TY  - JOUR
AU  - Krunić, Mihajlo
AU  - Penjišević, Jelena
AU  - Suručić, Relja
AU  - Šegan, Sandra
AU  - Kostić-Rajačić, Slađana
AU  - Jevtić, Ivana
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5634
AB  - Fourteen novel N-benzylpiperidine and N,N-diarylpiperazine conjugates were synthesized and pharmacologically evaluated as donepezil analogs, in a ligand-based drug design approach. All compounds possessed high to moderate in vitro inhibitory activity with IC50 in range 2.3–20 µM and selectivity towards acetylcholinesterase, while being inactive towards butyrylcholinesterase. Structure-activity relationship analysis revealed the influence of N,N-diarylpiperazine moiety and the linker connecting two pharmacophores on the inhibitory activity. Kinetic studies on the two most active compounds 7g and 8g (IC50 = 2.3 and 4 µM, respectively) revealed mixed type mode of inhibition, binding to both, free enzyme and enzyme-substrate complex. For further understanding of mechanism of action and binding orientations, molecular docking was performed for all compounds, while the ligand transport simulation and molecular dynamics simulations were performed for 7g and 8g. Computational results corroborated well with in vitro activities and kinetic studies.
PB  - Elsevier B.V.
T2  - Journal of Molecular Structure
T1  - Structure-activity and binding orientations analysis of potent, newly synthesized, acetylcholinesterase inhibitors
VL  - 1276
SP  - 134809
DO  - 10.1016/j.molstruc.2022.134809
ER  - 

@article{
author = "Krunić, Mihajlo and Penjišević, Jelena and Suručić, Relja and Šegan, Sandra and Kostić-Rajačić, Slađana and Jevtić, Ivana",
year = "2023",
abstract = "Fourteen novel N-benzylpiperidine and N,N-diarylpiperazine conjugates were synthesized and pharmacologically evaluated as donepezil analogs, in a ligand-based drug design approach. All compounds possessed high to moderate in vitro inhibitory activity with IC50 in range 2.3–20 µM and selectivity towards acetylcholinesterase, while being inactive towards butyrylcholinesterase. Structure-activity relationship analysis revealed the influence of N,N-diarylpiperazine moiety and the linker connecting two pharmacophores on the inhibitory activity. Kinetic studies on the two most active compounds 7g and 8g (IC50 = 2.3 and 4 µM, respectively) revealed mixed type mode of inhibition, binding to both, free enzyme and enzyme-substrate complex. For further understanding of mechanism of action and binding orientations, molecular docking was performed for all compounds, while the ligand transport simulation and molecular dynamics simulations were performed for 7g and 8g. Computational results corroborated well with in vitro activities and kinetic studies.",
publisher = "Elsevier B.V.",
journal = "Journal of Molecular Structure",
title = "Structure-activity and binding orientations analysis of potent, newly synthesized, acetylcholinesterase inhibitors",
volume = "1276",
pages = "134809",
doi = "10.1016/j.molstruc.2022.134809"
}

Krunić, M., Penjišević, J., Suručić, R., Šegan, S., Kostić-Rajačić, S.,& Jevtić, I.. (2023). Structure-activity and binding orientations analysis of potent, newly synthesized, acetylcholinesterase inhibitors. in Journal of Molecular Structure
Elsevier B.V.., 1276, 134809.
https://doi.org/10.1016/j.molstruc.2022.134809

Krunić M, Penjišević J, Suručić R, Šegan S, Kostić-Rajačić S, Jevtić I. Structure-activity and binding orientations analysis of potent, newly synthesized, acetylcholinesterase inhibitors. in Journal of Molecular Structure. 2023;1276:134809.
doi:10.1016/j.molstruc.2022.134809 .

Krunić, Mihajlo, Penjišević, Jelena, Suručić, Relja, Šegan, Sandra, Kostić-Rajačić, Slađana, Jevtić, Ivana, "Structure-activity and binding orientations analysis of potent, newly synthesized, acetylcholinesterase inhibitors" in Journal of Molecular Structure, 1276 (2023):134809,
https://doi.org/10.1016/j.molstruc.2022.134809 . .

TY  - CONF
AU  - Simić, Aleksandar
AU  - Tosti, Tomislav
AU  - Dramićanin, Aleksandra M.
AU  - Šegan, Sandra
AU  - Milojković-Opsenica, Dušanka
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6735
AB  - Sadržaj limunske kiseline u medu može da pruži informacije za procenu autenticnosti
meda. Me utim, važeci Codexalimentarius kao i Pravilnik o kvalitetu meda ne pružaju
informacije o sadržaju limunske kiseline u medu. Imajuci to u vidu, predmet ovog rada je
razvoj i validacija metode za odre ivanje citrata u medu. Analiza citrata ura ena je
primenom jonske hromatografijesa konduktometrijskom detekcijom na DIONEX AS 15
analitickoj koloni uz upotrebu 30 mM kalijum-hidroksida kao mobilne faze.Validovana
metoda se može primeniti za odre ivanje sadržaja citrata u medu u intervalu 1 – 100 mg/kg
s agranicom detekcije od 0,36 mg/kg igranicomkvantifikacije 1,20 mg/kg.Tacnost metode
je proverena testom obogacenja (95 – 101%), a preciznost ponovljenim analizama u toku
više dana. Metoda je proverena analizom 25 uzoraka bagremovog meda pri cemu je
sadržaj citrata bio u opsegu 10,82 – 55,74 mg/kg. Parametri validacije metode potvr uju
mogucnost primene jonskehromatografije sa konduktometrijskom detekcijom za brzo i
tacno odre ivanje citrata u uzorcima bagremovog meda.
AB  - The citric acid content can give useful information about honey authenticity. However, Codex Alimentarius and the Serbian regulation do not provide information on the content of citric acid in honey. Hence,the object of this paper is the method development and validation for the determination of citrate content in honey. The concentration of citrate in honey was determined by ion chromatography with conductivity detection on DIONEX AS 15 column and 30 mM potassium-hydroxide as mobile phase. The method validation revealed that method can be used for determination of citrate in acaciahoney from 1 to100 mg/kg. The limit of detection was 0.36 mg/kg and limit of quantification 1.20 mg/kg. The accuracy was determined with recovery test (95–101%), and precision with repeat analysis during few days. Analysis of 25 acacia honey samples confirmed applicability of method and revealed that amount of citrate was10.82 – 55.74 mg/kg. The statistical parameters of method validation pointed out that the ion chromatography with conductometry detection enabled rapid and accurate determination of citrate in acacia honey.
PB  - Belgrade : Serbian Chemical Society
C3  - Kratki izvodi radova, knjiga radova - 58. Savetovanje Srpskog hemijskog društva, 9. i 10. jun 2022. godine, Beograd / Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, June 9-10, 2023, Belgrade, Serbia
T1  - Validacija metode za određivanje sadržaja citrata u bagremovom medu jonskom hromatografijom
T1  - Method validation for determining the citrate content in acacia honey by ion  chromatography
SP  - 56
EP  - 56
UR  - https://hdl.handle.net/21.15107/rcub_cer_6735
ER  - 

@conference{
author = "Simić, Aleksandar and Tosti, Tomislav and Dramićanin, Aleksandra M. and Šegan, Sandra and Milojković-Opsenica, Dušanka",
year = "2022",
abstract = "Sadržaj limunske kiseline u medu može da pruži informacije za procenu autenticnosti
meda. Me utim, važeci Codexalimentarius kao i Pravilnik o kvalitetu meda ne pružaju
informacije o sadržaju limunske kiseline u medu. Imajuci to u vidu, predmet ovog rada je
razvoj i validacija metode za odre ivanje citrata u medu. Analiza citrata ura ena je
primenom jonske hromatografijesa konduktometrijskom detekcijom na DIONEX AS 15
analitickoj koloni uz upotrebu 30 mM kalijum-hidroksida kao mobilne faze.Validovana
metoda se može primeniti za odre ivanje sadržaja citrata u medu u intervalu 1 – 100 mg/kg
s agranicom detekcije od 0,36 mg/kg igranicomkvantifikacije 1,20 mg/kg.Tacnost metode
je proverena testom obogacenja (95 – 101%), a preciznost ponovljenim analizama u toku
više dana. Metoda je proverena analizom 25 uzoraka bagremovog meda pri cemu je
sadržaj citrata bio u opsegu 10,82 – 55,74 mg/kg. Parametri validacije metode potvr uju
mogucnost primene jonskehromatografije sa konduktometrijskom detekcijom za brzo i
tacno odre ivanje citrata u uzorcima bagremovog meda., The citric acid content can give useful information about honey authenticity. However, Codex Alimentarius and the Serbian regulation do not provide information on the content of citric acid in honey. Hence,the object of this paper is the method development and validation for the determination of citrate content in honey. The concentration of citrate in honey was determined by ion chromatography with conductivity detection on DIONEX AS 15 column and 30 mM potassium-hydroxide as mobile phase. The method validation revealed that method can be used for determination of citrate in acaciahoney from 1 to100 mg/kg. The limit of detection was 0.36 mg/kg and limit of quantification 1.20 mg/kg. The accuracy was determined with recovery test (95–101%), and precision with repeat analysis during few days. Analysis of 25 acacia honey samples confirmed applicability of method and revealed that amount of citrate was10.82 – 55.74 mg/kg. The statistical parameters of method validation pointed out that the ion chromatography with conductometry detection enabled rapid and accurate determination of citrate in acacia honey.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Kratki izvodi radova, knjiga radova - 58. Savetovanje Srpskog hemijskog društva, 9. i 10. jun 2022. godine, Beograd / Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, June 9-10, 2023, Belgrade, Serbia",
title = "Validacija metode za određivanje sadržaja citrata u bagremovom medu jonskom hromatografijom, Method validation for determining the citrate content in acacia honey by ion  chromatography",
pages = "56-56",
url = "https://hdl.handle.net/21.15107/rcub_cer_6735"
}

Simić, A., Tosti, T., Dramićanin, A. M., Šegan, S.,& Milojković-Opsenica, D.. (2022). Validacija metode za određivanje sadržaja citrata u bagremovom medu jonskom hromatografijom. in Kratki izvodi radova, knjiga radova - 58. Savetovanje Srpskog hemijskog društva, 9. i 10. jun 2022. godine, Beograd / Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, June 9-10, 2023, Belgrade, Serbia
Belgrade : Serbian Chemical Society., 56-56.
https://hdl.handle.net/21.15107/rcub_cer_6735

Simić A, Tosti T, Dramićanin AM, Šegan S, Milojković-Opsenica D. Validacija metode za određivanje sadržaja citrata u bagremovom medu jonskom hromatografijom. in Kratki izvodi radova, knjiga radova - 58. Savetovanje Srpskog hemijskog društva, 9. i 10. jun 2022. godine, Beograd / Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, June 9-10, 2023, Belgrade, Serbia. 2022;:56-56.
https://hdl.handle.net/21.15107/rcub_cer_6735 .

