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Volumn 65, Issue 3, 2005, Pages 364-374

Water-soluble prodrugs of cyclosporine A with tailored conversion rates

Author keywords

Conversion rates; Cyclosporine A; Drug delivery; Enzyme triggered release; Prodrugs; Solubilization

Indexed keywords

3 HYDROXY 4 METHYL 2 METHYLAMINO 6 OCTENOIC ACID; CYCLOPHILIN A; CYCLOSPORIN A; CYCLOSPORIN DERIVATIVE; PRODRUG;

EID: 16444369438     PISSN: 1397002X     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1399-3011.2005.00234.x     Document Type: Article
Times cited : (4)

References (30)
  • 2
  • 3
    • 0035238531 scopus 로고    scopus 로고
    • Cyclosporin. An updated review of the pharmacokinetic properties, clinical efficacy and tolerability of a microemulsion-based formulation (Neoral) in organ transplantation
    • Dunn, C.J., Wagstaff, A.J., Perry, C.M., Plosker, G.L. Goa, K.L. (2001) Cyclosporin. An updated review of the pharmacokinetic properties, clinical efficacy and tolerability of a microemulsion-based formulation (Neoral) in organ transplantation. Drugs 61, 1957-2016.
    • (2001) Drugs , vol.61 , pp. 1957-2016
    • Dunn, C.J.1    Wagstaff, A.J.2    Perry, C.M.3    Plosker, G.L.4    Goa, K.L.5
  • 6
    • 0026607879 scopus 로고
    • Prodrugs of peptides: 16. Isocyclosporin A as a potential prodrug of cyclosporin A
    • Bundgaard, H. & Friis, G.J. (1992) Prodrugs of peptides: 16. Isocyclosporin A as a potential prodrug of cyclosporin A. Int. J. Pharm. 82, 85-90.
    • (1992) Int. J. Pharm. , vol.82 , pp. 85-90
    • Bundgaard, H.1    Friis, G.J.2
  • 7
    • 1542511351 scopus 로고    scopus 로고
    • Cyclosporin A prodrugs: Design, synthesis and biophysical properties
    • Hamel, A.R., Hubler, F., Carrupt, A., Wenger, R.M. & Mutter, M. (2004) Cyclosporin A prodrugs: design, synthesis and biophysical properties. J. Pept, Res. 63, 147-154.
    • (2004) J. Pept. Res. , vol.63 , pp. 147-154
    • Hamel, A.R.1    Hubler, F.2    Carrupt, A.3    Wenger, R.M.4    Mutter, M.5
  • 8
    • 5144229966 scopus 로고
    • Practical aspects of two-dimensional transverse NOE spectroscopy
    • Bax, A. & Davis, D.G. (1985) Practical aspects of two-dimensional transverse NOE spectroscopy. J. Magn. Reson. 63, 207-213.
    • (1985) J. Magn. Reson. , vol.63 , pp. 207-213
    • Bax, A.1    Davis, D.G.2
  • 9
    • 33845378943 scopus 로고
    • Assignment of complex proton NMR spectra via two-dimensional homonuclear Hartmann-Hahn spectroscopy
    • Bax, A. & Davis, D.G. (1985) Assignment of complex proton NMR spectra via two-dimensional homonuclear Hartmann-Hahn spectroscopy. J. Am. Chem. Soc. 107, 2820-2821.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 2820-2821
    • Bax, A.1    Davis, D.G.2
  • 10
    • 44949290287 scopus 로고
    • Rapid-pulse artifacts in double-quantum-filtered COSY
    • Derome, A.E. &. Williamson, M.P. (1990) Rapid-pulse artifacts in double-quantum-filtered COSY. J. Magn. Res. 88, 177-185.
    • (1990) J. Magn. Res. , vol.88 , pp. 177-185
    • Derome, A.E.1    Williamson, M.P.2
  • 11
    • 0002891484 scopus 로고
    • Multiple quantum spin-echo spectroscopy
    • Bodenhausen, G., Vold, R.L. & Vold, R.R. (1980) Multiple quantum spin-echo spectroscopy. J. Mag. Res. 37, 93-106.
    • (1980) J. Mag. Res , vol.37 , pp. 93-106
