Kerem Buran, Yiğit İnan, Abdullahi Ibrahim Uba, Gökhan Zengin
{"title":"新型苯磺酰胺-哌嗪杂化化合物:设计、合成、抗氧化、酶抑制活性和对接、ADME 分析研究。","authors":"Kerem Buran, Yiğit İnan, Abdullahi Ibrahim Uba, Gökhan Zengin","doi":"10.1515/znc-2024-0062","DOIUrl":null,"url":null,"abstract":"<p><p>Benzene sulfonamides are an important biological substituent for several activities. In this study, hybridization of benzene sulfonamide with piperazine derivatives were investigated for their antioxidant capacity and enzyme inhibitory potencies. Six molecules were synthesized and characterized. DPPH, ABTS, FRAP, CUPRAC, chelating and phosphomolybdemum assays were applied to evaluate antioxidant capacities. Results show that compounds have high antioxidant capacity and compound <b>4</b> has the best antioxidant activity among them. Compound <b>4</b> has higher antioxidant activity than references for FRAP (IC<sub>50</sub>: 0.08 mM), CUPRAC (IC<sub>50</sub>: 0.21 mM) and phosphomolybdenum (IC<sub>50</sub>: 0.22 mM) assays. Besides this, compound <b>4</b> has moderate DPPH and ABTS antioxidant capacity. Furthermore, enzyme inhibition activities of these molecules were investigated against AChE, BChE, tyrosinase, <i>α</i>-amylase and <i>α</i>-glucosidase enzymes. It was revealed that all compounds have good enzyme inhibitory potential except for <i>α</i>-amylase enzyme. The best inhibitory activities were observed for AChE with compound <b>5</b> the same value (IC<sub>50</sub>: 1.003 mM), for BChE with compounds <b>2</b> and <b>5</b> the same value (IC<sub>50</sub>: 1.008 mM), for tyrosinase compound <b>4</b> (IC<sub>50</sub>: 1.19 mM), and for <i>α</i>-glucosidase with compound <b>3</b> (IC<sub>50</sub>: 1.000 mM). Docking studies have been conducted with these molecules, and the results correlate well with the inhibitory assays.</p>","PeriodicalId":49344,"journal":{"name":"Zeitschrift Fur Naturforschung Section C-A Journal of Biosciences","volume":null,"pages":null},"PeriodicalIF":1.8000,"publicationDate":"2024-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Novel benzene sulfonamide-piperazine hybrid compounds: design, synthesis, antioxidant, enzyme inhibition activities and docking, ADME profiling studies.\",\"authors\":\"Kerem Buran, Yiğit İnan, Abdullahi Ibrahim Uba, Gökhan Zengin\",\"doi\":\"10.1515/znc-2024-0062\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Benzene sulfonamides are an important biological substituent for several activities. In this study, hybridization of benzene sulfonamide with piperazine derivatives were investigated for their antioxidant capacity and enzyme inhibitory potencies. Six molecules were synthesized and characterized. DPPH, ABTS, FRAP, CUPRAC, chelating and phosphomolybdemum assays were applied to evaluate antioxidant capacities. Results show that compounds have high antioxidant capacity and compound <b>4</b> has the best antioxidant activity among them. Compound <b>4</b> has higher antioxidant activity than references for FRAP (IC<sub>50</sub>: 0.08 mM), CUPRAC (IC<sub>50</sub>: 0.21 mM) and phosphomolybdenum (IC<sub>50</sub>: 0.22 mM) assays. Besides this, compound <b>4</b> has moderate DPPH and ABTS antioxidant capacity. Furthermore, enzyme inhibition activities of these molecules were investigated against AChE, BChE, tyrosinase, <i>α</i>-amylase and <i>α</i>-glucosidase enzymes. It was revealed that all compounds have good enzyme inhibitory potential except for <i>α</i>-amylase enzyme. The best inhibitory activities were observed for AChE with compound <b>5</b> the same value (IC<sub>50</sub>: 1.003 mM), for BChE with compounds <b>2</b> and <b>5</b> the same value (IC<sub>50</sub>: 1.008 mM), for tyrosinase compound <b>4</b> (IC<sub>50</sub>: 1.19 mM), and for <i>α</i>-glucosidase with compound <b>3</b> (IC<sub>50</sub>: 1.000 mM). Docking studies have been conducted with these molecules, and the results correlate well with the inhibitory assays.</p>\",\"PeriodicalId\":49344,\"journal\":{\"name\":\"Zeitschrift Fur Naturforschung Section C-A Journal of Biosciences\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.8000,\"publicationDate\":\"2024-06-24\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Zeitschrift Fur Naturforschung Section C-A Journal of Biosciences\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://doi.org/10.1515/znc-2024-0062\",\"RegionNum\":4,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Zeitschrift Fur Naturforschung Section C-A Journal of Biosciences","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1515/znc-2024-0062","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Benzene sulfonamides are an important biological substituent for several activities. In this study, hybridization of benzene sulfonamide with piperazine derivatives were investigated for their antioxidant capacity and enzyme inhibitory potencies. Six molecules were synthesized and characterized. DPPH, ABTS, FRAP, CUPRAC, chelating and phosphomolybdemum assays were applied to evaluate antioxidant capacities. Results show that compounds have high antioxidant capacity and compound 4 has the best antioxidant activity among them. Compound 4 has higher antioxidant activity than references for FRAP (IC50: 0.08 mM), CUPRAC (IC50: 0.21 mM) and phosphomolybdenum (IC50: 0.22 mM) assays. Besides this, compound 4 has moderate DPPH and ABTS antioxidant capacity. Furthermore, enzyme inhibition activities of these molecules were investigated against AChE, BChE, tyrosinase, α-amylase and α-glucosidase enzymes. It was revealed that all compounds have good enzyme inhibitory potential except for α-amylase enzyme. The best inhibitory activities were observed for AChE with compound 5 the same value (IC50: 1.003 mM), for BChE with compounds 2 and 5 the same value (IC50: 1.008 mM), for tyrosinase compound 4 (IC50: 1.19 mM), and for α-glucosidase with compound 3 (IC50: 1.000 mM). Docking studies have been conducted with these molecules, and the results correlate well with the inhibitory assays.
期刊介绍:
A Journal of Biosciences: Zeitschrift für Naturforschung C (ZNC) is an international scientific journal and a community resource for the emerging field of natural and natural-like products. The journal publishes original research on the isolation (including structure elucidation), bio-chemical synthesis and bioactivities of natural products, their biochemistry, pharmacology, biotechnology, and their biological activity and innovative developed computational methods for predicting the structure and/or function of natural products. A Journal of Biosciences: Zeitschrift für Naturforschung C (ZNC) welcomes research papers in fields on the chemistry-biology boundary which address scientific ideas and approaches to generate and understand natural compounds on a molecular level and/or use them to stimulate and manipulate biological processes.