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Soluble Polymers as Targetable Drug Carriers

  • Chapter
Targeted Drug Delivery

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 100))

Abstract

The efficiency of drugs would increase considerably if we were able to direct them selectively to their cellular targets. The need for targetable drug carriers was realized a long time ago. It was P. Ehrlich, in 1906, who coined the phrase “the magic bullet” describing drugs which might be selectively directed to their specific site of action. But it is only in the last 20 years that natural science has developed to such a level that several laboratories have started to try to translate this dream to reality.

The support of NIH (grant DK 39544) is greatfully acknowledged.

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References

  • Abuchowski A, van Es T, Palczuk NC, Davis FF (1977) Alteration of immunological properties of bovine serum albumin by covalent attachment of polyethylene glycol. J Biol Chem 252: 3578–3581

    PubMed  CAS  Google Scholar 

  • Ajioka RS (1987) The biochemistry and physiology of endocytic apparatus. Thesis, University of Utah

    Google Scholar 

  • Alam F, Soloway, McGuire JE, Barth RF, Carey WE, Adams DM (1985) Dicesium N- succinimidyl 3-(undecahydro-closo-dodecaboranyldithio) propionate, a novel heterobifunctional boronating agent. J Med Chem 28: 522–525

    Article  PubMed  CAS  Google Scholar 

  • Alam F, Soloway AH, Barth RF, Mafune N, Adams DM, Knoth WH (1989) Boron neutron capture therapy: linkage of a boronated macromolecule to monoclonal antibodies directed against tumor-associated antigens. J Med Chem 32: 2326–2330

    Article  PubMed  CAS  Google Scholar 

  • Alvarez VL, Wen M-L, Lee C, Lopes AW, Rodwell JD, McKearn TJ (1986) Site specifically modified mIn labelled antibodies give low liver background and improved radioimmunoscintigraphy. Nucl Med Biol 13: 347–352

    CAS  Google Scholar 

  • Ammon R (1963) The occurrence of dextranase in human tissues (in German). Enzymologia 25: 245–251

    PubMed  CAS  Google Scholar 

  • Anghileri LJ, Heidbreder M, Mathas R (1976) Accumulation of 57Co-poly-L-lysine by tumors: an effect of the tumor electrical charge. J Nucl Biol Med 20: 79–80

    PubMed  CAS  Google Scholar 

  • Armstrong BK, Smith Q, Rapoport SI, Strohalm J, Kopecek J, Duncan R (1989) Osmotic opening of the blood-brain barrier permeability to Af-(2-hydroxy-ropyl)methacrylamide copolymers. Effect of polymer Mw, charge and hydro- phobicity. J Control Release 10: 27–35

    Google Scholar 

  • Artursson P, O’Mullane J (1989) Cellular and biological interaction of macromolecular drug delivery systems. Adv Drug Delivery Rev 3: 165–189

    Article  CAS  Google Scholar 

  • Ashkenazi S (1986) Adherence of non-fimbriate entero-invasive Escherichia coli 0124 to guinea pig intestinal tract in vitro and in vivo. J Med Microbiol 21: 117–123

    Article  PubMed  CAS  Google Scholar 

  • Ashwell G, Harford J (1982) Carbohydrate specific receptors of targeting of the liver. Annu Rev Biochem 51: 531–554

    Article  PubMed  CAS  Google Scholar 

  • Ashwell G, Morell AG (1974) The role of surface carbohydrates in the hepatic recognition and transport of circulating glycoproteins. Adv Enzymol 41: 99–128

    PubMed  CAS  Google Scholar 

  • Bader H, Ringsdorf H, Schmidt B (1984) Water soluble polymers in medicine. Makromol Chem 123 /124: 457–485

    Google Scholar 

  • Bagshawe KD (1989) Towards generating cytotoxic agents at cancer sites. Br J Cancer 60: 275–281

    Article  PubMed  CAS  Google Scholar 

  • Baldwin RW, Byers VS (1986) Monoclonal antibody targeting of anti-cancer cells. Springer Semin Immunopathol 9: 39–50

    Article  PubMed  CAS  Google Scholar 

  • Banks W, Greenwood CT, Muir DD (1972) Hydroxyethylstarch.I. Review of the chemistry of hydroxyethylstarch with reference to its use as a blood plasma volume expander. Staerke 24: 181–187

    Google Scholar 

  • Basu SK, Goldstein JL, Anderson RGW, Brown MS (1981) Monesin interrupts the recycling of low density lipoprotein receptors in human fibroblasts. Cell 24: 493–502

    Article  PubMed  CAS  Google Scholar 

  • Blattler WA, Kuenzi BS, Lambert JM, Senter PD (1985) New heterobifunctional protein cross-linking reagent that forms an acid-labile link. Biochemistry 24: 1517–1524

    Article  CAS  Google Scholar 

  • Blow DM (1974) Stereochemistry of substrate binding and hydrolysis in the trypsin family of enzymes. Bayer Symp 5: 473

    CAS  Google Scholar 

  • Brasseur N, Ali H, Langlois R, Wagner JR, Rosseau J, van Lier JE (1987) Biological activities of phthalocyanines V. Photodynamic therapy of EMT-6 mammary tumors in mice with sulfonated phthalocyanines. Photochem Photobiol 45: 581–586

    Article  PubMed  CAS  Google Scholar 

  • Bridges JF, Woodley JF, Duncan R, Kopecek J (1988) Soluble N-(2-hydroxypropyl)- methacrylamide copolymers as potential oral, controlled release, drug delivery system. I. Bioadhesion to the rat intestine in vitro. Int J Pharm 44: 213–223

    Google Scholar 

  • Brodsky FM (1988) Living with clathrin: its role in intracellular membrane traffic. Science 242: 1396–1402

