Inhibition of β-carbonic anhydrases from Brucella suis with C-cinnamoyl glycosides incorporating the phenol moiety

J Enzyme Inhib Med Chem. 2015 Dec;30(6):1017-20. doi: 10.3109/14756366.2014.986120. Epub 2015 Feb 13.

Abstract

A small series of C-glycosides containing the phenol moiety was tested for the inhibition of the β-class carbonic anhydrases (βCAs, EC 4.2.1.1) from Brucella suis. Many compounds showed activities in the micromolar or submicromolar range and excellent selectivity for pathogen CAs over human isozymes. Glycosides incorporating the 3-hydroxyphenyl moiety showed the best inhibition profile, and therefore this functionality represents lead for the development of novel anti-infectives with a new mechanism of action.

Keywords: Antibacterial; carbohydrate; carbonic anhydrase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Brucella suis / enzymology*
  • Carbonic Anhydrase Inhibitors / chemical synthesis
  • Carbonic Anhydrase Inhibitors / chemistry
  • Carbonic Anhydrase Inhibitors / pharmacology*
  • Carbonic Anhydrases / metabolism*
  • Dose-Response Relationship, Drug
  • Glycosides / chemistry
  • Glycosides / pharmacology*
  • Molecular Structure
  • Phenols / chemistry
  • Phenols / pharmacology*
  • Structure-Activity Relationship

Substances

  • Carbonic Anhydrase Inhibitors
  • Glycosides
  • Phenols
  • Carbonic Anhydrases