Synthesis and evaluation of a modified mucoadhesive polymer protecting from α-chymotrypsinic degradation

International Journal of Pharmaceutics

Volumn 146, Issue 2, 1997, Pages 247-254

  Bernkop Schnurch A ^a   Apprich, I ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Chymotrypsin; Chymostatin; Luminal degradation; Mucoadhesive polymer; Peroral administration of (poly)peptides

Indexed keywords

CHYMOSTATIN; CHYMOTRYPSIN; POLYACRYLIC ACID; POLYMER;

ADHESION; ANIMAL TISSUE; ARTICLE; CONJUGATE; CONTROLLED STUDY; DRUG DEGRADATION; DRUG SYNTHESIS; INTESTINE MUCOSA; NONHUMAN; PRIORITY JOURNAL; SWINE; TENSILE STRENGTH;

EID: 0031056746     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-5173(96)04832-6     Document Type: Article

References (31)

1. Aungst, B.J. and Phang, S., Metabolism of a neurotensin (8-13) analog by intestinal and nasal enzymes, and approaches to stabilize this peptide at these absorption sites. Int. J. Pharm., 117 (1995) 95-100.
2. Bernkop-Schnürch, A. and Dundalek, K., Novel bioadhesive drug delivery system protecting (poly)peptides from gastric enzymatic degradation. Int. J. Pharm., 138 (1996) 75-83.
3. Bernkop-Schnürch, A. and Fragner, R., Investigations into the diffusion behaviour of polypeptides in native intestinal mucus with regard to their peroral administration. Pharm. Sci., 2 (1996) 361-363.
4. Bernkop-Schnürch, A. and Göckel, N.C., Novel drug delivery system protecting from luminal enzymatic degradation caused by chymotrypsin. Drug Dev. Ind. Pharm., accepted for publication (1997).
5. Birk, Y., The Bowman-Birk inhibitor. Int. J. Pept. Protein Res., 25 (1985) 113-131.
6. Fukunaga, K., Hijikata, S., Ishimura, K., Sonoda, R., Irie, T. and Uekama, K., Albumin β-Cyclodextrin Sulphate as a stabilizer and sustained-release carrier for basic fibrinoblast growth factor. J. Pharm. Pharmacol. 46 (1994) 168-171.
7. Grinde, B. and Seglen, P.O., Differential effects of proteinase inhibitors and amines on the lysosomal and non-lysosomal pathways of protein degradation in isolated rat hepatocytes. Biochim. Biophys. Acta. 632 (1980) 73-86.
8. Hedstrom, L., Perona, J.J. and Rutter, W.J., Converting trypsin to chymotrypsin: residue 172 is a substrate specifity determinant. Biochemistry, 33 (1994) 8757-8763.
9. Jabbari, E., Wisniewski, N. and Peppas, N.A., Evidence of mucoadhesion by chain interpenetration at a poly(acrylic acid) mucin interface using ATR-FTIR spectroscopy. J. Control. Release, 26 (1993) 99-108.
10. Junginger, H.E., Bioadhesive polymer systems for peptide delivery. Acta Pharm. Technol., 36 (1990) 110-126.
11. Kambara, H., Hishida, S. and Naganawa, H., Secondary Ion Mass Spectra of Oligopeptides. Org. Mass Spectr., 17 (1982) 67-73.
12. Kobayashi, S., Kondo, S. and Juni, K., Study on pulmonary delivery of salmon calcitonin in rats: effects of protease inhibitors and absorption enhancers. Pharm. Res., 11 (1994) 1239-1243.
13. Lehr, C.-M., Bioadhesion technologies for the delivery of peptide and protein drugs to the gastrointestinal tract. Crit. Rev. Ther. Drug, 11 (1994) 119-160.
14. Leung, S.S. and Robinson, J.R., Polymer structure features contributing to mucoadhesion: II. J. Control. Release, 12 (1990) 187-194.