    Article  PubMed  CAS  Google Scholar 

  • Brondsted H, Kopecek J (1991) Hydrogels for site-specific oral delivery. Synthesis and characterization. Biomaterials (in press)

    Google Scholar 

  • Brown JP, McGarraugh GV, Parkinson TM, Wingard RE Jr, Onderdonk AB (1983) A polymeric drug for treatment of inflammatory bowel disease. J Med Chem 26: 1300–1307

    Article  PubMed  CAS  Google Scholar 

  • Byers VS, Pawluczyk I, Berry N, Durrant L, Robins RA, Garnett MC, Price MR, Baldwin RW (1988) Potentiation of anti-carcinoembryonic antigen immunotoxin cytotoxicity by monoclonal antibodies reacting with co-expressed carcino- embryonic antigen epitopes. J Immunol 140: 4050 - 4055

    PubMed  CAS  Google Scholar 

  • Carroll AM, Zalutsky MR (1984) Receptor mediated pharmaceuticals. In: Lamble JW, Abbott AC (eds) Receptors again. Elsevier, New York, pp 39–45

    Google Scholar 

  • Cartlidge SA, Duncan R, Lloyd JB, Kopeckova-Rejmanova P, Kopecek J (1987) Soluble, crosslinked Ar-(2-hydroxypropyl)methacrylamide copolymers as potential drug carriers. III. Targeting by incorporation of galactosamine residues. Effect of route of administration. J Control Release 4: 265–278

    Google Scholar 

  • Cassidy J, Duncan R, Morrison GJ, Strohalm J, Plocova D, Kopecek J, Kaye SB (1989) Activity of A-(2-hydroxypropyl)methacrylamide copolymers containing daunomycin against a rat tumor model. Biochem Pharmacol 38: 875–879

    Article  PubMed  CAS  Google Scholar 

  • Cawley DB, Simpson DL, Herschman HR (1981) Asialoglycoprotein receptor mediates the toxic effects of and asialofetuin-diphtheria toxin fragment A conjugate on cultured rat hepatocytes. Proc Natl Acad Sci USA 78: 3383–3387

    Article  PubMed  CAS  Google Scholar 

  • Chakraboty P, Bhaduri AN, Das PK (1990) Sugar receptor mediated drug delivery to macrophages in the therapy of experimental visceral leishmaniasis. Biochem Biophys Res Commun 166: 404–410

    Article  Google Scholar 

  • Chaves MS, Arranz F (1985) Water-insoluble dextrans by grafting. II. Reaction of dextrans with iV-alkyl chloroformates. Chemical and enzymatic hydrolysis. Makromol Chem 186: 17–29

    Google Scholar 

  • Courtoy PJ, Quintart J, Baudhuin P (1984) Shift of equilibrium density induced by 3,3′-diaminobenzidine cytochemistry: a new procedure for the analysis and purification of peroxidase containing organelles. J Cell Biol 98: 870–876

    Article  PubMed  CAS  Google Scholar 

  • Crepon B, Chytry V, Rfhova, B, Kopecek J, Jozefonvicz J (1991) Enzymatic degradation and immunogenic properties of substituted dextrans. Biomaterials (in press) De Duve C (1983) Lysosomes revisited. Eur J Biochem 137:391–397

    Google Scholar 

  • De Duve C, de Barsy T, Poole B, Trouet A, Tulkens P, van Hoof F (1974) Lysosomotropic agents. Biochem Pharmacol 23: 2495–2531

    Article  PubMed  Google Scholar 

  • Diaz R, Mayorga LS, Weidman PJ, Rothman JE, Stahl PD (1989) Vesicle fusion following receptor-mediated endocytosis requires a protein active in Golgi transport. Nature 339: 398–400

    Article  PubMed  CAS  Google Scholar 

  • Dorn K, Horpel G, Ringsdorf H (1985) Polymeric antitumor agents on a molecular and cellullar level. In: Gebelein CG, Carraher CE (eds) Bioactive polymeric systems. Plenum, New York, pp 531–585

    Google Scholar 

  • Drobnfk J (1989) Biodegradable soluble macromolecules as drug carriers. Adv Drug Delivery Res 3: 229–245

    Article  Google Scholar 

  • Drobnfk J, Rypacek F (1984) Soluble synthetic polymers in biological systems. Adv Polym Sci 57: 1–50

    Google Scholar 

  • Duncan R (1986) Lysosomal degradation of polymers used as drug carriers. CRC Crit Rev Biocomp 2: 127–145

    CAS  Google Scholar 

  • Duncan D, Kopecek J (1984) Soluble synthetic polymers as potential drug carriers. Adv Polym Sci 57: 51–101

    CAS  Google Scholar 

  • Duncan R, Starling D, Rypacek F, Drobnfk J, Lloyd JB (1982a) Pinocytosis of poly(a,P-(Af-2-hydroxyethyl))-DL-aspartamide and a tyramine derivative by rat visceral yolk sac cultured in vitro. Ability of hydrophobic residues to enhance the rate of pinocytic capture of a macromolecule. Biochim Biophys Acta 717: 248–254

    Google Scholar 

  • Duncan R, Cable HC, Lloyd JB, Rejmanova, P, Kopecek J (1982b) Degradation of side-chains of 7V-(2-hydroxypropyl)methacrylamide copolymers by lysosomal thiol-proteinases. Biosci Rep 2: 1041–1046

    Article  PubMed  CAS  Google Scholar 

  • Duncan R, Cable HC, Lloyd JB, Rejmanova P, Kopecek J (1983) Polymers containing enzymatically degradable bonds. VII. Design of oligopeptide side-chains in poly[Ar-(2-hydroxypropyl)methacrylamide] copolymers to promote efficient degradation by lysosomal enzymes. Makromol Chem 184: 1997–2008

