TY  - JOUR
AU  - Pogrebnoi, Serghei
AU  - Radul, Oleg
AU  - Stingaci, Eugenia
AU  - Lupascu, Lucian
AU  - Valica, Vladimir
AU  - Uncu, Livia
AU  - Smetanscaia, Anastasia
AU  - Petrou, Anthi
AU  - Ćirić, Ana
AU  - Glamočlija, Jasmina
AU  - Soković, Marina
AU  - Geronikaki, Athina
AU  - Macaev, Fliur Z.
PY  - 2022
UR  - https://www.mdpi.com/2079-6382/11/5/588
UR  - http://radar.ibiss.bg.ac.rs/handle/123456789/4982
AB  - The control of fungal pathogens is increasingly difficult due to the limited number of effective drugs available for antifungal therapy. In addition, both humans and fungi are eukaryotic organisms; antifungal drugs may have significant toxicity due to the inhibition of related human targets. Furthermore, another problem is increased incidents of fungal resistance to azoles, such as fluconazole, ketoconazole, voriconazole, etc. Thus, the interest in developing new azoles with an extended spectrum of activity still attracts the interest of the scientific community. Herein, we report the synthesis of a series of triazolium salts, an evaluation of their antifungal activity, and docking studies. Ketoconazole and bifonazole were used as reference drugs. All compounds showed good antifungal activity with MIC/MFC in the range of 0.0003 to 0.2/0.0006-0.4 mg/mL. Compound 19 exhibited the best activity among all tested with MIC/MFC in the range of 0.009 to 0.037 mg/mL and 0.0125-0.05 mg/mL, respectively. All compounds appeared to be more potent than both reference drugs. The docking studies are in accordance with experimental results.
PB  - Basel: MDPI
T2  - Antibiotics (Basel, Switzerland)
T1  - The Synthesis of Triazolium Salts as Antifungal Agents: A Biological and In Silico Evaluation.
IS  - 5
VL  - 11
DO  - 10.3390/antibiotics11050588
SP  - 588
ER  - 

@article{
author = "Pogrebnoi, Serghei and Radul, Oleg and Stingaci, Eugenia and Lupascu, Lucian and Valica, Vladimir and Uncu, Livia and Smetanscaia, Anastasia and Petrou, Anthi and Ćirić, Ana and Glamočlija, Jasmina and Soković, Marina and Geronikaki, Athina and Macaev, Fliur Z.",
year = "2022",
abstract = "The control of fungal pathogens is increasingly difficult due to the limited number of effective drugs available for antifungal therapy. In addition, both humans and fungi are eukaryotic organisms; antifungal drugs may have significant toxicity due to the inhibition of related human targets. Furthermore, another problem is increased incidents of fungal resistance to azoles, such as fluconazole, ketoconazole, voriconazole, etc. Thus, the interest in developing new azoles with an extended spectrum of activity still attracts the interest of the scientific community. Herein, we report the synthesis of a series of triazolium salts, an evaluation of their antifungal activity, and docking studies. Ketoconazole and bifonazole were used as reference drugs. All compounds showed good antifungal activity with MIC/MFC in the range of 0.0003 to 0.2/0.0006-0.4 mg/mL. Compound 19 exhibited the best activity among all tested with MIC/MFC in the range of 0.009 to 0.037 mg/mL and 0.0125-0.05 mg/mL, respectively. All compounds appeared to be more potent than both reference drugs. The docking studies are in accordance with experimental results.",
publisher = "Basel: MDPI",
journal = "Antibiotics (Basel, Switzerland)",
title = "The Synthesis of Triazolium Salts as Antifungal Agents: A Biological and In Silico Evaluation.",
number = "5",
volume = "11",
doi = "10.3390/antibiotics11050588",
pages = "588"
}

Pogrebnoi, S., Radul, O., Stingaci, E., Lupascu, L., Valica, V., Uncu, L., Smetanscaia, A., Petrou, A., Ćirić, A., Glamočlija, J., Soković, M., Geronikaki, A.,& Macaev, F. Z.. (2022). The Synthesis of Triazolium Salts as Antifungal Agents: A Biological and In Silico Evaluation.. in Antibiotics (Basel, Switzerland)
Basel: MDPI., 11(5), 588.
https://doi.org/10.3390/antibiotics11050588

Pogrebnoi S, Radul O, Stingaci E, Lupascu L, Valica V, Uncu L, Smetanscaia A, Petrou A, Ćirić A, Glamočlija J, Soković M, Geronikaki A, Macaev FZ. The Synthesis of Triazolium Salts as Antifungal Agents: A Biological and In Silico Evaluation.. in Antibiotics (Basel, Switzerland). 2022;11(5):588.
doi:10.3390/antibiotics11050588 .

