TY  - JOUR
AU  - Radaković, Nataša
AU  - Nikolić, Andrea
AU  - Terzić-Jovanović, Nataša
AU  - Stojković, Pavle
AU  - Stanković, Nada
AU  - Šolaja, Bogdan
AU  - Opsenica, Igor
AU  - Pavić, Aleksandar
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5235
AB  - Candida albicans remains the main causal agent of candidiasis, the most common fungal infection with disturbingly high mortality rates worldwide. The limited diversity and efficacy of clinical antifungal drugs, exacerbated by emerging drug resistance, have resulted in the failure of current antifungal therapies. This imposes an urgent demand for the development of innovative strategies for effective eradication of candidal infections. While the existing clinical drugs display fungicidal or fungistatic activity, the strategy specifically targeting C. albicans filamentation, as the most important virulence trait, represents an attractive approach for overcoming the drawbacks related to clinical antifungals. The results acquired in this study revealed the significant potential of 5-aminotetrazoles as a new class of effective and safe anti-virulence agents. Moreover, these novel agents were active when applied both alone and in combination with clinically approved polyenes. Complete prevention of C. albicans morphogenetic yeast-to-hyphae transition was achieved at doses as low as 1.3 μM under conditions mimicking various filamentation-responsive stimuli in the human body, while no cardio- or hepatotoxicity was observed at doses as high as 200 μM. The treatment of C. albicans-infected zebrafish embryos with nystatin alone had low efficacy, while the combination of nystatin and selected 5-aminotetrazoles prevented fungal filamentation, successfully eliminating the infection and rescuing the infected embryos from lethal disseminated candidiasis. In addition, the most potent anti-virulence 5-aminotetrazole prevented C. albicans in developing the resistance to nystatin when applied in combination, keeping the fungus sensitive to the antifungal drug.
PB  - Elsevier
T2  - European Journal of Medicinal Chemistry
T1  - Unraveling the anti-virulence potential and antifungal efficacy of 5-aminotetrazoles using the zebrafish model of disseminated candidiasis
VL  - 230
SP  - 114137
DO  - 10.1016/j.ejmech.2022.114137
ER  - 

@article{
author = "Radaković, Nataša and Nikolić, Andrea and Terzić-Jovanović, Nataša and Stojković, Pavle and Stanković, Nada and Šolaja, Bogdan and Opsenica, Igor and Pavić, Aleksandar",
year = "2022",
abstract = "Candida albicans remains the main causal agent of candidiasis, the most common fungal infection with disturbingly high mortality rates worldwide. The limited diversity and efficacy of clinical antifungal drugs, exacerbated by emerging drug resistance, have resulted in the failure of current antifungal therapies. This imposes an urgent demand for the development of innovative strategies for effective eradication of candidal infections. While the existing clinical drugs display fungicidal or fungistatic activity, the strategy specifically targeting C. albicans filamentation, as the most important virulence trait, represents an attractive approach for overcoming the drawbacks related to clinical antifungals. The results acquired in this study revealed the significant potential of 5-aminotetrazoles as a new class of effective and safe anti-virulence agents. Moreover, these novel agents were active when applied both alone and in combination with clinically approved polyenes. Complete prevention of C. albicans morphogenetic yeast-to-hyphae transition was achieved at doses as low as 1.3 μM under conditions mimicking various filamentation-responsive stimuli in the human body, while no cardio- or hepatotoxicity was observed at doses as high as 200 μM. The treatment of C. albicans-infected zebrafish embryos with nystatin alone had low efficacy, while the combination of nystatin and selected 5-aminotetrazoles prevented fungal filamentation, successfully eliminating the infection and rescuing the infected embryos from lethal disseminated candidiasis. In addition, the most potent anti-virulence 5-aminotetrazole prevented C. albicans in developing the resistance to nystatin when applied in combination, keeping the fungus sensitive to the antifungal drug.",
publisher = "Elsevier",
journal = "European Journal of Medicinal Chemistry",
title = "Unraveling the anti-virulence potential and antifungal efficacy of 5-aminotetrazoles using the zebrafish model of disseminated candidiasis",
volume = "230",
pages = "114137",
doi = "10.1016/j.ejmech.2022.114137"
}

Radaković, N., Nikolić, A., Terzić-Jovanović, N., Stojković, P., Stanković, N., Šolaja, B., Opsenica, I.,& Pavić, A.. (2022). Unraveling the anti-virulence potential and antifungal efficacy of 5-aminotetrazoles using the zebrafish model of disseminated candidiasis. in European Journal of Medicinal Chemistry
Elsevier., 230, 114137.
https://doi.org/10.1016/j.ejmech.2022.114137

Radaković N, Nikolić A, Terzić-Jovanović N, Stojković P, Stanković N, Šolaja B, Opsenica I, Pavić A. Unraveling the anti-virulence potential and antifungal efficacy of 5-aminotetrazoles using the zebrafish model of disseminated candidiasis. in European Journal of Medicinal Chemistry. 2022;230:114137.
doi:10.1016/j.ejmech.2022.114137 .

Radaković, Nataša, Nikolić, Andrea, Terzić-Jovanović, Nataša, Stojković, Pavle, Stanković, Nada, Šolaja, Bogdan, Opsenica, Igor, Pavić, Aleksandar, "Unraveling the anti-virulence potential and antifungal efficacy of 5-aminotetrazoles using the zebrafish model of disseminated candidiasis" in European Journal of Medicinal Chemistry, 230 (2022):114137,
https://doi.org/10.1016/j.ejmech.2022.114137 . .

TY  - JOUR
AU  - Kop, Tatjana
AU  - Terzić-Jovanović, Nataša
AU  - Žižak, Željko
AU  - Šolaja, Bogdan
AU  - Milić, Dragana R.
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5356
AB  - Iron salt-promoted reaction of estrone and its derivatives with              meta              -chloroperoxybenzoic acid was developed and epoxyquinols were further transformed. Most compounds showed              in vitro              antiproliferative activity.                      ,                           A new oxidant, containing              m              -chloroperoxybenzoic acid (MCPBA) and an iron salt, was developed and used for oxidation of steroidal phenols to a quinol/epoxyquinol mixture. Reaction was optimized for estrone, by varying initiators (Fe-salts), reaction temperature, time and mode of MCPBA application. A series of five more substrates (17β-estradiol and its hydrophobized derivatives) was subjected to the optimized oxidation, providing corresponding              p              -quinols and 4β,5β-epoxyquinols in good to moderate yields. The obtained epoxyquinols were additionally transformed by oxidation, as well as the acid-catalyzed oxirane opening. In a preliminary study of the antiproliferative activity against human cancer cell lines, all newly synthesized compounds expressed moderate to high activity.
PB  - Royal Society of Chemistry
T2  - RSC Advances
T1  - Iron salt-promoted oxidation of steroidal phenols by m -chloroperbenzoic acid: a route to possible antitumor agents
VL  - 12
IS  - 32
SP  - 20649
EP  - 20655
DO  - 10.1039/D2RA03717C
ER  - 

@article{
author = "Kop, Tatjana and Terzić-Jovanović, Nataša and Žižak, Željko and Šolaja, Bogdan and Milić, Dragana R.",
year = "2022",
abstract = "Iron salt-promoted reaction of estrone and its derivatives with              meta              -chloroperoxybenzoic acid was developed and epoxyquinols were further transformed. Most compounds showed              in vitro              antiproliferative activity.                      ,                           A new oxidant, containing              m              -chloroperoxybenzoic acid (MCPBA) and an iron salt, was developed and used for oxidation of steroidal phenols to a quinol/epoxyquinol mixture. Reaction was optimized for estrone, by varying initiators (Fe-salts), reaction temperature, time and mode of MCPBA application. A series of five more substrates (17β-estradiol and its hydrophobized derivatives) was subjected to the optimized oxidation, providing corresponding              p              -quinols and 4β,5β-epoxyquinols in good to moderate yields. The obtained epoxyquinols were additionally transformed by oxidation, as well as the acid-catalyzed oxirane opening. In a preliminary study of the antiproliferative activity against human cancer cell lines, all newly synthesized compounds expressed moderate to high activity.",
publisher = "Royal Society of Chemistry",
journal = "RSC Advances",
title = "Iron salt-promoted oxidation of steroidal phenols by m -chloroperbenzoic acid: a route to possible antitumor agents",
volume = "12",
number = "32",
pages = "20649-20655",
doi = "10.1039/D2RA03717C"
}

Kop, T., Terzić-Jovanović, N., Žižak, Ž., Šolaja, B.,& Milić, D. R.. (2022). Iron salt-promoted oxidation of steroidal phenols by m -chloroperbenzoic acid: a route to possible antitumor agents. in RSC Advances
Royal Society of Chemistry., 12(32), 20649-20655.
https://doi.org/10.1039/D2RA03717C

Kop T, Terzić-Jovanović N, Žižak Ž, Šolaja B, Milić DR. Iron salt-promoted oxidation of steroidal phenols by m -chloroperbenzoic acid: a route to possible antitumor agents. in RSC Advances. 2022;12(32):20649-20655.
doi:10.1039/D2RA03717C .

Kop, Tatjana, Terzić-Jovanović, Nataša, Žižak, Željko, Šolaja, Bogdan, Milić, Dragana R., "Iron salt-promoted oxidation of steroidal phenols by m -chloroperbenzoic acid: a route to possible antitumor agents" in RSC Advances, 12, no. 32 (2022):20649-20655,
https://doi.org/10.1039/D2RA03717C . .

