluorescence quenching at three temperatures (20, 25, and 37 degrees C) was analyzed using classical Stern-Volmer equation, and a static quenching mechanism was proposed. The enthalpy and entropy changes upon sulphur-containing compound-HSA interactions were calculated using Van't Hoff equation. Positive values of enthalpy and entropy changes indicate that non-specific, hydrophobic interactions are the main contributors to HSA-compound interaction. Molecular docking and calculated lipophilicity descriptors indicate the same, pointing out that the increased lipophilicity of sulphur-containing compounds might be a reason for their better binding to HSA. Obtained results might contribute to design of novel derivatives with improved-pharmacokinetic properties and drug efficacy.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy",
title = "Human serum albumin binding of certain antimalarials",
volume = "192",
pages = "128-139",
doi = "10.1016/j.saa.2017.10.061"
}

Marković, O., Cvijetić, I., Zlatović, M., Opsenica, I., Konstantinović, J. M., Terzić-Jovanović, N., Šolaja, B.,& Verbić, T.. (2018). Human serum albumin binding of certain antimalarials. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
Oxford : Pergamon-Elsevier Science Ltd., 192, 128-139.
https://doi.org/10.1016/j.saa.2017.10.061

Marković O, Cvijetić I, Zlatović M, Opsenica I, Konstantinović JM, Terzić-Jovanović N, Šolaja B, Verbić T. Human serum albumin binding of certain antimalarials. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy. 2018;192:128-139.
doi:10.1016/j.saa.2017.10.061 .

Marković, Olivera, Cvijetić, Ilija, Zlatović, Mario, Opsenica, Igor, Konstantinović, Jelena M., Terzić-Jovanović, Nataša, Šolaja, Bogdan, Verbić, Tatjana, "Human serum albumin binding of certain antimalarials" in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 192 (2018):128-139,
https://doi.org/10.1016/j.saa.2017.10.061 . .

TY  - JOUR
AU  - Ribić, Vesna
AU  - Stojanović, Srđan
AU  - Zlatović, Mario
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2457
AB  - We investigated 1060 possible anion-pi interactions in a data set of 41 superoxide dismutase active centers. Our observations indicate that majority of the aromatic residues are capable to form anion-pi interactions, mainly by long-range contacts, and that there is preference of Trp over other aromatic residues in these interactions. Furthermore, 68% of total predicted interactions in the dataset are multiple anion-pi interactions. Anion-pi interactions are distance and orientation dependent. We analyzed the energy contribution resulting from anion-pi interactions using ab initio calculations. The results showed that, while most of their interaction energies lay in the range from -0 to -4 kcal mol(-1), those energies can be up to -9 kcal mol(-1) and about 34% of interactions were found to be repulsive. Majority of the suggested anion-pi interacting residues in ternary complexes are metal-assisted. Stabilization centers for these proteins showed that all the six residues found in predicted anion-pi interactions are important in locating one or more of such centers. The anion-pi interacting residues in these proteins were found to be highly conserved. We hope that these studies might contribute useful information regarding structural stability and its interaction in future designs of novel metalloproteins.
PB  - Elsevier
T2  - International Journal of Biological Macromolecules
T1  - Anion-pi interactions in active centers of superoxide dismutases
VL  - 106
SP  - 559
EP  - 568
DO  - 10.1016/j.ijbiomac.2017.08.050
ER  - 

@article{
author = "Ribić, Vesna and Stojanović, Srđan and Zlatović, Mario",
year = "2018",
abstract = "We investigated 1060 possible anion-pi interactions in a data set of 41 superoxide dismutase active centers. Our observations indicate that majority of the aromatic residues are capable to form anion-pi interactions, mainly by long-range contacts, and that there is preference of Trp over other aromatic residues in these interactions. Furthermore, 68% of total predicted interactions in the dataset are multiple anion-pi interactions. Anion-pi interactions are distance and orientation dependent. We analyzed the energy contribution resulting from anion-pi interactions using ab initio calculations. The results showed that, while most of their interaction energies lay in the range from -0 to -4 kcal mol(-1), those energies can be up to -9 kcal mol(-1) and about 34% of interactions were found to be repulsive. Majority of the suggested anion-pi interacting residues in ternary complexes are metal-assisted. Stabilization centers for these proteins showed that all the six residues found in predicted anion-pi interactions are important in locating one or more of such centers. The anion-pi interacting residues in these proteins were found to be highly conserved. We hope that these studies might contribute useful information regarding structural stability and its interaction in future designs of novel metalloproteins.",
publisher = "Elsevier",
journal = "International Journal of Biological Macromolecules",
title = "Anion-pi interactions in active centers of superoxide dismutases",
volume = "106",
pages = "559-568",
doi = "10.1016/j.ijbiomac.2017.08.050"
}