    Article  CAS  Google Scholar 

  • Duncan R, Cable HC, Rejmanova P, Kopecek J, Lloyd JB (1984) Tyrosinamide residues enhance pinocytic capture of A-(2-hydroxypropyl)methacrylamide copolymers. Biochim Biophys Acta 799: 1–8

    PubMed  CAS  Google Scholar 

  • Duncan R, Seymour LCW, Scarlett L, Lloyd JB, Rejmanova P, Kopecek J (1986) Fate of 7V-(2-hydroxypropyl)methacrylamide copolymers with pendent galac-tosamine residues after intravenous administration to rats. Biochim Biophys Acta 880: 62–71

    PubMed  CAS  Google Scholar 

  • Duncan R, Kopeckova-Rejmanova, P, Strohalm J, Hume I, Cable HC, Pohl J, Lloyd JB, Kopecek J (1987) Anticancer agents coupled to JV-(2-hydroxypropyl)- methacrylamide copolymers. I. Evaluation of daunomycin and puromycin con¬jugates in vitro. Br J Cancer 55: 165–174

    Google Scholar 

  • Duncan R, Kopeckova, P, Strohalm J, Hume IC, Lloyd JB, Kopecek J (1988) Anticancer agents coupled to 7V-(2-hydroxypropyl)methacrylamide copolymers. II. Evaluation of daunomycin conjugates in vivo against L1210 leukemia. Br J Cancer 57: 147–156

    Article  PubMed  CAS  Google Scholar 

  • Duncan R, Hume IC, Kopeckova P, Ulbrich K, Strohalm J, Kopecek J (1989) Anticancer agents coupled to 7V-(2-hydroxypropyl)methacrylamide copolymers. III. Evaluation of adriamycin conjugates against mouse leukemia L1210 in vivo. J Control Release 10: 51–63

    Article  CAS  Google Scholar 

  • Durrant LG, Garnett MC, Gallego J, Armitage NC, Ballantyne KC, Marksman RA, Hardcastle JD, Baldwin RW (1987) Sensitivity of newly established colorectal cell lines to cytotoxic drugs and monoclonal antibody drug conjugated. Br J Cancer 56: 722–726

    Article  PubMed  CAS  Google Scholar 

  • Feizi T (1984) Monoclonal antibodies reveal saccharide structures of glycoproteins and glycolipids as differentiation and tumour-associated antigens. Biochem Soc Trans 12: 545–549

    PubMed  CAS  Google Scholar 

  • Ferrutti P, Tanzi MC (1986) New polymeric and oligomeric matrices as drug carriers. CRC Crit Rev Ther Drug Carrier Syst 2: 175–244

    Google Scholar 

  • Fersht A (1985) Enzyme structure and mechanism, 2nd edn. Freeman, New York

    Google Scholar 

  • Fischer E, Stein E (1960) Dextranases. In: Boyer PD, Lardy H, Myrback K (eds) The enzymes, vol 4A. Academic, New York, p 304

    Google Scholar 

  • Fiume L, Busi C, Mattioli A (1982) Lactosaminated human serum albumin as hepatropic drug carrier. Rate of uptake by mouse liver. FEBS Lett 146: 42–46

    Google Scholar 

  • Fiume L, Busi C, Mattioli A (1983) Targeting of antiviral drugs by coupling with protein carriers. FEBS Lett 153: 6–9

    Article  PubMed  CAS  Google Scholar 

  • Fiume L, Busi C Mattioli A, Spinoza G (1988) Targeting of antiviral drugs bound to protein carriers. CRC Crit Rev Ther Drug Carrier Syst 4: 265–284

    CAS  Google Scholar 

  • Flanagan PA, Kopeckova P, Kopecek J, Duncan R (1989) Evaluation of protein-Ar-(2- hydroxypropyl)methacrylamide copolymer conjugates as targetable drug-carriers. I. Binding, pinocytic uptake and intracellular distribution of transferrin and anti- transferrin receptor antibody conjugates. Biochim Biophys Acta 993: 83–91

    Google Scholar 

  • Flanagan PA, Duncan R, Rihova B, Subr V, Kopecek J, (1990) Immunogenicity of protein-A-(2-hydroxypropyl)methacrylamide copolymer conjugates in A/J and B10 mice. J Bioact Compat Polym 5: 151–166

    Article  CAS  Google Scholar 

  • Fleisher D, Stewart BH, Amidon GL (1985) Design of prodrugs for improved gastrointestinal absorption by intestinal enzyme targeting. Methods Enzymol 112: 360–381

    Article  PubMed  CAS  Google Scholar 

  • Fornusek L, Grim Y, Duncan R, Woodley JF, Kopecek J (1989) Bioadhesive water-soluble polymeric drug carriers for site-specific oral delivery. II. Body distribution after oral administration. Proc Int Symp Control Release Bioact Mater 16: 398–399

    Google Scholar 

  • Forster S, Lloyd JB (1988) Solute translocation across the mammalian lysosome membrane. Biochim Biophys Acta 947: 465–491

    PubMed  CAS  Google Scholar 

  • Friend DR, Chang GW (1984) A colon-specific drug-delivery system based on drug glycosides and the glycosidases of colon bacteria. J Med Chem 27: 261–266

    Article  PubMed  CAS  Google Scholar 

  • Fuertges F, Abuchowski A (1990) The clinical efficacy of poly(ethylene glycol)-modified proteins. J Control Release 11: 139–148

    Article  CAS  Google Scholar 

  • Garnett MC, Embleton MJ, Jacobs E, Baldwin RW (1985) Studies on the mechanism of action of an antibody-targeted drug-carrier conjugate. Anticancer Drug Design 1: 3–12

