Carboxyl-glucuronidation of mitiglinide by human UDP-glucuronosyltransferases

Biochem Pharmacol. 2007 Jun 1;73(11):1842-51. doi: 10.1016/j.bcp.2007.02.004. Epub 2007 Feb 11.

Abstract

Mitiglinide (MGN) is a new potassium channel antagonist for the treatment of type 2 diabetes mellitus. In the present study, a potential metabolic pathway of MGN, via carboxyl-linked glucuronic acid conjugation, was found. MGN carboxyl-glucuronide was isolated from a reaction mixture consisting of MGN and human liver microsomes fortified with UDP-glucuronic acid (UDPGA) and identified by a hydrolysis reaction with beta-glucuronidase and HPLC-MS/MS. Kinetic analysis indicated that MGN from four species had the highest affinity for the rabbit liver microsomal enzyme (K(m)=0.202 mM) and the lowest affinity for the dog liver microsomal enzyme (K(m)=1.164 mM). The metabolic activity (V(max)/K(m)) of MGN to the carboxyl-glucuronidation was in the following order: rabbit>dog>rat>human. With the assessment of MGN glucuronide formation across a panel of recombinant UDP-glucuronosyltransferase (UGT) isoforms (UGT1A3, UGT1A4, UGT1A6, UGT1A9, and UGT2B7), only UGT1A3 and UGT2B7 exhibited high MGN glucuronosyltransferase activity. The K(m) values of MGN glucuronidation in recombinant UGT1A3 and UGT2B7 microsomes were close to those in human liver microsomes. The formation of MGN glucuronidation by human liver microsomes was effectively inhibited by quercetin (substrate for UGT1A3) and diclofenac (substrate for UGT2B7), respectively. The MGN glucuronidation activities in 15 human liver microsomes were significantly correlated with quercetin (r(2)=0.806) and diclofenac glucuronidation activities (r(2)=0.704), respectively. These results demonstrate that UGT1A3 and UGT2B7 are catalytic enzymes in MGN carboxyl-glucuronidation in human liver.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glucuronidase / metabolism
  • Glucuronides / metabolism*
  • Glucuronosyltransferase / metabolism*
  • Humans
  • Hydrolysis
  • Indoles / metabolism*
  • Isoindoles
  • Kinetics
  • Microsomes, Liver / metabolism*
  • Recombinant Proteins / genetics
  • Recombinant Proteins / metabolism
  • Statistics as Topic

Substances

  • Glucuronides
  • Indoles
  • Isoindoles
  • Recombinant Proteins
  • mitiglinide
  • Glucuronosyltransferase
  • Glucuronidase