TY  - JOUR
AU  - Srbljanović, Jelena
AU  - Bobić, Branko
AU  - Štajner, Tijana
AU  - Uzelac, Aleksandra
AU  - Opsenica, Igor
AU  - Terzić-Jovanović, Nataša
AU  - Bauman, Neda
AU  - Šolaja, Bogdan
AU  - Đurković-Đaković, Olgica
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3721
AB  - Objectives: Malaria treatment is impeded by increasing resistance to conventional antimalarial drugs. Here we explored the activity of ten novel benzothiophene, thiophene and benzene aminoquinolines. Methods: In vitro testing was performed by the lactate dehydrogenase assay in chloroquine (CQ)-sensitive Plasmodium falciparum strain 3D7 and CQ-resistant (CQR) P. falciparum strain Dd2. In vivo activity was evaluated by a modified Thompson test using C57BL/6 mice infected with Plasmodium berghei ANKA strain. Results: Nine of the ten compounds had a lower 50% inhibitory concentration (IC50) than CQ against the CQR strain Dd2. Five of these compounds that were available for in vivo evaluation were shown to be non-toxic. All five compounds administered at a dose of 160 mg/kg/day for 3 days prolonged the survival of treated compared with untreated mice. Untreated control mice died by Day 7 with a mean parasitaemia of 15%. Among treated mice, a dichotomous outcome was observed, with a two-third majority of treated mice dying by Day 17 with a low mean parasitaemia of 5%, whilst one-third survived longer with a mean hyperparasitaemia of 70%; specifically, five of these mice survived a mean of 25 days, whilst two even survived past Day 31. Conclusions: The significant antimalarial potential of this aminoquinoline series is illustrated by its excellent in vitro activity against the CQR P. falciparum strain and significant in vivo activity. Interestingly, compounds ClAQ7, ClAQ9 and ClAQ11 were able to confer resistance to cerebral malaria and afford a switch to hyperparasitaemia to mice prone to the neurological syndrome.
PB  - Elsevier
T2  - Journal of Global Antimicrobial Resistance
T1  - Aminoquinolines afford resistance to cerebral malaria in susceptible mice
VL  - 23
SP  - 20
EP  - 25
DO  - 10.1016/j.jgar.2020.07.027
ER  - 

@article{
author = "Srbljanović, Jelena and Bobić, Branko and Štajner, Tijana and Uzelac, Aleksandra and Opsenica, Igor and Terzić-Jovanović, Nataša and Bauman, Neda and Šolaja, Bogdan and Đurković-Đaković, Olgica",
year = "2020",
abstract = "Objectives: Malaria treatment is impeded by increasing resistance to conventional antimalarial drugs. Here we explored the activity of ten novel benzothiophene, thiophene and benzene aminoquinolines. Methods: In vitro testing was performed by the lactate dehydrogenase assay in chloroquine (CQ)-sensitive Plasmodium falciparum strain 3D7 and CQ-resistant (CQR) P. falciparum strain Dd2. In vivo activity was evaluated by a modified Thompson test using C57BL/6 mice infected with Plasmodium berghei ANKA strain. Results: Nine of the ten compounds had a lower 50% inhibitory concentration (IC50) than CQ against the CQR strain Dd2. Five of these compounds that were available for in vivo evaluation were shown to be non-toxic. All five compounds administered at a dose of 160 mg/kg/day for 3 days prolonged the survival of treated compared with untreated mice. Untreated control mice died by Day 7 with a mean parasitaemia of 15%. Among treated mice, a dichotomous outcome was observed, with a two-third majority of treated mice dying by Day 17 with a low mean parasitaemia of 5%, whilst one-third survived longer with a mean hyperparasitaemia of 70%; specifically, five of these mice survived a mean of 25 days, whilst two even survived past Day 31. Conclusions: The significant antimalarial potential of this aminoquinoline series is illustrated by its excellent in vitro activity against the CQR P. falciparum strain and significant in vivo activity. Interestingly, compounds ClAQ7, ClAQ9 and ClAQ11 were able to confer resistance to cerebral malaria and afford a switch to hyperparasitaemia to mice prone to the neurological syndrome.",
publisher = "Elsevier",
journal = "Journal of Global Antimicrobial Resistance",
title = "Aminoquinolines afford resistance to cerebral malaria in susceptible mice",
volume = "23",
pages = "20-25",
doi = "10.1016/j.jgar.2020.07.027"
}

Srbljanović, J., Bobić, B., Štajner, T., Uzelac, A., Opsenica, I., Terzić-Jovanović, N., Bauman, N., Šolaja, B.,& Đurković-Đaković, O.. (2020). Aminoquinolines afford resistance to cerebral malaria in susceptible mice. in Journal of Global Antimicrobial Resistance
Elsevier., 23, 20-25.
https://doi.org/10.1016/j.jgar.2020.07.027

Srbljanović J, Bobić B, Štajner T, Uzelac A, Opsenica I, Terzić-Jovanović N, Bauman N, Šolaja B, Đurković-Đaković O. Aminoquinolines afford resistance to cerebral malaria in susceptible mice. in Journal of Global Antimicrobial Resistance. 2020;23:20-25.
doi:10.1016/j.jgar.2020.07.027 .

Srbljanović, Jelena, Bobić, Branko, Štajner, Tijana, Uzelac, Aleksandra, Opsenica, Igor, Terzić-Jovanović, Nataša, Bauman, Neda, Šolaja, Bogdan, Đurković-Đaković, Olgica, "Aminoquinolines afford resistance to cerebral malaria in susceptible mice" in Journal of Global Antimicrobial Resistance, 23 (2020):20-25,
https://doi.org/10.1016/j.jgar.2020.07.027 . .

TY  - JOUR
AU  - Konstantinović, Jelena M.
AU  - Kiris, Erkan
AU  - Kota, Krishna P.
AU  - Kugelman-Tonos, Johanny
AU  - Videnović, Milica
AU  - Cazares, Lisa H.
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Anđelković, Boban D.
AU  - Duplantier, Allen J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2325
AB  - The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative 16 showed remarkable protection (up to 89% of uncleaved SNAP-25) even when administered 30 min postintoxication. This appears to be the first example of LC inhibitors antagonizing BoNT intoxication in mouse embryonic stem cell derived motor neurons (mES-MNs) in a postexposure model. Oral administration of 16 was well tolerated in the mouse up to 600 mg/kg, q.d. Although adequate unbound drug levels were not achieved at this dose, the favorable in vitro ADMET results strongly support further work in this series.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model
VL  - 61
IS  - 4
SP  - 1595
EP  - 1608
DO  - 10.1021/acs.jmedchem.7b01710
ER  - 

@article{
author = "Konstantinović, Jelena M. and Kiris, Erkan and Kota, Krishna P. and Kugelman-Tonos, Johanny and Videnović, Milica and Cazares, Lisa H. and Terzić-Jovanović, Nataša and Verbić, Tatjana and Anđelković, Boban D. and Duplantier, Allen J. and Bavari, Sina and Šolaja, Bogdan",
year = "2018",
abstract = "The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative 16 showed remarkable protection (up to 89% of uncleaved SNAP-25) even when administered 30 min postintoxication. This appears to be the first example of LC inhibitors antagonizing BoNT intoxication in mouse embryonic stem cell derived motor neurons (mES-MNs) in a postexposure model. Oral administration of 16 was well tolerated in the mouse up to 600 mg/kg, q.d. Although adequate unbound drug levels were not achieved at this dose, the favorable in vitro ADMET results strongly support further work in this series.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model",
volume = "61",
number = "4",
pages = "1595-1608",
doi = "10.1021/acs.jmedchem.7b01710"
}

Konstantinović, J. M., Kiris, E., Kota, K. P., Kugelman-Tonos, J., Videnović, M., Cazares, L. H., Terzić-Jovanović, N., Verbić, T., Anđelković, B. D., Duplantier, A. J., Bavari, S.,& Šolaja, B.. (2018). New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 61(4), 1595-1608.
https://doi.org/10.1021/acs.jmedchem.7b01710

Konstantinović JM, Kiris E, Kota KP, Kugelman-Tonos J, Videnović M, Cazares LH, Terzić-Jovanović N, Verbić T, Anđelković BD, Duplantier AJ, Bavari S, Šolaja B. New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. in Journal of Medicinal Chemistry. 2018;61(4):1595-1608.
doi:10.1021/acs.jmedchem.7b01710 .

Konstantinović, Jelena M., Kiris, Erkan, Kota, Krishna P., Kugelman-Tonos, Johanny, Videnović, Milica, Cazares, Lisa H., Terzić-Jovanović, Nataša, Verbić, Tatjana, Anđelković, Boban D., Duplantier, Allen J., Bavari, Sina, Šolaja, Bogdan, "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model" in Journal of Medicinal Chemistry, 61, no. 4 (2018):1595-1608,
https://doi.org/10.1021/acs.jmedchem.7b01710 . .

TY  - JOUR
AU  - Konstantinović, Jelena M.
AU  - Videnović, Milica
AU  - Orsini, Stefania
AU  - Bogojević, Katarina
AU  - D'Alessandro, Sarah
AU  - Scaccabarozzi, Diletta
AU  - Terzić-Jovanović, Nataša
AU  - Gradoni, Luigi
AU  - Basilico, Nicoletta
AU  - Šolaja, Bogdan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2428
AB  - In this Letter, a detailed analysis of 30 4-aminoquinoline-based compounds with regard to their potential as antileishmanial drugs has been carried out. Ten compounds demonstrated IC50  LT  1 mu M against promastigote stages of L. infantum and L. tropica, and five compounds showed IC50  LT  1 mu M against intramacrophage L. infantum amastigotes. Two compounds showed dose-dependent enhancement of NO and ROS production by bone marrow-derived macrophages and remarkable reduction of parasite load in vivo, with advantage of being short-term and orally active. To the best of our knowledge, this is the first example of 4-amino-7-chloroquinoline derivatives active in Leishmania infantum infected mice.
PB  - American Chemical Society (ACS)
T2  - Acs Medicinal Chemistry Letters
T1  - Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice
VL  - 9
IS  - 7
SP  - 629
EP  - 634
DO  - 10.1021/acsmedchemlett.8b00053
ER  - 

@article{
author = "Konstantinović, Jelena M. and Videnović, Milica and Orsini, Stefania and Bogojević, Katarina and D'Alessandro, Sarah and Scaccabarozzi, Diletta and Terzić-Jovanović, Nataša and Gradoni, Luigi and Basilico, Nicoletta and Šolaja, Bogdan",
year = "2018",
abstract = "In this Letter, a detailed analysis of 30 4-aminoquinoline-based compounds with regard to their potential as antileishmanial drugs has been carried out. Ten compounds demonstrated IC50  LT  1 mu M against promastigote stages of L. infantum and L. tropica, and five compounds showed IC50  LT  1 mu M against intramacrophage L. infantum amastigotes. Two compounds showed dose-dependent enhancement of NO and ROS production by bone marrow-derived macrophages and remarkable reduction of parasite load in vivo, with advantage of being short-term and orally active. To the best of our knowledge, this is the first example of 4-amino-7-chloroquinoline derivatives active in Leishmania infantum infected mice.",
publisher = "American Chemical Society (ACS)",
journal = "Acs Medicinal Chemistry Letters",
title = "Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice",
volume = "9",
number = "7",
pages = "629-634",
doi = "10.1021/acsmedchemlett.8b00053"
}

Konstantinović, J. M., Videnović, M., Orsini, S., Bogojević, K., D'Alessandro, S., Scaccabarozzi, D., Terzić-Jovanović, N., Gradoni, L., Basilico, N.,& Šolaja, B.. (2018). Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice. in Acs Medicinal Chemistry Letters
American Chemical Society (ACS)., 9(7), 629-634.
https://doi.org/10.1021/acsmedchemlett.8b00053

Konstantinović JM, Videnović M, Orsini S, Bogojević K, D'Alessandro S, Scaccabarozzi D, Terzić-Jovanović N, Gradoni L, Basilico N, Šolaja B. Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice. in Acs Medicinal Chemistry Letters. 2018;9(7):629-634.
doi:10.1021/acsmedchemlett.8b00053 .

