{"title":"Synthesis and Anticancer Activity of Metformin-Phenolic Acid Conjugates.","authors":"Biswajit Banerjee, Tripti Sharma, Sabyasachi Banerjee, Subhasis Banerjee, Arijit Mondal","doi":"10.1002/cbdv.202403199","DOIUrl":null,"url":null,"abstract":"<p><p>The leading cause of death worldwide is cancer. Several studies suggest phenolic acids and metformin as potential cancer treatment options because of their biological and therapeutic properties. So, we synthesized some novel metformin-phenolic acid conjugates. We used an acid-base neutralization method to extract the metformin-free base. N, N`-dicyclohexylcarbodiimide (DCC)-4-dimethylaminopyridine (DMAP) coupling of phenolic/aromatic acids (benzoic acid, cinnamic acid, caffeic acid, ferulic acid, gallic acid, para-hydroxybenzoic acid, para coumaric acid, protocatechuic acid, salicylic acid, and vanillic acid) with metformin was performed to produce metformin phenolic acid conjugates (M1-M10). We evaluated the structures using 1H-NMR, 13C-NMR, FT-IR, and MS. All newly synthesized metformin phenolic acid conjugates were evaluated for their in vitro anti-cancer activity. Metformin phenolic acid conjugates were synthesized and showed a range of inhibitory effects. The metformin-caffeic acid conjugate [(E)-3-(3,4-dihydroxyphenyl)-N-(N,N-dimethylcarbamimidoyl)carbamimidoyl)acrylamide] (M3) (IC50: 5.47±2.72 μg/ml and 4.42±2.15 μg/ml) showed the best anticancer activity against MDA-MB-468 and A549 cancer cell lines.</p>","PeriodicalId":9878,"journal":{"name":"Chemistry & Biodiversity","volume":" ","pages":"e202403199"},"PeriodicalIF":2.3000,"publicationDate":"2025-02-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry & Biodiversity","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/cbdv.202403199","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
The leading cause of death worldwide is cancer. Several studies suggest phenolic acids and metformin as potential cancer treatment options because of their biological and therapeutic properties. So, we synthesized some novel metformin-phenolic acid conjugates. We used an acid-base neutralization method to extract the metformin-free base. N, N`-dicyclohexylcarbodiimide (DCC)-4-dimethylaminopyridine (DMAP) coupling of phenolic/aromatic acids (benzoic acid, cinnamic acid, caffeic acid, ferulic acid, gallic acid, para-hydroxybenzoic acid, para coumaric acid, protocatechuic acid, salicylic acid, and vanillic acid) with metformin was performed to produce metformin phenolic acid conjugates (M1-M10). We evaluated the structures using 1H-NMR, 13C-NMR, FT-IR, and MS. All newly synthesized metformin phenolic acid conjugates were evaluated for their in vitro anti-cancer activity. Metformin phenolic acid conjugates were synthesized and showed a range of inhibitory effects. The metformin-caffeic acid conjugate [(E)-3-(3,4-dihydroxyphenyl)-N-(N,N-dimethylcarbamimidoyl)carbamimidoyl)acrylamide] (M3) (IC50: 5.47±2.72 μg/ml and 4.42±2.15 μg/ml) showed the best anticancer activity against MDA-MB-468 and A549 cancer cell lines.
期刊介绍:
Chemistry & Biodiversity serves as a high-quality publishing forum covering a wide range of biorelevant topics for a truly international audience. This journal publishes both field-specific and interdisciplinary contributions on all aspects of biologically relevant chemistry research in the form of full-length original papers, short communications, invited reviews, and commentaries. It covers all research fields straddling the border between the chemical and biological sciences, with the ultimate goal of broadening our understanding of how nature works at a molecular level.
Since 2017, Chemistry & Biodiversity is published in an online-only format.