The chemical modification of human liver UDP-glucuronosyltransferase UGT1*6 reveals the involvement of a carboxyl group in catalysis

FEBS Lett. 1994 Jun 13;346(2-3):146-50. doi: 10.1016/0014-5793(94)00453-6.

Abstract

The treatment of UDP-glucuronosyltransferase UGT1*6 stably expressed in V79 cells with three carboxyl-specific reagents, dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide and N-ethyl-5-phenylisoxazolium-3'-sulfonate (Woodward's reagent K), resulted in a fast, dose-dependent decrease of the 4-methylumbelliferone glucuronidation. The inactivation reactions followed pseudo-first order kinetics. The pKa of the modified residue was close to 5.0. A partial protection against inactivation by Woodward's reagent was observed at pH 7.4 in the presence of UDP-glucuronic acid, UDP, and, to a lesser extent, in the presence of 4-methylumbelliferone. Dicyclohexylcarbodiimide significantly decreased the Vmax, without affecting the apparent Km towards UDP-glucuronic acid and 4-methylumbelliferone. The results support the involvement of a carboxyl group in the catalytic process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cell Line
  • Cross-Linking Reagents / pharmacology
  • Dicyclohexylcarbodiimide / pharmacology
  • Ethyldimethylaminopropyl Carbodiimide / pharmacology
  • Glucuronates / metabolism
  • Glucuronosyltransferase / antagonists & inhibitors
  • Glucuronosyltransferase / chemistry*
  • Glucuronosyltransferase / metabolism
  • Hydrogen-Ion Concentration
  • Hymecromone / metabolism
  • Indicators and Reagents
  • Isoxazoles / pharmacology
  • Kinetics
  • Liver / enzymology*
  • Recombinant Proteins / antagonists & inhibitors
  • Recombinant Proteins / metabolism
  • Structure-Activity Relationship

Substances

  • Cross-Linking Reagents
  • Glucuronates
  • Indicators and Reagents
  • Isoxazoles
  • Recombinant Proteins
  • N-ethyl-5-phenylisoxazolium-3'-sulfonate
  • Hymecromone
  • Dicyclohexylcarbodiimide
  • Glucuronosyltransferase
  • Ethyldimethylaminopropyl Carbodiimide