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Article

Antimicrobial Activity of Nitrogen-Containing 5-α-Androstane Derivatives: In Silico and Experimental Studies

1
TSMU I. Kutateladze Institute of Pharmacochemistry, P. Sarajishvili str. 36, Tbilisi 0159, Georgia
2
University of Patras, 26500 Patra, Greece
3
School of Pharmacy, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece
4
Institute of Biomedical Chemistry, 119121 Moscow, Russia
5
Mycological Laboratory, Department of Plant Physiology, Institute for Biological Research “Siniša Stanković”, University of Belgrade, 11060 Beograd, Serbia
*
Author to whom correspondence should be addressed.
Antibiotics 2020, 9(5), 224; https://doi.org/10.3390/antibiotics9050224
Received: 5 April 2020 / Revised: 25 April 2020 / Accepted: 27 April 2020 / Published: 30 April 2020
We evaluated the antimicrobial activity of thirty-one nitrogen-containing 5-α-androstane derivatives in silico using computer program PASS (Prediction of Activity Spectra for Substances) and freely available PASS-based web applications (such as Way2Drug). Antibacterial activity was predicted for 27 out of 31 molecules; antifungal activity was predicted for 25 out of 31 compounds. The results of experiments, which we conducted to study the antimicrobial activity, are in agreement with the predictions. All compounds were found to be active with MIC (Minimum Inhibitory Concentration) and MBC (Minimum Bactericidal Concentration) values in the range of 0.0005–0.6 mg/mL. The activity of all studied 5-α-androstane derivatives exceeded or was equal to those of Streptomycin and, except for the 3β-hydroxy-17α-aza-d-homo-5α-androstane-17-one, all molecules were more active than Ampicillin. Activity against the resistant strains of E. coli, P. aeruginosa, and methicillin-resistant Staphylococcus aureus was also shown in experiments. Antifungal activity was determined with MIC and MFC (Minimum Fungicidal Concentration) values varying from 0.007 to 0.6 mg/mL. Most of the compounds were found to be more potent than the reference drugs Bifonazole and Ketoconazole. According to the results of docking studies, the putative targets for antibacterial and antifungal activity are UDP-N-acetylenolpyruvoylglucosamine reductase and 14-α-demethylase, respectively. In silico assessments of the acute rodent toxicity and cytotoxicity obtained using GUSAR (General Unrestricted Structure-Activity Relationships) and CLC-Pred (Cell Line Cytotoxicity Predictor) web-services were low for the majority of compounds under study, which contributes to the chances for those compounds to advance in the development. View Full-Text
Keywords: antibacterial activity; antifungal activity; potency against the resistant strains; PASS; GUSAR; CLC-Pred; molecular docking; UDP-N-acetylenolpyruvoylglucosamine reductase inhibition; 14α-demethylase inhibition antibacterial activity; antifungal activity; potency against the resistant strains; PASS; GUSAR; CLC-Pred; molecular docking; UDP-N-acetylenolpyruvoylglucosamine reductase inhibition; 14α-demethylase inhibition
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MDPI and ACS Style

Amiranashvili, L.; Nadaraia, N.; Merlani, M.; Kamoutsis, C.; Petrou, A.; Geronikaki, A.; Pogodin, P.; Druzhilovskiy, D.; Poroikov, V.; Ciric, A.; Glamočlija, J.; Sokovic, M. Antimicrobial Activity of Nitrogen-Containing 5-α-Androstane Derivatives: In Silico and Experimental Studies. Antibiotics 2020, 9, 224. https://doi.org/10.3390/antibiotics9050224

AMA Style

Amiranashvili L, Nadaraia N, Merlani M, Kamoutsis C, Petrou A, Geronikaki A, Pogodin P, Druzhilovskiy D, Poroikov V, Ciric A, Glamočlija J, Sokovic M. Antimicrobial Activity of Nitrogen-Containing 5-α-Androstane Derivatives: In Silico and Experimental Studies. Antibiotics. 2020; 9(5):224. https://doi.org/10.3390/antibiotics9050224

Chicago/Turabian Style

Amiranashvili, Lela, Nanuli Nadaraia, Maia Merlani, Charalampos Kamoutsis, Anthi Petrou, Athina Geronikaki, Pavel Pogodin, Dmitry Druzhilovskiy, Vladimir Poroikov, Ana Ciric, Jasmina Glamočlija, and Marina Sokovic. 2020. "Antimicrobial Activity of Nitrogen-Containing 5-α-Androstane Derivatives: In Silico and Experimental Studies" Antibiotics 9, no. 5: 224. https://doi.org/10.3390/antibiotics9050224

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