Anion inhibition studies of the β-carbonic anhydrase from the pathogenic bacterium Vibrio cholerae

Bioorg Med Chem Lett. 2016 Mar 1;26(5):1406-10. doi: 10.1016/j.bmcl.2016.01.072. Epub 2016 Jan 27.

Abstract

The genome of the pathogenic bacterium Vibrio cholerae encodes for three carbonic anhydrases (CAs, EC 4.2.1.1) belonging to the α-, β- and γ-classes. Here we report and anion inhibition study of the β-CA, VchCAβ with anions and other small molecules which inhibit metalloenzymes. The best VchCAβ anion inhibitors were sulfamide, sulfamate, phenylboronic acid and phenylarsonic acid, which showed KIs in the range of 54-86μM. Diethyldithiocarbonate was also an effective VchCAβ inhibitor, with an inhibition constant of 0.73mM. The halides, cyanate, thiocyanate, cyanide, bicarbonate, carbonate, nitrate, nitrite, stannate, selenate, tellurate, divanadate, tetraborate, perrhenate, perruthenate, peroxydisulfate, selenocyanide, trithiocarbonate, and fluorosulfonate showed affinity in the low millimolar range, with KIs of 2.3-9.5mM. Identification of selective inhibitors of VchCAβ (over the human CA isoforms) may lead to pharmacological tools useful for understanding the physiological role(s) of this under-investigated enzyme.

Keywords: Anions; Carbonic anhydrase; Hydratase activity; Inhibitors; Metalloenzymes; Pathogenic bacteria; Vibrio cholerae.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions / chemistry
  • Anions / pharmacology
  • Arsenicals / chemistry
  • Arsenicals / pharmacology
  • Boronic Acids / chemistry
  • Boronic Acids / pharmacology
  • Carbonic Anhydrase Inhibitors / chemistry
  • Carbonic Anhydrase Inhibitors / pharmacology*
  • Carbonic Anhydrases / metabolism*
  • Dose-Response Relationship, Drug
  • Models, Molecular
  • Structure-Activity Relationship
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology
  • Sulfonic Acids / chemistry
  • Sulfonic Acids / pharmacology
  • Vibrio cholerae / enzymology*

Substances

  • Anions
  • Arsenicals
  • Boronic Acids
  • Carbonic Anhydrase Inhibitors
  • Sulfonamides
  • Sulfonic Acids
  • sulfamic acid
  • Carbonic Anhydrases
  • benzeneboronic acid