Ribić, V., Stojanović, S.,& Zlatović, M.. (2018). Anion-pi interactions in active centers of superoxide dismutases. in International Journal of Biological Macromolecules
Elsevier., 106, 559-568.
https://doi.org/10.1016/j.ijbiomac.2017.08.050

Ribić V, Stojanović S, Zlatović M. Anion-pi interactions in active centers of superoxide dismutases. in International Journal of Biological Macromolecules. 2018;106:559-568.
doi:10.1016/j.ijbiomac.2017.08.050 .

Ribić, Vesna, Stojanović, Srđan, Zlatović, Mario, "Anion-pi interactions in active centers of superoxide dismutases" in International Journal of Biological Macromolecules, 106 (2018):559-568,
https://doi.org/10.1016/j.ijbiomac.2017.08.050 . .

TY  - JOUR
AU  - Ribić, Vesna
AU  - Stojanović, Srđan
AU  - Zlatović, Mario
PY  - 2018
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3151
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3140
AB  - We investigated 1060 possible anion-pi interactions in a data set of 41 superoxide dismutase active centers. Our observations indicate that majority of the aromatic residues are capable to form anion-pi interactions, mainly by long-range contacts, and that there is preference of Trp over other aromatic residues in these interactions. Furthermore, 68% of total predicted interactions in the dataset are multiple anion-pi interactions. Anion-pi interactions are distance and orientation dependent. We analyzed the energy contribution resulting from anion-pi interactions using ab initio calculations. The results showed that, while most of their interaction energies lay in the range from -0 to -4 kcal mol(-1), those energies can be up to -9 kcal mol(-1) and about 34% of interactions were found to be repulsive. Majority of the suggested anion-pi interacting residues in ternary complexes are metal-assisted. Stabilization centers for these proteins showed that all the six residues found in predicted anion-pi interactions are important in locating one or more of such centers. The anion-pi interacting residues in these proteins were found to be highly conserved. We hope that these studies might contribute useful information regarding structural stability and its interaction in future designs of novel metalloproteins. (C) 2017 Elsevier B.V. All rights reserved.
PB  - Elsevier
T2  - International Journal of Biological Macromolecules
T1  - Anion-pi interactions in active centers of superoxide dismutases
VL  - 106
SP  - 559
EP  - 568
DO  - 10.1016/j.ijbiomac.2017.08.050
ER  - 

@article{
author = "Ribić, Vesna and Stojanović, Srđan and Zlatović, Mario",
year = "2018",
abstract = "We investigated 1060 possible anion-pi interactions in a data set of 41 superoxide dismutase active centers. Our observations indicate that majority of the aromatic residues are capable to form anion-pi interactions, mainly by long-range contacts, and that there is preference of Trp over other aromatic residues in these interactions. Furthermore, 68% of total predicted interactions in the dataset are multiple anion-pi interactions. Anion-pi interactions are distance and orientation dependent. We analyzed the energy contribution resulting from anion-pi interactions using ab initio calculations. The results showed that, while most of their interaction energies lay in the range from -0 to -4 kcal mol(-1), those energies can be up to -9 kcal mol(-1) and about 34% of interactions were found to be repulsive. Majority of the suggested anion-pi interacting residues in ternary complexes are metal-assisted. Stabilization centers for these proteins showed that all the six residues found in predicted anion-pi interactions are important in locating one or more of such centers. The anion-pi interacting residues in these proteins were found to be highly conserved. We hope that these studies might contribute useful information regarding structural stability and its interaction in future designs of novel metalloproteins. (C) 2017 Elsevier B.V. All rights reserved.",
publisher = "Elsevier",
journal = "International Journal of Biological Macromolecules",
title = "Anion-pi interactions in active centers of superoxide dismutases",
volume = "106",
pages = "559-568",
doi = "10.1016/j.ijbiomac.2017.08.050"
}