    CAS  Google Scholar 

  • Geuze HJ, Slot JW, Strous GJAM, Lodish HF, Schwartz AL (1983) Intracellular site of asialoglycoprotein receptor-ligand uncoupling: double label immunoelectron microscopy during receptor-mediated endocytosis. Cell 32: 277–287

    Article  PubMed  CAS  Google Scholar 

  • Geuze HJ, Slot JW, Strous JAM, Peppard J, von Figura K, Haslik A, Schwartz AL (1984) Intracellular receptor sorting during endocytosis: comparative immunoelectron microscopy of multiple receptors in rat liver. Cell 37: 195–204

    Article  PubMed  CAS  Google Scholar 

  • Glenney JR Jr, Chen WS, Lazar CS, Walton GM, Zokas LM, Rosenfeld MG, Gill GN (1988) Ligand-induced endocytosis of the EGF receptor is blocked by mutational inactivation and by microinjection of antiphosphotyrosine antibodies. Cell 52: 675–684

    Article  PubMed  CAS  Google Scholar 

  • Goddard P, Petrak K (1989) Biodegradation of drug-modified polymers in drug delivery — a critical analysis. J Bioact Compat Polym 4: 372–402

    Article  CAS  Google Scholar 

  • Grim Y, Kopecek J (1989) Bioadhesive water-soluble polymeric drug carriers for site- specific oral delivery. I. Synthesis, characterization and 5-aminosalicylic acid release in vitro. Proc Int Symp Control Release Bioact Mater 16: 211–212

    Google Scholar 

  • Grim Y, Kopecek J (1991) Bioadhesive water-soluble polymeric drug carriers for site- specific oral delivery. Synthesis, characterization and 5-aminosalicylic acid release in vitro. New Polym Mater (in press)

    Google Scholar 

  • Hagan PL, Halpern SE, Dillman RO, Shawler DL, Johnson DE, Chen A, Krishnan K, Frincke J, Bartholomew RM, David GS, Carlo D (1986) Tumor size: effect on monoclonal antibody uptake in tumor models. J Nucl Med 27: 422–427

    PubMed  CAS  Google Scholar 

  • Hanover JA, Beguinot L, Willingham MC, Pastan IH (1985) Transit of receptors for epidermal growth factor and transferrin through clathrin-coated pits. J Biol Chem 260: 15938–15945

    PubMed  CAS  Google Scholar 

  • Hasan T, Lin A, Yarmush D, Oseroff A, Yarmush M (1989) Monoclonal antibody- chromophore conjugates as selective phototoxins. J Control Release 10: 107–117

    Article  CAS  Google Scholar 

  • Haylett T, Thilo L (1986) Limited and selective transfer of plasma membrane glycoproteins to membrane of secondary lysosome. J Cell Biol 103: 1249–1256

    Article  PubMed  CAS  Google Scholar 

  • Helenius A, Mellman I, Wall D, Hubbard A (1983) Endosomes. TIBS 8: 245–250

    CAS  Google Scholar 

  • Henderson BW, Farrell G (1989) Possible implications of vascular damage for tumor cell inactivation in vivo: comparison of different photosensitizers. Proc SPIE 1065: 2–10

    CAS  Google Scholar 

  • Henderson BW, Dougherty TJ, Malone PB (1984) Studies on the mechanism of tumor destruction by photoradiation therapy. In: Doiron DR, Gomer CJ (eds) Porphyrin localization and treatment of tumors. Liss, New York, pp 601–612

    Google Scholar 

  • Hespe W, Meier AM, Blankwater YJ (1977) Excretion and distribution studies in rats with two forms of 14C-labelled polyvinylpyrrolidone with a relatively low mean molecular weight after intraveneous administration. Drug Res 27: 1158–1162

    CAS  Google Scholar 

  • Heuser JE, Anderson RGW (1989) Hypertonic media inhibit receptor-mediated endocytosis by blocking clathrin-coated pit formation. J Cell Biol 108: 389–400

    Article  PubMed  CAS  Google Scholar 

  • Heuser JE, Kirchhausen T (1985) Deep-etch views of clathrin assemblies. J Ultrastruct Res 92: 1–27

    Article  PubMed  CAS  Google Scholar 

  • Hoag K, Rigod J, Gungon R, Tozer TN, Friend DR (1989) Colonic drug delivery: glycoside produgs in the guinea pig. Proc Int Symp Control Release Bioact Mater 16: 54–55

    Google Scholar 

  • Hoes CJT, Feijen J (1989) The application of drug-polymer conjugates in chemo-therapy. In: Roerdink FG, Kroo AM (eds) Drug carrier systems. Wiley, New York, pp 57–109

    Google Scholar 

  • Hoes CJT, Potman W, van Heeswijk WAR, Mud J, de Grooth BG, Greve J, Feijen J (1985) Optimization of macromolecular prodrugs of the antitumor antibiotic adriamycin. J Control Release 2: 205–213

    CAS  Google Scholar 

  • Hoes CJT, Potman W, de Grooth BG, Greve J, Feijen J (1986) Chemical control of drug delivery. In: Harms AF (ed) Innovative approaches in drug research. Elsevier, Amsterdam, pp 267–283

    Google Scholar 

  • Horpel G, Klesse W, Ringsdorf H, Schmidt B (1982) Micelle forming co- and block copolymers for sustained drug release. IUPAC Int Symp on Macromolecules, Amherst, p 346

    Google Scholar 

  • Hurwitz E, Levy R, Maron R, Wilchek M, Arnon R, Sela M (1975) The covalent binding of daunomycin and adriamycin to antibodies with retention of both drug and antibody activities. Cancer Res 35: 1175–1181

    PubMed  CAS  Google Scholar 

  • Hurwitz E, Maron R, Arnon R, Sela M (1976) Fab dimers of antitumor immunoglobulins as covalent carriers of daunomycin. Cancer Biochem Biophys 1: 197–202

