Synthesis, in vitro Antitrichomonal Activity, and Docking Study of N-(4-substituted phenyl)-1,3-thiazol-2-yl-4-substituted Benzenesulfonamides
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| Format: | Artículo científico |
| Language: | en |
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Sociedad Química de México
2024
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| _version_ | 1876481617700061184 |
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| author | Rubén M. Carballo |
| author_facet | Rubén M. Carballo |
| contents | Synthesis, in vitro Antitrichomonal Activity, and Docking Study of N-(4-substituted phenyl)-1,3-thiazol-2-yl-4-substituted Benzenesulfonamides Rubén M. Carballo Héctor A. Peniche-Pavía Ramiro Quijano-Quiñones David Cáceres-Castillo Gumersindo Mirón-López Manlio Graniel-Sabido Andrea Reyes-Cuapio Rosa E. Moo-Puc Lía Valencia-Chan Gonzalo J. Mena-Rejón Multidisciplinaria (Ciencias Naturales y Exactas) phenylthiazole trichomoniasis docking studies benzenesulfonamide Trichomonas vaginalis Infection by Trichomonas vaginalis has a high incidence/prevalence worldwide. It has been associated with a predisposition to cervical neoplasia or prostate cancer and an increased risk of acquisition of human papillomavirus (HPV) and human immunodeficiency virus (HIV). Besides, resistance to the drugs used for trichomoniasis treatment has increased in the last 30 years. Herein, thirteen phenylthiazolylbenzene sulfonamides were synthesized and evaluated for their in vitro activity against Trichomonas vaginalis. Among them, four derivatives showed higher anti-trichomonal activity than metronidazole (IC50 = 0.93 µM), while their cytotoxicity levels were not significant. These compounds were subject to molecular docking studies using Trichomonas vaginalis ferredoxin as target. The results revealed that the orientation of the nitro group of the active derivatives is toward 2Fe-2S, the cluster responsible for high reactive oxygen species generation. Finally, it was evident that the presence of a nitro group in the structure of the synthesized phenylthiazolylbenzene sulfonamides is essential for their trichomonicidal activity. 2024 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47581848009 https://www.redalyc.org/journal/475/47581848009/ https://www.redalyc.org/journal/475/47581848009/html/ https://www.redalyc.org/journal/475/47581848009/47581848009.epub https://www.redalyc.org/journal/475/47581848009/movil 10.29356/jmcs.v68i1.1975 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.1 Vol.68 |
| format | Artículo científico |
| id | redalyc_47581848009 |
| institution | Redalyc |
| language | en |
| publishDate | 2024 |
| publisher | Sociedad Química de México |
| spellingShingle | Synthesis, in vitro Antitrichomonal Activity, and Docking Study of N-(4-substituted phenyl)-1,3-thiazol-2-yl-4-substituted Benzenesulfonamides Rubén M. Carballo Multidisciplinaria (Ciencias Naturales y Exactas) phenylthiazole trichomoniasis docking studies benzenesulfonamide Trichomonas vaginalis Synthesis, in vitro Antitrichomonal Activity, and Docking Study of N-(4-substituted phenyl)-1,3-thiazol-2-yl-4-substituted Benzenesulfonamides Rubén M. Carballo Héctor A. Peniche-Pavía Ramiro Quijano-Quiñones David Cáceres-Castillo Gumersindo Mirón-López Manlio Graniel-Sabido Andrea Reyes-Cuapio Rosa E. Moo-Puc Lía Valencia-Chan Gonzalo J. Mena-Rejón Multidisciplinaria (Ciencias Naturales y Exactas) phenylthiazole trichomoniasis docking studies benzenesulfonamide Trichomonas vaginalis Infection by Trichomonas vaginalis has a high incidence/prevalence worldwide. It has been associated with a predisposition to cervical neoplasia or prostate cancer and an increased risk of acquisition of human papillomavirus (HPV) and human immunodeficiency virus (HIV). Besides, resistance to the drugs used for trichomoniasis treatment has increased in the last 30 years. Herein, thirteen phenylthiazolylbenzene sulfonamides were synthesized and evaluated for their in vitro activity against Trichomonas vaginalis. Among them, four derivatives showed higher anti-trichomonal activity than metronidazole (IC50 = 0.93 µM), while their cytotoxicity levels were not significant. These compounds were subject to molecular docking studies using Trichomonas vaginalis ferredoxin as target. The results revealed that the orientation of the nitro group of the active derivatives is toward 2Fe-2S, the cluster responsible for high reactive oxygen species generation. Finally, it was evident that the presence of a nitro group in the structure of the synthesized phenylthiazolylbenzene sulfonamides is essential for their trichomonicidal activity. 2024 artículo científico 1870-249X https://www.redalyc.org/articulo.oa?id=47581848009 https://www.redalyc.org/journal/475/47581848009/ https://www.redalyc.org/journal/475/47581848009/html/ https://www.redalyc.org/journal/475/47581848009/47581848009.epub https://www.redalyc.org/journal/475/47581848009/movil 10.29356/jmcs.v68i1.1975 en http://www.redalyc.org/revista.oa?id=475 Journal of the Mexican Chemical Society application/pdf Sociedad Química de México Journal of the Mexican Chemical Society (México) Num.1 Vol.68 |
| title | Synthesis, in vitro Antitrichomonal Activity, and Docking Study of N-(4-substituted phenyl)-1,3-thiazol-2-yl-4-substituted Benzenesulfonamides |
| topic | Multidisciplinaria (Ciencias Naturales y Exactas) phenylthiazole trichomoniasis docking studies benzenesulfonamide Trichomonas vaginalis |
| url | https://www.redalyc.org/articulo.oa?id=47581848009 https://www.redalyc.org/journal/475/47581848009/ https://www.redalyc.org/journal/475/47581848009/html/ https://www.redalyc.org/journal/475/47581848009/47581848009.epub https://www.redalyc.org/journal/475/47581848009/movil |