Ribić, V., Stojanović, S.,& Zlatović, M.. (2018). Anion-pi interactions in active centers of superoxide dismutases. in International Journal of Biological Macromolecules
Elsevier., 106, 559-568.
https://doi.org/10.1016/j.ijbiomac.2017.08.050

Ribić V, Stojanović S, Zlatović M. Anion-pi interactions in active centers of superoxide dismutases. in International Journal of Biological Macromolecules. 2018;106:559-568.
doi:10.1016/j.ijbiomac.2017.08.050 .

Ribić, Vesna, Stojanović, Srđan, Zlatović, Mario, "Anion-pi interactions in active centers of superoxide dismutases" in International Journal of Biological Macromolecules, 106 (2018):559-568,
https://doi.org/10.1016/j.ijbiomac.2017.08.050 . .

TY  - JOUR
AU  - Đorđević, Ivana
AU  - Vukasinovic, Jelena
AU  - Todorović, Tamara
AU  - Filipovic, Nenad R.
AU  - Rodić, Marko V.
AU  - Lolić, Aleksandar
AU  - Portalone, Gustavo
AU  - Zlatović, Mario
AU  - Grubišić, Sonja
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2166
AB  - Cobalt(III) complexes derived from thio-and selenosemicarbazone ligands have been studied to elucidate the nature and consequences of S to Se substitution on their possible biological activity. Solid state structures of cobalt(III) complexes with bis-tridentate coordinated 2-quinolinecarboxaldehyde thio-and selenosemicarbazone were determined by single crystal X-ray diffraction analysis. The complexes were also characterized by spectroscopic methods and cyclic voltammetry. Electronic properties of the complexes were studied using DFT and TD-DFT methods. Finally, evident in vitro antioxidant activity of the complexes was demonstrated.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study
VL  - 82
IS  - 7-8
SP  - 825
EP  - 839
DO  - 10.2298/JSC170412062D
ER  - 

@article{
author = "Đorđević, Ivana and Vukasinovic, Jelena and Todorović, Tamara and Filipovic, Nenad R. and Rodić, Marko V. and Lolić, Aleksandar and Portalone, Gustavo and Zlatović, Mario and Grubišić, Sonja",
year = "2017",
abstract = "Cobalt(III) complexes derived from thio-and selenosemicarbazone ligands have been studied to elucidate the nature and consequences of S to Se substitution on their possible biological activity. Solid state structures of cobalt(III) complexes with bis-tridentate coordinated 2-quinolinecarboxaldehyde thio-and selenosemicarbazone were determined by single crystal X-ray diffraction analysis. The complexes were also characterized by spectroscopic methods and cyclic voltammetry. Electronic properties of the complexes were studied using DFT and TD-DFT methods. Finally, evident in vitro antioxidant activity of the complexes was demonstrated.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study",
volume = "82",
number = "7-8",
pages = "825-839",
doi = "10.2298/JSC170412062D"
}

Đorđević, I., Vukasinovic, J., Todorović, T., Filipovic, N. R., Rodić, M. V., Lolić, A., Portalone, G., Zlatović, M.,& Grubišić, S.. (2017). Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 82(7-8), 825-839.
https://doi.org/10.2298/JSC170412062D

Đorđević I, Vukasinovic J, Todorović T, Filipovic NR, Rodić MV, Lolić A, Portalone G, Zlatović M, Grubišić S. Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study. in Journal of the Serbian Chemical Society. 2017;82(7-8):825-839.
doi:10.2298/JSC170412062D .