    PubMed  CAS  Google Scholar 

  • Iacopetta BJ, Rothenberger S, Kuhn LC (1988) A role for the cytoplasmic domain in transferrin receptor sorting and coated pit formation during endocytosis. Cell 54: 485–489

    Article  PubMed  CAS  Google Scholar 

  • Iveson GP, Bird SJ, Lloyd JB (1989) Passive diffusion of non-electrolytes across the lysosome membrane. Biochem J 261: 451–456

    PubMed  CAS  Google Scholar 

  • Izhar M, Nuchamowitz Y, Mirelman D (1982) Adherence of Shigella flexneri to guinea pig intestinal cells is mediated by mucosal adhesin. Infect Immun 35: 1110–1118

    PubMed  CAS  Google Scholar 

  • Kasafirek E, Fric P, Slaby J, Malis F (1976) p-Nitroanilides of 3-carboxypropionyl- peptides. Their cleavage by elastase, trypsin and chymotrypsin. Eur J Biochem 69: 1–13

    Google Scholar 

  • Katchalski E, Levin Y, Neumann H, Riesel E, Sharon N (1961) Studies on the enzymatic hydrolysis of poly-a-amino acids. Bull Res Counc Isr [A] 10: 159–171

    Google Scholar 

  • Katre NV, Knauf MJ, Laird WJ (1987) Chemical modification of recombinant interleukin-2 by polyethylene glycol increases its potency in the murine Meth A sarcoma model. Proc Natl Acad Sci USA 84: 1487–1491

    Article  PubMed  CAS  Google Scholar 

  • Kopecek J (1981) Soluble polymers in medicine. In: Williams DF (ed) Systemic aspects of biocompatibility, vol 2. CRC, Boca Raton, pp 159–180

    Google Scholar 

  • Kopecek J (1982) Biodegradation of polymers for biomedical use. In: Benoit H, Rempp P (eds) IUPAC macromolecules. Pergamon, Oxford, pp 305–320

    Google Scholar 

  • Kopecek J (1984a) Synthesis of tailor-made soluble polymeric drug carriers. In: Anderson JM, Kim SW (eds) Recent advances in drug delivery systems. Plenum, New York, pp 41–62

    Chapter  Google Scholar 

  • Kopecek J (1984b) Controlled biodegradability of polymers - a key to drug delivery systems. Biomaterials 5: 19–25

    Article  PubMed  CAS  Google Scholar 

  • Kopecek J (1988) Development of tailor-made polymeric prodrugs for systemic and oral delivery. J Bioact Compat Polym 3: 16–26

    Article  CAS  Google Scholar 

  • Kopecek J (1990) The potential of water-soluble polymeric carriers in targeted and site-specific drug delivery. J Control Release 11: 279–290

    Article  CAS  Google Scholar 

  • Kopecek J (1991) Targetable polymeric anticancer drugs: temporal control of drug activity. Ann NY Acad Sci 618: 335–344

    Article  PubMed  Google Scholar 

  • Kopecek J, Duncan R (1987) Targetable polymeric drugs. J Control Release 6: 315–327

    Article  CAS  Google Scholar 

  • Kopecek J, Rejmanova P (1979) Reactive copolymers of A-(2-hydroxypropyl)- methacrylamide with TV-methacryloylated derivatives of L-leucine and L- phenylalanine. II. Reaction with the polymeric amine and stability of crosslinks towards chymotrypsin in vitro. J Polym Sci Polym Symp 66: 209–219

    Google Scholar 

  • Kopecek J, Rejmanova P (1983) Enzymatically degradable bonds in synthetic polymers. In: Bruck SD (ed) Controlled drug delivery, vol 1. CRC, Boca Raton, pp 81–124

    Google Scholar 

  • Kopecek J, Rejmanova P, Chytry V (1981) Polymers containing enzymatically degradable bonds. I. Chymotrypsin catalyzed hydrolysis of p-nitroanilides of phenylalanine and tyrosine attached to side-chains of copolymers of N-(2- hydroxypropyl)methacrylamide. Makromol Chem 182: 799–809

    Article  CAS  Google Scholar 

  • Kopecek J, Rejmanova P, Strohalm J, Ulbrich K, Ftihova B, Chytry V, Duncan R, Lloyd JB (1985) Synthetic polymeric drugs. Br Pat Appl 8 500 209 (4.1 1985)

    Google Scholar 

  • Kopeckova P, Kopecek J (1990) Release of 5-aminosalicylic acid from bioadhesive N- (2-hydroxypropyl)methacrylamide copolymers by azoreductases in vitro. Makromol Chem 191: 2037–2045

    Article  CAS  Google Scholar 

  • Kopeckova P, Longer MA, Woodley JF, Duncan R, Kopecek J (1991a) Release of p- nitroaniline from oligopeptide side-chains attached to N-(2-hydroxyproply) methacrylamide copolymers by rat intestinal brush border membrane enzymes. Makromol Chem Rapid Commun 12: 601–606

    Google Scholar 

  • Kopeckova P, ftfhova B, Rathi R, Kopecek J (1991b) Bioadhesive polymers for colon specific drug delivery. Proc Int Symp Control Release Bioact Mater 18: 341–342

    Google Scholar 

  • Kornfeld S (1987) Trafficking of lysosomal enzymes. FASEB J 1: 462–468

    PubMed  CAS  Google Scholar 

  • Kralovec J, Spencer G, Blair AH, Mammen M, Singh M, Ghose T (1989) Synthesis of methotrexate-antibody conjugates by regiospecific coupling and assessment of drug and antitumor activities. J Med Chem 32: 2426–2431