Konstantinović, Jelena M., Videnović, Milica, Orsini, Stefania, Bogojević, Katarina, D'Alessandro, Sarah, Scaccabarozzi, Diletta, Terzić-Jovanović, Nataša, Gradoni, Luigi, Basilico, Nicoletta, Šolaja, Bogdan, "Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice" in Acs Medicinal Chemistry Letters, 9, no. 7 (2018):629-634,
https://doi.org/10.1021/acsmedchemlett.8b00053 . .

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

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

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

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

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

TY  - JOUR
AU  - Konstantinović, Jelena M.
AU  - Kiris, Erkan
AU  - Kota, Krishna P.
AU  - Kugelman-Tonos, Johanny
AU  - Videnović, Milica
AU  - Cazares, Lisa H.
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Anđelković, Boban D.
AU  - Duplantier, Allen J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2935
AB  - The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative 16 showed remarkable protection (up to 89% of uncleaved SNAP-25) even when administered 30 min postintoxication. This appears to be the first example of LC inhibitors antagonizing BoNT intoxication in mouse embryonic stem cell derived motor neurons (mES-MNs) in a postexposure model. Oral administration of 16 was well tolerated in the mouse up to 600 mg/kg, q.d. Although adequate unbound drug levels were not achieved at this dose, the favorable in vitro ADMET results strongly support further work in this series.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model
VL  - 61
IS  - 4
SP  - 1595
EP  - 1608
DO  - 10.1021/acs.jmedchem.7b01710
ER  - 

@article{
author = "Konstantinović, Jelena M. and Kiris, Erkan and Kota, Krishna P. and Kugelman-Tonos, Johanny and Videnović, Milica and Cazares, Lisa H. and Terzić-Jovanović, Nataša and Verbić, Tatjana and Anđelković, Boban D. and Duplantier, Allen J. and Bavari, Sina and Šolaja, Bogdan",
year = "2018",
abstract = "The synthesis and inhibitory potencies against botulinum neurotoxin serotype A light chain (BoNT/A LC) using in vitro HPLC based enzymatic assay for various steroidal, benzothiophene, thiophene, and adamantane 4-aminoquinoline derivatives are described. In addition, the compounds were evaluated for the activity against BoNT/A holotoxin in mouse embryonic stem cell derived motor neurons. Steroidal derivative 16 showed remarkable protection (up to 89% of uncleaved SNAP-25) even when administered 30 min postintoxication. This appears to be the first example of LC inhibitors antagonizing BoNT intoxication in mouse embryonic stem cell derived motor neurons (mES-MNs) in a postexposure model. Oral administration of 16 was well tolerated in the mouse up to 600 mg/kg, q.d. Although adequate unbound drug levels were not achieved at this dose, the favorable in vitro ADMET results strongly support further work in this series.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model",
volume = "61",
number = "4",
pages = "1595-1608",
doi = "10.1021/acs.jmedchem.7b01710"
}

Konstantinović, J. M., Kiris, E., Kota, K. P., Kugelman-Tonos, J., Videnović, M., Cazares, L. H., Terzić-Jovanović, N., Verbić, T., Anđelković, B. D., Duplantier, A. J., Bavari, S.,& Šolaja, B.. (2018). New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 61(4), 1595-1608.
https://doi.org/10.1021/acs.jmedchem.7b01710

Konstantinović JM, Kiris E, Kota KP, Kugelman-Tonos J, Videnović M, Cazares LH, Terzić-Jovanović N, Verbić T, Anđelković BD, Duplantier AJ, Bavari S, Šolaja B. New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model. in Journal of Medicinal Chemistry. 2018;61(4):1595-1608.
doi:10.1021/acs.jmedchem.7b01710 .

Konstantinović, Jelena M., Kiris, Erkan, Kota, Krishna P., Kugelman-Tonos, Johanny, Videnović, Milica, Cazares, Lisa H., Terzić-Jovanović, Nataša, Verbić, Tatjana, Anđelković, Boban D., Duplantier, Allen J., Bavari, Sina, Šolaja, Bogdan, "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model" in Journal of Medicinal Chemistry, 61, no. 4 (2018):1595-1608,
https://doi.org/10.1021/acs.jmedchem.7b01710 . .

TY  - JOUR
AU  - Konstantinović, Jelena M.
AU  - Videnović, Milica
AU  - Orsini, Stefania
AU  - Bogojević, Katarina
AU  - D'Alessandro, Sarah
AU  - Scaccabarozzi, Diletta
AU  - Terzić-Jovanović, Nataša
AU  - Gradoni, Luigi
AU  - Basilico, Nicoletta
AU  - Šolaja, Bogdan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3626
AB  - In this Letter, a detailed analysis of 30 4-aminoquinoline-based compounds with regard to their potential as antileishmanial drugs has been carried out. Ten compounds demonstrated IC50  LT  1 mu M against promastigote stages of L. infantum and L. tropica, and five compounds showed IC50  LT  1 mu M against intramacrophage L. infantum amastigotes. Two compounds showed dose-dependent enhancement of NO and ROS production by bone marrow-derived macrophages and remarkable reduction of parasite load in vivo, with advantage of being short-term and orally active. To the best of our knowledge, this is the first example of 4-amino-7-chloroquinoline derivatives active in Leishmania infantum infected mice.
PB  - American Chemical Society (ACS)
T2  - Acs Medicinal Chemistry Letters
T1  - Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice
VL  - 9
IS  - 7
SP  - 629
EP  - 634
DO  - 10.1021/acsmedchemlett.8b00053
ER  - 

@article{
author = "Konstantinović, Jelena M. and Videnović, Milica and Orsini, Stefania and Bogojević, Katarina and D'Alessandro, Sarah and Scaccabarozzi, Diletta and Terzić-Jovanović, Nataša and Gradoni, Luigi and Basilico, Nicoletta and Šolaja, Bogdan",
year = "2018",
abstract = "In this Letter, a detailed analysis of 30 4-aminoquinoline-based compounds with regard to their potential as antileishmanial drugs has been carried out. Ten compounds demonstrated IC50  LT  1 mu M against promastigote stages of L. infantum and L. tropica, and five compounds showed IC50  LT  1 mu M against intramacrophage L. infantum amastigotes. Two compounds showed dose-dependent enhancement of NO and ROS production by bone marrow-derived macrophages and remarkable reduction of parasite load in vivo, with advantage of being short-term and orally active. To the best of our knowledge, this is the first example of 4-amino-7-chloroquinoline derivatives active in Leishmania infantum infected mice.",
publisher = "American Chemical Society (ACS)",
journal = "Acs Medicinal Chemistry Letters",
title = "Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice",
volume = "9",
number = "7",
pages = "629-634",
doi = "10.1021/acsmedchemlett.8b00053"
}

Konstantinović, J. M., Videnović, M., Orsini, S., Bogojević, K., D'Alessandro, S., Scaccabarozzi, D., Terzić-Jovanović, N., Gradoni, L., Basilico, N.,& Šolaja, B.. (2018). Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice. in Acs Medicinal Chemistry Letters
American Chemical Society (ACS)., 9(7), 629-634.
https://doi.org/10.1021/acsmedchemlett.8b00053

Konstantinović JM, Videnović M, Orsini S, Bogojević K, D'Alessandro S, Scaccabarozzi D, Terzić-Jovanović N, Gradoni L, Basilico N, Šolaja B. Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice. in Acs Medicinal Chemistry Letters. 2018;9(7):629-634.
doi:10.1021/acsmedchemlett.8b00053 .

Konstantinović, Jelena M., Videnović, Milica, Orsini, Stefania, Bogojević, Katarina, D'Alessandro, Sarah, Scaccabarozzi, Diletta, Terzić-Jovanović, Nataša, Gradoni, Luigi, Basilico, Nicoletta, Šolaja, Bogdan, "Novel Aminoquinoline Derivatives Significantly Reduce Parasite Load in Leishmania infantum Infected Mice" in Acs Medicinal Chemistry Letters, 9, no. 7 (2018):629-634,
https://doi.org/10.1021/acsmedchemlett.8b00053 . .