Đorđević, Ivana, Vukasinovic, Jelena, Todorović, Tamara, Filipovic, Nenad R., Rodić, Marko V., Lolić, Aleksandar, Portalone, Gustavo, Zlatović, Mario, Grubišić, Sonja, "Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study" in Journal of the Serbian Chemical Society, 82, no. 7-8 (2017):825-839,
https://doi.org/10.2298/JSC170412062D . .

TY  - JOUR
AU  - Popović-Đorđević, Jelena B.
AU  - Jevtić, Ivana
AU  - Grozdanic, Nadja Dj
AU  - Šegan, Sandra
AU  - Zlatović, Mario
AU  - Ivanović, Milovan D.
AU  - Stanojković, Tatjana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2063
AB  - The inhibitory activities of selected cyclic urea and carbamate derivatives (1-13) toward alpha-glucosidase (alpha-Gls) in in vitro assay were examined in this study. All examined compounds showed higher inhibitory activity (IC50) against alpha-Gls compared to standard antidiabetic drug acarbose. The most potent was benzyl (3,4,5-trimethoxyphenyl) carbamate (12) with IC50 = 49.85 +/- 0.10 mu M. In vitro cytotoxicity of the investigated compounds was tested on three human cancer cell lines HeLa, A549 and MDA-MB-453 using MTT assay. The best antitumour activity was achieved with compound 2 (trans-5-phenethyl-1-phenylhexahydro-1H-imidazo[4,5-c] pyridin-2(3H)-one) against MDA-MB-453 human breast cancer cell line (IC50 = 83.41 +/- 1.60 mu M). Cyclic ureas and carbamates showed promising anti-alpha-glucosidase activity and should be further tested as potential antidiabetic drugs. The PLS model of preliminary QSAR study indicated that, in planing the future synthesis of more potent compounds, the newly designed should have the substituents capable of polar interactions with receptor sites in various positions, while avoiding the increase of their lipophilicity.
PB  - Taylor & Francis Ltd, Abingdon
T2  - Journal of Enzyme Inhibition and Medicinal Chemistry
T1  - alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives
VL  - 32
IS  - 1
SP  - 298
EP  - 303
DO  - 10.1080/14756366.2016.1250754
ER  - 

@article{
author = "Popović-Đorđević, Jelena B. and Jevtić, Ivana and Grozdanic, Nadja Dj and Šegan, Sandra and Zlatović, Mario and Ivanović, Milovan D. and Stanojković, Tatjana",
year = "2017",
abstract = "The inhibitory activities of selected cyclic urea and carbamate derivatives (1-13) toward alpha-glucosidase (alpha-Gls) in in vitro assay were examined in this study. All examined compounds showed higher inhibitory activity (IC50) against alpha-Gls compared to standard antidiabetic drug acarbose. The most potent was benzyl (3,4,5-trimethoxyphenyl) carbamate (12) with IC50 = 49.85 +/- 0.10 mu M. In vitro cytotoxicity of the investigated compounds was tested on three human cancer cell lines HeLa, A549 and MDA-MB-453 using MTT assay. The best antitumour activity was achieved with compound 2 (trans-5-phenethyl-1-phenylhexahydro-1H-imidazo[4,5-c] pyridin-2(3H)-one) against MDA-MB-453 human breast cancer cell line (IC50 = 83.41 +/- 1.60 mu M). Cyclic ureas and carbamates showed promising anti-alpha-glucosidase activity and should be further tested as potential antidiabetic drugs. The PLS model of preliminary QSAR study indicated that, in planing the future synthesis of more potent compounds, the newly designed should have the substituents capable of polar interactions with receptor sites in various positions, while avoiding the increase of their lipophilicity.",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Journal of Enzyme Inhibition and Medicinal Chemistry",
title = "alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives",
volume = "32",
number = "1",
pages = "298-303",
doi = "10.1080/14756366.2016.1250754"
}

Popović-Đorđević, J. B., Jevtić, I., Grozdanic, N. D., Šegan, S., Zlatović, M., Ivanović, M. D.,& Stanojković, T.. (2017). alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives. in Journal of Enzyme Inhibition and Medicinal Chemistry
Taylor & Francis Ltd, Abingdon., 32(1), 298-303.
https://doi.org/10.1080/14756366.2016.1250754

Popović-Đorđević JB, Jevtić I, Grozdanic ND, Šegan S, Zlatović M, Ivanović MD, Stanojković T. alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives. in Journal of Enzyme Inhibition and Medicinal Chemistry. 2017;32(1):298-303.
doi:10.1080/14756366.2016.1250754 .

