5-Fluorouracil acetic acid/β-cyclodextrin conjugates: Drug release behavior in enzymatic and rat cecal media

International Journal of Pharmaceutics

Volumn 388, Issue 1-2, 2010, Pages 95-100

  Udo, Koichi ^a   Hokonohara, Kazuhiro ^a   Motoyama, Keiichi ^a   Arima, Hidetoshi ^a   Hirayama, Fumitoshi ^b   Uekama, Kaneto ^b  

^a KUMAMOTO UNIVERSITY   (Japan)

^b SOJO UNIVERSITY   (Japan)

Author keywords

Cyclodextrin conjugate; 5 Fluorouracil 1 acetic acid; Colon specific delivery; Prodrug

Indexed keywords

5 FLUOROURACIL 1 ACETIC ACID; AMYLASE; ANTINEOPLASTIC AGENT; BETA CYCLODEXTRIN; CARBOXYLESTERASE; MALTOSE; SODIUM HYDROXIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AQUEOUS SOLUTION; ARTICLE; CECUM; CONTROLLED STUDY; DRUG DEGRADATION; DRUG RELEASE; DRUG TISSUE LEVEL; HYDROLYSIS; MALE; NONHUMAN; PH; PRIORITY JOURNAL; RAT;

ACETIC ACID; ADMINISTRATION, ORAL; ANIMALS; ANTIMETABOLITES, ANTINEOPLASTIC; BETA-CYCLODEXTRINS; CECUM; DRUG CARRIERS; ENZYMES; FLUOROURACIL; HALF-LIFE; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; MALE; PRODRUGS; RATS; TIME FACTORS;

EID: 76549090085     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2009.12.039     Document Type: Article

References (33)