TY  - DATA
AU  - Konstantinović, Jelena M.
AU  - Kiris, Erkan
AU  - Kota, Krishna P.
AU  - Kugelman-Tonos, Johanny
AU  - Videnović, Milica
AU  - Cazares, Lisa H.
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Anđelković, Boban D.
AU  - Duplantier, Allen J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4515
AB  - Inhibitory activities against BoNT/A LC and holotoxin in proteolytic and cell-based assay for all tested compounds; fluorescence and UV–vis spectra for determination of 16 binding to HSA and AGP; ligand interaction diagrams, docking scores, and docking–in vitro inhibitory activity correlations; spectral and analytical data for all synthesized compounds; detailed procedures for the determination of the HPLC purity.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Supporting Information I for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"
DO  - 10.1021/acs.jmedchem.7b01710.s001
ER  - 

@misc{
author = "Konstantinović, Jelena M. and Kiris, Erkan and Kota, Krishna P. and Kugelman-Tonos, Johanny and Videnović, Milica and Cazares, Lisa H. and Terzić-Jovanović, Nataša and Verbić, Tatjana and Anđelković, Boban D. and Duplantier, Allen J. and Bavari, Sina and Šolaja, Bogdan",
year = "2018",
abstract = "Inhibitory activities against BoNT/A LC and holotoxin in proteolytic and cell-based assay for all tested compounds; fluorescence and UV–vis spectra for determination of 16 binding to HSA and AGP; ligand interaction diagrams, docking scores, and docking–in vitro inhibitory activity correlations; spectral and analytical data for all synthesized compounds; detailed procedures for the determination of the HPLC purity.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Supporting Information I for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"",
doi = "10.1021/acs.jmedchem.7b01710.s001"
}

Konstantinović, J. M., Kiris, E., Kota, K. P., Kugelman-Tonos, J., Videnović, M., Cazares, L. H., Terzić-Jovanović, N., Verbić, T., Anđelković, B. D., Duplantier, A. J., Bavari, S.,& Šolaja, B.. (2018). Supporting Information I for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model". in Journal of Medicinal Chemistry
American Chemical Society (ACS)..
https://doi.org/10.1021/acs.jmedchem.7b01710.s001

Konstantinović JM, Kiris E, Kota KP, Kugelman-Tonos J, Videnović M, Cazares LH, Terzić-Jovanović N, Verbić T, Anđelković BD, Duplantier AJ, Bavari S, Šolaja B. Supporting Information I for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model". in Journal of Medicinal Chemistry. 2018;.
doi:10.1021/acs.jmedchem.7b01710.s001 .

Konstantinović, Jelena M., Kiris, Erkan, Kota, Krishna P., Kugelman-Tonos, Johanny, Videnović, Milica, Cazares, Lisa H., Terzić-Jovanović, Nataša, Verbić, Tatjana, Anđelković, Boban D., Duplantier, Allen J., Bavari, Sina, Šolaja, Bogdan, "Supporting Information I for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"" in Journal of Medicinal Chemistry (2018),
https://doi.org/10.1021/acs.jmedchem.7b01710.s001 . .

TY  - DATA
AU  - Konstantinović, Jelena M.
AU  - Kiris, Erkan
AU  - Kota, Krishna P.
AU  - Kugelman-Tonos, Johanny
AU  - Videnović, Milica
AU  - Cazares, Lisa H.
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Anđelković, Boban D.
AU  - Duplantier, Allen J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4516
AB  - NMR spectra and HPLC purity spectra of all tested compounds
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Supporting Information II for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"
DO  - 10.1021/acs.jmedchem.7b01710.s002
ER  - 

@misc{
author = "Konstantinović, Jelena M. and Kiris, Erkan and Kota, Krishna P. and Kugelman-Tonos, Johanny and Videnović, Milica and Cazares, Lisa H. and Terzić-Jovanović, Nataša and Verbić, Tatjana and Anđelković, Boban D. and Duplantier, Allen J. and Bavari, Sina and Šolaja, Bogdan",
year = "2018",
abstract = "NMR spectra and HPLC purity spectra of all tested compounds",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Supporting Information II for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"",
doi = "10.1021/acs.jmedchem.7b01710.s002"
}

Konstantinović, J. M., Kiris, E., Kota, K. P., Kugelman-Tonos, J., Videnović, M., Cazares, L. H., Terzić-Jovanović, N., Verbić, T., Anđelković, B. D., Duplantier, A. J., Bavari, S.,& Šolaja, B.. (2018). Supporting Information II for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model". in Journal of Medicinal Chemistry
American Chemical Society (ACS)..
https://doi.org/10.1021/acs.jmedchem.7b01710.s002

Konstantinović JM, Kiris E, Kota KP, Kugelman-Tonos J, Videnović M, Cazares LH, Terzić-Jovanović N, Verbić T, Anđelković BD, Duplantier AJ, Bavari S, Šolaja B. Supporting Information II for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model". in Journal of Medicinal Chemistry. 2018;.
doi:10.1021/acs.jmedchem.7b01710.s002 .

Konstantinović, Jelena M., Kiris, Erkan, Kota, Krishna P., Kugelman-Tonos, Johanny, Videnović, Milica, Cazares, Lisa H., Terzić-Jovanović, Nataša, Verbić, Tatjana, Anđelković, Boban D., Duplantier, Allen J., Bavari, Sina, Šolaja, Bogdan, "Supporting Information II for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"" in Journal of Medicinal Chemistry (2018),
https://doi.org/10.1021/acs.jmedchem.7b01710.s002 . .

TY  - DATA
AU  - Konstantinović, Jelena M.
AU  - Kiris, Erkan
AU  - Kota, Krishna P.
AU  - Kugelman-Tonos, Johanny
AU  - Videnović, Milica
AU  - Cazares, Lisa H.
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Anđelković, Boban D.
AU  - Duplantier, Allen J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4517
AB  - Molecular formula strings (smiles) and additional data: In vitro proteolytic assay % inh BoNT/A LC at 20 uM; In vitro proteolytic assay IC50 (uM); mES-MNs pre intoxication % of full length SNAP-25 (10 uM; 20 uM); mES-MNs post intoxication at 20 uM % of full length SNAP-25 (30 min; 60 min)
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Supporting Information III for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"
DO  - 10.1021/acs.jmedchem.7b01710.s003
ER  - 

@misc{
author = "Konstantinović, Jelena M. and Kiris, Erkan and Kota, Krishna P. and Kugelman-Tonos, Johanny and Videnović, Milica and Cazares, Lisa H. and Terzić-Jovanović, Nataša and Verbić, Tatjana and Anđelković, Boban D. and Duplantier, Allen J. and Bavari, Sina and Šolaja, Bogdan",
year = "2018",
abstract = "Molecular formula strings (smiles) and additional data: In vitro proteolytic assay % inh BoNT/A LC at 20 uM; In vitro proteolytic assay IC50 (uM); mES-MNs pre intoxication % of full length SNAP-25 (10 uM; 20 uM); mES-MNs post intoxication at 20 uM % of full length SNAP-25 (30 min; 60 min)",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Supporting Information III for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"",
doi = "10.1021/acs.jmedchem.7b01710.s003"
}

Konstantinović, J. M., Kiris, E., Kota, K. P., Kugelman-Tonos, J., Videnović, M., Cazares, L. H., Terzić-Jovanović, N., Verbić, T., Anđelković, B. D., Duplantier, A. J., Bavari, S.,& Šolaja, B.. (2018). Supporting Information III for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model". in Journal of Medicinal Chemistry
American Chemical Society (ACS)..
https://doi.org/10.1021/acs.jmedchem.7b01710.s003

Konstantinović JM, Kiris E, Kota KP, Kugelman-Tonos J, Videnović M, Cazares LH, Terzić-Jovanović N, Verbić T, Anđelković BD, Duplantier AJ, Bavari S, Šolaja B. Supporting Information III for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model". in Journal of Medicinal Chemistry. 2018;.
doi:10.1021/acs.jmedchem.7b01710.s003 .

Konstantinović, Jelena M., Kiris, Erkan, Kota, Krishna P., Kugelman-Tonos, Johanny, Videnović, Milica, Cazares, Lisa H., Terzić-Jovanović, Nataša, Verbić, Tatjana, Anđelković, Boban D., Duplantier, Allen J., Bavari, Sina, Šolaja, Bogdan, "Supporting Information III for: "New Steroidal 4-Aminoquinolines Antagonize Botulinum Neurotoxin Serotype A in Mouse Embryonic Stem Cell Derived Motor Neurons in Postintoxication Model"" in Journal of Medicinal Chemistry (2018),
https://doi.org/10.1021/acs.jmedchem.7b01710.s003 . .

TY  - JOUR
AU  - Srbljanović, Jelena
AU  - Štajner, Tijana
AU  - Konstantinović, Jelena M.
AU  - Terzić-Jovanović, Nataša
AU  - Uzelac, Aleksandra
AU  - Bobic, Branko
AU  - Šolaja, Bogdan
AU  - Djurkovic-Djakovic, Olgica
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2172
AB  - Malaria remains a major disease in the developing world and globally is the most important parasitic disease causing significant morbidity and mortality. Because of widespread resistance to conventional antimalarials, including chloroquine (CQ), new drugs are urgently needed. Here we report on the antimalarial efficacy, both in vitro and in vivo, of a series of aminoquinoline derivatives with adamantane or benzothiophene as a carrier. In vitro efficacy was evaluated by a lactate dehydrogenase (LDH) assay in cultures of a CQ-sensitive (3D7) and CQ-resistant (Dd2) strain of Plasmodium falcipanim. Of a series of 26 screened compounds, 12 that exerted a growth inhibition rate of >= 5% were further examined in vitro to determine the 50% inhibitory concentration (IC50) values. Nine compounds shown in preliminary experiments to be non-toxic in vivo were evaluated in C57BL/6 mice infected with Plasmodium herghei ANKA strain using a modified Thompson test. All nine compounds examined in vivo prolonged the survival of treated versus untreated mice, four of which afforded >= 60% survival. Most notably, two of these compounds, both with the adamantane carrier, afforded complete cure (100% survival and parasite clearance). Interestingly, one of these compounds had no in vitro effect against the CQ resistant P. falciparum strain. Better in vivo compared with in vitro results suggest a role for compound metabolites rather than the compounds themselves. The results presented here point to adamantane as a carrier that enhances the antimalarial potential of aminoquinolines.
PB  - Elsevier
T2  - International Journal of Antimicrobial Agents
T1  - Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy
VL  - 50
IS  - 3
SP  - 461
EP  - 466
DO  - 10.1016/j.ijantimicag.2017.06.002
ER  - 