Popović-Đorđević, Jelena B., Jevtić, Ivana, Grozdanic, Nadja Dj, Šegan, Sandra, Zlatović, Mario, Ivanović, Milovan D., Stanojković, Tatjana, "alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives" in Journal of Enzyme Inhibition and Medicinal Chemistry, 32, no. 1 (2017):298-303,
https://doi.org/10.1080/14756366.2016.1250754 . .

TY  - JOUR
AU  - Aleksić, Ivana
AU  - Šegan, Sandra
AU  - Andrić, Filip
AU  - Zlatović, Mario
AU  - Moric, Ivana
AU  - Opsenica, Dejan
AU  - Senerovic, Lidija
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2270
AB  - Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC) > 400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean topological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species.
PB  - American Chemical Society (ACS)
T2  - Acs Chemical Biology
T1  - Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa
VL  - 12
IS  - 5
SP  - 1425
EP  - 1434
DO  - 10.1021/acschembio.6b01149
ER  - 

@article{
author = "Aleksić, Ivana and Šegan, Sandra and Andrić, Filip and Zlatović, Mario and Moric, Ivana and Opsenica, Dejan and Senerovic, Lidija",
year = "2017",
abstract = "Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC) > 400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean topological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species.",
publisher = "American Chemical Society (ACS)",
journal = "Acs Chemical Biology",
title = "Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa",
volume = "12",
number = "5",
pages = "1425-1434",
doi = "10.1021/acschembio.6b01149"
}

Aleksić, I., Šegan, S., Andrić, F., Zlatović, M., Moric, I., Opsenica, D.,& Senerovic, L.. (2017). Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa. in Acs Chemical Biology
American Chemical Society (ACS)., 12(5), 1425-1434.
https://doi.org/10.1021/acschembio.6b01149

Aleksić I, Šegan S, Andrić F, Zlatović M, Moric I, Opsenica D, Senerovic L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa. in Acs Chemical Biology. 2017;12(5):1425-1434.
doi:10.1021/acschembio.6b01149 .

Aleksić, Ivana, Šegan, Sandra, Andrić, Filip, Zlatović, Mario, Moric, Ivana, Opsenica, Dejan, Senerovic, Lidija, "Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa" in Acs Chemical Biology, 12, no. 5 (2017):1425-1434,
https://doi.org/10.1021/acschembio.6b01149 . .

TY  - JOUR
AU  - Aleksić, Ivana
AU  - Šegan, Sandra
AU  - Andrić, Filip
AU  - Zlatović, Mario
AU  - Moric, Ivana
AU  - Opsenica, Dejan
AU  - Senerovic, Lidija
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2983
AB  - Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC) > 400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean topological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species.
PB  - American Chemical Society (ACS)
T2  - Acs Chemical Biology
T1  - Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa
VL  - 12
IS  - 5
SP  - 1425
EP  - 1434
DO  - 10.1021/acschembio.6b01149
ER  - 

