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, <i>Candida parapsilosis</i>, <i>Candida albicans</i>, <i>Candida tropicalis</i>, <i>Aspergillus niger</i>, and <i...
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MDPI AG
2020-06-01
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| Series: | Antibiotics |
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| Online Access: | https://www.mdpi.com/2079-6382/9/6/350 |
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| author | Katharigatta N. Venugopala Mohammed A. Khedr Yarabahally R. Girish Subhrajyoti Bhandary Deepak Chopra Mohamed A. Morsy Bandar E. Aldhubiab Pran Kishore Deb Mahesh Attimarad Anroop B. Nair Nagaraja Sreeharsha Rashmi V Mahmoud Kandeel Sabah H. Akrawi Madhusudana Reddy M B Sheena Shashikanth Osama I. Alwassil Viresh Mohanlall |
| author_facet | Katharigatta N. Venugopala Mohammed A. Khedr Yarabahally R. Girish Subhrajyoti Bhandary Deepak Chopra Mohamed A. Morsy Bandar E. Aldhubiab Pran Kishore Deb Mahesh Attimarad Anroop B. Nair Nagaraja Sreeharsha Rashmi V Mahmoud Kandeel Sabah H. Akrawi Madhusudana Reddy M B Sheena Shashikanth Osama I. Alwassil Viresh Mohanlall |
| author_sort | Katharigatta N. Venugopala |
| collection | DOAJ |
| description | A series of 2,4,5 trisubstituted-1,2,3-triazole analogues have been screened for their antifungal activity against five fungal strains, <i>Candida parapsilosis</i>, <i>Candida albicans</i>, <i>Candida tropicalis</i>, <i>Aspergillus niger</i>, and <i>Trichophyton rubrum</i>, 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 <i>Candida albicans</i> 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. |
| first_indexed | 2024-03-10T19:00:31Z |
| format | Article |
| id | doaj.art-ad540e01a94d4a088b8f1a757c24e83c |
| institution | Directory Open Access Journal |
| issn | 2079-6382 |
| language | English |
| last_indexed | 2024-03-10T19:00:31Z |
| publishDate | 2020-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antibiotics |
| spelling | doaj.art-ad540e01a94d4a088b8f1a757c24e83c2023-11-20T04:28:10ZengMDPI AGAntibiotics2079-63822020-06-019635010.3390/antibiotics9060350Crystallography, in Silico Studies, and In Vitro Antifungal Studies of 2,4,5 Trisubstituted 1,2,3-Triazole AnaloguesKatharigatta N. Venugopala0Mohammed A. Khedr1Yarabahally R. Girish2Subhrajyoti Bhandary3Deepak Chopra4Mohamed A. Morsy5Bandar E. Aldhubiab6Pran Kishore Deb7Mahesh Attimarad8Anroop B. Nair9Nagaraja Sreeharsha10Rashmi V11Mahmoud Kandeel12Sabah H. Akrawi13Madhusudana Reddy M B14Sheena Shashikanth15Osama I. Alwassil16Viresh Mohanlall17Department of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi ArabiaDepartment of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi ArabiaACU-Center for Research and Innovations, BGSIT Campus, Adichunchanagiri University, B.G. Nagara, Mandya District 571448, IndiaDepartment of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal By-pass Road, Bhauri, Bhopal 462066, IndiaDepartment of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal By-pass Road, Bhauri, Bhopal 462066, IndiaDepartment of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi ArabiaDepartment of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi ArabiaFaculty of Pharmacy, Philadelphia University, Amman 19392, JordanDepartment of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi ArabiaDepartment of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi ArabiaDepartment of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi ArabiaDepartment of Public health Medicine, University of KwaZulu-Natal, Howard College Campus, Durban 4041, South AfricaDepartment of Biomedical Sciences, College of Veterinary Medicine, King Faisal University, Al-Ahsa 31982, Saudi ArabiaDepartment of Pharmaceutical Sciences, College of Clinical Pharmacy, King Faisal University, Al-Ahsa 31982, Saudi ArabiaDepartment of Chemistry, School of Applied Sciences, REVA University, Bangalore 560064, IndiaDepartment of Studies in Organic Chemistry, University of Mysore, Manasagangotri, Mysore 570006, IndiaDepartment of Pharmaceutical Sciences, College of Pharmacy, King Saud bin Abdulaziz University for Health Sciences, Riyadh 11481, Saudi ArabiaDepartment of Biotechnology and Food Technology, Durban University of Technology, Durban 4001, South AfricaA series of 2,4,5 trisubstituted-1,2,3-triazole analogues have been screened for their antifungal activity against five fungal strains, <i>Candida parapsilosis</i>, <i>Candida albicans</i>, <i>Candida tropicalis</i>, <i>Aspergillus niger</i>, and <i>Trichophyton rubrum</i>, 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 <i>Candida albicans</i> 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.https://www.mdpi.com/2079-6382/9/6/3502,4,5 trisubstituted 1,2,3-triazolesantifungal activitysingle-crystal X-ray diffractionminimum inhibitory concentrationmolecular dockingdynamic studies |
| spellingShingle | Katharigatta N. Venugopala Mohammed A. Khedr Yarabahally R. Girish Subhrajyoti Bhandary Deepak Chopra Mohamed A. Morsy Bandar E. Aldhubiab Pran Kishore Deb Mahesh Attimarad Anroop B. Nair Nagaraja Sreeharsha Rashmi V Mahmoud Kandeel Sabah H. Akrawi Madhusudana Reddy M B Sheena Shashikanth Osama I. Alwassil Viresh Mohanlall Crystallography, in Silico Studies, and In Vitro Antifungal Studies of 2,4,5 Trisubstituted 1,2,3-Triazole Analogues Antibiotics 2,4,5 trisubstituted 1,2,3-triazoles antifungal activity single-crystal X-ray diffraction minimum inhibitory concentration molecular docking dynamic studies |
| 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 | 2,4,5 trisubstituted 1,2,3-triazoles antifungal activity single-crystal X-ray diffraction minimum inhibitory concentration molecular docking dynamic studies |
| url | https://www.mdpi.com/2079-6382/9/6/350 |
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