Release from polymeric prodrugs: linkages and their degradation.
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[1] R. Borchardt,et al. Prodrug strategies based on intramolecular cyclization reactions. , 1997, Journal of pharmaceutical sciences.
[2] R. Duncan. Polymer-Drug Conjugates: Targeting Cancer , 2002 .
[3] P Buchwald,et al. Structure-metabolism relationships: steric effects and the enzymatic hydrolysis of carboxylic esters. , 2001, Mini reviews in medicinal chemistry.
[4] A. J. Kirby,et al. Structure and efficiency in intramolecular and enzymic catalysis. Catalysis of amide hydrolysis by the carboxy-group of substituted maleamic acids , 1972 .
[5] E. A. Bekturov,et al. Synthetic water-soluble polymers in solution , 1986 .
[6] C. G. Pitt,et al. Manipulation of the rate of hydrolysis of polymer-drug conjugates: The secondary structure of the polymer , 1996 .
[7] C. Larsen,et al. Macromolecular Prodrugs. XVI. Colon-Targeted Delivery—Comparison of the Rate of Release of Naproxen from Dextran Ester Prodrugs in Homogenates of Various Segments of the Pig Gastrointestinal (GI) Tract , 1989, Pharmaceutical Research.
[8] K. Krisch,et al. [Carboxylesterases from beef liver microsomes, II. Dissociation and association, molecular weight, reaction with E 600]. , 1967, Hoppe-Seyler's Zeitschrift fur physiologische Chemie.
[9] Wim E. Hennink,et al. Degradation and release behavior of dextran-based hydrogels , 1997 .
[10] Ashutosh Chilkoti,et al. Targeted drug delivery by thermally responsive polymers. , 2002, Advanced drug delivery reviews.
[11] K. Ulbrich,et al. Macromolecular prodrugs for use in targeted cancer chemotherapy: melphalan covalently coupled to N- (2-hydroxypropyl) methacrylamide copolymers , 1991 .
[12] R. Mashelkar,et al. Pendent chain linked delivery systems: II. Facile hydrolysis through molecular imprinting effects , 1997 .
[13] D. Kerr,et al. Preliminary clinical study of the distribution of HPMA copolymers bearing doxorubicin and galactosamine. , 1999, Journal of controlled release : official journal of the Controlled Release Society.
[14] Y. Ikada,et al. Distribution and tissue uptake of poly(ethylene glycol) with different molecular weights after intravenous administration to mice. , 1994, Journal of pharmaceutical sciences.
[15] J. Sussman,et al. Relationship between sequence conservation and three‐dimensional structure in a large family of esterases, lipases, and related proteins , 1993, Protein science : a publication of the Protein Society.
[16] A. Schindler,et al. The kinetics of drug cleavage and release from matrices containing covalent polymer-drug conjugates , 1995 .
[17] M. Royzen,et al. Anticancer drug delivery systems: N4-acyl poly(ethyleneglycol) prodrugs of ara-C. I. Efficacy in solid tumors. , 2002, Journal of controlled release : official journal of the Controlled Release Society.
[18] F. Horkay,et al. Tailoring the swelling pressure of degrading dextran hydroxyethyl methacrylate hydrogels. , 2003, Biomacromolecules.
[19] J. Kopeček. Controlled biodegradability of polymers--a key to drug delivery systems. , 1984, Biomaterials.
[20] E. Hoffmann,et al. Kinetics of Hydrolysis of Hydroxy and Methoxy Derivatives of N-Benzylidene-2-aminopropane , 1966 .
[21] L. Dittert,et al. Acetaminophen prodrugs. 3. Hydrolysis of carbonate and carboxylic acid esters in aqueous buffers. , 1970, Journal of pharmaceutical sciences.
[22] C. Meares,et al. Cathepsin substrates as cleavable peptide linkers in bioconjugates, selected from a fluorescence quench combinatorial library. , 1998, Bioconjugate chemistry.
[23] K. Ulbrich,et al. Synthesis of Biodegradable Polymers for Controlled Drug Release a , 1997, Annals of the New York Academy of Sciences.
[24] E. Schacht,et al. Synthesis of polyglutamine and dextran conjugates of streptomycin with an acid-sensitive drug-carrier linkage. , 1996 .
[25] S. Furukawa,et al. Synthesis of water-soluble polymeric prodrugs possessing 4-methylcatechol derivatives by mechanochemical solid-state copolymerization and nature of drug release. , 2002, Chemical & pharmaceutical bulletin.