@article{
author = "Aleksić, Ivana and Šegan, Sandra and Andrić, Filip and Zlatović, Mario and Moric, Ivana and Opsenica, Dejan and Senerovic, Lidija",
year = "2017",
abstract = "Antibiotic resistance has become a serious global threat to public health; therefore, improved strategies and structurally novel antimicrobials are urgently needed to combat infectious diseases. Here we report a new type of highly potent 4-aminoquinoline derivatives as quorum sensing inhibitors in Serratia marcescens and Pseudomonas aeruginosa, exhibiting weak bactericidal activities (minimum inhibitory concentration (MIC) > 400 mu M). Through detailed structure-activity study, we have identified 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines (5 and 10) as biofilm formation inhibitors with 50% biofilm inhibition at 69 mu M and 63 mu M in S. marcescens and P. aeruginosa, respectively. These two compounds, 5 and 10, are the first quinoline derivatives with anti-biofilm formation activity reported in S. marcescens. Quantitative structure-activity relationship (QSAR) analysis identified structural descriptors such as Wiener indices, hyper-distance-path index (HDPI), mean topological charge (MTC), topological charge index (TCI), and log D(o/w)exp as the most influential in biofilm inhibition in this bacterial species. Derivative 10 is one of the most potent quinoline type inhibitors of pyocyanin production described so far (IC50 = 2.5 mu M). While we have demonstrated that 5 and 10 act as Pseudomonas quinolone system (PQS) antagonists, the mechanism of inhibition of S. marcescens biofilm formation with these compounds remains open since signaling similar to P. aeruginosa PQS system has not yet been described in Serratia and activity of these compounds on acylhomoserine lactone (AHL) signaling has not been detected. Our data show that 7-Cl and 7-CF3 substituted N-dodecylamino-4-aminoquinolines present the promising scaffolds for developing antivirulence and anti-biofilm formation agents against multidrug-resistant bacterial species.",
publisher = "American Chemical Society (ACS)",
journal = "Acs Chemical Biology",
title = "Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa",
volume = "12",
number = "5",
pages = "1425-1434",
doi = "10.1021/acschembio.6b01149"
}

Aleksić, I., Šegan, S., Andrić, F., Zlatović, M., Moric, I., Opsenica, D.,& Senerovic, L.. (2017). Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa. in Acs Chemical Biology
American Chemical Society (ACS)., 12(5), 1425-1434.
https://doi.org/10.1021/acschembio.6b01149

Aleksić I, Šegan S, Andrić F, Zlatović M, Moric I, Opsenica D, Senerovic L. Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa. in Acs Chemical Biology. 2017;12(5):1425-1434.
doi:10.1021/acschembio.6b01149 .

Aleksić, Ivana, Šegan, Sandra, Andrić, Filip, Zlatović, Mario, Moric, Ivana, Opsenica, Dejan, Senerovic, Lidija, "Long-Chain 4-Aminoquinolines as Quorum Sensing Inhibitors in Serratia marcescens and Pseudomonas aeruginosa" in Acs Chemical Biology, 12, no. 5 (2017):1425-1434,
https://doi.org/10.1021/acschembio.6b01149 . .

TY  - JOUR
AU  - Terzić-Jovanović, Nataša
AU  - Konstantinović, Jelena M.
AU  - Tot, Miklos
AU  - Burojevic, Jovana
AU  - Djurkovic-Djakovic, Olgica
AU  - Srbljanović, Jelena
AU  - Štajner, Tijana
AU  - Verbić, Tatjana
AU  - Zlatović, Mario
AU  - Machado, Marta
AU  - Albuquerque, Ines S
AU  - Prudencio, Miguel
AU  - Sciotii, Richard J
AU  - Pecic, Stevan
AU  - DAlessandro, Sarah
AU  - Taramelli, Donatella
AU  - Šolaja, Bogdan
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1953
AB  - The syntheses and antiplasmodial activities of various substituted aminoquinolines coupled to an adamantane carrier are described. The compounds exhibited pronounced in vitro and in vivo activity against Plasmodium berghei in the Thompson test. Tethering a fluorine atom to the aminoquinoline C(3) position afforded fluoroaminoquinolines that act as intrahepatocytic parasite inhibitors, with compound 25 having an IC50 = 0.31 mu M and reducing the liver load in mice by up to 92% at 80 mg/kg dose. Screening our peroxides as inhibitors of liver stage infection revealed that the tetraoxane pharmacophore itself is also an excellent liver stage P. berghei inhibitor (78: IC50 = 0.33 mu M). Up to 91% reduction of the parasite liver load in mice was achieved at 100 mg/kg. Examination of tetraoxane 78 against the transgenic 3D7 strain expressing luciferase under a gametocyte-specific promoter revealed its activity against stage IV-V Plasmodium falciparum gametocytes (IC50 = 1.16 +/- 0.37 mu M). To the best of our knowledge, compounds 25 and 78 are the first examples of either an 4-aminoquinoline or a tetraoxane liver stage inhibitors.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?
VL  - 59
IS  - 1
SP  - 264
EP  - 281
DO  - 10.1021/acs.jmedchem.5b01374
ER  - 