    • Bodenhausen, G.1    Vold, R.L.2    Vold, R.R.3
  • 12
    • 0021114895 scopus 로고
    • Application of phase sensitive two-dimensional correlated spectroscopy (COSY) for measurements of proton-proton spin-spin coupling constants in proteins
    • Marion, D. &. Wuetrich, K. (1983) Application of phase sensitive two-dimensional correlated spectroscopy (COSY) for measurements of proton-proton spin-spin coupling constants in proteins. Biochem. Biophys. Res. Comm. 113, 967-974.
    • (1983) Biochem. Biophys. Res. Comm. , vol.113 , pp. 967-974
    • Marion, D.1    Wuetrich, K.2
  • 13
    • 0028547263 scopus 로고
    • SwaN-NMR: A complete and expansible NMR software for the Macintosh
    • Balacco, G. (1994) SwaN-NMR: A Complete and Expansible NMR Software for the Macintosh. J. Chem. Inf. Comput. Sci. 34, 1235-1241.
    • (1994) J. Chem. Inf. Comput. Sci. , vol.34 , pp. 1235-1241
    • Balacco, G.1
  • 14
    • 0002427748 scopus 로고    scopus 로고
    • SwaN-MR from infancy to maturity
    • Balacco, G. (2000) SwaN-MR from infancy to maturity. Mol. Biol. Today 1, 23-28.
    • (2000) Mol. Biol. Today , vol.1 , pp. 23-28
    • Balacco, G.1
  • 15
    • 4544275536 scopus 로고    scopus 로고
    • Synthesis of peptides and peptidomimetics
    • (Goodman, M., ed.), Georg Thieme Verlag Stuttgart, New York
    • Felix, A., Moroder, L. &. Toniolo, C. (2002) Synthesis of peptides and peptidomimetics. In: Houben-Weyl - Methods of Organic Chemistry, Vol. E22 (Goodman, M., ed.), Georg Thieme Verlag Stuttgart, New York.
    • (2002) Houben-Weyl - Methods of Organic Chemistry , vol.E22
    • Felix, A.1    Moroder, L.2    Toniolo, C.3
  • 18
    • 0023605394 scopus 로고
    • N-(Acyloxyalkoxycarbonyl) derivates as potential prodrugs of amines. II. Esterase-catalysed release of parent amines from model prodrugs
    • Gogate, U.S. &. Repta, A.J. (1987) N-(Acyloxyalkoxycarbonyl) derivates as potential prodrugs of amines. II. Esterase-catalysed release of parent amines from model prodrugs. Int. J. Pharm. 40, 249-255.
    • (1987) Int. J. Pharm. , vol.40 , pp. 249-255
    • Gogate, U.S.1    Repta, A.J.2
  • 19
    • 0023605117 scopus 로고
    • N-(acyloxyalkoxycarbonyl) derivatives as potential prodrugs of amines. I. Kinetics and mechanism of degradation in aqueous solutions
    • Gogate, U.S., Repta, A.J. & Alexander, J. (1987) N- (acyloxyalkoxycarbonyl) derivatives as potential prodrugs of amines. I. Kinetics and mechanism of degradation in aqueous solutions. Int. J. Pharm. 40, 235-248.
    • (1987) Int. J. Pharm. , vol.40 , pp. 235-248
    • Gogate, U.S.1    Repta, A.J.2    Alexander, J.3
  • 20
    • 0000658454 scopus 로고
    • (Acyloxy)alkyl carbamates as novel bioreversible prodrugs for amines: Increased permeation through biological membranes
    • Alexander, J., Cargill, R., Michelson, S.R. & Schwam, H. (1988) (Acyloxy)alkyl carbamates as novel bioreversible prodrugs for amines: increased permeation through biological membranes. J. Med. Chem. 31, 318-322.
    • (1988) J. Med. Chem. , vol.31 , pp. 318-322
    • Alexander, J.1    Cargill, R.2    Michelson, S.R.3    Schwam, H.4
  • 23
    • 0025868143 scopus 로고
    • Determination of kinetic constants for peptidyl prolyl cis-trans isomerases by an improved spectrophotometric assay
