Water Soluble Coumarin Quaternary Ammonium Chlorides: Synthesis and Biological Evaluation

• Published in: Chemistry & biodiversity 2020-09, Vol.17 (9), p.e2000258-n/a
• Main Authors: Karataş, Mert O., Noma, Samir A. A., Gürses, Canbolat, Balcıoğlu, Sevgi, Ateş, Burhan, Alıcı, Bülent, Çakır, Ümit
• Format: Article
• Language: English
• Subjects: Acetazolamide; Allopurinol; Ammonium; Ammonium chloride; Ammonium Chloride - chemical synthesis; Ammonium Chloride - chemistry; Ammonium Chloride - pharmacology; Ammonium salts; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial activity; antimicrobial activity; Antimicrobial agents; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Bacillus subtilis - drug effects; Bacteria; Biological effects; Cancer; Carbonic anhydrase; Carbonic anhydrase I; Carbonic Anhydrases - metabolism; Cell Line, Tumor; Cell Proliferation - drug effects; Cisplatin; Colorectal carcinoma; Coumarin; Coumarins - chemical synthesis; Coumarins - chemistry; Coumarins - pharmacology; Cytotoxicity; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; E coli; enzyme inhibition; Enzyme Inhibitors - chemical synthesis; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - pharmacology; Enzymes; Escherichia coli - drug effects; Humans; Liver cancer; Microbial Sensitivity Tests; Molecular Structure; NMR; Nuclear magnetic resonance; Properties (attributes); Pyridinium; Salts; Solubility; Structure-Activity Relationship; Toxicity; Water - chemistry; Xanthine oxidase; Xanthine Oxidase - antagonists & inhibitors; Xanthine Oxidase - metabolism
• ISSN: 1612-1872; 1612-1880
• DOI: 10.1002/cbdv.202000258

In the present study, coumarin‐bearing three pyridinium and three tetra‐alkyl ammonium salts were synthesized. The compounds were fully characterized by 1H‐ and 13C‐NMR, LC/MS and IR spectroscopic methods and elemental analyses. The cytotoxic properties of all compounds were tested against human liver cancer (HepG2), human colorectal cancer (Caco‐2) and non‐cancer mouse fibroblast (L‐929) cell lines. Some compounds performed comparable cytotoxicity with standard drug cisplatin. Antibacterial properties of the compounds were tested against Gram‐negative Escherichia coli and Gram‐positive Bacillus subtilis bacteria, but the compounds did not have any antibacterial effect against both bacteria. Enzyme inhibitory properties of all compounds were tested on the activities of human carbonic anhydrase I and II, and xanthine oxidase. All compounds inhibited both enzymes more effectively than standard drugs, acetazolamide and allopurinol, respectively. The biological evaluation results showed that ionic and water soluble coumarin derivatives are promising structures for further investigations especially on enzyme inhibition field.