Esterase-sensitive cyclic prodrugs of peptides: Evaluation of an acyloxyalkoxy promoiety in a model hexapeptide

Pharmaceutical Research

Volumn 13, Issue 11, 1996, Pages 1615-1623

  Pauletti, Giovanni M ^a   Gangwar, Sanjeev ^a   Okumu, Franklin W ^a   Siahaan, Teruna J ^a   Stella, Valentino J ^a   Borchardt, Ronald T ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

Caco 2 cells; Chemical stability; Enzymatic stability; Esterase sensitive prodrug; Membrane permeability; Peptide delivery

Indexed keywords

CYCLOPEPTIDE; ESTERASE; HEXAPEPTIDE; PRODRUG;

ANIMAL TISSUE; ARTICLE; CELL MEMBRANE PERMEABILITY; CELL STRAIN CACO 2; CONFORMATION; DRUG DEGRADATION; DRUG STABILITY; DRUG TRANSPORT; HUMAN; HUMAN TISSUE; INTESTINE MUCOSA; NONHUMAN; PRIORITY JOURNAL; RAT; TRANSPORT KINETICS;

ANIMALS; BIOLOGICAL TRANSPORT; CACO-2 CELLS; CARBAMATES; CELL MEMBRANE PERMEABILITY; CHEMISTRY, PHYSICAL; DRUG STABILITY; ENZYME STABILITY; ESTERASES; EVALUATION STUDIES; HUMANS; INTESTINAL MUCOSA; MALE; OLIGOPEPTIDES; PEPTIDES, CYCLIC; PRODRUGS; RATS; RATS, SPRAGUE-DAWLEY; SENSITIVITY AND SPECIFICITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030470532     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1016472119387     Document Type: Article

References (25)

1. V. H. L. Lee and A. Yamamoto. Adv. Drug Delivery Rev. 4:171-207 (1990).
2. V. Bocci. Adv. Drug Delivery Rev. 4:149-169 (1990).
3. X. H. Zhou. J. Controlled Release 29:239-252 (1994).
4. G. M. Pauletti, S. Gangwar, G. T. Knipp, M. M. Nerurkar, F. W. Okumu, K. Tamura, T. J. Siahaan, and R. T. Borchardt. J. Controlled Release 41:3-17 (1996).
5. R. A. Gray, D. G. Vander Velde, C. J. Burke, M. C. Manning, C. R. Middaugh, and R. T. Borchadt. Biochemistry 33:1323-1331 (1994).
6. W. A. Banks, A. J. Kastin, D. H. Coy, and E. Angulo. Brain. Res. Bull. 17:155-158 (1986).
7. H. Bundgaard. Adv. Drug Delivery Rev. 8:1-38 (1992).
8. R. Oliyai and V. J. Stella. Ann. Rev. Pharmacol. Toxicol. 32:521-544 (1993).
9. J. K. McDonald and A. J. Barrett. Mammalian Proteases: A Glossary and Bibliography, Vol. 2, Exopeptidases, Academic Press, New York, 1986.
10. F. W. Okumu, G. M. Pauletti, D. G. Vander Velde, T. J. Siahaan, and R. T. Borchardt. Pharm. Res. 12:S-302 (1995).
11. S. Gangwar, G. M. Pauletti, T. J. Siahaan, V. J. Stella, and R. T. Borchardt. J. Org. Chem. (submitted).
12. M. Inoue, M. Morikawa, M. Tsuboi, and M. Sugiura. Jpn. J. Pharmacol. 29:9-16 (1979).
13. F. M. Williams. Clin. Pharmacokinet. 10:392-403 (1985).
14. I. J. Hidalgo, T. J. Raub, and R. T. Borchardt. Gastroenterology 96:736-749 (1989).
15. P. Artursson. J. Pharm. Sci. 79:476-482 (1990).
16. M. Pinto, S. Robine-Leon, M.-D. Appay, M. Kedinger, N. Tradou, E. Dussaulx, B. Lacroix, P. Simon-Assmann, K. Haffen, J. Fogh, and A. Zweibaum. Biol. Cell 47:323-330 (1983).
17. G. Wilson, I. F. Hassan, C. J. Dix, I. Williamson, R. Shah, and M. Mackay. J. Controlled Release 11:25-40 (1990).
18. H. Liu, S. Ong, L. Glunz, and C. Pidgeon. Anal. Chem. 67:3550-3557 (1995).
19. P. F. Augustijns and R. T. Borchardt. Drug Metab. Dispos. 23:1372-1378 (1995).
20. C. S. Cook, P. J. Karabatsos, G. L. Schoenhard, and A. Karim. Pharm. Res. 12:1158-1164 (1995).
21. W. N. Aldridge. Biochem. J. 53:117-124 (1953).
22. K. Takahashi, S. Tamagawa, H. Sakano, T. Katagi, and N. Mizuno. Biol. Pharm. Bull. 18:1401-1404 (1995).
23. W. N. Aldridge. Biochem. J. 53:110-117 (1953).
24. D. S. Auld and B. Holmquist. Biochemistry 13:4355-4361 (1974).
25. S. Gangwar, S. D. S. Jois, T. J. Siahaan, D. G. Vander Velde, V. J. Stella, and R. T. Borchardt. Pharm. Res. 13: 1657-1662 (1996).