@article{
author = "Srbljanović, Jelena and Štajner, Tijana and Konstantinović, Jelena M. and Terzić-Jovanović, Nataša and Uzelac, Aleksandra and Bobic, Branko and Šolaja, Bogdan and Djurkovic-Djakovic, Olgica",
year = "2017",
abstract = "Malaria remains a major disease in the developing world and globally is the most important parasitic disease causing significant morbidity and mortality. Because of widespread resistance to conventional antimalarials, including chloroquine (CQ), new drugs are urgently needed. Here we report on the antimalarial efficacy, both in vitro and in vivo, of a series of aminoquinoline derivatives with adamantane or benzothiophene as a carrier. In vitro efficacy was evaluated by a lactate dehydrogenase (LDH) assay in cultures of a CQ-sensitive (3D7) and CQ-resistant (Dd2) strain of Plasmodium falcipanim. Of a series of 26 screened compounds, 12 that exerted a growth inhibition rate of >= 5% were further examined in vitro to determine the 50% inhibitory concentration (IC50) values. Nine compounds shown in preliminary experiments to be non-toxic in vivo were evaluated in C57BL/6 mice infected with Plasmodium herghei ANKA strain using a modified Thompson test. All nine compounds examined in vivo prolonged the survival of treated versus untreated mice, four of which afforded >= 60% survival. Most notably, two of these compounds, both with the adamantane carrier, afforded complete cure (100% survival and parasite clearance). Interestingly, one of these compounds had no in vitro effect against the CQ resistant P. falciparum strain. Better in vivo compared with in vitro results suggest a role for compound metabolites rather than the compounds themselves. The results presented here point to adamantane as a carrier that enhances the antimalarial potential of aminoquinolines.",
publisher = "Elsevier",
journal = "International Journal of Antimicrobial Agents",
title = "Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy",
volume = "50",
number = "3",
pages = "461-466",
doi = "10.1016/j.ijantimicag.2017.06.002"
}

Srbljanović, J., Štajner, T., Konstantinović, J. M., Terzić-Jovanović, N., Uzelac, A., Bobic, B., Šolaja, B.,& Djurkovic-Djakovic, O.. (2017). Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy. in International Journal of Antimicrobial Agents
Elsevier., 50(3), 461-466.
https://doi.org/10.1016/j.ijantimicag.2017.06.002

Srbljanović J, Štajner T, Konstantinović JM, Terzić-Jovanović N, Uzelac A, Bobic B, Šolaja B, Djurkovic-Djakovic O. Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy. in International Journal of Antimicrobial Agents. 2017;50(3):461-466.
doi:10.1016/j.ijantimicag.2017.06.002 .

Srbljanović, Jelena, Štajner, Tijana, Konstantinović, Jelena M., Terzić-Jovanović, Nataša, Uzelac, Aleksandra, Bobic, Branko, Šolaja, Bogdan, Djurkovic-Djakovic, Olgica, "Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy" in International Journal of Antimicrobial Agents, 50, no. 3 (2017):461-466,
https://doi.org/10.1016/j.ijantimicag.2017.06.002 . .

TY  - JOUR
AU  - Srbljanović, Jelena
AU  - Štajner, Tijana
AU  - Konstantinović, Jelena M.
AU  - Terzić-Jovanović, Nataša
AU  - Uzelac, Aleksandra
AU  - Bobic, Branko
AU  - Šolaja, Bogdan
AU  - Djurkovic-Djakovic, Olgica
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2172
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3033
AB  - Malaria remains a major disease in the developing world and globally is the most important parasitic disease causing significant morbidity and mortality. Because of widespread resistance to conventional antimalarials, including chloroquine (CQ), new drugs are urgently needed. Here we report on the antimalarial efficacy, both in vitro and in vivo, of a series of aminoquinoline derivatives with adamantane or benzothiophene as a carrier. In vitro efficacy was evaluated by a lactate dehydrogenase (LDH) assay in cultures of a CQ-sensitive (3D7) and CQ-resistant (Dd2) strain of Plasmodium falcipanim. Of a series of 26 screened compounds, 12 that exerted a growth inhibition rate of >= 5% were further examined in vitro to determine the 50% inhibitory concentration (IC50) values. Nine compounds shown in preliminary experiments to be non-toxic in vivo were evaluated in C57BL/6 mice infected with Plasmodium herghei ANKA strain using a modified Thompson test. All nine compounds examined in vivo prolonged the survival of treated versus untreated mice, four of which afforded >= 60% survival. Most notably, two of these compounds, both with the adamantane carrier, afforded complete cure (100% survival and parasite clearance). Interestingly, one of these compounds had no in vitro effect against the CQ resistant P. falciparum strain. Better in vivo compared with in vitro results suggest a role for compound metabolites rather than the compounds themselves. The results presented here point to adamantane as a carrier that enhances the antimalarial potential of aminoquinolines.
PB  - Elsevier
T2  - International Journal of Antimicrobial Agents
T1  - Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy
VL  - 50
IS  - 3
SP  - 461
EP  - 466
DO  - 10.1016/j.ijantimicag.2017.06.002
ER  - 

@article{
author = "Srbljanović, Jelena and Štajner, Tijana and Konstantinović, Jelena M. and Terzić-Jovanović, Nataša and Uzelac, Aleksandra and Bobic, Branko and Šolaja, Bogdan and Djurkovic-Djakovic, Olgica",
year = "2017",
abstract = "Malaria remains a major disease in the developing world and globally is the most important parasitic disease causing significant morbidity and mortality. Because of widespread resistance to conventional antimalarials, including chloroquine (CQ), new drugs are urgently needed. Here we report on the antimalarial efficacy, both in vitro and in vivo, of a series of aminoquinoline derivatives with adamantane or benzothiophene as a carrier. In vitro efficacy was evaluated by a lactate dehydrogenase (LDH) assay in cultures of a CQ-sensitive (3D7) and CQ-resistant (Dd2) strain of Plasmodium falcipanim. Of a series of 26 screened compounds, 12 that exerted a growth inhibition rate of >= 5% were further examined in vitro to determine the 50% inhibitory concentration (IC50) values. Nine compounds shown in preliminary experiments to be non-toxic in vivo were evaluated in C57BL/6 mice infected with Plasmodium herghei ANKA strain using a modified Thompson test. All nine compounds examined in vivo prolonged the survival of treated versus untreated mice, four of which afforded >= 60% survival. Most notably, two of these compounds, both with the adamantane carrier, afforded complete cure (100% survival and parasite clearance). Interestingly, one of these compounds had no in vitro effect against the CQ resistant P. falciparum strain. Better in vivo compared with in vitro results suggest a role for compound metabolites rather than the compounds themselves. The results presented here point to adamantane as a carrier that enhances the antimalarial potential of aminoquinolines.",
publisher = "Elsevier",
journal = "International Journal of Antimicrobial Agents",
title = "Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy",
volume = "50",
number = "3",
pages = "461-466",
doi = "10.1016/j.ijantimicag.2017.06.002"
}

Srbljanović, J., Štajner, T., Konstantinović, J. M., Terzić-Jovanović, N., Uzelac, A., Bobic, B., Šolaja, B.,& Djurkovic-Djakovic, O.. (2017). Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy. in International Journal of Antimicrobial Agents
Elsevier., 50(3), 461-466.
https://doi.org/10.1016/j.ijantimicag.2017.06.002

Srbljanović J, Štajner T, Konstantinović JM, Terzić-Jovanović N, Uzelac A, Bobic B, Šolaja B, Djurkovic-Djakovic O. Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy. in International Journal of Antimicrobial Agents. 2017;50(3):461-466.
doi:10.1016/j.ijantimicag.2017.06.002 .

Srbljanović, Jelena, Štajner, Tijana, Konstantinović, Jelena M., Terzić-Jovanović, Nataša, Uzelac, Aleksandra, Bobic, Branko, Šolaja, Bogdan, Djurkovic-Djakovic, Olgica, "Examination of the antimalarial potential of experimental aminoquinolines: poor in vitro effect does not preclude in vivo efficacy" in International Journal of Antimicrobial Agents, 50, no. 3 (2017):461-466,
https://doi.org/10.1016/j.ijantimicag.2017.06.002 . .

TY  - CONF
AU  - Marković, Olivera
AU  - Konstantinović, Jelena M.
AU  - Cvijetić, Ilija
AU  - Amézqueta, Susana
AU  - Valko, Klara
AU  - Ràfols, Clara
AU  - Polović, Natalija
AU  - Šolaja, Bogdan
AU  - Verbić, Tatjana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3403
AB  - Drug molecules in vivo may be bound to proteins and lipids in plasma and/or in tissues, or free (unbound) in diffusion among the aqueous environment of the blood and tissues. Data from in vitro plasma protein binding experiments that determine the fraction of protein-bound drug are  frequently used in drug discovery. Methods used for drug –  plasma protein binding (PPB) studies are numerous and can be divided into two main groups: separation methods (enabling the calculation of binding parameters, i.e. the number of binding sites and their respective affinity constants) and non-separation methods (describing predominantly qualitative parameters of the ligand-protein complex).
PB  - International Association of Physical Chemists
C3  - 6th World Conference on Physico-Chemical Methods in Drug Discovery, Zagreb, Croatia, September 4-7, 2017 - Book of Abstracts
T1  - Measurements of plasma protein binding – variety of experimental techniques
SP  - 30
EP  - 30
UR  - https://hdl.handle.net/21.15107/rcub_cer_3403
ER  - 

@conference{
author = "Marković, Olivera and Konstantinović, Jelena M. and Cvijetić, Ilija and Amézqueta, Susana and Valko, Klara and Ràfols, Clara and Polović, Natalija and Šolaja, Bogdan and Verbić, Tatjana",
year = "2017",
abstract = "Drug molecules in vivo may be bound to proteins and lipids in plasma and/or in tissues, or free (unbound) in diffusion among the aqueous environment of the blood and tissues. Data from in vitro plasma protein binding experiments that determine the fraction of protein-bound drug are  frequently used in drug discovery. Methods used for drug –  plasma protein binding (PPB) studies are numerous and can be divided into two main groups: separation methods (enabling the calculation of binding parameters, i.e. the number of binding sites and their respective affinity constants) and non-separation methods (describing predominantly qualitative parameters of the ligand-protein complex).",
publisher = "International Association of Physical Chemists",
journal = "6th World Conference on Physico-Chemical Methods in Drug Discovery, Zagreb, Croatia, September 4-7, 2017 - Book of Abstracts",
title = "Measurements of plasma protein binding – variety of experimental techniques",
pages = "30-30",
url = "https://hdl.handle.net/21.15107/rcub_cer_3403"
}

Marković, O., Konstantinović, J. M., Cvijetić, I., Amézqueta, S., Valko, K., Ràfols, C., Polović, N., Šolaja, B.,& Verbić, T.. (2017). Measurements of plasma protein binding – variety of experimental techniques. in 6th World Conference on Physico-Chemical Methods in Drug Discovery, Zagreb, Croatia, September 4-7, 2017 - Book of Abstracts
International Association of Physical Chemists., 30-30.
https://hdl.handle.net/21.15107/rcub_cer_3403

Marković O, Konstantinović JM, Cvijetić I, Amézqueta S, Valko K, Ràfols C, Polović N, Šolaja B, Verbić T. Measurements of plasma protein binding – variety of experimental techniques. in 6th World Conference on Physico-Chemical Methods in Drug Discovery, Zagreb, Croatia, September 4-7, 2017 - Book of Abstracts. 2017;:30-30.
https://hdl.handle.net/21.15107/rcub_cer_3403 .

