Synthesis of theophylline-polyrotaxane conjugates and their drug release via supramolecular dissociation

Journal of Controlled Release

Volumn 58, Issue 3, 1999, Pages 251-269

  Ooya, Tooru ^a   Yui, Nobuhiko ^a  

^a JAPAN ADVANCED INSTITUTE OF SCIENCE AND TECHNOLOGY   (Japan)

Author keywords

Degradation controlled drug release; Drug conjugate; Polyrotaxane; Solution property; Supramolecular structure

Indexed keywords

ACEFYLLINE; ALPHA CYCLODEXTRIN; CHYMOTRYPSIN A; PAPAIN; POLYMER; POLYROTAXANE; THEOPHYLLINE POLYROTAXANE; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATE; DRUG RELEASE; IN VITRO STUDY; PRIORITY JOURNAL; SYNTHESIS;

ALPHA-CYCLODEXTRINS; BRONCHODILATOR AGENTS; CHEMISTRY, PHARMACEUTICAL; CHYMOTRYPSIN; CYCLODEXTRINS; DELAYED-ACTION PREPARATIONS; DRUG CARRIERS; ETHYLENEDIAMINES; NITROPHENOLS; PAPAIN; PHENYLALANINE; POLYETHYLENE GLYCOLS; POLYMERS; SOLUBILITY; THEOPHYLLINE;

EID: 0033036238     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0168-3659(98)00163-1     Document Type: Article

References (33)