Simić, Aleksandar, Tosti, Tomislav, Dramićanin, Aleksandra M., Šegan, Sandra, Milojković-Opsenica, Dušanka, "Validacija metode za određivanje sadržaja citrata u bagremovom medu jonskom hromatografijom" in Kratki izvodi radova, knjiga radova - 58. Savetovanje Srpskog hemijskog društva, 9. i 10. jun 2022. godine, Beograd / Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, June 9-10, 2023, Belgrade, Serbia (2022):56-56,
https://hdl.handle.net/21.15107/rcub_cer_6735 .

TY  - JOUR
AU  - Šegan, Sandra
AU  - Jevtić, Ivana
AU  - Tosti, Tomislav
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Kostić Rajačić, Slađana
AU  - Milojković-Opsenica, Dušanka
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5413
AB  - Lipophilicity and ionization constant of sixteen fentanyl analogues were investigated by reversed-phase thin-layer chromatography (RP-TLC). Fourteen compounds have nitrogen containing groups at C-3 position of the piperidine ring and two compounds are 3-carbomethoxy derivatives of fentanyl. Among them, five are diastereomeric cis/trans couples and six novel trans diastereomers. In addition, the lipophilicity and ionization constant of fentanyl were also determined by the same method, as a reference. The physicochemical property, lipophilicity, expressed as retention indices RM0, b, and C0, as well as PC1, was determined and correlated with in silico values. Ionization constants were determined on the basis of the relationships between analyte's retention expressed as RF and mobile phase pH. Calculated structural descriptors together with the retention indices, were subjected to the principal component analysis – PCA and hierarchical cluster analysis – HCA, in order to provide basic insights into the similarities among the studied compounds. The blood – brain barrier (BBB) permeation was investigated in the function of experimentally obtained values of lipophilicity, polar surface area and molecular weight. In general, results of the present research corroborate well with previously determined antinociceptive activities of the investigated compounds, pointing out that besides the cis/trans isomerism, another set of important parameters should be taken into account when designing new derivatives of C-3 substituted fentanyl, especially lipophilicity, voluminosity and HBD/A character of the substituents. Accordingly, RP-TLC can be considered as a valuable asset in the ligand-based drug design.
PB  - Elsevier
T2  - Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences
T1  - Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography
VL  - 1211
SP  - 123481
DO  - 10.1016/j.jchromb.2022.123481
ER  - 

@article{
author = "Šegan, Sandra and Jevtić, Ivana and Tosti, Tomislav and Penjišević, Jelena and Šukalović, Vladimir and Kostić Rajačić, Slađana and Milojković-Opsenica, Dušanka",
year = "2022",
abstract = "Lipophilicity and ionization constant of sixteen fentanyl analogues were investigated by reversed-phase thin-layer chromatography (RP-TLC). Fourteen compounds have nitrogen containing groups at C-3 position of the piperidine ring and two compounds are 3-carbomethoxy derivatives of fentanyl. Among them, five are diastereomeric cis/trans couples and six novel trans diastereomers. In addition, the lipophilicity and ionization constant of fentanyl were also determined by the same method, as a reference. The physicochemical property, lipophilicity, expressed as retention indices RM0, b, and C0, as well as PC1, was determined and correlated with in silico values. Ionization constants were determined on the basis of the relationships between analyte's retention expressed as RF and mobile phase pH. Calculated structural descriptors together with the retention indices, were subjected to the principal component analysis – PCA and hierarchical cluster analysis – HCA, in order to provide basic insights into the similarities among the studied compounds. The blood – brain barrier (BBB) permeation was investigated in the function of experimentally obtained values of lipophilicity, polar surface area and molecular weight. In general, results of the present research corroborate well with previously determined antinociceptive activities of the investigated compounds, pointing out that besides the cis/trans isomerism, another set of important parameters should be taken into account when designing new derivatives of C-3 substituted fentanyl, especially lipophilicity, voluminosity and HBD/A character of the substituents. Accordingly, RP-TLC can be considered as a valuable asset in the ligand-based drug design.",
publisher = "Elsevier",
journal = "Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences",
title = "Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography",
volume = "1211",
pages = "123481",
doi = "10.1016/j.jchromb.2022.123481"
}

Šegan, S., Jevtić, I., Tosti, T., Penjišević, J., Šukalović, V., Kostić Rajačić, S.,& Milojković-Opsenica, D.. (2022). Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography. in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences
Elsevier., 1211, 123481.
https://doi.org/10.1016/j.jchromb.2022.123481

Šegan S, Jevtić I, Tosti T, Penjišević J, Šukalović V, Kostić Rajačić S, Milojković-Opsenica D. Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography. in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences. 2022;1211:123481.
doi:10.1016/j.jchromb.2022.123481 .

Šegan, Sandra, Jevtić, Ivana, Tosti, Tomislav, Penjišević, Jelena, Šukalović, Vladimir, Kostić Rajačić, Slađana, Milojković-Opsenica, Dušanka, "Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography" in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, 1211 (2022):123481,
https://doi.org/10.1016/j.jchromb.2022.123481 . .

TY  - JOUR
AU  - Djokic, Lidija
AU  - Stankovic, Nada
AU  - Galic, Ivana
AU  - Moric, Ivana
AU  - Radakovic, Natasa
AU  - Šegan, Sandra
AU  - Pavic, Aleksandar
AU  - Senerovic, Lidija
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5579
AB  - Bacterial infections have become increasingly difficult to treat due to the occurrence of antibiotic-resistant strains. A promising strategy to increase the efficacy of therapy is to combine antibacterials with agents that decrease pathogen virulence via the modulation of the quorum sensing (QS). Lactonases inhibit acylated homoserine lactone (AHL)-mediated QS in Gram-negative bacteria, including the leading nosocomial pathogen Pseudomonas aeruginosa. Here we describe the characteristics of heterologously expressed YtnP lactonase from Bacillus paralicheniformis ZP1 (YtnP-ZP1) isolated from agricultural soil using the culture enrichment method. Purified YtnP-ZP1 hydrolyzed different AHLs with preference to substrates with long acyl residues as evaluated in assays with biosensors and HPLC. The enzyme showed good thermostability and activity in a wide temperature range. YtnP-ZP1 in 50 μg mL–1 concentration reduced the amount of P. aeruginosa-produced long-chain AHLs by 85%, while it hydrolyzed 50% of short-chain AHLs. Incubation of P. aeruginosa PAO1 with YtnP-ZP1 reduced its swarming motility and elastolytic activity without bactericidal effect. YtnP-ZP1 caused the inhibition of biofilm formation and disintegration of mature biofilms in P. aeruginosa PAO1 and multiresistant clinical strain BR5H that was visualized by crystal violet staining. The treatment with YtnP-ZP1 in concentrations higher than 25 μg mL–1 improved the survival of P. aeruginosa PAO1-infected zebrafish (Danio rerio), rescuing 80% of embryos, while in combination with tobramycin or gentamicin survival rate increased to 100%. The treatment of P. aeruginosa PAO1 biofilms on infected zebrafish tail wounds with 50 μg mL–1 YtnP-ZP1 and 2 × MIC tobramycin led to infection clearing in 2 days. The extensive toxicity studies proved YtnP-ZP1 was non-toxic to human cells and zebrafish. In conclusion, novel YtnP-ZP1 lactonase with its effective anti-virulence activity could be used to increase the efficacy of clinically approved antibiotics in clearing both systemic and biofilm-associated P. aeruginosa infections.
PB  - Frontiers Media SA
T2  - Frontiers in Microbiology
T1  - Novel Quorum Quenching YtnP Lactonase From Bacillus paralicheniformis Reduces Pseudomonas aeruginosa Virulence and Increases Antibiotic Efficacy in vivo
VL  - 13
SP  - 906312
DO  - 10.3389/fmicb.2022.906312
ER  - 