Marković, Olivera, Konstantinović, Jelena M., Cvijetić, Ilija, Amézqueta, Susana, Valko, Klara, Ràfols, Clara, Polović, Natalija, Šolaja, Bogdan, Verbić, Tatjana, "Measurements of plasma protein binding – variety of experimental techniques" in 6th World Conference on Physico-Chemical Methods in Drug Discovery, Zagreb, Croatia, September 4-7, 2017 - Book of Abstracts (2017):30-30,
https://hdl.handle.net/21.15107/rcub_cer_3403 .

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

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

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

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

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

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

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

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

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

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

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  - Bozinovic, Nina
AU  - Novaković, Irena
AU  - Kostić Rajačić, Slađana
AU  - Opsenica, Igor
AU  - Šolaja, Bogdan
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1702
AB  - A series of new pyridobenzazepine and pyridobenzothiepine derivatives was synthesized by Pd-catalyzed formation of C-N and C-S bonds. All synthesized compounds were tested for their in vitro antimicrobial activity. The pyridobenzazepine derivatives showed better antibacterial and antifungal activity than the corresponding dipyridoazepine analogue. Among the synthesized azepines, derivative 8 displayed potent activity against the tested bacteria (MIC ranged 39-78 mu g mL(-1)), while azepine 12 showed promising antifungal activity (MIC ranged 156-313 mu g mL(-1)). The synthesized thiepine derivatives exhibited weak antibacterial activity, but showed pronounced antifungal activity.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis and antimicrobial activity of azepine and thiepine derivatives
VL  - 80
IS  - 7
SP  - 839
EP  - 852
DO  - 10.2298/JSC150116013B
ER  - 

@article{
author = "Bozinovic, Nina and Novaković, Irena and Kostić Rajačić, Slađana and Opsenica, Igor and Šolaja, Bogdan",
year = "2015",
abstract = "A series of new pyridobenzazepine and pyridobenzothiepine derivatives was synthesized by Pd-catalyzed formation of C-N and C-S bonds. All synthesized compounds were tested for their in vitro antimicrobial activity. The pyridobenzazepine derivatives showed better antibacterial and antifungal activity than the corresponding dipyridoazepine analogue. Among the synthesized azepines, derivative 8 displayed potent activity against the tested bacteria (MIC ranged 39-78 mu g mL(-1)), while azepine 12 showed promising antifungal activity (MIC ranged 156-313 mu g mL(-1)). The synthesized thiepine derivatives exhibited weak antibacterial activity, but showed pronounced antifungal activity.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis and antimicrobial activity of azepine and thiepine derivatives",
volume = "80",
number = "7",
pages = "839-852",
doi = "10.2298/JSC150116013B"
}

Bozinovic, N., Novaković, I., Kostić Rajačić, S., Opsenica, I.,& Šolaja, B.. (2015). Synthesis and antimicrobial activity of azepine and thiepine derivatives. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 80(7), 839-852.
https://doi.org/10.2298/JSC150116013B

Bozinovic N, Novaković I, Kostić Rajačić S, Opsenica I, Šolaja B. Synthesis and antimicrobial activity of azepine and thiepine derivatives. in Journal of the Serbian Chemical Society. 2015;80(7):839-852.
doi:10.2298/JSC150116013B .

Bozinovic, Nina, Novaković, Irena, Kostić Rajačić, Slađana, Opsenica, Igor, Šolaja, Bogdan, "Synthesis and antimicrobial activity of azepine and thiepine derivatives" in Journal of the Serbian Chemical Society, 80, no. 7 (2015):839-852,
https://doi.org/10.2298/JSC150116013B . .

TY  - JOUR
AU  - Opsenica, Dejan
AU  - Radivojevic, Jelena
AU  - Matić, Ivana Z.
AU  - Štajner, Tijana
AU  - Knezevic-Usaj, Slavica
AU  - Djurkovic-Djakovic, Olgica
AU  - Šolaja, Bogdan
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1795
AB  - New cyclohexylidene 1,2,4,5-tetraoxanes with polar guanidine and urea based groups were synthesized and evaluated for their antimalarial activity against chloroquine resistant and susceptible Plasmodium falciparum strains. The derivatives showed moderate, nM range antimalarial activities and low cytotoxicity. The N-phenylurea derivative 24 exhibited the best resistance indices (RIW2 = 0.44, RITM91C235 = 0.80) and was not toxic against human normal peripheral blood mononuclear cells (IC50 > 200 mu M). Seven derivatives were tested in vitro against four human cancer cell lines and they demonstrated high selectivity toward leukaemia K562 cells. One compound, derivative 21 with a primary amino group, was the first tetraoxane tested in vivo against Toxoplasma gondii as another apicomplexan parasite. Subcutaneous administration at a dose of 10 mg kg(-1) day(-1) for 8 days allowed the survival of 20 % of infected mice, thus demonstrating the high potential of tetraoxanes for the treatment of apicomplexan parasites.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Tetraoxanes as inhibitors of apicomplexan parasites Plasmodium falciparum and Toxoplasma gondii growth and anti-cancer molecules
VL  - 80
IS  - 11
SP  - 1339
DO  - 10.2298/JSC150430063O
ER  - 

@article{
author = "Opsenica, Dejan and Radivojevic, Jelena and Matić, Ivana Z. and Štajner, Tijana and Knezevic-Usaj, Slavica and Djurkovic-Djakovic, Olgica and Šolaja, Bogdan",
year = "2015",
abstract = "New cyclohexylidene 1,2,4,5-tetraoxanes with polar guanidine and urea based groups were synthesized and evaluated for their antimalarial activity against chloroquine resistant and susceptible Plasmodium falciparum strains. The derivatives showed moderate, nM range antimalarial activities and low cytotoxicity. The N-phenylurea derivative 24 exhibited the best resistance indices (RIW2 = 0.44, RITM91C235 = 0.80) and was not toxic against human normal peripheral blood mononuclear cells (IC50 > 200 mu M). Seven derivatives were tested in vitro against four human cancer cell lines and they demonstrated high selectivity toward leukaemia K562 cells. One compound, derivative 21 with a primary amino group, was the first tetraoxane tested in vivo against Toxoplasma gondii as another apicomplexan parasite. Subcutaneous administration at a dose of 10 mg kg(-1) day(-1) for 8 days allowed the survival of 20 % of infected mice, thus demonstrating the high potential of tetraoxanes for the treatment of apicomplexan parasites.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Tetraoxanes as inhibitors of apicomplexan parasites Plasmodium falciparum and Toxoplasma gondii growth and anti-cancer molecules",
volume = "80",
number = "11",
pages = "1339",
doi = "10.2298/JSC150430063O"
}

Opsenica, D., Radivojevic, J., Matić, I. Z., Štajner, T., Knezevic-Usaj, S., Djurkovic-Djakovic, O.,& Šolaja, B.. (2015). Tetraoxanes as inhibitors of apicomplexan parasites Plasmodium falciparum and Toxoplasma gondii growth and anti-cancer molecules. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 80(11), 1339.
https://doi.org/10.2298/JSC150430063O

Opsenica D, Radivojevic J, Matić IZ, Štajner T, Knezevic-Usaj S, Djurkovic-Djakovic O, Šolaja B. Tetraoxanes as inhibitors of apicomplexan parasites Plasmodium falciparum and Toxoplasma gondii growth and anti-cancer molecules. in Journal of the Serbian Chemical Society. 2015;80(11):1339.
doi:10.2298/JSC150430063O .

Opsenica, Dejan, Radivojevic, Jelena, Matić, Ivana Z., Štajner, Tijana, Knezevic-Usaj, Slavica, Djurkovic-Djakovic, Olgica, Šolaja, Bogdan, "Tetraoxanes as inhibitors of apicomplexan parasites Plasmodium falciparum and Toxoplasma gondii growth and anti-cancer molecules" in Journal of the Serbian Chemical Society, 80, no. 11 (2015):1339,
https://doi.org/10.2298/JSC150430063O . .

