Identification of carboxylesterases expressed in rat intestine and effects of their hydrolyzing activity in predicting first-pass metabolism of ester prodrugs

Pharmazie. 2011 Nov;66(11):888-93.

Abstract

Carboxylesterases (CESs) located in the intestine play an unique role in the absorption of many drugs especially ester prodrugs. In order to determine the expression and hydrolyzing activity of CESs isozymes (CES1 and CES2) located in rat intestine, the activities of CES1 and CES2 were evaluated by the intestinal S9 incubation with imidapril and irinotecan (CPT-11), the substrates of CES1 and CES2, respectively. The distribution characteristics of CES1, CES2, Pregnane X Receptor (PXR) and Constitutive Androstane Receptor were analyzed by real-time polymerase chain reaction (RT-PCR) or Western blot. Imidaprilat metabolized from imidapril by CES1 was too low to be detected in rat intestinal S9 fractions, while there was little and even no expression of CES1 mRNA in intestinal segments. In contrast, Vmax values for CPT-11 diminished gradually from proximal to distal segments within the rat intestine which was consistent with the mRNA expression level of CES2. These results indicated that CES2 represents the major CESs isoform in the rat complete intestine and decreased from duodenum to colon, whereas the expression of CES1 was too low to influence the metabolism of ester prodrugs. The expression of PXR and CAR decreased slightly along the entire intestine on both mRNA and protein levels which indicated that PXR and CAR may be one of the major factors which contribute to the expression of CES1 and CES2. Thus, the knowledge about the characteristic and site-specific expression of CES1 and CES2 in rat intestine will help to predict the oral bioavailability of ester prodrugs.

MeSH terms

  • Actins / metabolism
  • Angiotensin-Converting Enzyme Inhibitors / pharmacokinetics
  • Animals
  • Biotransformation
  • Blotting, Western
  • Camptothecin / analogs & derivatives
  • Camptothecin / pharmacokinetics
  • Carboxylic Ester Hydrolases / biosynthesis*
  • Constitutive Androstane Receptor
  • Esters / chemistry
  • Esters / pharmacokinetics*
  • Hydrolysis
  • Imidazolidines / pharmacokinetics
  • Intestines / enzymology*
  • Irinotecan
  • Male
  • Nitrophenols / pharmacology
  • Organophosphorus Compounds / pharmacology
  • Parasympathomimetics / pharmacokinetics
  • Pregnane X Receptor
  • Prodrugs / chemistry
  • Prodrugs / pharmacokinetics*
  • RNA, Messenger / biosynthesis
  • RNA, Messenger / genetics
  • Rats
  • Rats, Sprague-Dawley
  • Real-Time Polymerase Chain Reaction
  • Receptors, Cytoplasmic and Nuclear / metabolism
  • Receptors, Steroid / metabolism

Substances

  • Actins
  • Angiotensin-Converting Enzyme Inhibitors
  • Constitutive Androstane Receptor
  • Esters
  • Imidazolidines
  • Nitrophenols
  • Organophosphorus Compounds
  • Parasympathomimetics
  • Pregnane X Receptor
  • Prodrugs
  • RNA, Messenger
  • Receptors, Cytoplasmic and Nuclear
  • Receptors, Steroid
  • nitrophenylphosphate
  • Irinotecan
  • imidapril
  • Carboxylic Ester Hydrolases
  • Camptothecin