Intestinal first-pass metabolism via carboxylesterase in rat jejunum and ileum

Drug Metabolism and Disposition

Volumn 35, Issue 7, 2007, Pages 1089-1095

  Masaki, Kenji ^a   Hashimoto, Mitsuru ^a   Imai, Teruko ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 NITROANILINE; 4 NITROPHENYL PHOSPHATE; CARBOXYLESTERASE;

ARTICLE; ENZYME ACTIVITY; ENZYME METABOLISM; FIRST PASS EFFECT; GENE EXPRESSION; ILEUM; JEJUNUM; MALE; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; RAT;

AMINOPEPTIDASES; ANILIDES; ANILINE COMPOUNDS; ANIMALS; BIOTRANSFORMATION; CARBOXYLIC ESTER HYDROLASES; ENZYME INHIBITORS; GENE EXPRESSION REGULATION, ENZYMOLOGIC; HYDROLYSIS; ILEUM; INTESTINAL ABSORPTION; INTESTINAL MUCOSA; ISOENZYMES; JEJUNUM; MALE; NITROPHENOLS; PROPRANOLOL; RATS; RATS, WISTAR; RNA, MESSENGER; SUBCELLULAR FRACTIONS;

RATTUS;

EID: 34250705787     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.106.013862     Document Type: Article

References (36)