    Article  PubMed  CAS  Google Scholar 

  • Kriniek NL, Ftihova B, Ulbrich K, Andrade JD, Kopecek J (1988) Targetable photoactivatable drugs: synthesis of water soluble galactosamine containing polymeric carriers of chlorin e6 and their photodynamic effect on PLC cells in vitro. Proc SPIE 997: 70–83

    Google Scholar 

  • Kriniek NL, fohova B, Ulbrich K, Strohalm J, Kopecek J (1990) Targetable photoactivatable drugs. II. Synthesis of 7V-(2-hydroxypropyl)methacrylamide copolymer-anti-Thy 1.2 antibody-chlorin e6 conjugates and a preliminary study of their photodynamic effect on mouse splenocytes in vitro. Makromol Chem 191: 839–856

    Article  Google Scholar 

  • Krolick K, Yuan D, Vitetta E (1981) Specific killing of a human breast carcinoma cell line by a monoclonal antibody coupled to the A-chain of ricin. Cancer Immunol Immunother 12: 39–41

    Article  Google Scholar 

  • Laane A, Aaviksaar A, Haga M, Chytry V, Kopecek J (1985) Preparation of polymer- modified enzymes of prolonged circulation times. Poly[7V-(2-hydroxypropyl)- methacrylamide]-bound acetylcholinesterase. Makromol Chem [Suppl] 9: 35–42

    Article  CAS  Google Scholar 

  • Lagueux J, Page M, Delorme F (1984) Daunorubicin-albumin copolymer targeting to leukemic cells in vitro and in vivo. Semin Oncol [Suppl 3] 2 (4): 59–63

    Google Scholar 

  • Lancaster CM, Wheatley MA (1989) Drug delivery to the colon: polymer susceptibility to degradation by colon contents. Polym Preprints 30: 480–481

    CAS  Google Scholar 

  • Larsen C, Harboe E, Johansen M, Olesen HP (1989) 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 gastro-intestinal tract. Pharm Res 6: 995–999

    Google Scholar 

  • Lee YC, Lee RT (1982) Neoglycoproteins as probes for binding and cellular uptake of glycoconjugates. In: Horowitz MI (ed) Glycoproteins, glycolipids and proteoglycans. Plenum, New York, pp 57–83 (The glycoconjugates, vol 43 )

    Google Scholar 

  • Lefrak EA, Pitha J, Rosenheim S, Gottlieb J A (1973) A clinicopathologic analysis of adriamycin cardiotoxicity. Cancer 32: 302–314

    Article  PubMed  CAS  Google Scholar 

  • Lenaz L, Page J A (1976) Cardiotoxicity of adriamycin and related anthracyclines. Cancer Treat Rev 3: 111–120

    Article  PubMed  CAS  Google Scholar 

  • Leung SHS, Robinson JR (1988) The contribution of anionic polymer structural features to mucoadhesion. J Control Release 5: 223–231

    Article  CAS  Google Scholar 

  • Limet JN, Quintart J, Schneider Y-J, Courtoy PJ (1985) Receptor mediated endocytosis of polymeric IgA and galactosylated serum albumin in rat liver. Evidence for intracellular ligand sorting and identification of distinct endosomal compartments. Eur J Biochem 146: 539–548

    Google Scholar 

  • Ling V (1987) Multidrug resistance and P-glycoprotein expression. Ann NY Acad Sci 507: 7–8

    Article  PubMed  CAS  Google Scholar 

  • Ling V, Juranka P, Endicott JA, Deuchars KL, Gerlach JH (1988) Multidrug resistance and P-glycoprotein expression. In: Woolen PV 3rd, Tew KD (eds) Mechanism of drug resistance in neoplastic cells. Academic, New York, pp 197–209

    Google Scholar 

  • Lloyd JB (1985) Macromolecules as vehicles for intracellular drug delivery. Pharm Int 6: 252–255

    CAS  Google Scholar 

  • Lloyd JB (1986) Endocytosis and lysosomes: recent progress in intracellular traffic. In: Gregoriadis G, Senior J, Poste G (eds) Targeting of drugs with synthetic systems. Plenum, New York, pp 57–63

    Google Scholar 

  • Lloyd JB (1989) Explorations in cell biology and pharmacology using synthetic polymers. Angew Makromol Chem 166 /167: 191–200

    Google Scholar 

  • Lloyd JB, Forster S (1986) The lysosome membrane. TIBS 11: 365–368

    CAS  Google Scholar 

  • Lobel P, Fujimoto K, Ye RD, Griffiths G, Kornfeld S (1989) Mutations in the cytoplasmic domain of the 275 kd mannose 6-phosphate receptor differentially alter lysosomal enzyme sorting and endocytosis. Cell 57: 787–796

    Article  PubMed  CAS  Google Scholar 

  • Longer MA, Robinson JR (1986) Fundamental aspects of bioadhesion. Pharm Int 7: 114–117

    CAS  Google Scholar 

  • Longer MA, Woodley JF, Duncan R (1989) Comparison of the activities of rat small intestine and colon brush border membrane peptidases. Proc Int Symp Control Release Bioact Mater 16: 54–55

    Google Scholar 

  • Maeda H, Oda T, Matsumura Y, Kimura M (1988) Improvement of pharmacological properties of protein-drugs by tailoring with synthetic polymers. J Bioact Compat Polym 3: 27–43

    Article  CAS  Google Scholar 

  • Manabe Y, Tsubota T, Haruta Y, Okazaki M, Haisa S, Nakamura K, Kimura I (1983) Production of a monoclonal antibody-bleomycin conjugate utilizing dextran T–40 and the antigen-targeting cytotoxicity of the conjugate. Biochem Biophys Res Commun 115: 1009–1014

    Article  PubMed  CAS  Google Scholar 

  • Masquelier M, Baurain R, Trouet A (1980) Amino acid and dipeptide derivatives of daunorubicin. Synthesis, physicochemical properties and lysosomal digestion. J Med Chem 23: 1166–1170

