Conjugation of poorly absorptive drugs with mucoadhesive polymers for the improvement of oral absorption of drugs

Journal of Controlled Release

Volumn 123, Issue 3, 2007, Pages 195-202

  Sakuma, Shinji ^a   Matsumoto, Takaomi ^a   Yamashita, Shinji ^a   Wang, Yanli ^b   Lu, Zheng Rong ^b  

^a SETSUNAN UNIVERSITY   (Japan)

^b UNIVERSITY OF UTAH   (United States)

Author keywords

Brush border peptidase; Conjugation; Mucoadhesive polymer; Oral absorption enhancement; Poorly absorptive drug

Indexed keywords

BRUSH BORDER PEPTIDASE; MUCOADHESIVE POLYMER; ORAL ABSORPTION ENHANCEMENT; POORLY ABSORPTIVE DRUG;

ABSORPTION; AMINO ACIDS; POLYMER BLENDS; VINYL RESINS;

DRUG DOSAGE;

ALANYLALENDRONIC ACID; ALANYLPROLYLALENDRONIC ACID; ALENDRONIC ACID; DIPEPTIDYL PEPTIDASE IV; MICROSOMAL AMINOPEPTIDASE; POLY(VINYLAMINE); POLYMER; SUCCINOYLGLYCYLGLYCYLPHENYLALANYLALANYLPROLINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BRUSH BORDER; CONTROLLED STUDY; DRUG ABSORPTION; DRUG BLOOD LEVEL; DRUG CONJUGATION; DRUG DESIGN; DRUG RELEASE; DRUG SYNTHESIS; MALE; MEMBRANE PERMEABILITY; NONHUMAN; PRIORITY JOURNAL; RAT;

ADHESIVENESS; ADMINISTRATION, ORAL; ALENDRONATE; ANIMALS; ANTIGENS, CD13; ANTIGENS, CD26; AREA UNDER CURVE; BONE DENSITY CONSERVATION AGENTS; CELL MEMBRANE PERMEABILITY; CHEMISTRY, PHARMACEUTICAL; DRUG CARRIERS; DRUG COMPOUNDING; INTESTINAL ABSORPTION; INTESTINES; MALE; MICROVILLI; MUCINS; OLIGOPEPTIDES; POLYVINYLS; RATS; RATS, WISTAR; SOLUBILITY; TECHNOLOGY, PHARMACEUTICAL;

EID: 35548954211     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jconrel.2007.08.011     Document Type: Article

References (33)

1. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P. Experimental and computational approaches to estimate solubility and permeability in drug delivery and development setting. Adv. Drug Deliv. Rev. 46 1-3 (2001) 3-26
2. Straughn A.B., Meyer M.C., Raghow G., and Rotenberg K. Bioavailability of microsize and ultramicrosize griseofulvin products in man. J. Pharmacokinet. Biopharm. 8 4 (1980) 347-362
3. Charman S.A., Charman W.N., Rogge M.C., Wilson T.D., Dutko F.J., and Pouton C.W. Self-emulsifying drug delivery systems: formulation and biopharmaceutic evaluation of an investigational lipophilic compound. Pharm. Res. 9 1 (1992) 87-93
4. Liu C., Wu J., Shi B., Zhang Y., Gao T., and Pei Y. Enhancing the bioavailability of cyclosporine a using solid dispersion containing polyoxyethylene (40) stearate. Drug Dev. Ind. Pharm. 32 1 (2006) 115-123
5. Sakuma S., Hayashi M., and Akashi M. Design of nanoparticles composed of graft copolymers for oral peptide delivery. Adv. Drug Deliv. Rev. 47 1 (2001) 21-37
6. Fujita T., Fujita T., Morikawa K., Tanaka H., Iemura O., Yamamoto A., and Muranishi S. Improvement of intestinal absorption of human calcitonin by chemical modification with fatty acids: synergistic effects of acylation and absorption enhancers. Int. J. Pharm. 134 (1996) 47-57
7. Tamai I., Nakanishi T., Nakahara H., Sai Y., Ganapathy V., Leibach F.H., and Tsuji A. Improvement of l-dopa absorption by dipeptidyl derivation, utilizing peptide transporter PepT1. J. Pharm. Sci. 87 12 (1998) 1542-1546
8. Han H.K., Oh D.M., and Amidon G.L. Cellular uptake mechanism of amino acid ester prodrugs in Caco-2/hPEPT1 cells overexpressing a human peptide transporter. Pharm. Res. 15 9 (1998) 1382-1386
9. Futaki S. Arginin-rich peptides: potential for intracellular delivery of macromolecules and the mystery of the translocation mechanisms. Int.J. Pharm. 245 1-2 (2002) 1-7
10. Lee V.H.L. Protease inhibitors and penetration enhancers as approaches to modify peptide absorption. J. Control. Release 13 (1990) 213-223
11. Shen Q., Lin Y., Handa T., Doi M., Sugie M., Wakayama K., Okada N., Fujita T., and Yamamoto A. Modulation of intestinal P-glycoprotein function by polyethylene glycols and their derivatives by in vitro transport and in situ absorption studies. Int. J. Pharm. 313 1-2 (2006) 49-56
12. Saffran M., Kumar G.S., Savariar C., Burnham J.C., Williams F., and Neckers D.C. A new approach to the oral administration of insulin and other peptide drugs. Science 233 4768 (1986) 1081-1084
13. Couvreur P., and Puisieux F. Nano- and microparicles for the delivery of polypeptides and proteins. Adv. Drug Deliv. Rev. 10 (1993) 141-162
14. Morishita M., Goto T., Nakamura K., Lowman A.M., Takayama K., and Peppas N.A. Novel oral insulin delivery systems based on complexation polymer hydrogels: single and multiple administration studies in type 1 and 2 diabetic rats. J. Control. Release 110 3 (2006) 587-594
15. Gabor F., Bogner E., Weissenboeck A., and Wirth M. The lectin-cell interaction and its implications to intestinal lectin-mediated drug delivery. Adv. Drug Deliv. Rev., 56 4 (2004) 459-480
16. Gu J.P., Robinson J.R., and Leung S.H.S. Binding of acrylic polymers to mucin/epithelial surfaces: structure-property relationships. Crit. Rev. Ther. Drug Carr. Syst. 5 1 (1988) 21-67
17. Sakuma S., Sudo R., Suzuki N., Kikuchi H., Takamori H., Sato T., Minamitake Y., Hayashi Y., Sugita O., Hiwatari K., Kishida A., and Akashi M. Human calcitonin delivered orally by means of nanoparticles composed of novel graft copolymers. J. Dispers. Sci. Technol. 24 3-4 (2003) 623-632
18. van der Merwe S.M., Verhoef J.C., Verheijden J.H., Kotze A.F., and Junginger H.E. Trimethylated chitosan as polymeric absorption enhancer for improved peroral delivery of peptide drugs. Eur. J. Pharm. Biopharm. 58 2 (2004) 225-235
19. Lin J.H., Chen I.W., and Deluna F.A. On the absorption of alendronate in rats. J. Pharm. Sci. 83 12 (1994) 1741-1746
20. Gertz B.J., Holland S.D., Cline W.F., Matuszeuski B.K., Freeman A., Quan H., Lasseter K.C., Mucklow J.C., and Porras A.G. Studies of the oral bioavailability of alendronate. Clin. Pharmacol. Ther. 58 3 (1995) 288-298
21. Sakuma S., Sudo R., Suzuki N., Kikuchi H., Akashi M., and Hayashi M. Mucoadhesion of polystyrene nanoparticles having surface hydrophilic polymeric chains in the gastrointestinal tract. Int. J. Pharm. 177 2 (1999) 161-172
22. Ezra A., Hoffman A., Breuer E., Alferiev I.S., Mönkkönen J., Hanany-Rozen N.E., Weiss G., Stepensky D., Gati I., Cohen H., Törmälehto S., Amidon G.L., and Golomb G. A peptide prodrug approach for improving bisphosphonate oral absorption. J. Med. Chem. 43 20 (2000) 3641-3652
23. Kopeček J., and Kopečková P. N-(2-hydroxypropyl)-methacrylamide copolymers for colon-specific drug delivery. In: Friend D.R. (Ed). Oral Colon Specific Delivery (1992), CRC Press, Boca Raton, FL 189-211
24. Sakuma S., Lu Z.-R., Kopečková P., and Kopeček J. Biorecognizable HPMA copolymer-drug conjugates for colon-specific delivery of 9-aminocamptothecin. J. Control. Release 75 3 (2001) 365-379
25. Langguth P., Bohner V., Biber J., and Merkle H.P. Metabolism and transport of the pentapeptide metkephamid by brush-border membrane vesicles of rat intestine. J. Pharm. Pharmacol. 46 1 (1994) 34-40
26. Stieger B., and Murer H. Heterogeneity of brush-border-membrane vesicles from rat small intestine prepared by a precipitation method using Mg/EGTA. Eur. J. Biochem. 135 1 (1983) 95-101
27. Kline W.F., and Matuszewski B.K. Improved determination of the bisphosphonate alendronate in human plasma and urine by automated precolumn derivatization and high-performance liquid chromatography with fluorescence and elelctrochemical detection. J. Chromatogr. 583 2 (1992) 183-193
28. Davis S.S. The design and evaluation of controlled release system for the gastrointestinal tract. J. Control. Release 2 (1985) 27-28
29. Kondo H., Takahashi Y., Watanabe T., Yokohama S., and Watanabe J. Gastrointestinal transit of liquids in unfed cynomolgus monkeys. Biopharm. Drug Dispos. 24 3 (2003) 131-140
30. Sakuma S., Sudo R., Suzuki N., Kikuchi H., Akashi M., Ishida Y., and Hayashi M. Behavior of mucoadhesive nanoparticles having hydrophilic polymeric chains in the intestine. J. Control. Release 81 3 (2002) 281-290
31. Woodley J.F. Enzymatic barriers for GI peptide and protein delivery. Crit. Rev. Ther. Drug Carr. Syst. 11 2-3 (1994) 61-95
32. Kopeček J., Rejmanová P., and Chytrý V. Polymers containing enzymatically degradable bonds. 1. Chymotrypsin catalyzed hydrolysis of p-nitroanilides of phenylalanine and tyrosine attached to side-chains of copolymers of N-(2-hydroxypropyl)methacrylamide. Macromol. Chem. 182 (1981) 799-809
33. Kopeček J., and Rejmanová P. Enzymatically degradable bonds in synthetic polymers. In: Bruck S.D. (Ed). Controlled Drug Delivery vol. I (1983), CRC Press, Boca Raton, FL 81-124