@article{
author = "Djokic, Lidija and Stankovic, Nada and Galic, Ivana and Moric, Ivana and Radakovic, Natasa and Šegan, Sandra and Pavic, Aleksandar and Senerovic, Lidija",
year = "2022",
abstract = "Bacterial infections have become increasingly difficult to treat due to the occurrence of antibiotic-resistant strains. A promising strategy to increase the efficacy of therapy is to combine antibacterials with agents that decrease pathogen virulence via the modulation of the quorum sensing (QS). Lactonases inhibit acylated homoserine lactone (AHL)-mediated QS in Gram-negative bacteria, including the leading nosocomial pathogen Pseudomonas aeruginosa. Here we describe the characteristics of heterologously expressed YtnP lactonase from Bacillus paralicheniformis ZP1 (YtnP-ZP1) isolated from agricultural soil using the culture enrichment method. Purified YtnP-ZP1 hydrolyzed different AHLs with preference to substrates with long acyl residues as evaluated in assays with biosensors and HPLC. The enzyme showed good thermostability and activity in a wide temperature range. YtnP-ZP1 in 50 μg mL–1 concentration reduced the amount of P. aeruginosa-produced long-chain AHLs by 85%, while it hydrolyzed 50% of short-chain AHLs. Incubation of P. aeruginosa PAO1 with YtnP-ZP1 reduced its swarming motility and elastolytic activity without bactericidal effect. YtnP-ZP1 caused the inhibition of biofilm formation and disintegration of mature biofilms in P. aeruginosa PAO1 and multiresistant clinical strain BR5H that was visualized by crystal violet staining. The treatment with YtnP-ZP1 in concentrations higher than 25 μg mL–1 improved the survival of P. aeruginosa PAO1-infected zebrafish (Danio rerio), rescuing 80% of embryos, while in combination with tobramycin or gentamicin survival rate increased to 100%. The treatment of P. aeruginosa PAO1 biofilms on infected zebrafish tail wounds with 50 μg mL–1 YtnP-ZP1 and 2 × MIC tobramycin led to infection clearing in 2 days. The extensive toxicity studies proved YtnP-ZP1 was non-toxic to human cells and zebrafish. In conclusion, novel YtnP-ZP1 lactonase with its effective anti-virulence activity could be used to increase the efficacy of clinically approved antibiotics in clearing both systemic and biofilm-associated P. aeruginosa infections.",
publisher = "Frontiers Media SA",
journal = "Frontiers in Microbiology",
title = "Novel Quorum Quenching YtnP Lactonase From Bacillus paralicheniformis Reduces Pseudomonas aeruginosa Virulence and Increases Antibiotic Efficacy in vivo",
volume = "13",
pages = "906312",
doi = "10.3389/fmicb.2022.906312"
}

Djokic, L., Stankovic, N., Galic, I., Moric, I., Radakovic, N., Šegan, S., Pavic, A.,& Senerovic, L.. (2022). Novel Quorum Quenching YtnP Lactonase From Bacillus paralicheniformis Reduces Pseudomonas aeruginosa Virulence and Increases Antibiotic Efficacy in vivo. in Frontiers in Microbiology
Frontiers Media SA., 13, 906312.
https://doi.org/10.3389/fmicb.2022.906312

Djokic L, Stankovic N, Galic I, Moric I, Radakovic N, Šegan S, Pavic A, Senerovic L. Novel Quorum Quenching YtnP Lactonase From Bacillus paralicheniformis Reduces Pseudomonas aeruginosa Virulence and Increases Antibiotic Efficacy in vivo. in Frontiers in Microbiology. 2022;13:906312.
doi:10.3389/fmicb.2022.906312 .

Djokic, Lidija, Stankovic, Nada, Galic, Ivana, Moric, Ivana, Radakovic, Natasa, Šegan, Sandra, Pavic, Aleksandar, Senerovic, Lidija, "Novel Quorum Quenching YtnP Lactonase From Bacillus paralicheniformis Reduces Pseudomonas aeruginosa Virulence and Increases Antibiotic Efficacy in vivo" in Frontiers in Microbiology, 13 (2022):906312,
https://doi.org/10.3389/fmicb.2022.906312 . .

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  - Šegan, Sandra
AU  - Živković-Radovanović, Vukosava
AU  - Tosti, Tomislav
AU  - Ristivojević, Petar
AU  - Milojković-Opsenica, Dušanka
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4770
AB  - Growing antibiotic resistance creates a need to find new antimicrobial agents characterized by diverse chemical structures and pharmaceutical activity. The higher plants synthesize many specialized metabolites as a part of their normal metabolic activity and have been extensively used for centuries in treatment of different diseases. They have a wide activity range depending on the species, topography and climate, and may have different categories of active principles. In contrast to conventional antimicrobial techniques, planar chromatography in combination with biological detection can be an appropriate method of choice for fast, simple, and low-cost screening of plant extract for successful detection of antimicrobial agents which can be good candidates for lead compounds. To date, all bioautography steps such as chromatographic separation, detection with bacteria cells, incubation, and visualization of bioactive bands were improved and optimized. This review gives an overview of bioautography procedure from extraction to structure elucidation of antimicrobial compounds from plants.
PB  - USA :Taylor & Francis INC
T2  - Journal of Liquid Chromatography & Related Technologies
T1  - Thin-layer chromatography in bioassays of antimicrobial compounds from plants
DO  - 10.1080/10826076.2021.1968429
ER  - 

@article{
author = "Šegan, Sandra and Živković-Radovanović, Vukosava and Tosti, Tomislav and Ristivojević, Petar and Milojković-Opsenica, Dušanka",
year = "2021",
abstract = "Growing antibiotic resistance creates a need to find new antimicrobial agents characterized by diverse chemical structures and pharmaceutical activity. The higher plants synthesize many specialized metabolites as a part of their normal metabolic activity and have been extensively used for centuries in treatment of different diseases. They have a wide activity range depending on the species, topography and climate, and may have different categories of active principles. In contrast to conventional antimicrobial techniques, planar chromatography in combination with biological detection can be an appropriate method of choice for fast, simple, and low-cost screening of plant extract for successful detection of antimicrobial agents which can be good candidates for lead compounds. To date, all bioautography steps such as chromatographic separation, detection with bacteria cells, incubation, and visualization of bioactive bands were improved and optimized. This review gives an overview of bioautography procedure from extraction to structure elucidation of antimicrobial compounds from plants.",
publisher = "USA :Taylor & Francis INC",
journal = "Journal of Liquid Chromatography & Related Technologies",
title = "Thin-layer chromatography in bioassays of antimicrobial compounds from plants",
doi = "10.1080/10826076.2021.1968429"
}

Šegan, S., Živković-Radovanović, V., Tosti, T., Ristivojević, P.,& Milojković-Opsenica, D.. (2021). Thin-layer chromatography in bioassays of antimicrobial compounds from plants. in Journal of Liquid Chromatography & Related Technologies
USA :Taylor & Francis INC..
https://doi.org/10.1080/10826076.2021.1968429

Šegan S, Živković-Radovanović V, Tosti T, Ristivojević P, Milojković-Opsenica D. Thin-layer chromatography in bioassays of antimicrobial compounds from plants. in Journal of Liquid Chromatography & Related Technologies. 2021;.
doi:10.1080/10826076.2021.1968429 .

Šegan, Sandra, Živković-Radovanović, Vukosava, Tosti, Tomislav, Ristivojević, Petar, Milojković-Opsenica, Dušanka, "Thin-layer chromatography in bioassays of antimicrobial compounds from plants" in Journal of Liquid Chromatography & Related Technologies (2021),
https://doi.org/10.1080/10826076.2021.1968429 . .

TY  - CONF
AU  - Milojković-Opsenica, Dušanka
AU  - Rosić, Anđelka
AU  - Krstić, Đurđa
AU  - Trifković, Jelena
AU  - Tosti, Tomislav
AU  - Šegan, Sandra
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6736
AB  - Honey is a natural sweet product of honeybees widely consumed by people as both a food and
a medicine. It is mainly composed of carbohydrates, primarily fructose and glucose, followed by
sucrose and other oligosaccharides present in lower quantity. Due to its nutritional and health
benefits and relatively high price, honey is frequently subjected to adulteration either by
addition of sugar syrups or cheaper and lower quality honey, or by mislabeling of declaration.
Numerous analytical methods, such as chromatographic, spectroscopic, isotopic, and
electrochemical, have been developed to detect honey adulterants.[1] Application of thin-layer
chromatography (TLC) in the detection of syrup adulterants is limited due to the hydrolysis of
polysaccharides and a presence of false positive components such as smaller oligosaccharides
(from 3 to 6 monosaccharide units). However, with the development of high-performance layers
and sophisticated instrumentation, high-performance TLC (HPTLC) should become a method of
choice in determination of honey authenticity.
PB  - Croatian Chemical Society
C3  - Book of abstracts - 27th Croatian Meeting of Chemists and Chemical Engineers / 5 th Symposium Vladimir Prelog, 5-8 October 2021, Veli Lošinj, Vitality Hotel Punta, Croatia
T1  - Development and validation of HPTLC method for determination of sugar profiles of honey and its syrup adulterants
SP  - 244
EP  - 244
UR  - https://hdl.handle.net/21.15107/rcub_cer_6736
ER  - 

@conference{
author = "Milojković-Opsenica, Dušanka and Rosić, Anđelka and Krstić, Đurđa and Trifković, Jelena and Tosti, Tomislav and Šegan, Sandra",
year = "2021",
abstract = "Honey is a natural sweet product of honeybees widely consumed by people as both a food and
a medicine. It is mainly composed of carbohydrates, primarily fructose and glucose, followed by
sucrose and other oligosaccharides present in lower quantity. Due to its nutritional and health
benefits and relatively high price, honey is frequently subjected to adulteration either by
addition of sugar syrups or cheaper and lower quality honey, or by mislabeling of declaration.
Numerous analytical methods, such as chromatographic, spectroscopic, isotopic, and
electrochemical, have been developed to detect honey adulterants.[1] Application of thin-layer
chromatography (TLC) in the detection of syrup adulterants is limited due to the hydrolysis of
polysaccharides and a presence of false positive components such as smaller oligosaccharides
(from 3 to 6 monosaccharide units). However, with the development of high-performance layers
and sophisticated instrumentation, high-performance TLC (HPTLC) should become a method of
choice in determination of honey authenticity.",
publisher = "Croatian Chemical Society",
journal = "Book of abstracts - 27th Croatian Meeting of Chemists and Chemical Engineers / 5 th Symposium Vladimir Prelog, 5-8 October 2021, Veli Lošinj, Vitality Hotel Punta, Croatia",
title = "Development and validation of HPTLC method for determination of sugar profiles of honey and its syrup adulterants",
pages = "244-244",
url = "https://hdl.handle.net/21.15107/rcub_cer_6736"
}