Pogrebnoi, Serghei, Radul, Oleg, Stingaci, Eugenia, Lupascu, Lucian, Valica, Vladimir, Uncu, Livia, Smetanscaia, Anastasia, Petrou, Anthi, Ćirić, Ana, Glamočlija, Jasmina, Soković, Marina, Geronikaki, Athina, Macaev, Fliur Z., "The Synthesis of Triazolium Salts as Antifungal Agents: A Biological and In Silico Evaluation." in Antibiotics (Basel, Switzerland), 11, no. 5 (2022):588,
https://doi.org/10.3390/antibiotics11050588 . .

TY  - JOUR
AU  - Zveaghintseva, Marina
AU  - Stingaci, Eugenia
AU  - Pogrebnoi, Sergei
AU  - Smetanscaia, Anastasia
AU  - Valica, Vladimir
AU  - Uncu, Livia
AU  - Kravtsov, Victor
AU  - Melnik, Elena
AU  - Petrou, Anthi
AU  - Glamočlija, Jasmina
AU  - Soković, Marina
AU  - Carazo, Alejandro
AU  - Mladěnka, Přemysl
AU  - Poroikov, Vladimir
AU  - Geronikaki, Athina
AU  - Macaev, Fliur
PY  - 2021
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/4305
AB  - Herein we report the synthesis of some new 1H-1,2,4-triazole functionalized chromenols
(3a–3n) via tandem reactions of 1-(alkyl/aryl)-2-(1H-1,2,4-triazole-1-yl) with salicylic aldehydes and
the evaluation of their antifungal activity. In silico prediction of biological activity spectra with
computer program PASS indicate that the compounds have a high novelty compared to the known
antifungal agents. We did not find any close analog among the over 580,000 pharmaceutical agents
in the Cortellis Drug Discovery Intelligence database at the similarity cutoff of 70%. The evaluation
of antifungal activity in vitro revealed that the highest activity was exhibited by compound 3k,
followed by 3n. Their MIC values for different fungi were 22.1–184.2 and 71.3–199.8  M, respectively.
Twelve from fourteen tested compounds were more active than the reference drugs ketoconazole and
bifonazole. The most sensitive fungus appeared to be Trichoderma viride, while Aspergillus fumigatus
was the most resistant one. It was found that the presence of the 2-(tert-butyl)-2H-chromen-2-ol
substituent on the 4th position of the triazole ring is very beneficial for antifungal activity. Molecular
docking studies on C. albicans sterol 14 -demethylase (CYP51) and DNA topoisomerase IV were used
to predict the mechanism of antifungal activities. According to the docking results, the inhibition
of CYP51 is a putative mechanism of antifungal activity of the novel chromenol derivatives. We
also showed that most active compounds have a low cytotoxicity, which allows us to consider them
promising antifungal agents for the subsequent testing activity in in vivo assays.
PB  - Basel: MDPI
T2  - Molecules
T1  - Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation
IS  - 14
VL  - 26
DO  - 10.3390/molecules26144304
SP  - 4304
ER  - 

@article{
author = "Zveaghintseva, Marina and Stingaci, Eugenia and Pogrebnoi, Sergei and Smetanscaia, Anastasia and Valica, Vladimir and Uncu, Livia and Kravtsov, Victor and Melnik, Elena and Petrou, Anthi and Glamočlija, Jasmina and Soković, Marina and Carazo, Alejandro and Mladěnka, Přemysl and Poroikov, Vladimir and Geronikaki, Athina and Macaev, Fliur",
year = "2021",
abstract = "Herein we report the synthesis of some new 1H-1,2,4-triazole functionalized chromenols
(3a–3n) via tandem reactions of 1-(alkyl/aryl)-2-(1H-1,2,4-triazole-1-yl) with salicylic aldehydes and
the evaluation of their antifungal activity. In silico prediction of biological activity spectra with
computer program PASS indicate that the compounds have a high novelty compared to the known
antifungal agents. We did not find any close analog among the over 580,000 pharmaceutical agents
in the Cortellis Drug Discovery Intelligence database at the similarity cutoff of 70%. The evaluation
of antifungal activity in vitro revealed that the highest activity was exhibited by compound 3k,
followed by 3n. Their MIC values for different fungi were 22.1–184.2 and 71.3–199.8  M, respectively.
Twelve from fourteen tested compounds were more active than the reference drugs ketoconazole and
bifonazole. The most sensitive fungus appeared to be Trichoderma viride, while Aspergillus fumigatus
was the most resistant one. It was found that the presence of the 2-(tert-butyl)-2H-chromen-2-ol
substituent on the 4th position of the triazole ring is very beneficial for antifungal activity. Molecular
docking studies on C. albicans sterol 14 -demethylase (CYP51) and DNA topoisomerase IV were used
to predict the mechanism of antifungal activities. According to the docking results, the inhibition
of CYP51 is a putative mechanism of antifungal activity of the novel chromenol derivatives. We
also showed that most active compounds have a low cytotoxicity, which allows us to consider them
promising antifungal agents for the subsequent testing activity in in vivo assays.",
publisher = "Basel: MDPI",
journal = "Molecules",
title = "Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation",
number = "14",
volume = "26",
doi = "10.3390/molecules26144304",
pages = "4304"
}