TY  - CONF
AU  - Marković, Olivera
AU  - Cvijetić, Ilija
AU  - Zlatović, Mario
AU  - Opsenica, Igor
AU  - Terzić-Jovanović, Nataša
AU  - Šolaja, Bogdan
AU  - Verbić, Tatjana
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3401
AB  - Tested compounds, previously synthesized, are derivatives of chloroquine, drug commonly used in the treatment and prevention of malaria. Interaction between tested compounds and Human serum albumin (HSA) has been studied by fluorescence spectroscopy in phosphate buffered saline (1× PBS, pH 7.4) . Molecular docking studies were used to determine HSA–compound binding mode.
PB  - International Association of Physical Chemists
C3  - 4th World Conference on Physico-Chemical Methods in Drug Discovery and Development Red Island, Croatia, September 21-24, 2015 - Book of Abstracts
T1  - Human serum albumin binding of certain antimalarials
SP  - 67
EP  - 67
UR  - https://hdl.handle.net/21.15107/rcub_cer_3401
ER  - 

@conference{
author = "Marković, Olivera and Cvijetić, Ilija and Zlatović, Mario and Opsenica, Igor and Terzić-Jovanović, Nataša and Šolaja, Bogdan and Verbić, Tatjana",
year = "2015",
abstract = "Tested compounds, previously synthesized, are derivatives of chloroquine, drug commonly used in the treatment and prevention of malaria. Interaction between tested compounds and Human serum albumin (HSA) has been studied by fluorescence spectroscopy in phosphate buffered saline (1× PBS, pH 7.4) . Molecular docking studies were used to determine HSA–compound binding mode.",
publisher = "International Association of Physical Chemists",
journal = "4th World Conference on Physico-Chemical Methods in Drug Discovery and Development Red Island, Croatia, September 21-24, 2015 - Book of Abstracts",
title = "Human serum albumin binding of certain antimalarials",
pages = "67-67",
url = "https://hdl.handle.net/21.15107/rcub_cer_3401"
}

Marković, O., Cvijetić, I., Zlatović, M., Opsenica, I., Terzić-Jovanović, N., Šolaja, B.,& Verbić, T.. (2015). Human serum albumin binding of certain antimalarials. in 4th World Conference on Physico-Chemical Methods in Drug Discovery and Development Red Island, Croatia, September 21-24, 2015 - Book of Abstracts
International Association of Physical Chemists., 67-67.
https://hdl.handle.net/21.15107/rcub_cer_3401

Marković O, Cvijetić I, Zlatović M, Opsenica I, Terzić-Jovanović N, Šolaja B, Verbić T. Human serum albumin binding of certain antimalarials. in 4th World Conference on Physico-Chemical Methods in Drug Discovery and Development Red Island, Croatia, September 21-24, 2015 - Book of Abstracts. 2015;:67-67.
https://hdl.handle.net/21.15107/rcub_cer_3401 .

Marković, Olivera, Cvijetić, Ilija, Zlatović, Mario, Opsenica, Igor, Terzić-Jovanović, Nataša, Šolaja, Bogdan, Verbić, Tatjana, "Human serum albumin binding of certain antimalarials" in 4th World Conference on Physico-Chemical Methods in Drug Discovery and Development Red Island, Croatia, September 21-24, 2015 - Book of Abstracts (2015):67-67,
https://hdl.handle.net/21.15107/rcub_cer_3401 .

TY  - JOUR
AU  - Videnović, Milica
AU  - Opsenica, Dejan
AU  - Burnett, James C.
AU  - Gomba, Laura
AU  - Nuss, Jonathan E.
AU  - Selaković, Života
AU  - Konstantinović, Jelena M.
AU  - Krstic, Maja
AU  - Šegan, Sandra
AU  - Zlatović, Mario
AU  - Sciotti, Richard J.
AU  - Bavari, Sina
AU  - Šolaja, Bogdan
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1580
AB  - Significantly more potent second generation 4-amino-7-chloroquinoline (4,7-ACQ) based inhibitors of the botulinum neurotoxin serotype A (BoNT/A) light chain were synthesized. Introducing an amino group at the C(3) position of the cholate component markedly increased potency (IC50 values for such derivatives ranged from 0.81 to 2.27 mu M). Two additional subclasses were prepared: bis(steroidal)-4,7-ACQ derivatives and bis(4,7-ACQ)cholate derivatives; both classes provided inhibitors with nanomolar-range potencies (e.g., the K-i of compound 67 is 0.10 mu M). During BoNT/A challenge using primary neurons, select derivatives protected SNAP-25 by up to 89%. Docking simulations were performed to rationalize the compounds' in vitro potencies. In addition to specific residue contacts, coordination of the enzyme's catalytic zinc and expulsion of the enzyme's catalytic water were a consistent theme. With respect to antimalarial activity, the compounds provided better IC90 activities against chloroquine resistant (CQR) malaria than CQ, and seven compounds were more active than mefloquine against CQR strain W2.
PB  - American Chemical Society (ACS)
T2  - Journal of Medicinal Chemistry
T1  - Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria
VL  - 57
IS  - 10
SP  - 4134
EP  - 4153
DO  - 10.1021/jm500033r
ER  - 

@article{
author = "Videnović, Milica and Opsenica, Dejan and Burnett, James C. and Gomba, Laura and Nuss, Jonathan E. and Selaković, Života and Konstantinović, Jelena M. and Krstic, Maja and Šegan, Sandra and Zlatović, Mario and Sciotti, Richard J. and Bavari, Sina and Šolaja, Bogdan",
year = "2014",
abstract = "Significantly more potent second generation 4-amino-7-chloroquinoline (4,7-ACQ) based inhibitors of the botulinum neurotoxin serotype A (BoNT/A) light chain were synthesized. Introducing an amino group at the C(3) position of the cholate component markedly increased potency (IC50 values for such derivatives ranged from 0.81 to 2.27 mu M). Two additional subclasses were prepared: bis(steroidal)-4,7-ACQ derivatives and bis(4,7-ACQ)cholate derivatives; both classes provided inhibitors with nanomolar-range potencies (e.g., the K-i of compound 67 is 0.10 mu M). During BoNT/A challenge using primary neurons, select derivatives protected SNAP-25 by up to 89%. Docking simulations were performed to rationalize the compounds' in vitro potencies. In addition to specific residue contacts, coordination of the enzyme's catalytic zinc and expulsion of the enzyme's catalytic water were a consistent theme. With respect to antimalarial activity, the compounds provided better IC90 activities against chloroquine resistant (CQR) malaria than CQ, and seven compounds were more active than mefloquine against CQR strain W2.",
publisher = "American Chemical Society (ACS)",
journal = "Journal of Medicinal Chemistry",
title = "Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria",
volume = "57",
number = "10",
pages = "4134-4153",
doi = "10.1021/jm500033r"
}

Videnović, M., Opsenica, D., Burnett, J. C., Gomba, L., Nuss, J. E., Selaković, Ž., Konstantinović, J. M., Krstic, M., Šegan, S., Zlatović, M., Sciotti, R. J., Bavari, S.,& Šolaja, B.. (2014). Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria. in Journal of Medicinal Chemistry
American Chemical Society (ACS)., 57(10), 4134-4153.
https://doi.org/10.1021/jm500033r

Videnović M, Opsenica D, Burnett JC, Gomba L, Nuss JE, Selaković Ž, Konstantinović JM, Krstic M, Šegan S, Zlatović M, Sciotti RJ, Bavari S, Šolaja B. Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria. in Journal of Medicinal Chemistry. 2014;57(10):4134-4153.
doi:10.1021/jm500033r .

Videnović, Milica, Opsenica, Dejan, Burnett, James C., Gomba, Laura, Nuss, Jonathan E., Selaković, Života, Konstantinović, Jelena M., Krstic, Maja, Šegan, Sandra, Zlatović, Mario, Sciotti, Richard J., Bavari, Sina, Šolaja, Bogdan, "Second Generation Steroidal 4-Aminoquinolines Are Potent, Dual-Target Inhibitors of the Botulinum Neurotoxin Serotype A Metalloprotease and P. falciparum Malaria" in Journal of Medicinal Chemistry, 57, no. 10 (2014):4134-4153,
https://doi.org/10.1021/jm500033r . .

TY  - JOUR
AU  - Šegan, Sandra
AU  - Terzić Jovanović, Nataša
AU  - Milojković-Opsenica, Dušanka
AU  - Trifković, Jelena
AU  - Šolaja, Bogdan
AU  - Opsenica, Dejan
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1599
AB  - The chromatographic behavior of mixed 1,2,4,5-tetraoxanes, cholic and deoxycholic acid derivatives with distinct biological activity, was examined by high-performance thin-layer chromatography in order to correlate their structure and retention. Chromatographic systems were consisted of RP-18 or CN-silica as stationary phase, and binary mixtures of water with methanol, dioxane or acetone as mobile phase. Based on the respective retentions, the lipophilicity of the investigated compounds was determined. Multiple linear regression and partial least squares have been used to select variables that best describe the behavior of the investigated compounds in chromatographic systems and to quantify influences of most important parameters. The validation and cross-validation of the QSRR model suggest its applicability for prediction and understanding of retention of congeners. The models indicate the importance of nonpolar properties of the solutes and their ability for hydrophobic interactions, as well as the importance of proton donating abilities, hydrophilic and,pi interactions pointing out on that way the possible separation mechanism in the studied chromatographic systems. Observed correlations between structure and biological activity of mixed 1,2,4,5-tetraoxanes, indicate that the antimalarial activity against W2 and D6 Plasmodium falciparum strains, is governed by hydrophobic feature (measured with lipophilicity parameter), hydrophilic feature (measured with HLB, %HS, HB and HBA descriptors), and electronic feature (HOMO).
PB  - Elsevier
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters
VL  - 97
SP  - 178
EP  - 183
DO  - 10.1016/j.jpba.2014.04.029
ER  - 

@article{
author = "Šegan, Sandra and Terzić Jovanović, Nataša and Milojković-Opsenica, Dušanka and Trifković, Jelena and Šolaja, Bogdan and Opsenica, Dejan",
year = "2014",
abstract = "The chromatographic behavior of mixed 1,2,4,5-tetraoxanes, cholic and deoxycholic acid derivatives with distinct biological activity, was examined by high-performance thin-layer chromatography in order to correlate their structure and retention. Chromatographic systems were consisted of RP-18 or CN-silica as stationary phase, and binary mixtures of water with methanol, dioxane or acetone as mobile phase. Based on the respective retentions, the lipophilicity of the investigated compounds was determined. Multiple linear regression and partial least squares have been used to select variables that best describe the behavior of the investigated compounds in chromatographic systems and to quantify influences of most important parameters. The validation and cross-validation of the QSRR model suggest its applicability for prediction and understanding of retention of congeners. The models indicate the importance of nonpolar properties of the solutes and their ability for hydrophobic interactions, as well as the importance of proton donating abilities, hydrophilic and,pi interactions pointing out on that way the possible separation mechanism in the studied chromatographic systems. Observed correlations between structure and biological activity of mixed 1,2,4,5-tetraoxanes, indicate that the antimalarial activity against W2 and D6 Plasmodium falciparum strains, is governed by hydrophobic feature (measured with lipophilicity parameter), hydrophilic feature (measured with HLB, %HS, HB and HBA descriptors), and electronic feature (HOMO).",
publisher = "Elsevier",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters",
volume = "97",
pages = "178-183",
doi = "10.1016/j.jpba.2014.04.029"
}

Šegan, S., Terzić Jovanović, N., Milojković-Opsenica, D., Trifković, J., Šolaja, B.,& Opsenica, D.. (2014). Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters. in Journal of Pharmaceutical and Biomedical Analysis
Elsevier., 97, 178-183.
https://doi.org/10.1016/j.jpba.2014.04.029

Šegan S, Terzić Jovanović N, Milojković-Opsenica D, Trifković J, Šolaja B, Opsenica D. Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters. in Journal of Pharmaceutical and Biomedical Analysis. 2014;97:178-183.
doi:10.1016/j.jpba.2014.04.029 .