@article{
author = "Terzić-Jovanović, Nataša and Konstantinović, Jelena M. and Tot, Miklos and Burojevic, Jovana and Djurkovic-Djakovic, Olgica and Srbljanović, Jelena and Štajner, Tijana and Verbić, Tatjana and Zlatović, Mario and Machado, Marta and Albuquerque, Ines S and Prudencio, Miguel and Sciotii, Richard J and Pecic, Stevan and DAlessandro, Sarah and Taramelli, Donatella and Šolaja, Bogdan",
year = "2016",
abstract = "The syntheses and antiplasmodial activities of various substituted aminoquinolines coupled to an adamantane carrier are described. The compounds exhibited pronounced in vitro and in vivo activity against Plasmodium berghei in the Thompson test. Tethering a fluorine atom to the aminoquinoline C(3) position afforded fluoroaminoquinolines that act as intrahepatocytic parasite inhibitors, with compound 25 having an IC50 = 0.31 mu M and reducing the liver load in mice by up to 92% at 80 mg/kg dose. Screening our peroxides as inhibitors of liver stage infection revealed that the tetraoxane pharmacophore itself is also an excellent liver stage P. berghei inhibitor (78: IC50 = 0.33 mu M). Up to 91% reduction of the parasite liver load in mice was achieved at 100 mg/kg. Examination of tetraoxane 78 against the transgenic 3D7 strain expressing luciferase under a gametocyte-specific promoter revealed its activity against stage IV-V Plasmodium falciparum gametocytes (IC50 = 1.16 +/- 0.37 mu M). To the best of our knowledge, compounds 25 and 78 are the first examples of either an 4-aminoquinoline or a tetraoxane liver stage inhibitors.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?",
volume = "59",
number = "1",
pages = "264-281",
doi = "10.1021/acs.jmedchem.5b01374"
}

Terzić-Jovanović, N., Konstantinović, J. M., Tot, M., Burojevic, J., Djurkovic-Djakovic, O., Srbljanović, J., Štajner, T., Verbić, T., Zlatović, M., Machado, M., Albuquerque, I. S., Prudencio, M., Sciotii, R. J., Pecic, S., DAlessandro, S., Taramelli, D.,& Šolaja, B.. (2016). Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 59(1), 264-281.
https://doi.org/10.1021/acs.jmedchem.5b01374

Terzić-Jovanović N, Konstantinović JM, Tot M, Burojevic J, Djurkovic-Djakovic O, Srbljanović J, Štajner T, Verbić T, Zlatović M, Machado M, Albuquerque IS, Prudencio M, Sciotii RJ, Pecic S, DAlessandro S, Taramelli D, Šolaja B. Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?. in Journal of Medicinal Chemistry. 2016;59(1):264-281.
doi:10.1021/acs.jmedchem.5b01374 .

Terzić-Jovanović, Nataša, Konstantinović, Jelena M., Tot, Miklos, Burojevic, Jovana, Djurkovic-Djakovic, Olgica, Srbljanović, Jelena, Štajner, Tijana, Verbić, Tatjana, Zlatović, Mario, Machado, Marta, Albuquerque, Ines S, Prudencio, Miguel, Sciotii, Richard J, Pecic, Stevan, DAlessandro, Sarah, Taramelli, Donatella, Šolaja, Bogdan, "Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?" in Journal of Medicinal Chemistry, 59, no. 1 (2016):264-281,
https://doi.org/10.1021/acs.jmedchem.5b01374 . .