Milojković-Opsenica, D., Rosić, A., Krstić, Đ., Trifković, J., Tosti, T.,& Šegan, S.. (2021). Development and validation of HPTLC method for determination of sugar profiles of honey and its syrup adulterants. in Book of abstracts - 27th Croatian Meeting of Chemists and Chemical Engineers / 5 th Symposium Vladimir Prelog, 5-8 October 2021, Veli Lošinj, Vitality Hotel Punta, Croatia
Croatian Chemical Society., 244-244.
https://hdl.handle.net/21.15107/rcub_cer_6736

Milojković-Opsenica D, Rosić A, Krstić Đ, Trifković J, Tosti T, Šegan S. Development and validation of HPTLC method for determination of sugar profiles of honey and its syrup adulterants. in Book of abstracts - 27th Croatian Meeting of Chemists and Chemical Engineers / 5 th Symposium Vladimir Prelog, 5-8 October 2021, Veli Lošinj, Vitality Hotel Punta, Croatia. 2021;:244-244.
https://hdl.handle.net/21.15107/rcub_cer_6736 .

Milojković-Opsenica, Dušanka, Rosić, Anđelka, Krstić, Đurđa, Trifković, Jelena, Tosti, Tomislav, Šegan, Sandra, "Development and validation of HPTLC method for determination of sugar profiles of honey and its syrup adulterants" in Book of abstracts - 27th Croatian Meeting of Chemists and Chemical Engineers / 5 th Symposium Vladimir Prelog, 5-8 October 2021, Veli Lošinj, Vitality Hotel Punta, Croatia (2021):244-244,
https://hdl.handle.net/21.15107/rcub_cer_6736 .

TY  - JOUR
AU  - Fotirić Akšić, Milica
AU  - Lazarević, Kristina
AU  - Šegan, Sandra
AU  - Natić, Maja
AU  - Tosti, Tomislav
AU  - Ćirić, Ivanka
AU  - Meland, Mekjell
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4771
AB  - Apple production generates large amounts of apple pomace including seeds, leading to high transportation costs, public health hazards and undesirable odor. A new reuse strategy of this kind of waste could solve environmental issues and/or create unconventional sources of health beneficial products. In total, seeds from 75 apple cultivars grown in Norway (both domestic and international) have been analyzed for the first time for oil content and fatty acid profile together with tocopherols and carotenoids quantification in defatted seeds. Seeds from cultivar Håkonseple had the highest oil content (22.10%), with linoleic, oleic acid, and palmitic acid as the most abundant fatty acids. The levels of β-carotene and lycopene carotenoids and α-tocopherol were the highest in defatted seeds of the cultivar Sureple Grøn. Principal component analysis separated cultivars according to the total oil content. The Norwegian apple cultivars Håkonseple, Kviteple, Tolleivseple, Vinterrosenstrips, and Tokheimseple are recommended for obtaining vegetable oil due to their high oil contents, while cultivar Sureple Grøn can be separated due to its high levels of β-carotene, lycopene and total tocopherols.
PB  - MDPI
T2  - Foods
T1  - Assessing the fatty acid, carotenoid, and tocopherol compositions of seeds from apple cultivars (Malus domestica borkh.) grown in norway
VL  - 10
IS  - 8
SP  - 1956
DO  - 10.3390/foods10081956
ER  - 

@article{
author = "Fotirić Akšić, Milica and Lazarević, Kristina and Šegan, Sandra and Natić, Maja and Tosti, Tomislav and Ćirić, Ivanka and Meland, Mekjell",
year = "2021",
abstract = "Apple production generates large amounts of apple pomace including seeds, leading to high transportation costs, public health hazards and undesirable odor. A new reuse strategy of this kind of waste could solve environmental issues and/or create unconventional sources of health beneficial products. In total, seeds from 75 apple cultivars grown in Norway (both domestic and international) have been analyzed for the first time for oil content and fatty acid profile together with tocopherols and carotenoids quantification in defatted seeds. Seeds from cultivar Håkonseple had the highest oil content (22.10%), with linoleic, oleic acid, and palmitic acid as the most abundant fatty acids. The levels of β-carotene and lycopene carotenoids and α-tocopherol were the highest in defatted seeds of the cultivar Sureple Grøn. Principal component analysis separated cultivars according to the total oil content. The Norwegian apple cultivars Håkonseple, Kviteple, Tolleivseple, Vinterrosenstrips, and Tokheimseple are recommended for obtaining vegetable oil due to their high oil contents, while cultivar Sureple Grøn can be separated due to its high levels of β-carotene, lycopene and total tocopherols.",
publisher = "MDPI",
journal = "Foods",
title = "Assessing the fatty acid, carotenoid, and tocopherol compositions of seeds from apple cultivars (Malus domestica borkh.) grown in norway",
volume = "10",
number = "8",
pages = "1956",
doi = "10.3390/foods10081956"
}

Fotirić Akšić, M., Lazarević, K., Šegan, S., Natić, M., Tosti, T., Ćirić, I.,& Meland, M.. (2021). Assessing the fatty acid, carotenoid, and tocopherol compositions of seeds from apple cultivars (Malus domestica borkh.) grown in norway. in Foods
MDPI., 10(8), 1956.
https://doi.org/10.3390/foods10081956

Fotirić Akšić M, Lazarević K, Šegan S, Natić M, Tosti T, Ćirić I, Meland M. Assessing the fatty acid, carotenoid, and tocopherol compositions of seeds from apple cultivars (Malus domestica borkh.) grown in norway. in Foods. 2021;10(8):1956.
doi:10.3390/foods10081956 .

Fotirić Akšić, Milica, Lazarević, Kristina, Šegan, Sandra, Natić, Maja, Tosti, Tomislav, Ćirić, Ivanka, Meland, Mekjell, "Assessing the fatty acid, carotenoid, and tocopherol compositions of seeds from apple cultivars (Malus domestica borkh.) grown in norway" in Foods, 10, no. 8 (2021):1956,
https://doi.org/10.3390/foods10081956 . .

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  - 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  - Šegan, Sandra
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Andrić, Deana
AU  - Milojković-Opsenica, Dušanka
AU  - Kostić Rajačić, Slađana
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2991
AB  - Reversed-phase thin-layer chromatography and micellar thin-layer chromatography were used in order to investigate retention behaviour and to determine lipophilicity of series of 2(methoxy)phenylpiperazine dopamine D2 ligands with different size, shape and rigidity. The retention mechanism was discussed. The lipophilicity parameters obtained in conventional reversed-phase systems expressed as RM0 and C0, as well as RM values
determined in microemulsion reversed-phase systems were correlated with in silico determined lipophilicity values. In silico pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands revealed the importance of experimentally determined lipophilicity values besides the molecular weight, on the blood–brain barrier permeability process. Also, the experimentally determined lipophilicity was found as a very important factor in plasma protein binding process of 2-(methoxy)phenylpiperazine dopamine D2 ligands. Besides, the Lipinski's rule of five indicates that examined ligands satisfy the criterion of drug-like molecules. The principal component analysis was performed on the experimentally determined and calculated lipophilicity values as well on the molecular descriptors which describe the pharmacokinetic properties in order to provide basic insights into similarities among the studied ligands.
PB  - Elsevier
T2  - Journal of Chromatography B
T1  - Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy) phenylpiperazine dopamine D2 ligands
VL  - 1124
SP  - 146
EP  - 153
DO  - 10.1016/j.jchromb.2019.06.006
ER  - 

@article{
author = "Šegan, Sandra and Penjišević, Jelena and Šukalović, Vladimir and Andrić, Deana and Milojković-Opsenica, Dušanka and Kostić Rajačić, Slađana",
year = "2019",
abstract = "Reversed-phase thin-layer chromatography and micellar thin-layer chromatography were used in order to investigate retention behaviour and to determine lipophilicity of series of 2(methoxy)phenylpiperazine dopamine D2 ligands with different size, shape and rigidity. The retention mechanism was discussed. The lipophilicity parameters obtained in conventional reversed-phase systems expressed as RM0 and C0, as well as RM values
determined in microemulsion reversed-phase systems were correlated with in silico determined lipophilicity values. In silico pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands revealed the importance of experimentally determined lipophilicity values besides the molecular weight, on the blood–brain barrier permeability process. Also, the experimentally determined lipophilicity was found as a very important factor in plasma protein binding process of 2-(methoxy)phenylpiperazine dopamine D2 ligands. Besides, the Lipinski's rule of five indicates that examined ligands satisfy the criterion of drug-like molecules. The principal component analysis was performed on the experimentally determined and calculated lipophilicity values as well on the molecular descriptors which describe the pharmacokinetic properties in order to provide basic insights into similarities among the studied ligands.",
publisher = "Elsevier",
journal = "Journal of Chromatography B",
title = "Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy) phenylpiperazine dopamine D2 ligands",
volume = "1124",
pages = "146-153",
doi = "10.1016/j.jchromb.2019.06.006"
}

Šegan, S., Penjišević, J., Šukalović, V., Andrić, D., Milojković-Opsenica, D.,& Kostić Rajačić, S.. (2019). Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy) phenylpiperazine dopamine D2 ligands. in Journal of Chromatography B
Elsevier., 1124, 146-153.
https://doi.org/10.1016/j.jchromb.2019.06.006

Šegan S, Penjišević J, Šukalović V, Andrić D, Milojković-Opsenica D, Kostić Rajačić S. Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy) phenylpiperazine dopamine D2 ligands. in Journal of Chromatography B. 2019;1124:146-153.
doi:10.1016/j.jchromb.2019.06.006 .