Šegan, Sandra, Terzić Jovanović, Nataša, Milojković-Opsenica, Dušanka, Trifković, Jelena, Šolaja, Bogdan, Opsenica, Dejan, "Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters" in Journal of Pharmaceutical and Biomedical Analysis, 97 (2014):178-183,
https://doi.org/10.1016/j.jpba.2014.04.029 . .

TY  - JOUR
AU  - Šegan, Sandra
AU  - Terzić-Jovanović, Nataša
AU  - Milojković-Opsenica, Dušanka
AU  - Trifković, Jelena
AU  - Šolaja, Bogdan
AU  - Opsenica, Dejan
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3166
AB  - The chromatographic behavior of mixed 1,2,4,5-tetraoxanes, cholic and deoxycholic acid derivatives with distinct biological activity, was examined by high-performance thin-layer chromatography in order to correlate their structure and retention. Chromatographic systems were consisted of RP-18 or CN-silica as stationary phase, and binary mixtures of water with methanol, dioxane or acetone as mobile phase. Based on the respective retentions, the lipophilicity of the investigated compounds was determined. Multiple linear regression and partial least squares have been used to select variables that best describe the behavior of the investigated compounds in chromatographic systems and to quantify influences of most important parameters. The validation and cross-validation of the QSRR model suggest its applicability for prediction and understanding of retention of congeners. The models indicate the importance of nonpolar properties of the solutes and their ability for hydrophobic interactions, as well as the importance of proton donating abilities, hydrophilic and,pi interactions pointing out on that way the possible separation mechanism in the studied chromatographic systems. Observed correlations between structure and biological activity of mixed 1,2,4,5-tetraoxanes, indicate that the antimalarial activity against W2 and D6 Plasmodium falciparum strains, is governed by hydrophobic feature (measured with lipophilicity parameter), hydrophilic feature (measured with HLB, %HS, HB and HBA descriptors), and electronic feature (HOMO).
PB  - Elsevier
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters
VL  - 97
SP  - 178
EP  - 183
DO  - 10.1016/j.jpba.2014.04.029
ER  - 

@article{
author = "Šegan, Sandra and Terzić-Jovanović, Nataša and Milojković-Opsenica, Dušanka and Trifković, Jelena and Šolaja, Bogdan and Opsenica, Dejan",
year = "2014",
abstract = "The chromatographic behavior of mixed 1,2,4,5-tetraoxanes, cholic and deoxycholic acid derivatives with distinct biological activity, was examined by high-performance thin-layer chromatography in order to correlate their structure and retention. Chromatographic systems were consisted of RP-18 or CN-silica as stationary phase, and binary mixtures of water with methanol, dioxane or acetone as mobile phase. Based on the respective retentions, the lipophilicity of the investigated compounds was determined. Multiple linear regression and partial least squares have been used to select variables that best describe the behavior of the investigated compounds in chromatographic systems and to quantify influences of most important parameters. The validation and cross-validation of the QSRR model suggest its applicability for prediction and understanding of retention of congeners. The models indicate the importance of nonpolar properties of the solutes and their ability for hydrophobic interactions, as well as the importance of proton donating abilities, hydrophilic and,pi interactions pointing out on that way the possible separation mechanism in the studied chromatographic systems. Observed correlations between structure and biological activity of mixed 1,2,4,5-tetraoxanes, indicate that the antimalarial activity against W2 and D6 Plasmodium falciparum strains, is governed by hydrophobic feature (measured with lipophilicity parameter), hydrophilic feature (measured with HLB, %HS, HB and HBA descriptors), and electronic feature (HOMO).",
publisher = "Elsevier",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters",
volume = "97",
pages = "178-183",
doi = "10.1016/j.jpba.2014.04.029"
}

Šegan, S., Terzić-Jovanović, N., Milojković-Opsenica, D., Trifković, J., Šolaja, B.,& Opsenica, D.. (2014). Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters. in Journal of Pharmaceutical and Biomedical Analysis
Elsevier., 97, 178-183.
https://doi.org/10.1016/j.jpba.2014.04.029

Šegan S, Terzić-Jovanović N, Milojković-Opsenica D, Trifković J, Šolaja B, Opsenica D. Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters. in Journal of Pharmaceutical and Biomedical Analysis. 2014;97:178-183.
doi:10.1016/j.jpba.2014.04.029 .

Šegan, Sandra, Terzić-Jovanović, Nataša, Milojković-Opsenica, Dušanka, Trifković, Jelena, Šolaja, Bogdan, Opsenica, Dejan, "Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters" in Journal of Pharmaceutical and Biomedical Analysis, 97 (2014):178-183,
https://doi.org/10.1016/j.jpba.2014.04.029 . .

TY  - CONF
AU  - Marković, Olivera
AU  - Cvijetić, Ilija
AU  - Zlatović, Mario
AU  - Opsenica, Igor
AU  - Terzić-Jovanović, Nataša
AU  - Verbić, Tatjana
AU  - Šolaja, Bogdan
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3399
AB  - Human serum albumin (HSA) is the most abundant protein in blood plasma and it transports
endogenous (fatty acids and bilirubin) and exogenous compounds (drugs) through the blood. In the
present study binding of several derivatives of our new antimalarials, and chloroquine, to HSA
was investigated by fluorescence spectroscopy (in 0.15 М HEPES, pH 7.35).
AB  - Хумани серум албумин (ХСА) је најзаступљенији протеин у крвној плазми који преноси
ендогенe (масне киселине и билирубин) и егзогенe супстанце (лекове) кроз крв.
Флуоресцентном спектроскопијом je проучавано везивање ХСА са хлорокином и неколико
наших нових аминохинолинских антималарика (у 0,15 М HEPES пуферу, pH 7,35).
PB  - Serbian Chemical Society, Belgrade / Srpsko hemijsko društvo, Beograd
C3  - 51st Meeting of the Serbian Chemical Society - Book of abstracts/ 51. Savetovanje Srpskog hemijskog društva - Kratki izvodi radova, Niš, 5-7.6.2014
T1  - Human serum albumin binding of certain antimalarials
T1  - Везивање неких антималарика за хумани серум албумин
SP  - 23
EP  - 23
UR  - https://hdl.handle.net/21.15107/rcub_cer_3399
ER  - 

@conference{
author = "Marković, Olivera and Cvijetić, Ilija and Zlatović, Mario and Opsenica, Igor and Terzić-Jovanović, Nataša and Verbić, Tatjana and Šolaja, Bogdan",
year = "2014",
abstract = "Human serum albumin (HSA) is the most abundant protein in blood plasma and it transports
endogenous (fatty acids and bilirubin) and exogenous compounds (drugs) through the blood. In the
present study binding of several derivatives of our new antimalarials, and chloroquine, to HSA
was investigated by fluorescence spectroscopy (in 0.15 М HEPES, pH 7.35)., Хумани серум албумин (ХСА) је најзаступљенији протеин у крвној плазми који преноси
ендогенe (масне киселине и билирубин) и егзогенe супстанце (лекове) кроз крв.
Флуоресцентном спектроскопијом je проучавано везивање ХСА са хлорокином и неколико
наших нових аминохинолинских антималарика (у 0,15 М HEPES пуферу, pH 7,35).",
publisher = "Serbian Chemical Society, Belgrade / Srpsko hemijsko društvo, Beograd",
journal = "51st Meeting of the Serbian Chemical Society - Book of abstracts/ 51. Savetovanje Srpskog hemijskog društva - Kratki izvodi radova, Niš, 5-7.6.2014",
title = "Human serum albumin binding of certain antimalarials, Везивање неких антималарика за хумани серум албумин",
pages = "23-23",
url = "https://hdl.handle.net/21.15107/rcub_cer_3399"
}

Marković, O., Cvijetić, I., Zlatović, M., Opsenica, I., Terzić-Jovanović, N., Verbić, T.,& Šolaja, B.. (2014). Human serum albumin binding of certain antimalarials. in 51st Meeting of the Serbian Chemical Society - Book of abstracts/ 51. Savetovanje Srpskog hemijskog društva - Kratki izvodi radova, Niš, 5-7.6.2014
Serbian Chemical Society, Belgrade / Srpsko hemijsko društvo, Beograd., 23-23.
https://hdl.handle.net/21.15107/rcub_cer_3399

Marković O, Cvijetić I, Zlatović M, Opsenica I, Terzić-Jovanović N, Verbić T, Šolaja B. Human serum albumin binding of certain antimalarials. in 51st Meeting of the Serbian Chemical Society - Book of abstracts/ 51. Savetovanje Srpskog hemijskog društva - Kratki izvodi radova, Niš, 5-7.6.2014. 2014;:23-23.
https://hdl.handle.net/21.15107/rcub_cer_3399 .

Marković, Olivera, Cvijetić, Ilija, Zlatović, Mario, Opsenica, Igor, Terzić-Jovanović, Nataša, Verbić, Tatjana, Šolaja, Bogdan, "Human serum albumin binding of certain antimalarials" in 51st Meeting of the Serbian Chemical Society - Book of abstracts/ 51. Savetovanje Srpskog hemijskog društva - Kratki izvodi radova, Niš, 5-7.6.2014 (2014):23-23,
https://hdl.handle.net/21.15107/rcub_cer_3399 .