Mouse liver and kidney carboxylesterase (M-LK) rapidly hydrolyzes antitumor prodrug irinotecan and the N-terminal three quarter sequence determines substrate selectivity

Drug Metab Dispos. 2003 Jan;31(1):21-7. doi: 10.1124/dmd.31.1.21.

Abstract

Antitumor prodrug irinotecan is used for a variety of malignancies such as colorectal cancer. It is hydrolyzed to the metabolite, 7-ethyl-10-hydroxycamptothecin (SN-38), which exerts its antineoplastic effect. Several human and rodent carboxylesterases are shown to hydrolyze irinotecan, but the overall activity varies from enzyme to enzyme. This report describes a novel mouse liver and kidney carboxylesterase (M-LK) that is highly active toward this prodrug. Northern analyses demonstrated that M-LK was abundantly expressed in the liver and kidney and slightly in the intestine and lung. Lysates from M-LK transfected cells exhibited a markedly higher activity on irinotecan hydrolysis than lysates from the cells transfected with mouse triacylglycerol hydrolase (TGH) (6.9 versus 1.3 pmol/mg/min). Based on the immunostaining intensity with purified rat hydrolase A, M-LK had a specific activity of 173 pmol/mg/min, which ranked it as one of the most efficient esterases known to hydrolyze irinotecan. A chimeric carboxylesterase and its wild-type enzyme (e.g., M-LKn and M-LK), sharing three quarters of the entire sequence from the N-terminus, exhibited the same substrate preference toward irinotecan and two other substrates, suggesting that the N-terminal sequence determines substrate selectivity. M-LK transfected cells manifested more severe cytotoxicity than TGH transfected cells upon being exposed to irinotecan. Topoisomerase I inhibitors such as irinotecan represent a promising class of anticancer drugs. Identification of M-LK as an efficient carboxylesterase to activate irinotecan provides additional sequence information to locate residues involved in irinotecan hydrolysis and thus facilitates the design of new analogs.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Amino Acid Sequence / physiology
  • Animals
  • Antineoplastic Agents, Phytogenic / metabolism*
  • Antineoplastic Agents, Phytogenic / pharmacokinetics
  • Camptothecin / analogs & derivatives*
  • Camptothecin / metabolism*
  • Camptothecin / pharmacokinetics
  • Carboxylesterase
  • Carboxylic Ester Hydrolases / genetics
  • Carboxylic Ester Hydrolases / metabolism*
  • Humans
  • Hydrolysis / drug effects
  • Irinotecan
  • Kidney / enzymology*
  • Lipase / metabolism
  • Lipase / pharmacokinetics
  • Liver / enzymology*
  • Mice
  • Molecular Sequence Data
  • Peptide Fragments / metabolism*
  • Peptide Fragments / physiology
  • Prodrugs / metabolism*
  • Prodrugs / pharmacokinetics
  • Sequence Homology, Amino Acid
  • Substrate Specificity / drug effects
  • Substrate Specificity / physiology

Substances

  • Antineoplastic Agents, Phytogenic
  • Peptide Fragments
  • Prodrugs
  • Irinotecan
  • Carboxylic Ester Hydrolases
  • Carboxylesterase
  • Lipase
  • Camptothecin