Zveaghintseva, M., Stingaci, E., Pogrebnoi, S., Smetanscaia, A., Valica, V., Uncu, L., Kravtsov, V., Melnik, E., Petrou, A., Glamočlija, J., Soković, M., Carazo, A., Mladěnka, P., Poroikov, V., Geronikaki, A.,& Macaev, F.. (2021). Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation. in Molecules
Basel: MDPI., 26(14), 4304.
https://doi.org/10.3390/molecules26144304

Zveaghintseva M, Stingaci E, Pogrebnoi S, Smetanscaia A, Valica V, Uncu L, Kravtsov V, Melnik E, Petrou A, Glamočlija J, Soković M, Carazo A, Mladěnka P, Poroikov V, Geronikaki A, Macaev F. Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation. in Molecules. 2021;26(14):4304.
doi:10.3390/molecules26144304 .

Zveaghintseva, Marina, Stingaci, Eugenia, Pogrebnoi, Sergei, Smetanscaia, Anastasia, Valica, Vladimir, Uncu, Livia, Kravtsov, Victor, Melnik, Elena, Petrou, Anthi, Glamočlija, Jasmina, Soković, Marina, Carazo, Alejandro, Mladěnka, Přemysl, Poroikov, Vladimir, Geronikaki, Athina, Macaev, Fliur, "Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation" in Molecules, 26, no. 14 (2021):4304,
https://doi.org/10.3390/molecules26144304 . .

TY  - JOUR
AU  - Stingaci, Eugenia
AU  - Zveaghinteva, Marina
AU  - Pogrebnoi, Serghei
AU  - Lupascu, Lucian
AU  - Valica, Vladimir
AU  - Uncu, Livia
AU  - Smetanscaia, Anastasia
AU  - Drumea, Maricica
AU  - Petrou, Anthi
AU  - Ćirić, Ana
AU  - Glamočlija, Jasmina
AU  - Soković, Marina
AU  - Kravtsov, Victor
AU  - Geronikaki, Athina
AU  - Macaev, Fliur
PY  - 2020
UR  - https://linkinghub.elsevier.com/retrieve/pii/S0960894X20304790
UR  - https://radar.ibiss.bg.ac.rs/handle/123456789/3761
AB  - 1,2,4-Triazole is a very important scaffold in medicinal chemistry due to the wide spectrum of biological activities and mainly antifungal activity of 1,2,4-triazole derivatives. The main mechanism of antifungal action of the latter is inhibition of 14-alpha-demethylase enzyme (CYP51). The current study presents synthesis and evaluation of eight triazole derivatives for their antimicrobial activity. Docking studies to elucidate the mechanism of action were also performed. The designed compounds were synthesized using classical methods of organic synthesis. The in vivo evaluation of antimicrobial activity was performed by microdilution method. All tested compounds showed good antibacterial activity with MIC and MBC values ranging from 0.0002 to 0.0069 mM. Compound 2 h appeared to be the most active among all tested with MIC at 0.0002–0.0033 mM and MBC at 0.0004–0.0033 mM followed by compounds 2f and 2g. The most sensitive bacterium appeared to be Xanthomonas campestris while Erwinia amylovora was the most resistant. The evaluation of antifungal activity revealed that all compounds showed good antifungal activity with MIC values ranging from 0.02 mM to 0.52 mM and MFC from 0.03 mM to 0.52 mM better than reference drugs ketoconazole (MIC and MFC values at 0.28–1.88 mM and 0.38 mM to 2.82 mM respectively) and bifonazole (MIC and MFC values at 0.32–0.64 mM and 0.64–0.81 mM). The best antifungal activity is displayed by compound 2 h with MIC at 0.02–0.04 mM and MFC at 0.03–0.06 mM while compound 2a showed the lowest activity. The results showed that these compounds could be lead compounds in search for new potent antimicrobial agents. Docking studies confirmed experimental results.
PB  - Elsevier BV
T2  - Bioorganic & Medicinal Chemistry Letters
T1  - New vinyl-1,2,4-triazole derivatives as antimicrobial agents: Synthesis, biological evaluation and molecular docking studies
IS  - 17
VL  - 30
DO  - 10.1016/j.bmcl.2020.127368
SP  - 127368
ER  - 