    Google Scholar 

  • Mattes J (1987) Biodistribution of antibodies after intraperitoneal or intravenous injection and effect of carbohydrate modifications. JNCI 79: 855–864

    PubMed  CAS  Google Scholar 

  • Maxfield FR (1985) Acidification of endosomic vesicles and lysosomes. In: Pastan I, Willingham MC (eds) Endocytosis. Plenum, New York, pp 235–257

    Google Scholar 

  • McCormick LA, Seymour LCW, Duncan R, Kopecek J (1986) Interaction of a cationic A-(2-hydroxypropyl)methacrylamide copolymer with rat visceral yolk sac cultured in vitro and rat liver in vivo. J Bioact Compat Polym 1: 4–9

    Article  CAS  Google Scholar 

  • Meijer AEFH, Willinghagen RGJ (1963) The activity of glucose-6-phosphatase, adenosine triphosphatase, succinic dehydrogenase, and acid phosphatase after dextran or polyvinylpyrrolidone uptake by liver in vivo. Biochem Pharmacol 12: 973–980

    Article  PubMed  CAS  Google Scholar 

  • Mew D, Wat C-K, Towers GHN, Levy J (1983) Photoimmunotherapy: treatment of animal tumors with tumor-specific monoclonal antibody-hematoporphyrin conjugates. J Immunol 130: 1473–1477

    PubMed  CAS  Google Scholar 

  • Mew D, Lum V, Wat C-K, Towers GHN, Sun C, Oh C, Walter RJ, Wright W, Berns MW, Levy JG (1985) Ability of specific monoclonal antibodies and conventional antisera conjugated to hematoporphyrin to label and kill selected cell lines subsequent to light activation. Cancer Res 45: 4380–4386

    PubMed  CAS  Google Scholar 

  • Miller WG (1961) Degradation of poly-a-L-glutamic acid. I. Degradation on high-molecular weight polyglutamic acid by papain. J Am Chem Soc 83: 259–265

    Article  CAS  Google Scholar 

  • Miller WG (1964a) Degradation of synthetic polypeptides. II. Degradation of poly-a- L-glutamic acid by proteolytic enzymes in 0.20 M sodium chloride. J Am Chem Soc 86: 3913–3918

    Article  CAS  Google Scholar 

  • Miller WG (1964b) Degradation of poly-a-L-lysine by proteolytic enzymes in 0.2 M sodium chloride. J Am Chem Soc 86: 3918–3922

    Article  CAS  Google Scholar 

  • Miller WG, Monroe J (1968) Enzymatic hydrolysis of synthetic polypeptides under high helical content. Biochemistry 7: 253–261

    Article  PubMed  CAS  Google Scholar 

  • Mirelman D, Izhar M, Eshdat Y (1982) Carbohydrate recognition mechanisms which mediate microbial adherence to mammalian mucosal surfaces. Tokai J Exp Clin Med [Suppl] 7: 177–183

    CAS  Google Scholar 

  • Monsigny M, Kieda C, Roche A-C (1983) Membrane glycoproteins, glycolipids and membrane lectins as recognition signals in normal and malignant cells. Biol Cell 47: 95–110

    CAS  Google Scholar 

  • Moore MS, Mahaffey DT, Brodsky FM, Anderson RGW (1987) Assembly of clathrin-coated pits onto purified plasma membranes. Science 236: 558–563

    Article  PubMed  CAS  Google Scholar 

  • Neufeld EF, Ashwell G (1980) Carbohydrate recognition systems for receptor mediated pinocytosis. In: Lennarz WJ (ed) The biochemistry of glycoproteins and proteo-glycans. Plenum, New York, pp 241–266

    Google Scholar 

  • Ohno H, Abe K, Tsuchida E (1981) Interaction of human serum proteins with synthetic polymers in homogeneous systems. Makromol Chem 182: 1253–1262

    Article  CAS  Google Scholar 

  • Oseroff AR, Ohuoha D, Hasan T, Bommer JC, Yarmush ML (1986) Antibody- targeted photolysis: selective photodestruction of human T-cell leukemia cells using monoclonal antibody-chlorin e6 conjugates. Proc Natl Acad Sci USA 83: 8744–8748

    Article  PubMed  CAS  Google Scholar 

  • Page M, Emond JP (1983) Daunomycin targeting using carrier monoclonal antibodies. In: Mathe G, Marl R, Dejager R (eds) Anthracyclines: current status and future developments. Masson, New York, pp 105–108

    Google Scholar 

  • Park K, Robinson JR (1984) Bioadhesive polymers as platforms for oral controlled drug delivery: methods to study bioadhesion. Int J Pharm 19: 107–127

    Article  CAS  Google Scholar 

  • Park K, Robinson JR (1985) Physico-chemical properties of water insoluble polymers important to mucin/epithelial adhesion. J Control Release 2: 47–57

    Article  CAS  Google Scholar 

  • Pastan I, Willingham MC (1983) Receptor mediated endocytosis: coated pits, receptosomes and the golgi, TIBS 8: 250–254

    CAS  Google Scholar 

  • Pastan I, Willingham MC (1985) The pathway of endocytosis. In: Pastan I, Willingham MC (eds) Endocytosis. Plenum, New York, pp 1–44

    Google Scholar 

  • Peppas NA, Buri PA (1985) Surface, interfacial and molecular aspects of polymer bioadhesion on soft tissues. J Control Release 2: 257–275

    Article  CAS  Google Scholar 

  • Petrak K, Goddard P (1989) Transport of macromolecules across the capillary walls. Adv Drug Delivery Rev 3: 191–214

    Article  CAS  Google Scholar 

  • Pimm MV (1988) Drug-monoclonal antibody conjugates for cancer therapy: potentials and limitations. CRC Crit Rev Ther Drug Carrier Syst 5: 189–227