Šegan, Sandra, Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Milojković-Opsenica, Dušanka, Kostić Rajačić, Slađana, "Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy) phenylpiperazine dopamine D2 ligands" in Journal of Chromatography B, 1124 (2019):146-153,
https://doi.org/10.1016/j.jchromb.2019.06.006 . .

TY  - JOUR
AU  - Šegan, Sandra
AU  - Opsenica, Dejan
AU  - Milojković-Opsenica, Dušanka
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3205
AB  - Among widely used chromatographic methods modern thin-layer chromatography is not only the
simplest to perform but is also considered as respectable analytical method in various phases of
drug discovery and development processes such as monitoring of synthesis, identification of bioactive
substances from various natural sources and their isolation and purification, determination
of lipophilicity and other physico-chemical parameters, quantitative structure-activity relationship
studies, bioautography, as well as qualitative and quantitative analysis of drugs and their metabolites. An overview of recently published papers dealing with application of thin-layer chromatography in medicinal chemistry is presented.
PB  - Taylor & Francis Inc.
T2  - Journal of Liquid Chromatography & Related Technologies
T1  - Thin-layer chromatography in medicinal chemistry
VL  - 42
IS  - 9-10
SP  - 238
EP  - 248
DO  - 10.1080/10826076.2019.1585615
ER  - 

@article{
author = "Šegan, Sandra and Opsenica, Dejan and Milojković-Opsenica, Dušanka",
year = "2019",
abstract = "Among widely used chromatographic methods modern thin-layer chromatography is not only the
simplest to perform but is also considered as respectable analytical method in various phases of
drug discovery and development processes such as monitoring of synthesis, identification of bioactive
substances from various natural sources and their isolation and purification, determination
of lipophilicity and other physico-chemical parameters, quantitative structure-activity relationship
studies, bioautography, as well as qualitative and quantitative analysis of drugs and their metabolites. An overview of recently published papers dealing with application of thin-layer chromatography in medicinal chemistry is presented.",
publisher = "Taylor & Francis Inc.",
journal = "Journal of Liquid Chromatography & Related Technologies",
title = "Thin-layer chromatography in medicinal chemistry",
volume = "42",
number = "9-10",
pages = "238-248",
doi = "10.1080/10826076.2019.1585615"
}

Šegan, S., Opsenica, D.,& Milojković-Opsenica, D.. (2019). Thin-layer chromatography in medicinal chemistry. in Journal of Liquid Chromatography & Related Technologies
Taylor & Francis Inc.., 42(9-10), 238-248.
https://doi.org/10.1080/10826076.2019.1585615

Šegan S, Opsenica D, Milojković-Opsenica D. Thin-layer chromatography in medicinal chemistry. in Journal of Liquid Chromatography & Related Technologies. 2019;42(9-10):238-248.
doi:10.1080/10826076.2019.1585615 .

Šegan, Sandra, Opsenica, Dejan, Milojković-Opsenica, Dušanka, "Thin-layer chromatography in medicinal chemistry" in Journal of Liquid Chromatography & Related Technologies, 42, no. 9-10 (2019):238-248,
https://doi.org/10.1080/10826076.2019.1585615 . .

TY  - JOUR
AU  - Milojković-Opsenica, Dušanka
AU  - Andrić, Filip
AU  - Šegan, Sandra
AU  - Trifković, Jelena
AU  - Tešić, Živoslav
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2475
AB  - The methods of correlating molecular structure of substances expressed as descriptors, to their biological activity are commonly denoted as Quantitative Structure-Activity Relationships (QSARs). This concept, typically applied in drug discovery processes, is also widely used for correlation of molecular structure and physicochemical properties of solutes in so-called quantitative structure-property relationship (QSPR) studies, as well as for explanation of chromatographic behavior, i.e., separation mechanisms of analytes, where is termed as quantitative structure-retention relationship (QSRR). Mathematical expressions of structural characteristics of substances, named as molecular descriptors, can be calculated by various computational techniques or experimentally determined by different analytical methods. Thin-layer chromatography as a rapid, sensitive, and economical liquid chromatographic method has been widely used for determination of various chromatographic descriptors applicable in QSAR/QSPR studies. An overview of recently published papers dealing with this concept is presented. [GRAPHICS] .
PB  - Taylor & Francis Inc, Philadelphia
T2  - Journal of Liquid Chromatography & Related Technologies
T1  - Thin-layer chromatography in quantitative structure-activity relationship studies
VL  - 41
IS  - 6
SP  - 272
EP  - 281
DO  - 10.1080/10826076.2018.1447892
ER  - 

@article{
author = "Milojković-Opsenica, Dušanka and Andrić, Filip and Šegan, Sandra and Trifković, Jelena and Tešić, Živoslav",
year = "2018",
abstract = "The methods of correlating molecular structure of substances expressed as descriptors, to their biological activity are commonly denoted as Quantitative Structure-Activity Relationships (QSARs). This concept, typically applied in drug discovery processes, is also widely used for correlation of molecular structure and physicochemical properties of solutes in so-called quantitative structure-property relationship (QSPR) studies, as well as for explanation of chromatographic behavior, i.e., separation mechanisms of analytes, where is termed as quantitative structure-retention relationship (QSRR). Mathematical expressions of structural characteristics of substances, named as molecular descriptors, can be calculated by various computational techniques or experimentally determined by different analytical methods. Thin-layer chromatography as a rapid, sensitive, and economical liquid chromatographic method has been widely used for determination of various chromatographic descriptors applicable in QSAR/QSPR studies. An overview of recently published papers dealing with this concept is presented. [GRAPHICS] .",
publisher = "Taylor & Francis Inc, Philadelphia",
journal = "Journal of Liquid Chromatography & Related Technologies",
title = "Thin-layer chromatography in quantitative structure-activity relationship studies",
volume = "41",
number = "6",
pages = "272-281",
doi = "10.1080/10826076.2018.1447892"
}

Milojković-Opsenica, D., Andrić, F., Šegan, S., Trifković, J.,& Tešić, Ž.. (2018). Thin-layer chromatography in quantitative structure-activity relationship studies. in Journal of Liquid Chromatography & Related Technologies
Taylor & Francis Inc, Philadelphia., 41(6), 272-281.
https://doi.org/10.1080/10826076.2018.1447892

Milojković-Opsenica D, Andrić F, Šegan S, Trifković J, Tešić Ž. Thin-layer chromatography in quantitative structure-activity relationship studies. in Journal of Liquid Chromatography & Related Technologies. 2018;41(6):272-281.
doi:10.1080/10826076.2018.1447892 .

Milojković-Opsenica, Dušanka, Andrić, Filip, Šegan, Sandra, Trifković, Jelena, Tešić, Živoslav, "Thin-layer chromatography in quantitative structure-activity relationship studies" in Journal of Liquid Chromatography & Related Technologies, 41, no. 6 (2018):272-281,
https://doi.org/10.1080/10826076.2018.1447892 . .

TY  - JOUR
AU  - Ajdačić, Vladimir
AU  - Lazić, Jelena
AU  - Mojicevic, Marija
AU  - Šegan, Sandra
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2138
AB  - A series of novel guanylhydrazones were designed, synthesized and characterized. All the compounds were screened for their antibacterial and antifungal activity. Compounds 26 and 27 showed excellent antibacterial activities against Staphylococcus aureus ATCC 25923 and Micrococcus luteus ATCC 379 with minimal inhibitory concentrations of 4 ae g mL(-1), and good antifungal activity against Candida parapsilosis ATCC 22019. These results suggested that the selected guanylhydrazones could serve as promising leads for improved antimicrobial development.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Antibacterial and antifungal properties of guanylhydrazones
VL  - 82
IS  - 6
SP  - 641
EP  - 649
DO  - 10.2298/JSC170213033A
ER  - 

@article{
author = "Ajdačić, Vladimir and Lazić, Jelena and Mojicevic, Marija and Šegan, Sandra and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2017",
abstract = "A series of novel guanylhydrazones were designed, synthesized and characterized. All the compounds were screened for their antibacterial and antifungal activity. Compounds 26 and 27 showed excellent antibacterial activities against Staphylococcus aureus ATCC 25923 and Micrococcus luteus ATCC 379 with minimal inhibitory concentrations of 4 ae g mL(-1), and good antifungal activity against Candida parapsilosis ATCC 22019. These results suggested that the selected guanylhydrazones could serve as promising leads for improved antimicrobial development.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Antibacterial and antifungal properties of guanylhydrazones",
volume = "82",
number = "6",
pages = "641-649",
doi = "10.2298/JSC170213033A"
}

Ajdačić, V., Lazić, J., Mojicevic, M., Šegan, S., Nikodinović-Runić, J.,& Opsenica, I.. (2017). Antibacterial and antifungal properties of guanylhydrazones. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 82(6), 641-649.
https://doi.org/10.2298/JSC170213033A

Ajdačić V, Lazić J, Mojicevic M, Šegan S, Nikodinović-Runić J, Opsenica I. Antibacterial and antifungal properties of guanylhydrazones. in Journal of the Serbian Chemical Society. 2017;82(6):641-649.
doi:10.2298/JSC170213033A .

Ajdačić, Vladimir, Lazić, Jelena, Mojicevic, Marija, Šegan, Sandra, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Antibacterial and antifungal properties of guanylhydrazones" in Journal of the Serbian Chemical Society, 82, no. 6 (2017):641-649,
https://doi.org/10.2298/JSC170213033A . .