[26] C. McCormick,et al. Synthesis, Characterization, and Release Mechanisms of Polymers Containing Pendant Herbicides , 1977 .
[27] J. Cassidy,et al. The place of polymer prodrugs in cancer therapy , 2000 .
[28] J. Keana,et al. Molecular amplifiers: synthesis and functionalization of a poly(aminopropyl)dextran bearing a uniquely reactive terminus for univalent attachment to biomolecules. , 1992, Bioconjugate chemistry.
[29] J. Kopecek,et al. Anticancer agents coupled to N-(2-hydroxypropyl)methacrylamide copolymers. I. Evaluation of daunomycin and puromycin conjugates in vitro. , 1987, British Journal of Cancer.
[30] S. Brocchini,et al. Competitive Reactions During Amine Addition to cis-Aconityl Anhydride , 2002 .
[31] Glen S. Kwon,et al. Methotrexate Esters of Poly(Ethylene Oxide)-Block-Poly(2-Hydroxyethyl-L-Aspartamide). Part I: Effects of the Level of Methotrexate Conjugation on the Stability of Micelles and on Drug Release , 2000, Pharmaceutical Research.
[32] H. Ringsdorf,et al. Effect of molecular size of 125I-labelled poly(vinylpyrrolidone) on its pinocytosis by rat visceral yolk sacs and rat peritoneal macrophages. , 1981, The Biochemical journal.
[33] Jan Feijen,et al. Effect of comonomer hydrophilicity and ionization on the lower critical solution temperature of N-isopropylacrylamide copolymers , 1993 .
[34] Zheng-Rong Lu,et al. Design of novel bioconjugates for targeted drug delivery. , 2002, Journal of controlled release : official journal of the Controlled Release Society.
[35] Jean Campbell,et al. Bioinspired pH-responsive polymers for the intracellular delivery of biomolecular drugs. , 2003, Bioconjugate chemistry.
[36] K. Ulbrich,et al. HPMA copolymers with pH-controlled release of doxorubicin: in vitro cytotoxicity and in vivo antitumor activity. , 2003, Journal of controlled release : official journal of the Controlled Release Society.
[37] R. Mülhaupt,et al. Acid-sensitive polyethylene glycol conjugates of doxorubicin: preparation, in vitro efficacy and intracellular distribution. , 1999, Bioorganic & medicinal chemistry.
[38] K. Ulbrich,et al. Poly[N-(2-hydroxypropyl)methacrylamide] conjugates of methotrexate: Synthesis and in vitro drug release , 1997 .
[39] K. Ulbrich,et al. Targeting of N-(2-hydroxypropyl)methacrylamide copolymer-doxorubicin conjugate to the hepatocyte galactose-receptor in mice: visualisation and quantification by gamma scintigraphy as a basis for clinical targeting studies. , 1993, Journal of drug targeting.
[40] N. Bodor,et al. Structure-based estimation of enzymatic hydrolysis rates and its application in computer-aided retrometabolic drug design. , 2000, Die Pharmazie.
[41] P. Andreasen,et al. The plasminogen activation system in tumor growth, invasion, and metastasis , 2000, Cellular and Molecular Life Sciences CMLS.
[42] C. Larsen,et al. Macromolecular prodrugs I. Kinetics and mechanism of hydrolysis of O-benzoyl dextran conjugates in aqueous buffer and in human plasma , 1985 .
[43] Chun Xing Li. Poly(L-glutamic acid)--anticancer drug conjugates. , 2002, Advanced drug delivery reviews.
[44] R. Mashelkar,et al. Pendent chain linked delivery systems: I facile hydrolysis through anchimeric effect , 1996 .
[45] J. Kopeček,et al. Degradation of side-chains ofN-(2-hydroxypropyl)methacrylamide copolymers by lysosomal thiol-proteinases , 1982, Bioscience reports.
[46] J. Collins,et al. Structure‐based subsite specificity mapping of human cathepsin D using statine‐based inhibitors , 1997, Protein science : a publication of the Protein Society.
[47] K. Petrak,et al. Transport of macromolecules across the capillary walls , 1989 .
[48] Bonnie F. Sloane,et al. Cell surface complex of cathepsin B/annexin II tetramer in malignant progression. , 2000, Biochimica et biophysica acta.
