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Design, synthesis, and molecular docking studies of N-substituted sulfonamides as potential anticancer therapeutics
OBJECTIVES: The goal of this study was to design and enable development of anticancer sulfonamides by coupling amines and dansyl chloride with strategically selected substituents. The synthesized structures were characterized by NMR and mass spectrometry. In addition, molecular docking analysis was...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Taibah University
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10692713/ https://www.ncbi.nlm.nih.gov/pubmed/38047237 http://dx.doi.org/10.1016/j.jtumed.2023.10.006 |
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author | Babalola, Ibrahim T. Suleiman, Garba |
author_facet | Babalola, Ibrahim T. Suleiman, Garba |
author_sort | Babalola, Ibrahim T. |
collection | PubMed |
description | OBJECTIVES: The goal of this study was to design and enable development of anticancer sulfonamides by coupling amines and dansyl chloride with strategically selected substituents. The synthesized structures were characterized by NMR and mass spectrometry. In addition, molecular docking analysis was used to determine the binding ability of sulfonamides toward 1AZM, a possible drug target, as compared with that of the well-known drug acetazolamide. METHODS: Sulfonamides were synthesized by coupling amines and dansyl chloride under highly favorable conditions. The designed sulfonamides incorporated strategically positioned substituents to impart diverse biological properties. The synthesized structures were validated with NMR and mass spectra. Molecular docking analysis was performed to evaluate the binding affinities of the synthesized sulfonamides with the potential drug target 1AZM. RESULTS: The synthesis of sulfonamides through the coupling of amines and dansyl chloride was successfully achieved. The validation of the synthesized structures with NMR and mass spectra confirmed their chemical identities. Molecular docking analysis revealed that the synthesized sulfonamides displayed binding affinities ranging from −6.8 to −8.2 kcal/mol toward the potential drug target 1AZM. Importantly, all derivatives exhibited superior binding affinities to acetazolamide (−5.25 kcal/mol). CONCLUSIONS: The coupling of amines and dansyl chloride enabled efficient, straightforward sulfonamide synthesis. The strategic design of sulfonamides with specific substituents endows diverse biological properties, including potential anti-cancer activity. The elucidation of the synthesized compounds with NMR and mass spectra confirmed their structures. Molecular docking analysis demonstrated that the synthesized sulfonamides exhibited favorable binding affinities toward the potential drug target 1AZM. Notably, all derivatives displayed higher binding affinities, ranging from −6.8 to −8.2 kcal/mol, than the recommended drug acetazolamide (−5.25 kcal/mol), thus suggesting their potential as highly effective analogues for further validation in cancer therapy. |
format | Online Article Text |
id | pubmed-10692713 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | Taibah University |
record_format | MEDLINE/PubMed |
spelling | pubmed-106927132023-12-03 Design, synthesis, and molecular docking studies of N-substituted sulfonamides as potential anticancer therapeutics Babalola, Ibrahim T. Suleiman, Garba J Taibah Univ Med Sci Original Article OBJECTIVES: The goal of this study was to design and enable development of anticancer sulfonamides by coupling amines and dansyl chloride with strategically selected substituents. The synthesized structures were characterized by NMR and mass spectrometry. In addition, molecular docking analysis was used to determine the binding ability of sulfonamides toward 1AZM, a possible drug target, as compared with that of the well-known drug acetazolamide. METHODS: Sulfonamides were synthesized by coupling amines and dansyl chloride under highly favorable conditions. The designed sulfonamides incorporated strategically positioned substituents to impart diverse biological properties. The synthesized structures were validated with NMR and mass spectra. Molecular docking analysis was performed to evaluate the binding affinities of the synthesized sulfonamides with the potential drug target 1AZM. RESULTS: The synthesis of sulfonamides through the coupling of amines and dansyl chloride was successfully achieved. The validation of the synthesized structures with NMR and mass spectra confirmed their chemical identities. Molecular docking analysis revealed that the synthesized sulfonamides displayed binding affinities ranging from −6.8 to −8.2 kcal/mol toward the potential drug target 1AZM. Importantly, all derivatives exhibited superior binding affinities to acetazolamide (−5.25 kcal/mol). CONCLUSIONS: The coupling of amines and dansyl chloride enabled efficient, straightforward sulfonamide synthesis. The strategic design of sulfonamides with specific substituents endows diverse biological properties, including potential anti-cancer activity. The elucidation of the synthesized compounds with NMR and mass spectra confirmed their structures. Molecular docking analysis demonstrated that the synthesized sulfonamides exhibited favorable binding affinities toward the potential drug target 1AZM. Notably, all derivatives displayed higher binding affinities, ranging from −6.8 to −8.2 kcal/mol, than the recommended drug acetazolamide (−5.25 kcal/mol), thus suggesting their potential as highly effective analogues for further validation in cancer therapy. Taibah University 2023-11-04 /pmc/articles/PMC10692713/ /pubmed/38047237 http://dx.doi.org/10.1016/j.jtumed.2023.10.006 Text en © 2023 The Authors https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Original Article Babalola, Ibrahim T. Suleiman, Garba Design, synthesis, and molecular docking studies of N-substituted sulfonamides as potential anticancer therapeutics |
title | Design, synthesis, and molecular docking studies of N-substituted sulfonamides as potential anticancer therapeutics |
title_full | Design, synthesis, and molecular docking studies of N-substituted sulfonamides as potential anticancer therapeutics |
title_fullStr | Design, synthesis, and molecular docking studies of N-substituted sulfonamides as potential anticancer therapeutics |
title_full_unstemmed | Design, synthesis, and molecular docking studies of N-substituted sulfonamides as potential anticancer therapeutics |
title_short | Design, synthesis, and molecular docking studies of N-substituted sulfonamides as potential anticancer therapeutics |
title_sort | design, synthesis, and molecular docking studies of n-substituted sulfonamides as potential anticancer therapeutics |
topic | Original Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10692713/ https://www.ncbi.nlm.nih.gov/pubmed/38047237 http://dx.doi.org/10.1016/j.jtumed.2023.10.006 |
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