TY  - JOUR
AU  - Šegan, Sandra
AU  - Opsenica, Igor
AU  - Zlatović, Mario
AU  - Milojković-Opsenica, Dušanka
AU  - Šolaja, Bogdan
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1960
AB  - The chromatographic behaviour of series of 4-amino-7-chloroquinoline (4,7-ACQ) based compounds was studied by reversed-phase thin-layer chromatography (RPTLC) with binary mobile phases containing water and the organic modifiers, DMSO or acetone. The lipophilicity of the studied compounds was determined by extrapolation of retention parameters R-M to pure water content in mobile phase. In order to obtain some basic insight into the chromatographic behaviour and structural features of investigated compounds, PCA was performed on both chromatographic data (R-M values) and calculated 2D and 3D structural descriptors. Both QSRR and QSAR models were built by means of the partial least squares (PLS) statistical method. It was found that descriptors which encode hydrophobic (dispersive) interactions have positive influence on retention, while influence of descriptors encoding polar interactions was negative. According to the obtained PLS model for inhibition of botulinum neurotoxin serotype A light chain, hydrophobic interactions influence positively on the mechanism of action of the investigated 4,7-ACQ while polar interactions are less favoured. Contrary, the results of PLS modelling of activity against Plasmodium falciparum strains (W2, D6 and TM91C235) indicate that higher polarity of 4,7-ACQ contribute to their higher antimalarial activity.
PB  - Elsevier
T2  - Journal of Chromatography B-Analytical Technologies in the Biomedical and Life Sciences
T1  - Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds
VL  - 1012
SP  - 144
EP  - 152
DO  - 10.1016/j.jchromb.2016.01.033
ER  - 

@article{
author = "Šegan, Sandra and Opsenica, Igor and Zlatović, Mario and Milojković-Opsenica, Dušanka and Šolaja, Bogdan",
year = "2016",
abstract = "The chromatographic behaviour of series of 4-amino-7-chloroquinoline (4,7-ACQ) based compounds was studied by reversed-phase thin-layer chromatography (RPTLC) with binary mobile phases containing water and the organic modifiers, DMSO or acetone. The lipophilicity of the studied compounds was determined by extrapolation of retention parameters R-M to pure water content in mobile phase. In order to obtain some basic insight into the chromatographic behaviour and structural features of investigated compounds, PCA was performed on both chromatographic data (R-M values) and calculated 2D and 3D structural descriptors. Both QSRR and QSAR models were built by means of the partial least squares (PLS) statistical method. It was found that descriptors which encode hydrophobic (dispersive) interactions have positive influence on retention, while influence of descriptors encoding polar interactions was negative. According to the obtained PLS model for inhibition of botulinum neurotoxin serotype A light chain, hydrophobic interactions influence positively on the mechanism of action of the investigated 4,7-ACQ while polar interactions are less favoured. Contrary, the results of PLS modelling of activity against Plasmodium falciparum strains (W2, D6 and TM91C235) indicate that higher polarity of 4,7-ACQ contribute to their higher antimalarial activity.",
publisher = "Elsevier",
journal = "Journal of Chromatography B-Analytical Technologies in the Biomedical and Life Sciences",
title = "Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds",
volume = "1012",
pages = "144-152",
doi = "10.1016/j.jchromb.2016.01.033"
}

Šegan, S., Opsenica, I., Zlatović, M., Milojković-Opsenica, D.,& Šolaja, B.. (2016). Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds. in Journal of Chromatography B-Analytical Technologies in the Biomedical and Life Sciences
Elsevier., 1012, 144-152.
https://doi.org/10.1016/j.jchromb.2016.01.033

Šegan S, Opsenica I, Zlatović M, Milojković-Opsenica D, Šolaja B. Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds. in Journal of Chromatography B-Analytical Technologies in the Biomedical and Life Sciences. 2016;1012:144-152.
doi:10.1016/j.jchromb.2016.01.033 .

Šegan, Sandra, Opsenica, Igor, Zlatović, Mario, Milojković-Opsenica, Dušanka, Šolaja, Bogdan, "Quantitative structure retention/activity relationships of biologically relevant 4-amino-7-chloroquinoline based compounds" in Journal of Chromatography B-Analytical Technologies in the Biomedical and Life Sciences, 1012 (2016):144-152,
https://doi.org/10.1016/j.jchromb.2016.01.033 . .