TY  - JOUR
AU  - Šegan, Sandra
AU  - Bozinovic, Nina
AU  - Opsenica, Igor
AU  - Andrić, Filip
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2243
AB  - Lipophilicity is one of the essential properties influencing drug absorption, excretion and metabolism. It is used for screening viable drug candidates. Chromatographic behavior of thiepino[3,2-c: 6,7-c'] dipyridine and 16 benzothiepino[3,2-c] pyridine derivatives as potential antifungal drugs was studied using thin-layer chromatography under typical reversed-phase conditions and two microemulsion chromatographic systems. Seventeen chromatographic and nine in silico lipophilicity measures were estimated. They were compared by classical multivariate approaches: principal component analysis, hierarchical cluster analysis, and ranked and grouped by the non-parametricmethod-Sum of ranking differences. Two computational and two chromatographic descriptors from the typical reversed-phase conditions using acetone/ water mixtures emerged as the best candidates for lipophilicity estimation. The principal component scores related to typical reversed-phase conditions using dioxane/ water were ranked as statistically insignificant ( the worst). Microemulsion systems were positioned in between, performing worse than in silico estimates. Thiepine derivatives were ranked and grouped by sum of ranking differences, fusing multiple lipophilicity measures. In multicriteria maximization ranking, the compound substituted by phenyl group at position 8 was selected as the most lipophilic one. It is also the most active against Candida albicans. The ranking confirmed that introduction of phenyl core is essential for increasing the lipophilicity of the studied compounds.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Journal of Separation Science
T1  - Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs
VL  - 40
IS  - 10
SP  - 2089
EP  - 2096
DO  - 10.1002/jssc.201601442
ER  - 

@article{
author = "Šegan, Sandra and Bozinovic, Nina and Opsenica, Igor and Andrić, Filip",
year = "2017",
abstract = "Lipophilicity is one of the essential properties influencing drug absorption, excretion and metabolism. It is used for screening viable drug candidates. Chromatographic behavior of thiepino[3,2-c: 6,7-c'] dipyridine and 16 benzothiepino[3,2-c] pyridine derivatives as potential antifungal drugs was studied using thin-layer chromatography under typical reversed-phase conditions and two microemulsion chromatographic systems. Seventeen chromatographic and nine in silico lipophilicity measures were estimated. They were compared by classical multivariate approaches: principal component analysis, hierarchical cluster analysis, and ranked and grouped by the non-parametricmethod-Sum of ranking differences. Two computational and two chromatographic descriptors from the typical reversed-phase conditions using acetone/ water mixtures emerged as the best candidates for lipophilicity estimation. The principal component scores related to typical reversed-phase conditions using dioxane/ water were ranked as statistically insignificant ( the worst). Microemulsion systems were positioned in between, performing worse than in silico estimates. Thiepine derivatives were ranked and grouped by sum of ranking differences, fusing multiple lipophilicity measures. In multicriteria maximization ranking, the compound substituted by phenyl group at position 8 was selected as the most lipophilic one. It is also the most active against Candida albicans. The ranking confirmed that introduction of phenyl core is essential for increasing the lipophilicity of the studied compounds.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Journal of Separation Science",
title = "Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs",
volume = "40",
number = "10",
pages = "2089-2096",
doi = "10.1002/jssc.201601442"
}

Šegan, S., Bozinovic, N., Opsenica, I.,& Andrić, F.. (2017). Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs. in Journal of Separation Science
Wiley-V C H Verlag Gmbh, Weinheim., 40(10), 2089-2096.
https://doi.org/10.1002/jssc.201601442

Šegan S, Bozinovic N, Opsenica I, Andrić F. Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs. in Journal of Separation Science. 2017;40(10):2089-2096.
doi:10.1002/jssc.201601442 .

Šegan, Sandra, Bozinovic, Nina, Opsenica, Igor, Andrić, Filip, "Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs" in Journal of Separation Science, 40, no. 10 (2017):2089-2096,
https://doi.org/10.1002/jssc.201601442 . .

TY  - JOUR
AU  - Šegan, Sandra
AU  - Bozinovic, Nina
AU  - Opsenica, Igor
AU  - Andrić, Filip
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2982
AB  - Lipophilicity is one of the essential properties influencing drug absorption, excretion and metabolism. It is used for screening viable drug candidates. Chromatographic behavior of thiepino[3,2-c: 6,7-c'] dipyridine and 16 benzothiepino[3,2-c] pyridine derivatives as potential antifungal drugs was studied using thin-layer chromatography under typical reversed-phase conditions and two microemulsion chromatographic systems. Seventeen chromatographic and nine in silico lipophilicity measures were estimated. They were compared by classical multivariate approaches: principal component analysis, hierarchical cluster analysis, and ranked and grouped by the non-parametricmethod-Sum of ranking differences. Two computational and two chromatographic descriptors from the typical reversed-phase conditions using acetone/ water mixtures emerged as the best candidates for lipophilicity estimation. The principal component scores related to typical reversed-phase conditions using dioxane/ water were ranked as statistically insignificant ( the worst). Microemulsion systems were positioned in between, performing worse than in silico estimates. Thiepine derivatives were ranked and grouped by sum of ranking differences, fusing multiple lipophilicity measures. In multicriteria maximization ranking, the compound substituted by phenyl group at position 8 was selected as the most lipophilic one. It is also the most active against Candida albicans. The ranking confirmed that introduction of phenyl core is essential for increasing the lipophilicity of the studied compounds.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Journal of Separation Science
T1  - Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs
VL  - 40
IS  - 10
SP  - 2089
EP  - 2096
DO  - 10.1002/jssc.201601442
ER  - 

@article{
author = "Šegan, Sandra and Bozinovic, Nina and Opsenica, Igor and Andrić, Filip",
year = "2017",
abstract = "Lipophilicity is one of the essential properties influencing drug absorption, excretion and metabolism. It is used for screening viable drug candidates. Chromatographic behavior of thiepino[3,2-c: 6,7-c'] dipyridine and 16 benzothiepino[3,2-c] pyridine derivatives as potential antifungal drugs was studied using thin-layer chromatography under typical reversed-phase conditions and two microemulsion chromatographic systems. Seventeen chromatographic and nine in silico lipophilicity measures were estimated. They were compared by classical multivariate approaches: principal component analysis, hierarchical cluster analysis, and ranked and grouped by the non-parametricmethod-Sum of ranking differences. Two computational and two chromatographic descriptors from the typical reversed-phase conditions using acetone/ water mixtures emerged as the best candidates for lipophilicity estimation. The principal component scores related to typical reversed-phase conditions using dioxane/ water were ranked as statistically insignificant ( the worst). Microemulsion systems were positioned in between, performing worse than in silico estimates. Thiepine derivatives were ranked and grouped by sum of ranking differences, fusing multiple lipophilicity measures. In multicriteria maximization ranking, the compound substituted by phenyl group at position 8 was selected as the most lipophilic one. It is also the most active against Candida albicans. The ranking confirmed that introduction of phenyl core is essential for increasing the lipophilicity of the studied compounds.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Journal of Separation Science",
title = "Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs",
volume = "40",
number = "10",
pages = "2089-2096",
doi = "10.1002/jssc.201601442"
}

Šegan, S., Bozinovic, N., Opsenica, I.,& Andrić, F.. (2017). Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs. in Journal of Separation Science
Wiley-V C H Verlag Gmbh, Weinheim., 40(10), 2089-2096.
https://doi.org/10.1002/jssc.201601442

Šegan S, Bozinovic N, Opsenica I, Andrić F. Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs. in Journal of Separation Science. 2017;40(10):2089-2096.
doi:10.1002/jssc.201601442 .

Šegan, Sandra, Bozinovic, Nina, Opsenica, Igor, Andrić, Filip, "Consensus-based comparison of chromatographic and computationally estimated lipophilicity of benzothiepino[3,2-c]pyridine derivatives as potential antifungal drugs" in Journal of Separation Science, 40, no. 10 (2017):2089-2096,
https://doi.org/10.1002/jssc.201601442 . .

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  - Bozinovic, Nina
AU  - Šegan, Sandra
AU  - Vojnovic, Sandra
AU  - Pavić, Aleksandar
AU  - Šolaja, Bogdan
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1887
AB  - A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.
PB  - Wiley, Hoboken
T2  - Chemical Biology & Drug Design
T1  - Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives
VL  - 88
IS  - 6
SP  - 795
EP  - 806
DO  - 10.1111/cbdd.12809
ER  - 

@article{
author = "Bozinovic, Nina and Šegan, Sandra and Vojnovic, Sandra and Pavić, Aleksandar and Šolaja, Bogdan and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2016",
abstract = "A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology & Drug Design",
title = "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives",
volume = "88",
number = "6",
pages = "795-806",
doi = "10.1111/cbdd.12809"
}

Bozinovic, N., Šegan, S., Vojnovic, S., Pavić, A., Šolaja, B., Nikodinović-Runić, J.,& Opsenica, I.. (2016). Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. in Chemical Biology & Drug Design
Wiley, Hoboken., 88(6), 795-806.
https://doi.org/10.1111/cbdd.12809

Bozinovic N, Šegan S, Vojnovic S, Pavić A, Šolaja B, Nikodinović-Runić J, Opsenica I. Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. in Chemical Biology & Drug Design. 2016;88(6):795-806.
doi:10.1111/cbdd.12809 .

Bozinovic, Nina, Šegan, Sandra, Vojnovic, Sandra, Pavić, Aleksandar, Šolaja, Bogdan, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives" in Chemical Biology & Drug Design, 88, no. 6 (2016):795-806,
https://doi.org/10.1111/cbdd.12809 . .

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 . .

