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Isolation and Evaluation of the Enantiospecific Antitubercular Activity of a Novel Triazole Compound
Cyclohex-3-enyl(5-phenyl-4H-1,2,4-triazol-3-yl)methanol (MSDRT 12) is a novel triazole-based antitubercular compound with two chiral centers. To evaluate the enantiospecific antitubercular activity, the four stereoisomers were isolated using preparative chiral chromatography and the individual stere...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Österreichische Apotheker-Verlagsgesellschaft
2014
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3951235/ https://www.ncbi.nlm.nih.gov/pubmed/24634844 http://dx.doi.org/10.3797/scipharm.1308-15 |
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author | Shekar, Radha Sinha, Barij Nayan Mukhopadhya, Arindam Degani, Mariam S. |
author_facet | Shekar, Radha Sinha, Barij Nayan Mukhopadhya, Arindam Degani, Mariam S. |
author_sort | Shekar, Radha |
collection | PubMed |
description | Cyclohex-3-enyl(5-phenyl-4H-1,2,4-triazol-3-yl)methanol (MSDRT 12) is a novel triazole-based antitubercular compound with two chiral centers. To evaluate the enantiospecific antitubercular activity, the four stereoisomers were isolated using preparative chiral chromatography and the individual stereoisomers were evaluated using the resazurin microtiter assay method (REMA) and a microbroth dilution technique against the Mycobacterium tuberculosis H37Rv strain. Isomer III of MSDRT 12 was found to be the most potent with a minimum inhibitory concentration (MIC) of 0.78 μg/mL, Isomer II had a MIC of 12.5 μg/mL, and isomers I and IV showed no activity. The diastereomeric mixture of MSDRT 12 showed a MIC of 3.125 μg/mL and isoniazid, used as the standard drug, showed a MIC of 0.4 μg/mL. This confirms the necessity of screening individual enantiomers for their pharmacological activity early in the discovery phase to identify the most potent isomer for further development efforts. |
format | Online Article Text |
id | pubmed-3951235 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | Österreichische Apotheker-Verlagsgesellschaft |
record_format | MEDLINE/PubMed |
spelling | pubmed-39512352014-03-14 Isolation and Evaluation of the Enantiospecific Antitubercular Activity of a Novel Triazole Compound Shekar, Radha Sinha, Barij Nayan Mukhopadhya, Arindam Degani, Mariam S. Sci Pharm Research Article Cyclohex-3-enyl(5-phenyl-4H-1,2,4-triazol-3-yl)methanol (MSDRT 12) is a novel triazole-based antitubercular compound with two chiral centers. To evaluate the enantiospecific antitubercular activity, the four stereoisomers were isolated using preparative chiral chromatography and the individual stereoisomers were evaluated using the resazurin microtiter assay method (REMA) and a microbroth dilution technique against the Mycobacterium tuberculosis H37Rv strain. Isomer III of MSDRT 12 was found to be the most potent with a minimum inhibitory concentration (MIC) of 0.78 μg/mL, Isomer II had a MIC of 12.5 μg/mL, and isomers I and IV showed no activity. The diastereomeric mixture of MSDRT 12 showed a MIC of 3.125 μg/mL and isoniazid, used as the standard drug, showed a MIC of 0.4 μg/mL. This confirms the necessity of screening individual enantiomers for their pharmacological activity early in the discovery phase to identify the most potent isomer for further development efforts. Österreichische Apotheker-Verlagsgesellschaft 2014 2013-10-21 /pmc/articles/PMC3951235/ /pubmed/24634844 http://dx.doi.org/10.3797/scipharm.1308-15 Text en © Shekar et al.; licensee Österreichische Apotheker-Verlagsgesellschaft m. b. H., Vienna, Austria. This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/3.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Research Article Shekar, Radha Sinha, Barij Nayan Mukhopadhya, Arindam Degani, Mariam S. Isolation and Evaluation of the Enantiospecific Antitubercular Activity of a Novel Triazole Compound |
title | Isolation and Evaluation of the Enantiospecific Antitubercular Activity of a Novel Triazole Compound |
title_full | Isolation and Evaluation of the Enantiospecific Antitubercular Activity of a Novel Triazole Compound |
title_fullStr | Isolation and Evaluation of the Enantiospecific Antitubercular Activity of a Novel Triazole Compound |
title_full_unstemmed | Isolation and Evaluation of the Enantiospecific Antitubercular Activity of a Novel Triazole Compound |
title_short | Isolation and Evaluation of the Enantiospecific Antitubercular Activity of a Novel Triazole Compound |
title_sort | isolation and evaluation of the enantiospecific antitubercular activity of a novel triazole compound |
topic | Research Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3951235/ https://www.ncbi.nlm.nih.gov/pubmed/24634844 http://dx.doi.org/10.3797/scipharm.1308-15 |
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