    • Kofron, J.L., Kuzmic, P., Kishore, V., Colon-Bonilla, E. &. Rich, D.H. (1991) Determination of kinetic constants for peptidyl prolyl cis-trans isomerases by an improved spectrophotometric assay. Biochemistry 30, 6127-6134.
    • (1991) Biochemistry , vol.30 , pp. 6127-6134
    • Kofron, J.L.1    Kuzmic, P.2    Kishore, V.3    Colon-Bonilla, E.4    Rich, D.H.5
  • 24
    • 0026651050 scopus 로고
    • Lithium chloride perturbation of cis-trans peptide bond equilibria: Effect on conformational equilibria in cyclosporin A and on time-dependent inhibition of cyclophilin
    • Kofron, J.L., Kuzmic, P., Kishore, V.; Gemmecker, G., Fesik, S.W. &. Rich, D.H. (1992) Lithium chloride perturbation of cis-trans peptide bond equilibria: effect on conformational equilibria in cyclosporin A and on time-dependent inhibition of cyclophilin. J. Am. Chem. Soc. 114, 2670-2675.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 2670-2675
    • Kofron, J.L.1    Kuzmic, P.2    Kishore, V.3    Gemmecker, G.4    Fesik, S.W.5    Rich, D.H.6
  • 25
    • 1542749547 scopus 로고
    • Cyclosporine: Chemistry, structure-activity relationships and mode of action
    • Wenger, R., Payne, T.G. & Schreier, M.H. (1985) Cyclosporine: chemistry, structure-activity relationships and mode of action. Prog. Clin. Biochem. Med. 3, 157-191.
    • (1985) Prog. Clin. Biochem. Med. , vol.3 , pp. 157-191
    • Wenger, R.1    Payne, T.G.2    Schreier, M.H.3
  • 26
    • 0006645882 scopus 로고
    • Prodrugs versus soft drugs
    • (Bundgaard, H., ed.). Elsevier Science, Amsterdam, New York, Oxford
    • Bodor, N. (1985) Prodrugs versus soft drugs. In: Design of Prodrug. (Bundgaard, H., ed.), pp. 333-354. Elsevier Science, Amsterdam, New York, Oxford.
    • (1985) Design of Prodrug , pp. 333-354
    • Bodor, N.1
  • 27
    • 0021800252 scopus 로고
    • Prodrugs. Do they have advantages in clinical practice?
    • Stella, V.J., Charman, W.N.A. & Naringtekar, V.H. (1985) Prodrugs. Do they have advantages in clinical practice? Drugs 29, 455-473
    • (1985) Drugs , vol.29 , pp. 455-473
    • Stella, V.J.1    Charman, W.N.A.2    Naringtekar, V.H.3
  • 28
    • 0002327694 scopus 로고
    • Design of prodrugs: Bioreversible derivates for various functional groups and chemical entities
    • (Bundgaard, H., ed.), Elsevier Science, Amsterdam, New York, Oxford
    • Bundgaard, H. (1985) Design of prodrugs: bioreversible derivates for various functional groups and chemical entities. In: Design of Prodrug (Bundgaard, H., ed.), Elsevier Science, Amsterdam, New York, Oxford.
    • (1985) Design of Prodrug
    • Bundgaard, H.1
  • 29
    • 0024603946 scopus 로고
    • The double prodrug concept and its applications
    • Bundgaard, H. (1989) The double prodrug concept and its applications. Adv. Drug Delivery Rev. 3, 39-65.
    • (1989) Adv. Drug Delivery Rev. , vol.3 , pp. 39-65
    • Bundgaard, H.1
  • 30
    • 16444381263 scopus 로고    scopus 로고
    • Water soluble cyclosporine monomethoxy poly (ethyleneglycol) conjugates as potential prodrugs
    • Cho, H. & Chung, Y. (2004) Water soluble cyclosporine monomethoxy poly (ethyleneglycol) conjugates as potential prodrugs. Arch. Pharm. Res. 27, 662-669.
    • (2004) Arch. Pharm. Res. , vol.27 , pp. 662-669
    • Cho, H.1    Chung, Y.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.