1. Antenucci R.N., and Palmer J.K. Enzymatic degradation of α- and β-cyclodextrins by bacteriodes of the human colon. J. Agric. Food Chem. 32 (1984) 1316-1321
2. Bellanger N., and Perly B. NMR investigations of the conformation of a new cyclodextrin-based amphiphilic transporter for hydrophobic drugs. J. Mol. Struct. 273 (1992) 215-226
3. Creminon C., Djedaini-Pilard F., Vienet R., Pean C., Grognet J.M., Grassi J., Perly B., and Pradelles P. A new specific enzyme immunoassay allowing an efficient pharmacokinetic evaluation of gamma-cyclodextrin after intravenous administration to rats. Pharm. Res. 16 (1999) 1407-1411
4. Flourie B., Molis C., Achour L., Dupas H., Hatat C., and Rambaud J.C. Fate of β-cyclodextrin in the human intestine. J. Nutr. 123 (1993) 676-680
5. In: Friend D.R. (Ed). Oral Colon-specific Drug Delivery (1992), CRC Press, Boca Raton
6. Friend D.R. New oral delivery systems for treatment of inflammatory bowel disease. Adv. Drug Deliv. Rev. 57 (2005) 247-265
7. Friend D.R., and Chang G.W. A colon-specific drug-delivery system based on drug glycosides and the glycosidases of colonic bacteria. J. Med. Chem. 27 (1984) 261-266
8. Friend D.R., and Chang G.W. Drug glycosides: potential prodrugs for colon-specific drug delivery. J. Med. Chem. 28 (1985) 51-57
9. Frijlink H.W., Visser J., Hefting N.R., Oosting R., Meijer D.K., and Lerk C.F. The pharmacokinetics of β-cyclodextrin and hydroxypropyl-β-cyclodextrin in the rat. Pharm. Res. 7 (1990) 1248-1252
10. Fujita K., Tahara T., Nagamura S., Imoto T., and Koga T. Synthesis of specifically modified maltooligosaccharides by enzymatic degradation of cyclodextrin derivatives. Substrate-based investigation of the active site of taka-amylase. J. Org. Chem. 52 (1987) 636-640
11. 14C-β-cyclodextrin in rat. Drug Res. 35 (1985) 1042-1047
12. He W., Du Q., Cao D.Y., Xiang B., and Fan L.F. Study on colon-specific pectin/ethylcellulose film-coated 5-fluorouracil pellets in rats. Int. J. Pharm. 348 (2008) 35-45
13. Hirayama F., Minami K., and Uekama K. In-vitro evaluation of biphenylyl acetic acid-β-cyclodextrin conjugates as colon-targeting prodrugs: drug release behaviour in rat biological media. J. Pharm. Pharmacol. 48 (1996) 27-31
14. Hirayama F., Ogata T., Yano H., Arima H., Udo K., Takano M., and Uekama K. Release characteristics of a short-chain fatty acid, n-butyric acid, from its β-cyclodextrin ester conjugate in rat biological media. J. Pharm. Sci. 89 (2000) 1486-1495
15. Ibekwe V.C., Fadda H.M., Parsons G.E., and Basit A.W. A comparative in vitro assessment of the drug release performance of pH-responsive polymers for ileo-colonic delivery. Int. J. Pharm. 308 (2006) 52-60
16. Jeong Y.I., Ohno T., Hu Z., Yoshikawa Y., Shibata N., Nagata S., and Takada K. Evaluation of an intestinal pressure-controlled colon delivery capsules prepared by a dipping method. J. Control. Release 71 (2001) 175-182
17. Kamada M., Hirayama F., Udo K., Yano H., Arima H., and Uekama K. Cyclodextrin conjugate-based controlled release system: repeated- and prolonged-releases of ketoprofen after oral administration in rats. J. Control. Release 82 (2002) 407-416
18. Klein S., Stein J., and Dressman J. Site-specific delivery of anti-inflammatory drugs in the gastrointestinal tract: an in-vitro release model. J. Pharm. Pharmacol. 57 (2005) 709-719
19. MacLoad A.D., Friend D.R., and Tozer T.N. Synthesis and chemical stability of glucocorticoid-dextran esters: potential prodrugs for colon-specific delivery. Int. J. Pharm. 92 (1993) 105-114
20. Minami K., Hirayama F., and Uekama K. Colon-specific drug delivery based on a cyclodextrin prodrug: release behavior of biphenylylacetic acid from its cyclodextrin conjugates in rat intestinal tracts after oral administration. J. Pharm. Sci. 87 (1998) 715-720
21. Ouchi T., Banba T., Fujimoto M., and Hamamoto S. Synthesis and antitumor activity of chitosan carrying 5-fluorouracils. Makromol. Chem. 190 (1991) 1817-1825
22. 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 (1986) 1081-1084
23. Stella V.J., and Rajewski R.A. Cyclodextrins: their future in drug formulation and delivery. Pharm. Res. 14 (1997) 556-567
24. Tada M. Antineoplastic agents. The preparation of 5-fluorouracil-1-acetic acid derivatives. Bull. Chem. Soc. Jpn. 48 (1975) 3427-3428
25. Tozaki H., Fujita T., Odoriba T., Terabe A., Okabe S., Muranishi S., and Yamamoto A. Validation of a pharmacokinetic model of colon-specific drug delivery and the therapeutic effects of chitosan capsules containing 5-aminosalicylic acid on 2,4,6-trinitrobenzenesulphonic acid-induced colitis in rats. J. Pharm. Pharmacol. 51 (1999) 1107-1112
26. Tozer T.N., Rigod J., Mcleod A.D., Gungon R., Hoag M.K., and Friend D.R. Colon-specific delivery of dexamethasone from a glucoside prodrug in the guinea pig. Pharm. Res. 8 (1991) 445-454
27. Uekama K., Hirayama F., and Irie T. Cyclodextrin drug carrier systems. Chem. Rev. 98 (1998) 2045-2076
28. Uekama K., Minami K., and Hirayama F. 6A-O-[(4-biphenylyl)acetyl]-α-, -β-, and -γ-cyclodextrins and 6A-deoxy-6A-[[(4-biphenylyl)acetyl]amino]-α-, -β-, and -γ-cyclodextrins: potential prodrugs for colon-specific delivery. J. Med. Chem. 40 (1997) 2755-2761
29. Xi M.M., Zhang S.Q., Wang X.Y., Fang K.Q., and Gu Y. Study on the characteristics of pectin-ketoprofen for colon targeting in rats. Int. J. Pharm. 298 (2005) 91-97
30. Yamamoto M., Aritomi H., Irie T., Hirayama F., and Uekama K. Biopharmaceutical evaluation of maltosyl-β-cyclodextrin as a parenteral drug carrier. STP Pharma Sci. 1 (1991) 397-402
31. Yano H., Hirayama F., Arima H., and Uekama K. Prednisolone-appended α-cyclodextrin: alleviation of systemic adverse effect of prednisolone after intracolonic administration in 2,4,6-trinitrobenzenesulfonic acid-induced colitis rats. J. Pharm. Sci. 90 (2001) 2103-2112
32. Yano H., Hirayama F., Arima H., and Uekama K. Preparation of prednisolone-appended α-, β- and γ-cyclodextrins: substitution at secondary hydroxyl groups and in vitro hydrolysis behavior. J. Pharm. Sci. 90 (2001) 493-503
33. Yano H., Hirayama F., Kamada M., Arima H., and Uekama K. Colon-specific delivery of prednisolone-appended α-cyclodextrin conjugate: alleviation of systemic side effect after oral administration. J. Control. Release 79 (2002) 103-112