1. Ulbrich K., Konak C., Tuzar Z., Kopeček J. Solution properties of drug carriers based on poly[N-(2-hydroxypropyl)methacrylamide] containing biodegradable bonds. Makromol. Chem. 188:1987;1261-1272.
2. Soyez H., Schacht E., Vanderkerken S. The crucial role of spacer groups in macromolecular prodrug design. Adv. Drug Deliv. Rev. 21:1996;81-106.
3. Nichifor M., Schacht E., Seymour L.W. Macromolecular prodrug of 5-fluorouracil. 2: Enzymatic degradation. J. Control. Release. 39:1996;79-92.
4. Nukui M., Hoes K., Berg H., Feijen J. Association of macromolecular prodrugs consisting of adriamycin bound to poly(L-glutamic acid). Makromol. Chem. 192:1991;2925-2942.
5. Hirayama F., Minami K., Uekama K. In-vitro evaluation of biphenylyl acetic acid-β-cyclodextrin conjugates as colon-targeting prodrugs: Drug release behavior in rat biological media. J. Pharm. Pharmacol. 48:1995;27-31.
6. Lopez H.P., Djedaïni F., Perly B., Coleman A.W., Galons H., Miocque M. An approach to vectorisation of pharmacologically active molecules: The covalent binding of Leu-enkephalin to a modified β-cyclodextrin. Tetrahedron Lett. 31:1990;1999-2002.
7. Pilard F.D., Désalos J., Perly B. Synthesis of a new molecular carrier: N-(Leu-enkephalin)yl 6-amino-6-deoxy-cyclomaltoheptaose. Tetrahedron Lett. 34:1993;2457-2460.
8. Tanaka H., Kominato K., Yamamoto R., Yoshioka T., Nishida H., Tone H., Okamoto R. Synthesis of doxorubicin-cyclodextrin conjugates. J. Antibiot. 47:1994;1025-1029.
9. Ohtani Y., Irie T., Uekama K., Fukunaga K., Pitha J. Differential effects of α-, β- and γ-cyclodextrins on human erythrocytes. Eur. J. Biochem. 186:1989;17-22.
10. Ooya T., Mori H., Terano M., Yui N. Synthesis of a biodegradable polymeric supramolecular assembly for drug delivery. Macromol. Rapid Commun. 16:1995;259-263.
11. Ooya T., Yui N. Synthesis and characterization of biodegradable polyrotaxane as a novel supramolecular-structured drug carrier. J. Biomater. Sci. Polym. Edn. 8:1997;437-455.
12. Yui N., Ooya T., Kumeno T. Effect of biodegradable polyrotaxane on platelet activation. Bioconjugate Chem. 9:1998;118-125.
13. Sriamornsak P., Prakongpan S., Puttipipatkhachorn S., Kennedy R.A. Development of sustained release theophylline pellets coated with calcium pectinate. J. Control. Release. 47:1997;221-232.
14. Mocanu G., Airinei A., Carpov A. Macromolecular drug conjugates. V. Theophylline-dextran. J. Control. Release. 40:1996;1-9.
15. Harada A., Li J., Kamachi M. Preparation and properties of inclusion complexes of poly(ethylene glycol) with α-cyclodextrin. Macromolecules. 26:1993;5698-5703.
16. Onozuka S., Kojima M., Hattori K., Toda F. The regiospecific mono tosylation of cyclodextrins. Bull. Chem. Soc. Jpn. 53:1980;3221-3224.
17. Nozaki T., Maeda Y., Ito K., Kitano H. Cyclodextrins modified with polymer chains which are responsive to external stimuli. Macromolecules. 28:1995;522-524.
18. Vandoorne F., Vercauteren R., Permentier D., Schacht E. Re-investigation of 4-nitrophenyl chloroformate activation of dextran. Evidence for the formation of different types of carbonate moieties. Makromol. Chem. 186:1985;2455-2460.
19. Vandoorne F., Bruneel D., Schacht E. Effect of chemical modification of dextran on the degradation by dextranase. Bioact. Compat. Polym. 5:1990;4-15.
20. Axén R., Ernback S. Chemical fixation of enzymes to cyanogen halide activated polysaccharide carriers. Eur. J. Biochem. 18:1971;351-360.
21. Laakso T., Stjärnkvist P., Sjöholm I. Biodegradable microspheres. VI: Lysosomal release of covalently bound antiparasitic drugs from starch microparticles. J. Pharm. Sci. 76:1987;134-140.
22. 5N-(2-hydroxyethyl)-L-glutamine] and coupling bioactive agents. Makromol. Chem. 193:1992;3023-3030.
23. Harada A., Li J., Kamachi M. Formation of inclusion complex of monodisperse oligo(ethylene glycol)s with α-cyclodextrin. Macromolecules. 27:1994;4538-4543.
24. Marre A.D., Soyez H., Schacht E. Synthesis of macromolecular mitomycin C derivatives. J. Control. Release. 32:1994;129-137.
25. Akashi M., Wada M., Yanase S., Miyauchi N. Polymer drugs and polymeric drugs. II. Synthesis of water dispersible microspheres having 5-fluorouracil and theophylline using a water soluble macromonomer. J. Polym. Sci., Part C: Polym. Lett. 27:1989;377-380.
26. Ooya T., Yui N. Supramolecular dissociation of biodegradable polyrotaxanes by enzymatic terminal hydrolysis. Macromol. Chem. Phys. 199:1998;2311-2320.
27. Ooya T., Yui N. Regulation of intracellular metabolism by biodegradable polyrotaxanes. J. Biomater. Sci. Polym. Edn. 52:1998;313-326.
28. Tanner D.W., Berry G.C. Properties of cellulose acetate in solution. I. Light scattering, osmometry, and viscometry on dilute solutions. J. Polym. Sci., Polym. Phys. Edn. 12:1974;941-975.
29. Orofino T.A., Mickey J.W. Jr. Dilute solution properties of linear polystyrene in θ-solvent media. J. Chem. Phys. 38:1963;2512-2520.
30. Outer P., Carr C.I., Zimm B.H. Light scattering investigation of the structure of polystyrene. J. Chem. Phys. 18:1950;830-839.
31. Schechter I., Berger A. The size of the active site in proteases. I. Papain. Biochim. Biophys. Res. Commun. 27(2):1967;157-162.
32. Ulbrich K., Stohalm J., Kopecěk J. Poly(ethylene glycol)s containing enzymatically degradable bonds. Makromol. Chem. 187:1986;1331-1441.
33. K. Park, W.S.W. Shalaby, H. Park, Enzyme-catalyzed degradation, in: K. Park, W.S.W. Shalaby, H. Park (Eds.), Biodegradable Hydrogels for Drug Delivery, Technomic Publishing Company, Lancaster, 1993, pp. 153-187.