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Crystallography, in Silico Studies, and In Vitro Antifungal Studies of 2,4,5 Trisubstituted 1,2,3-Triazole Analogues
A series of 2,4,5 trisubstituted-1,2,3-triazole analogues have been screened for their antifungal activity against five fungal strains, Candida parapsilosis, Candida albicans, Candida tropicalis, Aspergillus niger, and Trichophyton rubrum, via a 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium b...
Autores principales: | , , , , , , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7344790/ https://www.ncbi.nlm.nih.gov/pubmed/32575727 http://dx.doi.org/10.3390/antibiotics9060350 |
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author | Venugopala, Katharigatta N. Khedr, Mohammed A. Girish, Yarabahally R. Bhandary, Subhrajyoti Chopra, Deepak Morsy, Mohamed A. Aldhubiab, Bandar E. Deb, Pran Kishore Attimarad, Mahesh Nair, Anroop B. Sreeharsha, Nagaraja V, Rashmi Kandeel, Mahmoud Akrawi, Sabah H. Reddy M B, Madhusudana Shashikanth, Sheena Alwassil, Osama I. Mohanlall, Viresh |
author_facet | Venugopala, Katharigatta N. Khedr, Mohammed A. Girish, Yarabahally R. Bhandary, Subhrajyoti Chopra, Deepak Morsy, Mohamed A. Aldhubiab, Bandar E. Deb, Pran Kishore Attimarad, Mahesh Nair, Anroop B. Sreeharsha, Nagaraja V, Rashmi Kandeel, Mahmoud Akrawi, Sabah H. Reddy M B, Madhusudana Shashikanth, Sheena Alwassil, Osama I. Mohanlall, Viresh |
author_sort | Venugopala, Katharigatta N. |
collection | PubMed |
description | A series of 2,4,5 trisubstituted-1,2,3-triazole analogues have been screened for their antifungal activity against five fungal strains, Candida parapsilosis, Candida albicans, Candida tropicalis, Aspergillus niger, and Trichophyton rubrum, via a 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) microdilution assay. Compounds GKV10, GKV11, and GKV15 emerged as promising antifungal agents against all the fungal strains used in the current study. One of the highly active antifungal compounds, GKV10, was selected for a single-crystal X-ray diffraction analysis to unequivocally establish its molecular structure, conformation, and to understand the presence of different intermolecular interactions in its crystal lattice. A cooperative synergy of the C-H···O, C-H···N, C-H···S, C-H···π, and π···π intermolecular interactions was present in the crystal structure, which contributed towards the overall stabilization of the lattice. A molecular docking study was conducted for all the test compounds against Candida albicans lanosterol-14α-demethylase (pdb = 5 tzl). The binding stability of the highly promising antifungal test compound, GKV15, from the series was then evaluated by molecular dynamics studies. |
format | Online Article Text |
id | pubmed-7344790 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-73447902020-07-09 Crystallography, in Silico Studies, and In Vitro Antifungal Studies of 2,4,5 Trisubstituted 1,2,3-Triazole Analogues Venugopala, Katharigatta N. Khedr, Mohammed A. Girish, Yarabahally R. Bhandary, Subhrajyoti Chopra, Deepak Morsy, Mohamed A. Aldhubiab, Bandar E. Deb, Pran Kishore Attimarad, Mahesh Nair, Anroop B. Sreeharsha, Nagaraja V, Rashmi Kandeel, Mahmoud Akrawi, Sabah H. Reddy M B, Madhusudana Shashikanth, Sheena Alwassil, Osama I. Mohanlall, Viresh Antibiotics (Basel) Article A series of 2,4,5 trisubstituted-1,2,3-triazole analogues have been screened for their antifungal activity against five fungal strains, Candida parapsilosis, Candida albicans, Candida tropicalis, Aspergillus niger, and Trichophyton rubrum, via a 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) microdilution assay. Compounds GKV10, GKV11, and GKV15 emerged as promising antifungal agents against all the fungal strains used in the current study. One of the highly active antifungal compounds, GKV10, was selected for a single-crystal X-ray diffraction analysis to unequivocally establish its molecular structure, conformation, and to understand the presence of different intermolecular interactions in its crystal lattice. A cooperative synergy of the C-H···O, C-H···N, C-H···S, C-H···π, and π···π intermolecular interactions was present in the crystal structure, which contributed towards the overall stabilization of the lattice. A molecular docking study was conducted for all the test compounds against Candida albicans lanosterol-14α-demethylase (pdb = 5 tzl). The binding stability of the highly promising antifungal test compound, GKV15, from the series was then evaluated by molecular dynamics studies. MDPI 2020-06-20 /pmc/articles/PMC7344790/ /pubmed/32575727 http://dx.doi.org/10.3390/antibiotics9060350 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Venugopala, Katharigatta N. Khedr, Mohammed A. Girish, Yarabahally R. Bhandary, Subhrajyoti Chopra, Deepak Morsy, Mohamed A. Aldhubiab, Bandar E. Deb, Pran Kishore Attimarad, Mahesh Nair, Anroop B. Sreeharsha, Nagaraja V, Rashmi Kandeel, Mahmoud Akrawi, Sabah H. Reddy M B, Madhusudana Shashikanth, Sheena Alwassil, Osama I. Mohanlall, Viresh Crystallography, in Silico Studies, and In Vitro Antifungal Studies of 2,4,5 Trisubstituted 1,2,3-Triazole Analogues |
title | Crystallography, in Silico Studies, and In Vitro Antifungal Studies of 2,4,5 Trisubstituted 1,2,3-Triazole Analogues |
title_full | Crystallography, in Silico Studies, and In Vitro Antifungal Studies of 2,4,5 Trisubstituted 1,2,3-Triazole Analogues |
title_fullStr | Crystallography, in Silico Studies, and In Vitro Antifungal Studies of 2,4,5 Trisubstituted 1,2,3-Triazole Analogues |
title_full_unstemmed | Crystallography, in Silico Studies, and In Vitro Antifungal Studies of 2,4,5 Trisubstituted 1,2,3-Triazole Analogues |
title_short | Crystallography, in Silico Studies, and In Vitro Antifungal Studies of 2,4,5 Trisubstituted 1,2,3-Triazole Analogues |
title_sort | crystallography, in silico studies, and in vitro antifungal studies of 2,4,5 trisubstituted 1,2,3-triazole analogues |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7344790/ https://www.ncbi.nlm.nih.gov/pubmed/32575727 http://dx.doi.org/10.3390/antibiotics9060350 |
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