Synthesis, Molecular Docking Analysis and Biological Evaluations of Saccharide-Modified Thiadiazole Sulfonamide Derivatives
A series of saccharide-modified thiadiazole sulfonamide derivatives has been designed and synthesized by the “tail approach” and evaluated for inhibitory activity against carbonic anhydrases II, IX, and XII. Most of the compounds showed high topological polar surface area (TPSA) values and excellent...
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MDPI AG
2021-05-01
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author | Zuo-Peng Zhang Ye Zhong Zhen-Bin Han Lin Zhou Hua-Sheng Su Jian Wang Yang Liu Mao-Sheng Cheng |
author_facet | Zuo-Peng Zhang Ye Zhong Zhen-Bin Han Lin Zhou Hua-Sheng Su Jian Wang Yang Liu Mao-Sheng Cheng |
author_sort | Zuo-Peng Zhang |
collection | DOAJ |
description | A series of saccharide-modified thiadiazole sulfonamide derivatives has been designed and synthesized by the “tail approach” and evaluated for inhibitory activity against carbonic anhydrases II, IX, and XII. Most of the compounds showed high topological polar surface area (TPSA) values and excellent enzyme inhibitory activity. The impacts of some compounds on the viability of HT-29, MDA-MB-231, and MG-63 human cancer cell lines were examined under both normoxic and hypoxic conditions, and they showed certain inhibitory effects on cell viability. Moreover, it was found that the series of compounds had the ability to raise the pH of the tumor cell microenvironment. All the results proved that saccharide-modified thiadiazole sulfonamides have important research prospects for the development of CA IX inhibitors. |
first_indexed | 2024-03-10T11:07:59Z |
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issn | 1661-6596 1422-0067 |
language | English |
last_indexed | 2024-03-10T11:07:59Z |
publishDate | 2021-05-01 |
publisher | MDPI AG |
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series | International Journal of Molecular Sciences |
spelling | doaj.art-0fa2a3c23ae5487c89c58e41c61bc9ab2023-11-21T20:57:23ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-05-012211548210.3390/ijms22115482Synthesis, Molecular Docking Analysis and Biological Evaluations of Saccharide-Modified Thiadiazole Sulfonamide DerivativesZuo-Peng Zhang0Ye Zhong1Zhen-Bin Han2Lin Zhou3Hua-Sheng Su4Jian Wang5Yang Liu6Mao-Sheng Cheng7Key Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, ChinaKey Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, ChinaKey Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, ChinaKey Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, ChinaKey Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, ChinaKey Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, ChinaKey Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, ChinaKey Laboratory of Structure-Based Drug Design & Discovery of Ministry of Education, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, ChinaA series of saccharide-modified thiadiazole sulfonamide derivatives has been designed and synthesized by the “tail approach” and evaluated for inhibitory activity against carbonic anhydrases II, IX, and XII. Most of the compounds showed high topological polar surface area (TPSA) values and excellent enzyme inhibitory activity. The impacts of some compounds on the viability of HT-29, MDA-MB-231, and MG-63 human cancer cell lines were examined under both normoxic and hypoxic conditions, and they showed certain inhibitory effects on cell viability. Moreover, it was found that the series of compounds had the ability to raise the pH of the tumor cell microenvironment. All the results proved that saccharide-modified thiadiazole sulfonamides have important research prospects for the development of CA IX inhibitors.https://www.mdpi.com/1422-0067/22/11/5482saccharidetail approachpH of the tumor cell microenvironmentCA IX inhibitors |
spellingShingle | Zuo-Peng Zhang Ye Zhong Zhen-Bin Han Lin Zhou Hua-Sheng Su Jian Wang Yang Liu Mao-Sheng Cheng Synthesis, Molecular Docking Analysis and Biological Evaluations of Saccharide-Modified Thiadiazole Sulfonamide Derivatives International Journal of Molecular Sciences saccharide tail approach pH of the tumor cell microenvironment CA IX inhibitors |
title | Synthesis, Molecular Docking Analysis and Biological Evaluations of Saccharide-Modified Thiadiazole Sulfonamide Derivatives |
title_full | Synthesis, Molecular Docking Analysis and Biological Evaluations of Saccharide-Modified Thiadiazole Sulfonamide Derivatives |
title_fullStr | Synthesis, Molecular Docking Analysis and Biological Evaluations of Saccharide-Modified Thiadiazole Sulfonamide Derivatives |
title_full_unstemmed | Synthesis, Molecular Docking Analysis and Biological Evaluations of Saccharide-Modified Thiadiazole Sulfonamide Derivatives |
title_short | Synthesis, Molecular Docking Analysis and Biological Evaluations of Saccharide-Modified Thiadiazole Sulfonamide Derivatives |
title_sort | synthesis molecular docking analysis and biological evaluations of saccharide modified thiadiazole sulfonamide derivatives |
topic | saccharide tail approach pH of the tumor cell microenvironment CA IX inhibitors |
url | https://www.mdpi.com/1422-0067/22/11/5482 |
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