Intestinal absorption and analgesic activity of aminopeptidase-resistant cellobiose-coupled leucine enkephalinamide

Biopharmaceutics and Drug Disposition

Volumn 19, Issue 9, 1998, Pages 605-610

  Mizuma, Takashi ^a   Ohta, Kunihiro ^a   Awazu, Shoji ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Analgesic; Intestinal absorption; Peptides; Sugar coupling

Indexed keywords

ACETIC ACID; AMASTATIN; AMINOPEPTIDASE; CELLOBIOSE; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; ENKEPHALINASE INHIBITOR; LEUCINE ENKEPHALINAMIDE;

ANALGESIC ACTIVITY; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ABSORPTION; DRUG CLEARANCE; DRUG STABILITY; HOT PLATE TEST; INTESTINE ABSORPTION; INTESTINE MUCOSA; MALE; MOUSE; NONHUMAN; RAT; SUBCUTANEOUS DRUG ADMINISTRATION; WRITHING TEST;

AMINOPEPTIDASES; ANALGESICS; ANIMALS; CELLOBIOSE; DRUG CARRIERS; ENKEPHALIN, LEUCINE; INTESTINAL ABSORPTION; MALE; MICE; MICE, INBRED ICR; RATS; RATS, WISTAR; TIME FACTORS;

EID: 0031768642     PISSN: 01422782     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-081X(199812)19:9<605::AID-BDD149>3.0.CO;2-W     Document Type: Article

References (18)

1. L.E. Geary, K.S. Wiley, W.L. Scot and M.L. Cohen, Degradation of exogenous enkephalin in the guinea-pig ileum: relative importance of aminopeptidase, enkephalinase and angiotensin converting enzyme activity. J. Pharmacol. Exp. Ther., 221, 104-111 (1982).
2. B.J. Aungst, J.A. Blake and M.A. Hussain, An in vitro evaluation of metabolism and poor membrane permeation impeding intestinal absorption of leucine enkephalin, and methods to increase absorption. J. Pharmacol. Exp. Ther., 259, 139-145 (1991).
3. P. Langguth, H.P. Merkle and G.L. Amidon, Oral absorption of peptides: the effect of absorption site and enzyme inhibition on the systemic availability of metkephamid. Pharm. Res., 11, 528-535 (1994).
4. +-dependent transport of aminopeptidase-resistant sugar-coupled tripeptides in rat intestine. Biochem. Biophys. Res. Commun., 203, 1412-1416 (1994).
5. T. Mizuma, K. Ohta, K. Koyanagi and S. Awazu, Improvement of intestinal absorption of leucine enkephalin by sugar coupling and peptidase inhibitors. J. Pharm. Sci., 85, 854-857 (1996).
6. B. Malfroy and J.-C. Schwartz, Comparison of dipeptidyl carboxypeptidase and endopeptidase activities in the three enkephalin-hydrolysing metallopeptidases: 'angiotensin-converting enzyme', thermolysin and 'enkephalinase'. Biochem. Biophys. Res. Commun., 130, 372-378 (1985).
7. T. Mizuma, K. Ohta and S. Awazu, Peripherally active analgesia of aminopeptidase-resistant sugar-coupled leucine enkephalin. Res. Commun. Mol. Path. Pharmacol., 95, 83-91 (1997).
8. T. Mizuma, K. Ohta, M. Hayashi and S. Awazu, Intestinal active absorption of sugar-conjugated compounds by glucose transport system: implication of improvement of poorly absorbable drugs. Biochem. Pharmacol., 43, 2037-2039 (1992).
9. K. Yamaoka, Y. Tanigawara, T. Nakagawa and T. Uno, A pharmacokinetic analysis program (MULTI) for microcomputer. J. Pharmacobio-Dyn., 4, 879-885 (1981).
10. T.W. Smith, P. Buchan, D.N. Parsons and S. Wilkinson, Peripheral antinociceptive effects of N-methyl morphine. Life Sci., 31, 1205-1208 (1982).
11. G.W. Hardy, L.A. Lowe, P.Y. Sang, D.S.A. Simpkin, S. Wilkinson, R.L. Follenfant and T.W. Smith, Peripherally acting enkephalin analogues. 1. Polar pentapeptides. J. Med. Chem., 31, 960-966 (1988).
12. S. Kaneko and M. Satoh, Experimental method for evaluation of analgesic drug. In Screening Methods for Drug Evaluation, H. Saito and Y. Nomura (Eds), Hirokawa, Tokyo, 1990, pp. 82-102.
13. M.B. Tyers, A classification of opiate receptors that mediate antinocieption in animals. Br. J. Pharmacol., 69, 503-512 (1989).
14. T. Oka, X.-F. Liu, T. Kajita, N. Ohgiya, K. Ghoda, T. Taniguchi, Y. Arai and T. Matsumiya, Effects of the subcutaneous administration of enkephalins on tail-flick response and righting reflex of developing rats. Dev. Brain Res., 69, 271-276 (1992).
15. D. Roemer and J. Pless, Structure activity relationship of orally active enkephalin analogues as analgesics. Life Sci., 24, 621-624 (1979).
16. R.E. Rodriguez, F.D. Rodriguez, M.P. Sacristan, J.L. Torres, F. Reig, J.M. Garcia Anton and G. Valencia, New glycosylpeptides with high antinociceptive activity. Psychopharmacology, 101, 222-225 (1990).
17. 5]enkephalin related glycoconjugates with amide type of linkage. Int. J. Peptide Protein Res., 39, 12-17 (1992).
18. R. Polt, F. Porreca, L.Z. Szabo, E.J. Bilsky, P. Davis, T.J. Abbruscato, T.P. Davis, R. Horvath, H.I. Yamamura and V.J. Hruby, Glycopeptide enkephalin analogues produce analgesia in mice: evidence for penetration of the bloodbrain barrier. Proc. Natl. Acad. Sci. USA, 91, 7114-7118 (1994).