[49] J. Kopeček,et al. Effect of molecular weight (Mw) of N-(2-hydroxypropyl)methacrylamide copolymers on body distribution and rate of excretion after subcutaneous, intraperitoneal, and intravenous administration to rats. , 1987, Journal of biomedical materials research.
[50] Y. Chow,et al. Intramolecular Catalysis of Hydrolytic Reactions. II. The Hydrolysis of Phthalamic Acid1,2 , 1958 .
[51] K. Zhu,et al. Blends of PVA and PGLA: control of the permeability and degradability of hydrogels by blending , 1992 .
[52] C. Larsen. Macromolecular prodrugs. XII. Kinetics of release of naproxen from various polysaccharide ester prodrugs in neutral and alkaline solution , 1989 .
[53] R. Duncan. The dawning era of polymer therapeutics , 2003, Nature Reviews Drug Discovery.
[54] T. Park,et al. Doxorubicin-conjugated biodegradable polymeric micelles having acid-cleavable linkages. , 2002, Journal of controlled release : official journal of the Controlled Release Society.
[55] L. G. Donaruma. Synthetic biologically active polymers , 1975 .
[56] K. Ulbrich,et al. Synthesis of HPMA Copolymers Containing Doxorubicin Bound via a Hydrazone Linkage. Effect of Spacer on Drug Release and in vitro Cytotoxicity , 2002 .
[57] K. Krisch,et al. [Carboxylesterases from beef liver microsomes. I. Isolation, properties and substrate specificity]. , 1967, Hoppe-Seyler's Zeitschrift fur physiologische Chemie.
[58] Zheng-Rong Lu,et al. Influence of the Structure of Drug Moieties on the in Vitro Efficacy of HPMA Copolymer–Geldanamycin Derivative Conjugates , 2002, Pharmaceutical Research.
[59] J. Kopeček,et al. Degradation of side chains of N-(2-hydroxypropyl) methacrylamide copolymers by lysosomal enzymes. , 1980, Biochemical and biophysical research communications.
[60] E. Schacht,et al. Polymeric prodrugs of 5-fluorouracil , 1997 .
[61] H. Zhao,et al. Drug delivery systems employing 1,4- or 1,6-elimination: poly(ethylene glycol) prodrugs of amine-containing compounds. , 1999, Journal of medicinal chemistry.
[62] K. Ulbrich,et al. Polymeric drugs based on conjugates of synthetic and natural macromolecules. II. Anti-cancer activity of antibody or (Fab')(2)-targeted conjugates and combined therapy with immunomodulators. , 2000, Journal of controlled release : official journal of the Controlled Release Society.
[63] C. Longley,et al. Utility of poly(ethylene glycol) conjugation to create prodrugs of amphotericin B. , 2003, Bioconjugate chemistry.
[64] Z. Lu,et al. Modification of cyclosporin A and conjugation of its derivative to HPMA copolymers. , 2001, Bioconjugate chemistry.
[65] Richard B Greenwald,et al. Effective drug delivery by PEGylated drug conjugates. , 2003, Advanced drug delivery reviews.
[66] R. Schowen,et al. Polyvinylpyrrolidone-drug conjugate: synthesis and release mechanism. , 2004, Journal of controlled release : official journal of the Controlled Release Society.
[67] Jindřich Kopeček,et al. Polymers containing enzymatically degradable bonds, 8. Degradation of oligopeptide sequences in N‐(2‐hydroxypropyl)methacrylamide copolymers by bovine spleen cathepsin B , 1983 .
[68] M Hosokawa,et al. The mammalian carboxylesterases: from molecules to functions. , 1998, Annual review of pharmacology and toxicology.
[69] Yokoyama Masayuki,et al. Polymer micelles as novel drug carrier: Adriamycin-conjugated poly(ethylene glycol)-poly(aspartic acid) block copolymer , 1990 .
[70] F. Kratz,et al. Drug-polymer conjugates containing acid-cleavable bonds. , 1999, Critical reviews in therapeutic drug carrier systems.
[71] H. Chiang,et al. Synthesis and properties of a naproxen polymeric prodrug , 2002, The Journal of pharmacy and pharmacology.
[72] M. Yokoyama. Drug Targeting with Polymeric Micelle Drug Carriers , 2002 .
[73] F. Veronese,et al. Bioconjugation in pharmaceutical chemistry. , 1999, Farmaco.
[74] J. Schug,et al. Correlation of nonadditive kinetic effects with molecular geometries. Structure and reactivity of alkyl- and cycloalkenylpyridines , 1984 .