TY  - JOUR
AU  - Bozinovic, Nina
AU  - Šegan, Sandra
AU  - Vojnovic, Sandra
AU  - Pavić, Aleksandar
AU  - Šolaja, Bogdan
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3192
AB  - A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.
PB  - Wiley, Hoboken
T2  - Chemical Biology & Drug Design
T1  - Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives
VL  - 88
IS  - 6
SP  - 795
EP  - 806
DO  - 10.1111/cbdd.12809
ER  - 

@article{
author = "Bozinovic, Nina and Šegan, Sandra and Vojnovic, Sandra and Pavić, Aleksandar and Šolaja, Bogdan and Nikodinović-Runić, Jasmina and Opsenica, Igor",
year = "2016",
abstract = "A novel series of thiepine derivatives were synthesized and evaluated as potential antimicrobials. All the synthesized compounds were evaluated for their antimicrobial activities in vitro against the fungi Candida albicans (ATCC 10231), C.parapsilosis (clinical isolate), Gram-negative bacterium Pseudomonas aeruginosa (ATCC 44752), and Gram-positive bacterium Staphylococcus aureus (ATCC 25923). Synthesized compounds showed higher antifungal activity than antibacterial activity, indicating that they could be used as selective antimicrobials. Selected thiepines efficiently inhibited Candida hyphae formation, a trait necessary for their pathogenicity. Thiepine 8-phenyl[1]benzothiepino[3,2-c]pyridine (16) efficiently killed Candida albicans at 15.6g/mL and showed no embryotoxicity at 75g/mL. Derivative 8-[4-(4,5-dihydro-1H-imidazol-2-yl)phenyl][1]benzothiepino[3,2-c]pyridine (23) caused significant hemolysis and in vitro DNA interaction. The position of the phenyl ring was essential for the antifungal activity, while the electronic effects of the substituents did not significantly influence activity. Results obtained from in vivo embryotoxicity on zebrafish (Danio rerio) encourage further structure optimizations.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology & Drug Design",
title = "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives",
volume = "88",
number = "6",
pages = "795-806",
doi = "10.1111/cbdd.12809"
}

Bozinovic, N., Šegan, S., Vojnovic, S., Pavić, A., Šolaja, B., Nikodinović-Runić, J.,& Opsenica, I.. (2016). Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. in Chemical Biology & Drug Design
Wiley, Hoboken., 88(6), 795-806.
https://doi.org/10.1111/cbdd.12809

Bozinovic N, Šegan S, Vojnovic S, Pavić A, Šolaja B, Nikodinović-Runić J, Opsenica I. Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives. in Chemical Biology & Drug Design. 2016;88(6):795-806.
doi:10.1111/cbdd.12809 .

Bozinovic, Nina, Šegan, Sandra, Vojnovic, Sandra, Pavić, Aleksandar, Šolaja, Bogdan, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Synthesis and anti-Candida activity of novel benzothiepino[3,2-c]pyridine derivatives" in Chemical Biology & Drug Design, 88, no. 6 (2016):795-806,
https://doi.org/10.1111/cbdd.12809 . .

TY  - JOUR
AU  - Andrić, Filip
AU  - Bajusz, David
AU  - Racz, Anita
AU  - Šegan, Sandra
AU  - Héberger, Karoly
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3182
AB  - Needs for fast, yet reliable means of assessing the lipophilicities of diverse compounds resulted in the development of various in silico and chromatographic approaches that are faster, cheaper, and greener compared to the traditional shake-flask method. However, at present no accepted "standard" approach exists for their comparison and selection of the most appropriate one(s). This is of utmost importance when it comes to the development of new lipophilicity indices, or the assessment of the lipophilicity of newly synthesized compounds. In this study, 50 well-known, diverse compounds of significant pharmaceutical and environmental importance have been selected and examined. Octanol-water partition coefficients have been measured with the shake-flask method for most of them. Their retentions have been studied in typical reversed thin-layer chromatographic systems, involving the most frequently employed stationary phases (octadecyl- and cyano-modified silica), and acetonitrile and methanol as mobile phase constituents. Twelve computationally estimated logP-s and twenty chromatographic indices together with the shake-flask octanol-water partition coefficient have been investigated with classical chemometric approaches such as principal component analysis (PCA), hierarchical cluster analysis (HCA), Pearson's and Spearman's correlation matrices, as well as novel non-parametric methods: sum of ranking differences (SRD) and generalized pairwise correlation method (GPCM). Novel SRD and GPCM methods have been introduced based on the Comparisons with One VAriable (lipophilicity metric) at a Time (COVAT). For the visualization of COVAT results, a heatmap format was introduced. Analysis of variance (ANOVA) was applied to reveal the dominant factors between computational logPs and various chromatographic measures. In consensus-based comparisons, the shake-flask method performed the best, closely followed by computational estimates, while the chromatographic estimates often overlap with in silico assessments, mostly with methods involving octadecyl-modified silica stationary phases. The ones that employ cyano-modified silica perform generally worse. The introduction of alternative coloring schemes for the covariance matrices and SRD/GPCM heatmaps enables the discovery of intrinsic relationships among lipophilicity scales and the selection of best/worst measures. Closest to the recommended logK(ow) values are ClogP and the first principal component scores obtained on octadecyl-silica stationary phase in combination with methanol-water mobile phase, while the usage of slopes derived from Soczewinski-Matyisik equation should be avoided. (C) 2016 Elsevier B.V. All rights reserved.
PB  - Elsevier
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Multivariate assessment of lipophilicity scales-computational and reversed phase thin-layer chromatographic indices
VL  - 127
SP  - 81
EP  - 93
DO  - 10.1016/j.jpba.2016.04.001
ER  - 

@article{
author = "Andrić, Filip and Bajusz, David and Racz, Anita and Šegan, Sandra and Héberger, Karoly",
year = "2016",
abstract = "Needs for fast, yet reliable means of assessing the lipophilicities of diverse compounds resulted in the development of various in silico and chromatographic approaches that are faster, cheaper, and greener compared to the traditional shake-flask method. However, at present no accepted "standard" approach exists for their comparison and selection of the most appropriate one(s). This is of utmost importance when it comes to the development of new lipophilicity indices, or the assessment of the lipophilicity of newly synthesized compounds. In this study, 50 well-known, diverse compounds of significant pharmaceutical and environmental importance have been selected and examined. Octanol-water partition coefficients have been measured with the shake-flask method for most of them. Their retentions have been studied in typical reversed thin-layer chromatographic systems, involving the most frequently employed stationary phases (octadecyl- and cyano-modified silica), and acetonitrile and methanol as mobile phase constituents. Twelve computationally estimated logP-s and twenty chromatographic indices together with the shake-flask octanol-water partition coefficient have been investigated with classical chemometric approaches such as principal component analysis (PCA), hierarchical cluster analysis (HCA), Pearson's and Spearman's correlation matrices, as well as novel non-parametric methods: sum of ranking differences (SRD) and generalized pairwise correlation method (GPCM). Novel SRD and GPCM methods have been introduced based on the Comparisons with One VAriable (lipophilicity metric) at a Time (COVAT). For the visualization of COVAT results, a heatmap format was introduced. Analysis of variance (ANOVA) was applied to reveal the dominant factors between computational logPs and various chromatographic measures. In consensus-based comparisons, the shake-flask method performed the best, closely followed by computational estimates, while the chromatographic estimates often overlap with in silico assessments, mostly with methods involving octadecyl-modified silica stationary phases. The ones that employ cyano-modified silica perform generally worse. The introduction of alternative coloring schemes for the covariance matrices and SRD/GPCM heatmaps enables the discovery of intrinsic relationships among lipophilicity scales and the selection of best/worst measures. Closest to the recommended logK(ow) values are ClogP and the first principal component scores obtained on octadecyl-silica stationary phase in combination with methanol-water mobile phase, while the usage of slopes derived from Soczewinski-Matyisik equation should be avoided. (C) 2016 Elsevier B.V. All rights reserved.",
publisher = "Elsevier",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Multivariate assessment of lipophilicity scales-computational and reversed phase thin-layer chromatographic indices",
volume = "127",
pages = "81-93",
doi = "10.1016/j.jpba.2016.04.001"
}

Andrić, F., Bajusz, D., Racz, A., Šegan, S.,& Héberger, K.. (2016). Multivariate assessment of lipophilicity scales-computational and reversed phase thin-layer chromatographic indices. in Journal of Pharmaceutical and Biomedical Analysis
Elsevier., 127, 81-93.
https://doi.org/10.1016/j.jpba.2016.04.001

Andrić F, Bajusz D, Racz A, Šegan S, Héberger K. Multivariate assessment of lipophilicity scales-computational and reversed phase thin-layer chromatographic indices. in Journal of Pharmaceutical and Biomedical Analysis. 2016;127:81-93.
doi:10.1016/j.jpba.2016.04.001 .

Andrić, Filip, Bajusz, David, Racz, Anita, Šegan, Sandra, Héberger, Karoly, "Multivariate assessment of lipophilicity scales-computational and reversed phase thin-layer chromatographic indices" in Journal of Pharmaceutical and Biomedical Analysis, 127 (2016):81-93,
https://doi.org/10.1016/j.jpba.2016.04.001 . .