1. 14C]phenylphosphate as carboxylesterases and amidases. Biochim Biophys Acta 524:85-93.
2. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254.
3. Brandt E, Heymann E, Mentlein R (1980) Selective inhibition of rat liver carboxylesterases by various organophosphorus diesters in vivo and in vitro. Biochem Pharmacol 29:1927-1931.
4. Callreus T, Lundahl J, Hoglund P, and Bengtsson P (1999) Changes in gastrointestinal motility influence the absorption of desmopressin. Eur J Clin Pharmacol 55:305-309.
5. de Waziers I, Cugnenc PH, Yang CS, Leroux JP, Beaune PH (1990) Cytochrome P-450 isoenzymes, epoxide hydrolase and glutathione transferases in rat and human hepatic and extrahepatic tissues. J Pharmacol Exp Ther 253:387-394.
6. Fleisher D, Stewart BH, and Amidon GL (1985) Design of prodrugs for improved gastrointestinal absorption by intestinal enzyme targeting. Methods Enzymol 112:360-381.
7. Furihata T, Hosokawa M, Fujii A, Derbel M, Satoh T, and Chiba K (2005) Dexamethasone-induced methylprednisolone hemisuccinate hydrolase: its identification as a member of the rat carboxylesterase 2 family and its unique existence in plasma. Biochem Pharmacol 69:1287-1297.
8. Heymann E and Krisch K (1967) Phosphoric acid-bis-(p-nitro- phenylester), a new inhibitor of microsomal carboxylesterases. Hoppe Seylers Z Physiol Chem 348:609-619.
9. Imai T, Taketani M, Shii M, Hosokawa M, and Chiba K (2006) Substrate specificity of carboxylesterase isozymes and their contribution to hydrolase activity in human liver and small intestine. Drug Metab Dispos 34:1734-1741.
10. Lin JH, Chiba M, and Baillie TA (1999) Is the role of the small intestine in first-pass metabolism overemphasized? Pharmacol Rev 51:135-158.
11. Liu S, Tam D, Chen X, and Pang KS (2006) P-glycoprotein and an unstirred water layer barring digoxin absorption in the vascularly perfused rat small intestine preparation: induction studies with pregnenolone-16α- carbonitrile. Drug Metab Dispos 34:1468-1476.
12. Masaki K, Taketani M, and Imai T (2006) First-pass hydrolysis of a propranolol ester derivative in rat small intestine. Drug Metab Dispos 34:398-404.
13. Mentlein R, Rix-Matzen H, and Heymann E (1988) Subcellular localization of non-specific carboxylesterases, acylcarnitine hydrolase, monoacylglycerol lipase and palmitoyl-CoA hydrolase in rat liver. Biochim Biophys Acta 964:319-328.
14. Mizen L and Burton G (1998) The use of esters as prodrugs for oral delivery of β-lactam antibiotics. Pharm Biotechnol 11:345-365.
15. Okudaira N, Tatebayashi T, Speirs GC, Komiya I, and Sugiyama Y (2000) A study of the intestinal absorption of an ester-type prodrug, ME3229, in rats: active efflux transport as a cause of poor bioavailability of the active drug. J Pharmacol Exp Ther 294:580-587.
16. Paine MF, Shen DD, Kunze KL, Perkins JD, Marsh CL, McVicar JP, Barr DM, Gillies BS, and Thummel KE (1996) First-pass metabolism of midazolam by the human intestine. Clin Pharmacol Ther 60:14-24.
17. Pang KS (2003) Modeling of intestinal drug absorption: roles of transporters and metabolic enzymes (for the Gillette Review Series). Drug Metab Dispos 31:1507-1519.
18. Pang KS, Yuen V, Fayz S, te Koppele JM, and Mulder GJ (1986) Absorption and metabolism of acetaminophen by the in situ perfused rat small intestine preparation. Drug Metab Dispos 14:102-111.
19. Prueksaritanont T, DeLuna P, Gorham LM, Ma B, Cohn D, Pang J, Xu X, Leung K, and Lin JH (1998) In vitro and in vivo evaluations of intestinal barriers for the zwitterion L-767,679 and its carboxyl ester prodrug L-775,318: roles of efflux and metabolism. Drug Metab Dispos 26:520-527.
20. Prueksaritanont T, Gorham LM, Hochman JH, Tran LO, and Vyas KP (1996) Comparative studies of drug-metabolizing enzymes in dog, monkey, and human small intestines, and in Caco-2 cells. Drug Metab Dispos 24:634-642.
21. Quinney SK, Sanghani SP, Davis WI, Hurley TD, Sun Z, Murry DJ, and Bosron WF (2005) Hydrolysis of capecitabine to 5′-deoxy-5-fluorocytidine by human carboxylesterases and inhibition by loperamide. J Pharmacol Exp Ther 313:1011-1016.
22. Rigtrup KM and Ong DE (1992) A retinyl ester hydrolase activity intrinsic to the brush border membrane of rat small intestine. Biochemistry 31:2920-2926.
23. Ruiz-Balaguer N, Nacher A, Casabo VG, and Merino Sanjuan M (2002) Intestinal transport of cefuroxime axetil in rats: absorption and hydrolysis processes. Int J Pharm 234:101-111.
24. Sanghani SP, Davis WI, Dumaual NG, Mahrenholz A, and Bosron WF (2002) Identification of microsomal rat liver carboxylesterases and their activity with retinyl palmitate. Eur J Biochem 269:4387-4398.
25. Satoh T and Hosokawa M (1998) The mammalian carboxylesterases: from molecules to functions. Annu Rev Pharmacol Toxicol 38:257-288.
26. Satoh T and Hosokawa M (2006) Structure, function and regulation of carboxylesterases. Chem Biol Interact 162:195-211.
27. Shameem M, Imai T, and Otagiri M (1993) An in-vitro and in-vivo correlative approach to the evaluation of ester prodrugs to improve oral delivery of propranolol. J Pharm Pharmacol 45:246-252.
28. Sone T and Wang CY (1997) Microsomal amidases and carboxylesterases. Comp Toxicol 3:265-281.
29. Tamura S, Tokunaga Y, Ibuki R, Amidon GL, Sezaki H, and Yamashita S (2003) The site-specific transport and metabolism of tacrolimus in rat small intestine. J Pharmacol Exp Ther 306:310-316.
30. Van Gelder J, Shafiee M, De Clercq E, Penninckx F, Van den Mooter G, Kinget R, and Augustijns P (2000) Species-dependent and site-specific intestinal metabolism of ester pro-drugs. Int J Pharm 205:93-100.
31. Walter E, Janich S, Roessler BJ, Hilfinger JM, and Amidon GL (1996) HT29-MTX/Caco-2 cocultures as an in vitro model for the intestinal epithelium: in vitro-in vivo correlation with permeability data from rats and humans. J Pharm Sci 85:1070-1076.
32. Yamaoka K, Tanigawara Y, Nakagawa T, and Uno T (1981) A pharmacokinetic analysis program (multi) for microcomputer. J Pharmacobiodyn 4:879-885.
33. Yamashita S, Tanaka Y, Endoh Y, Taki Y, Sakane T, Nadai T, and Sezaki H (1997) Analysis of drug permeation across Caco-2 monolayer: implication for predicting in vivo drug absorption. Pharm Res 14:486-491.
34. Yoshigae Y, Imai T, Horita A, Matsukane H, and Otagiri M (1998) Species differences in stereoselective hydrolase activity in intestinal mucosa. Pharm Res 15:626-631.
35. Yoshigae Y, Imai T, Horita A, and Otagiri M (1997) Species differences for stereoselective hydrolysis of propranolol prodrugs in plasma and liver. Chirality 9:661-666.
36. Zimmerman CL, Wen Y, and Remmel RP (2000) First-pass disposition of (-)-6-aminocarbovir in rats: II. Inhibition of intestinal first-pass metabolism. Drug Metab Dispos 28:672-679.