@article{
author = "Stingaci, Eugenia and Zveaghinteva, Marina and Pogrebnoi, Serghei and Lupascu, Lucian and Valica, Vladimir and Uncu, Livia and Smetanscaia, Anastasia and Drumea, Maricica and Petrou, Anthi and Ćirić, Ana and Glamočlija, Jasmina and Soković, Marina and Kravtsov, Victor and Geronikaki, Athina and Macaev, Fliur",
year = "2020",
abstract = "1,2,4-Triazole is a very important scaffold in medicinal chemistry due to the wide spectrum of biological activities and mainly antifungal activity of 1,2,4-triazole derivatives. The main mechanism of antifungal action of the latter is inhibition of 14-alpha-demethylase enzyme (CYP51). The current study presents synthesis and evaluation of eight triazole derivatives for their antimicrobial activity. Docking studies to elucidate the mechanism of action were also performed. The designed compounds were synthesized using classical methods of organic synthesis. The in vivo evaluation of antimicrobial activity was performed by microdilution method. All tested compounds showed good antibacterial activity with MIC and MBC values ranging from 0.0002 to 0.0069 mM. Compound 2 h appeared to be the most active among all tested with MIC at 0.0002–0.0033 mM and MBC at 0.0004–0.0033 mM followed by compounds 2f and 2g. The most sensitive bacterium appeared to be Xanthomonas campestris while Erwinia amylovora was the most resistant. The evaluation of antifungal activity revealed that all compounds showed good antifungal activity with MIC values ranging from 0.02 mM to 0.52 mM and MFC from 0.03 mM to 0.52 mM better than reference drugs ketoconazole (MIC and MFC values at 0.28–1.88 mM and 0.38 mM to 2.82 mM respectively) and bifonazole (MIC and MFC values at 0.32–0.64 mM and 0.64–0.81 mM). The best antifungal activity is displayed by compound 2 h with MIC at 0.02–0.04 mM and MFC at 0.03–0.06 mM while compound 2a showed the lowest activity. The results showed that these compounds could be lead compounds in search for new potent antimicrobial agents. Docking studies confirmed experimental results.",
publisher = "Elsevier BV",
journal = "Bioorganic & Medicinal Chemistry Letters",
title = "New vinyl-1,2,4-triazole derivatives as antimicrobial agents: Synthesis, biological evaluation and molecular docking studies",
number = "17",
volume = "30",
doi = "10.1016/j.bmcl.2020.127368",
pages = "127368"
}

Stingaci, E., Zveaghinteva, M., Pogrebnoi, S., Lupascu, L., Valica, V., Uncu, L., Smetanscaia, A., Drumea, M., Petrou, A., Ćirić, A., Glamočlija, J., Soković, M., Kravtsov, V., Geronikaki, A.,& Macaev, F.. (2020). New vinyl-1,2,4-triazole derivatives as antimicrobial agents: Synthesis, biological evaluation and molecular docking studies. in Bioorganic & Medicinal Chemistry Letters
Elsevier BV., 30(17), 127368.
https://doi.org/10.1016/j.bmcl.2020.127368

Stingaci E, Zveaghinteva M, Pogrebnoi S, Lupascu L, Valica V, Uncu L, Smetanscaia A, Drumea M, Petrou A, Ćirić A, Glamočlija J, Soković M, Kravtsov V, Geronikaki A, Macaev F. New vinyl-1,2,4-triazole derivatives as antimicrobial agents: Synthesis, biological evaluation and molecular docking studies. in Bioorganic & Medicinal Chemistry Letters. 2020;30(17):127368.
doi:10.1016/j.bmcl.2020.127368 .

Stingaci, Eugenia, Zveaghinteva, Marina, Pogrebnoi, Serghei, Lupascu, Lucian, Valica, Vladimir, Uncu, Livia, Smetanscaia, Anastasia, Drumea, Maricica, Petrou, Anthi, Ćirić, Ana, Glamočlija, Jasmina, Soković, Marina, Kravtsov, Victor, Geronikaki, Athina, Macaev, Fliur, "New vinyl-1,2,4-triazole derivatives as antimicrobial agents: Synthesis, biological evaluation and molecular docking studies" in Bioorganic & Medicinal Chemistry Letters, 30, no. 17 (2020):127368,
https://doi.org/10.1016/j.bmcl.2020.127368 . .