[75] J. Kopeček,et al. Polymers containing enzymatically degradable bonds, 7. Design of oligopeptide side-chains in poly[N-(2-hydroxypropyl)methacrylamide] copolymers to promote efficient degradation by lysosomal enzymes† , 1983 .
[76] H. Maeda,et al. Factors and mechanism of "EPR" effect and the enhanced antitumor effects of macromolecular drugs including SMANCS. , 2003, Advances in experimental medicine and biology.
[77] R. S. Brown. Studies in Amide Hydrolysis: Acid, Base, and Water Reactions , 2000 .
[78] J. M. Harris,et al. Effect of pegylation on pharmaceuticals , 2003, Nature Reviews Drug Discovery.
[79] T. Park,et al. Biodegradable Nanoparticles Containing Doxorubicin-PLGA Conjugate for Sustained Release , 1999, Pharmaceutical Research.
[80] Hans Bundgaard,et al. Design of prodrugs , 1985 .
[81] R. M. Fitch,et al. Controlled release of pendant bioactive materials from acrylic polymer colloids , 1986 .
[82] C. Larsen,et al. Macromolecular prodrugs. IV: Kinetics of hydrolysis of metronidazole monosuccinate dextran ester conjugates in aqueous solution and in plasma ― sequential release of metronidazole from the conjugates at physiological pH , 1987 .
[83] K. Ulbrich,et al. Polymers containing enzymatically degradable bonds, XII. Effect of spacer structure on the rate of release of daunomycin and adriamycin from poly [N-(2-hydroxypropyl)-methacrylamide] copolymer drag carriers in vitro and antitumour activity measured in vivo , 1992 .
[84] R. Duncan,et al. Synthesis, controlled release properties and antitumour activity of alginate-cis-aconityl-daunomycin conjugates , 1995 .
[85] W. Rutter,et al. Role of the S' subsites in serine protease catalysis. Active-site mapping of rat chymotrypsin, rat trypsin, alpha-lytic protease, and cercarial protease from Schistosoma mansoni. , 1994, Biochemistry.
[86] K. Breddam,et al. Interdependency of the binding subsites in subtilisin. , 1992, Biochemistry.
[87] P. Dettmar,et al. Prognostic value of the cysteine proteases cathepsins B and cathepsin L in human breast cancer. , 1995, Clinical cancer research : an official journal of the American Association for Cancer Research.
[88] J. Kopeček,et al. Stability in rat plasma and serum of lysosomally degradable oligopeptide sequences in N-(2-hydroxypropyl) methacrylamide copolymers. , 1985, Biomaterials.
[89] W. Shen,et al. cis-Aconityl spacer between daunomycin and macromolecular carriers: a model of pH-sensitive linkage releasing drug from a lysosomotropic conjugate. , 1981, Biochemical and biophysical research communications.
[90] M. Tuttle,et al. Controlled release of water-soluble macromolecules from bioerodible hydrogels. , 1983, Biomaterials.
[91] H. G. Schild. Poly(N-isopropylacrylamide): experiment, theory and application , 1992 .
[92] E. Schacht,et al. EVALUATION OF THE HYDROLYTIC AND ENZYMATIC STABILITY OF MACROMOLECULAR MITOMYCIN-C DERIVATIVES. , 1994 .
[93] K. Zhu,et al. Controlled Delivery System for Norethindrone Based on Biodegradable Poly- α, β -(Hydroxyalkyl)-DL-Aspartamide , 2002 .
[94] A. Berger,et al. On the size of the active site in proteases. I. Papain. , 1967, Biochemical and biophysical research communications.
[95] 前田 浩. Polymer drugs in the clinical stage : advantages and prospects , 2003 .
[96] E. Schacht,et al. The crucial role of spacer groups in macromolecular prodrug design , 1996 .
[97] E. Schacht,et al. Macromolecular derivatives of N,N-di-(2-chloroethyl)-4-phenylene diamine mustard. 2. In vitro cytotoxicity and in vivo anticancer efficacy. , 1999, Journal of controlled release : official journal of the Controlled Release Society.
[98] R. Mehvar,et al. Molecular-weight-dependent pharmacokinetics of fluorescein-labeled dextrans in rats. , 1992, Journal of pharmaceutical sciences.
[99] N. Bodor,et al. Physicochemical aspects of the enzymatic hydrolysis of carboxylic esters. , 2002, Die Pharmazie.