Synthesis, Anticholinesterase, Antioxidant, and Anti-Aflatoxigenic Activity of Novel Coumarin Carbamate Derivatives

KURT B., Gazioglu I., KANDAS N. O., Sonmez F.

CHEMISTRYSELECT, vol.3, no.14, pp.3978-3983, 2018 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 3 Issue: 14
  • Publication Date: 2018
  • Doi Number: 10.1002/slct.201800142
  • Journal Name: CHEMISTRYSELECT
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.3978-3983
  • Keywords: Aflatoxin B1, antioxidant activity, carbamate, coumarin, glutathione-s-transferase, western blot, GLUTATHIONE-S-TRANSFERASE, CARBONIC-ANHYDRASE I, ALZHEIMERS-DISEASE, BIOLOGICAL EVALUATION, COUMARYLTHIAZOLE DERIVATIVES, CHOLINESTERASE-INHIBITORS, MULTITARGET AGENTS, MOLECULAR DOCKING, DESIGN, VITRO
  • Bezmialem Vakıf University Affiliated: Yes

Abstract

New coumarin derivatives with the carbamate moiety were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. 4-methyl-2-oxo-2H-chromen-7-yl cycloheptylcarbamate (4h) showed the strongest inhibition against AChE with IC50 values of 2.30 mu M, and 2-oxo-2H-chromen-7-yl-(cyclohexylmethyl)carbamate (4c) and 4-methyl-2-oxo-2H-chromen-7-yl-(cyclohexylmethyl)carbamate (4g) were found to be the most potent BuChE inhibitors with IC50 value of 0.003 mu M and 0.004 mu M, respectively. Moreover antioxidant, anti-aflatoxigenic activities, protective effects against aflatoxin-B1 (AFB1) in H4IIE-C3 cells and effects on glutathione s-transferase of the synthesized compounds were investigated. The synthesized coumarin carbamates inhibited AFB1 in H4IIE-C3 cells. Western blot analyses confirmed that GST alpha protein was induced in cells treated with coumarin carbamates and AFB1. These results showed that the synthesized coumarin carbamates possess a potent protective effect against AFB1.