Evaluation of antimicrobial, antibiofilm and carbonic anhydrase inhibition profiles of 1,3-bis-chalcone derivatives

J Biochem Mol Toxicol. 2019 Apr;33(4):e22281. doi: 10.1002/jbt.22281. Epub 2018 Dec 31.

Abstract

A series of 1,3-bis-chalcone derivatives (3a-i, 6a-i and 8) were synthesized and evaluated antimicrobial, antibiofilm and carbonic anhydrase inhibition activities. In this evaluation, 6f was found to be the most active compound showing the same effect as the positive control against Bacillus subtilis and Streptococcus pyogenes in terms of antimicrobial activity. Biofilm structures formed by microorganisms were damaged by compounds at the minimum inhibitory concentration value between 0.5% and 97%.1,3-bis-chalcones ( 3a-i, 6a-i and 8) showed good inhibitory action against human (h) carbonic anhydrase (CA) isoforms I and II. hCA I and II were effectively inhibited by these compounds, with K i values in the range of 94.33 ± 13.26 to 787.38 ± 82.64 nM for hCA I, and of 100.37 ± 11.41 to 801.76 ± 91.11 nM for hCA II, respectively. In contrast, acetazolamide clinically used as CA inhibitor showed K i value of 1054.38 ± 207.33 nM against hCA I, and 983.78 ± 251.08 nM against hCA II, respectively.

Keywords: 1,3-bis-chalcone; antibiofilm; antifungal; antimicrobial; carbonic anhydrase.

MeSH terms

  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology
  • Bacillus subtilis / drug effects
  • Biofilms / drug effects
  • Candida albicans / drug effects
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Carbonic Anhydrase Inhibitors / chemistry
  • Carbonic Anhydrase Inhibitors / pharmacology*
  • Chalcones / chemistry
  • Chalcones / pharmacology*
  • Drug Evaluation, Preclinical
  • Humans
  • Isoenzymes / antagonists & inhibitors*
  • Microbial Sensitivity Tests
  • Proton Magnetic Resonance Spectroscopy
  • Pseudomonas aeruginosa / drug effects
  • Shigella boydii / drug effects
  • Streptococcus pyogenes / drug effects

Substances

  • Anti-Infective Agents
  • Carbonic Anhydrase Inhibitors
  • Chalcones
  • Isoenzymes