TY  - JOUR
AU  - Andrić, Filip
AU  - Šegan, Sandra
AU  - Dramićanin, Aleksandra M.
AU  - Majstorović, Helena
AU  - Milojković-Opsenica, Dušanka
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3156
AB  - Soil-water partition coefficient normalized to the organic carbon.content (K-OC) is one of the crucial properties influencing the fate of organic compounds in the environment. Chromatographic methods are well established alternative for direct sorption techniques used for K-OC determination. The present work proposes reversed-phase thin-layer chromatography (RP-TLC) as a simpler, yet equally accurate method as officially recommended HPLC technique. Several TLC systems were studied including octadecyl-(RP18) and cyano-(CN) modified silica layers in combination with methanol-water and acetonitrile-water mixtures as mobile phases. In total 50 compounds of different molecular shape, size, and various ability to establish specific interactions were selected (phenols, beznodiazepines, triazine herbicides, and polyaromatic hydrocarbons). Calibration set of 29 compounds with known logK(OC) values determined by sorption experiments was used to build simple univariate calibrations, Principal Component Regression (PCR) and Partial Least Squares (PLS) models between logK(OC) and TLC retention parameters. Models exhibit good statistical performance, indicating that CN-layers contribute better to logK(OC) modeling than RP18-silica. The most promising TLC methods, officially recommended HPLC method, and four in silico estimation approaches have been compared by non-parametric Sum of Ranking Differences approach (SRD). The best estimations of logK(OC) values were achieved by simple univariate calibration of TLC retention data involving CN-silica layers and moderate content of methanol (40-50% v/v). They were ranked far well compared to the officially recommended HPLC method which was ranked in the middle. The worst estimates have been obtained from in silico computations based on octanol-water partition coefficient. Linear Solvation Energy Relationship study revealed that increased polarity of CN-layers over RP18 in combination with methanol-water mixtures is the key to better modeling of logK(OC) through significant diminishing of dipolar and proton accepting influence of the mobile phase as well as enhancing molar refractivity in excess of the chromatographic systems. (C) 2016 Elsevier B.V. All rights reserved.
PB  - Elsevier
T2  - Journal of Chromatography A
T1  - Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography
VL  - 1458
SP  - 136
EP  - 144
DO  - 10.1016/j.chroma.2016.06.063
ER  - 

@article{
author = "Andrić, Filip and Šegan, Sandra and Dramićanin, Aleksandra M. and Majstorović, Helena and Milojković-Opsenica, Dušanka",
year = "2016",
abstract = "Soil-water partition coefficient normalized to the organic carbon.content (K-OC) is one of the crucial properties influencing the fate of organic compounds in the environment. Chromatographic methods are well established alternative for direct sorption techniques used for K-OC determination. The present work proposes reversed-phase thin-layer chromatography (RP-TLC) as a simpler, yet equally accurate method as officially recommended HPLC technique. Several TLC systems were studied including octadecyl-(RP18) and cyano-(CN) modified silica layers in combination with methanol-water and acetonitrile-water mixtures as mobile phases. In total 50 compounds of different molecular shape, size, and various ability to establish specific interactions were selected (phenols, beznodiazepines, triazine herbicides, and polyaromatic hydrocarbons). Calibration set of 29 compounds with known logK(OC) values determined by sorption experiments was used to build simple univariate calibrations, Principal Component Regression (PCR) and Partial Least Squares (PLS) models between logK(OC) and TLC retention parameters. Models exhibit good statistical performance, indicating that CN-layers contribute better to logK(OC) modeling than RP18-silica. The most promising TLC methods, officially recommended HPLC method, and four in silico estimation approaches have been compared by non-parametric Sum of Ranking Differences approach (SRD). The best estimations of logK(OC) values were achieved by simple univariate calibration of TLC retention data involving CN-silica layers and moderate content of methanol (40-50% v/v). They were ranked far well compared to the officially recommended HPLC method which was ranked in the middle. The worst estimates have been obtained from in silico computations based on octanol-water partition coefficient. Linear Solvation Energy Relationship study revealed that increased polarity of CN-layers over RP18 in combination with methanol-water mixtures is the key to better modeling of logK(OC) through significant diminishing of dipolar and proton accepting influence of the mobile phase as well as enhancing molar refractivity in excess of the chromatographic systems. (C) 2016 Elsevier B.V. All rights reserved.",
publisher = "Elsevier",
journal = "Journal of Chromatography A",
title = "Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography",
volume = "1458",
pages = "136-144",
doi = "10.1016/j.chroma.2016.06.063"
}

Andrić, F., Šegan, S., Dramićanin, A. M., Majstorović, H.,& Milojković-Opsenica, D.. (2016). Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography. in Journal of Chromatography A
Elsevier., 1458, 136-144.
https://doi.org/10.1016/j.chroma.2016.06.063

Andrić F, Šegan S, Dramićanin AM, Majstorović H, Milojković-Opsenica D. Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography. in Journal of Chromatography A. 2016;1458:136-144.
doi:10.1016/j.chroma.2016.06.063 .

Andrić, Filip, Šegan, Sandra, Dramićanin, Aleksandra M., Majstorović, Helena, Milojković-Opsenica, Dušanka, "Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography" in Journal of Chromatography A, 1458 (2016):136-144,
https://doi.org/10.1016/j.chroma.2016.06.063 . .

TY  - JOUR
AU  - Andrić, Filip
AU  - Šegan, Sandra
AU  - Dramićanin, Aleksandra
AU  - Majstorovic, Helena
AU  - Milojković-Opsenica, Dušanka
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1849
AB  - Soil-water partition coefficient normalized to the organic carbon.content (K-OC) is one of the crucial properties influencing the fate of organic compounds in the environment. Chromatographic methods are well established alternative for direct sorption techniques used for K-OC determination. The present work proposes reversed-phase thin-layer chromatography (RP-TLC) as a simpler, yet equally accurate method as officially recommended HPLC technique. Several TLC systems were studied including octadecyl-(RP18) and cyano-(CN) modified silica layers in combination with methanol-water and acetonitrile-water mixtures as mobile phases. In total 50 compounds of different molecular shape, size, and various ability to establish specific interactions were selected (phenols, beznodiazepines, triazine herbicides, and polyaromatic hydrocarbons). Calibration set of 29 compounds with known logK(OC) values determined by sorption experiments was used to build simple univariate calibrations, Principal Component Regression (PCR) and Partial Least Squares (PLS) models between logK(OC) and TLC retention parameters. Models exhibit good statistical performance, indicating that CN-layers contribute better to logK(OC) modeling than RP18-silica. The most promising TLC methods, officially recommended HPLC method, and four in silico estimation approaches have been compared by non-parametric Sum of Ranking Differences approach (SRD). The best estimations of logK(OC) values were achieved by simple univariate calibration of TLC retention data involving CN-silica layers and moderate content of methanol (40-50% v/v). They were ranked far well compared to the officially recommended HPLC method which was ranked in the middle. The worst estimates have been obtained from in silico computations based on octanol-water partition coefficient. Linear Solvation Energy Relationship study revealed that increased polarity of CN-layers over RP18 in combination with methanol-water mixtures is the key to better modeling of logK(OC) through significant diminishing of dipolar and proton accepting influence of the mobile phase as well as enhancing molar refractivity in excess of the chromatographic systems.
PB  - Elsevier
T2  - Journal of Chromatography A
T1  - Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography
VL  - 1458
SP  - 136
EP  - 144
DO  - 10.1016/j.chroma.2016.06.063
ER  - 

@article{
author = "Andrić, Filip and Šegan, Sandra and Dramićanin, Aleksandra and Majstorovic, Helena and Milojković-Opsenica, Dušanka",
year = "2016",
abstract = "Soil-water partition coefficient normalized to the organic carbon.content (K-OC) is one of the crucial properties influencing the fate of organic compounds in the environment. Chromatographic methods are well established alternative for direct sorption techniques used for K-OC determination. The present work proposes reversed-phase thin-layer chromatography (RP-TLC) as a simpler, yet equally accurate method as officially recommended HPLC technique. Several TLC systems were studied including octadecyl-(RP18) and cyano-(CN) modified silica layers in combination with methanol-water and acetonitrile-water mixtures as mobile phases. In total 50 compounds of different molecular shape, size, and various ability to establish specific interactions were selected (phenols, beznodiazepines, triazine herbicides, and polyaromatic hydrocarbons). Calibration set of 29 compounds with known logK(OC) values determined by sorption experiments was used to build simple univariate calibrations, Principal Component Regression (PCR) and Partial Least Squares (PLS) models between logK(OC) and TLC retention parameters. Models exhibit good statistical performance, indicating that CN-layers contribute better to logK(OC) modeling than RP18-silica. The most promising TLC methods, officially recommended HPLC method, and four in silico estimation approaches have been compared by non-parametric Sum of Ranking Differences approach (SRD). The best estimations of logK(OC) values were achieved by simple univariate calibration of TLC retention data involving CN-silica layers and moderate content of methanol (40-50% v/v). They were ranked far well compared to the officially recommended HPLC method which was ranked in the middle. The worst estimates have been obtained from in silico computations based on octanol-water partition coefficient. Linear Solvation Energy Relationship study revealed that increased polarity of CN-layers over RP18 in combination with methanol-water mixtures is the key to better modeling of logK(OC) through significant diminishing of dipolar and proton accepting influence of the mobile phase as well as enhancing molar refractivity in excess of the chromatographic systems.",
publisher = "Elsevier",
journal = "Journal of Chromatography A",
title = "Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography",
volume = "1458",
pages = "136-144",
doi = "10.1016/j.chroma.2016.06.063"
}

Andrić, F., Šegan, S., Dramićanin, A., Majstorovic, H.,& Milojković-Opsenica, D.. (2016). Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography. in Journal of Chromatography A
Elsevier., 1458, 136-144.
https://doi.org/10.1016/j.chroma.2016.06.063

Andrić F, Šegan S, Dramićanin A, Majstorovic H, Milojković-Opsenica D. Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography. in Journal of Chromatography A. 2016;1458:136-144.
doi:10.1016/j.chroma.2016.06.063 .

Andrić, Filip, Šegan, Sandra, Dramićanin, Aleksandra, Majstorovic, Helena, Milojković-Opsenica, Dušanka, "Linear modeling of the soil-water partition coefficient normalized to organic carbon content by reversed-phase thin-layer chromatography" in Journal of Chromatography A, 1458 (2016):136-144,
https://doi.org/10.1016/j.chroma.2016.06.063 . .