15. Lueßen, H.L., Verhoef, J.C., Lehr, C.-M., de Boer, A.G. and Junginger, H.E., Mucoadhesive poly(acrylates) are inhibitors of the intestinal proteases trypsin and carboxypeptidase A. Proc. Int. Symp. Control Rel. Bioact. Mater., 21 (1994) 130-131.
16. Lueßen, H.L., Verhoef, J.C., Borchard, G., Lehr, C.-M., de Boer, A.G. and Junginger, H.E., Mucoadhesive polymers in the peroral peptide drug delivery: 2. Carbomer and polycarbophil are potent inhibitors of the intestinal proteolytic enzyme trypsin. Pharm. Res., 12 (1995) 1293-1298.
17. Lueßen, H.L., de Leeuw, B.J., Pérard, D., Lehr, C.-M., de Boer, A.G., Verhoef, J.C. and Junginger, E.H., Mucoadhesive polymers in peroral peptide drug delivery. I. Influence of mucoadhesive excipients on the proteolytic activity of intestinal enzymes. Eur. J. Pharm. Sci., 4 (1996) 117-128.
18. Morishita, I., Morishita, M., Takayama, K., Machida, Y. and Nagai, T., Hypoglycemic effect of novel oral microspheres of insulin with protease inhibitor in normal and diabetic rats. Int. J. Pharm., 78 (1992a) 9-16.
19. Morishita, M., Morishita, I., Takayama, K., Machida, Y. and Nagai, T., Novel oral microspheres of insulin with protease inhibitor protecting from enzymatic degradation. Int. J. Pharm., 78 (1992b) 1-7.
20. Mortazavi, S.A. and Smart, J.D., An investigation of some factors influencing the in vitro assessment of mucoadhesion. Int. J. Pharm., 116 (1995) 223-230.
21. Nitsan, Z. and Nir, I., Accentuated response to soybean inhibitors by meal-feeding in various species. Adv. Exp. Med. Biol., 199 (1986) 199-222.
22. Ponchel, G., Touchard, F., Duchêne, D. and Peppas, N., Bioadhesive analysis of controlled release systems: I. Fracture and interpenetration analysis in poly(acrylic acid)-containing systems. J. Control. Release, 5 (1987) 129-141.
23. Sanzgiri, Y.D. Topp, E.M., Benedetti, L. and Stella, V.J., Evaluation of mucoadhesive properties of hyaluronic acid benzyl esters. Int. J. Pharrm., 107 (1994) 91-97.
24. Schilling, R.J. and Mitra, A.K., Degradation of insulin by trypsin and α-chymotrypsin. Pharm. Rex., 8 (1991) 721-727.
25. Smart, J.D., Kellaway, J.W. and Worthington E.C., An in-vitro investigation of mucosa-adhesivc materials for use in controlled drug delivery. J. Pharm. Pharmacol., 36 (1984) 295-299.
26. Staros, J.V., Wright, R.W. and Swingle, D.M., Enhancement by N-hydroxysulfosuccinimide of water-soluble carbodiimide-mediated coupling reactions. Anal. Biochem., 156 (1986) 220-222.
27. Suenaga, H., Mikami, M., Yamamoto, H., Harada, T. and Shinkai, S., Strong inhibitory effect of sugar biphenylylboronic acid complexes on the hydrolytic activity of α-chymotrypsin. J. Chem. Soc., 13 (1995) 1733-1738.
28. Umezawa, H., Aoyagi, T., Morishima, H., Kunimoto, S. and Matsuzaki, M., Chymostatin, a new chymotrypsin inhibitor produced by actinomycetes. J. Antibiot., 23 (1970) 425-427.
29. Watanabe, S., Takeuchi, T. and Chey, W.Y., Mediation of trypsin inhibitor-induced pancreatic hypersecretion by secretin and cholecystokinin in rats. Gastroenterology, 102 (1992) 621-628.
30. Woodley, J.F., Enzymatic barriers for G1 peptide and protein delivery. Crit. Rev. Ther. Drug, 11 (1994) 61-95.
31. Yagi, T., Ishizaki, K. and Takebe, H., Cytotoxic effects of protease inhibitors on human cells. 2. Effect of Elastatinal. Cancer Lett., 10 (1980) 301-307.