    CAS  Google Scholar 

  • Pitha J (1980) Nucleic acids and sulfate and phosphate polyanions. In: Donaruma IG, Ottenbrite RM, Vogl D (eds) Anionic polymeric drugs. Wiley, New York, p 277

    Google Scholar 

  • Pitha J (1981) Effects of polyvinyl analogs of nucleic acids on cells, animals and their viral infections. In: Gebelein CG, Koblitz FF (eds) Biomedical and dental applications of polymers, Plenum, New York, pp 203–313

    Google Scholar 

  • Poretz RD, Vucenik I, Bergstrom L, Segelman A, Sigel G Jr, Chernomorsky S (1989) Intracellular distribution of porphyrin-based photosensitizers in in vitro cultured human bladder tumor cells. SPIE 1065: 197–203

    CAS  Google Scholar 

  • Poznansky MJ (1984) Enzyme-albumin polymers. New approaches to the use of enzymes in medicine. Appl Biochem Biotechnol 10: 41–56

    Article  PubMed  CAS  Google Scholar 

  • Poznansky MJ (1986) Tailoring enzymes for more effective use as therapeutic agents. In: Feeny RE, Whitaker JR (eds) Protein Tailoring for Food and Medical Uses. Dekker, New York, pp 317–337

    Google Scholar 

  • Poznansky MJ, Juliano RL (1984) Biological approaches to the controlled delivery of drugs: a critical review. Pharmacol Rev 36: 277–336

    PubMed  CAS  Google Scholar 

  • Poznansky MJ, Shandling M, Salkie MA, Elliott J, Lau E (1982) Advances in the use of L-asparaginase-albumin polymer as an antitumor agent. Cancer Res 42: 1020–1025

    PubMed  CAS  Google Scholar 

  • Pratesi G, Savi G, Pezzoni G, Bellini O, Penco S, Tinelli S, Zunino F (1985) Poly-L- aspartic acid as a carrier for doxorubicin: a comparative in vivo study of free and polymer-bound drug. Br J Cancer 52: 841–848

    Article  PubMed  CAS  Google Scholar 

  • Pusztai A (1989) Transport of proteins through the membranes of the adult gastrointestinal tract-a potential for drug delivery. Adv Drug Delivery Rev 3: 215–228

    Article  CAS  Google Scholar 

  • Pytela J, Saudek V, Drobnfk J, Rypacek F (1989) Poly(A-hydroxyalkylglutamines). IV. Enzymatic degradation of 7V-(2-hydroxyethyl)-L-glutamine homopolymers and copolymers. J Control Release 10: 17–25

    Article  CAS  Google Scholar 

  • Rathi RC, Kopeckova P, Rfhova B, Kopecek J (1991) N-(2-Hydroxypropyl)metha- crylamide copolymers containing pendant saccharide moieties. Synthesis and bioadhesive properties. J Polym Sci, A: Polym Chem (in press)

    Google Scholar 

  • Reichner JS, Whiteheart SW, Hart GW (1988) Intracellular trafficking of cell surface sialoglycoconjugates. J Biol Chem 263: 16316–16326

    PubMed  CAS  Google Scholar 

  • Rejmanova P, Kopecek J, Pohl J, Baudys M, Kostka V (1983) Polymers containing enzymatically degradable bonds. VIII. Degradation of oligopeptide sequences in 7V-(2-hydroxypropyl)methacrylamide copolymers by bovine spleen cathepsin B. Makromol Chem 184: 2009–2020

    Article  CAS  Google Scholar 

  • Rennke HG, Venkatachalam MA, Patel Y (1979) Glomerular permeability of macro- molecules. Effect of molecular configuration on the fractional clearance of uncharged dextran and neutral horseradish peroxidase in the rat. J Clin Invest 63: 713–717

    Google Scholar 

  • Řihová B, Kopecek J (1985) Biological properties of targetable poly[7V-(2- hydroxypropyl)methacrylamide]-antibody conjugates. J Control Release 2: 289–310

    Article  Google Scholar 

  • Řihová B, Ulbrich K, Kopecek J, Mancal P (1983) Immunogenicity of N-(2- hydroxypropyl)methacrylamide copolymers-potential hapten or drug carriers. Folia Microbiol (Praha) 28: 217–227

    Article  Google Scholar 

  • Řihová B, Kopecek J, Ulbrich K, Pospfsil M, Mancal P (1984) Effect of the chemical structure of 7V-(2-hydroxypropyl)methacrylamide copolymers on their ability to induce antibody formation in inbred strains of mice. Biomaterials 5: 143–148

    Article  PubMed  Google Scholar 

  • Řihová B, Kopecek J, Ulbrich K, Chytry V (1985) Immunogenicity of N-(2-hydroxy-propyl)methacrylamide copolymers. Makromol Chem [Suppl] 9: 13–24

    Article  Google Scholar 

  • Řihová B, Kopecek J, Kopeckova-Rejmanova P, Strohalm J, Plocova D, Semoradova H (1986) Bioaffinity therapy with antibodies and drugs bound to soluble synthetic polymers. J Chromatogr Biomed Appl 376: 221–233

    Article  Google Scholar 

  • Řihová B, Kopeckova P, Strohalm J, Rossmann P, Vetvicka V, Kopecek J (1988) Antibody-directed affinity therapy applied to the immune system: in vivo effectiveness and limited toxicity of daunomycin conjugated to HPMA copolymers and targeting antibody. Clin Immunol Immunopathol 46: 100–114

    Article  PubMed  Google Scholar 

  • Řihová B, Veres K, Fornusek L, Ulbrich K, Strohalm J, Bilej M, Kopecek J (1989a) Action of polymeric prodrugs based on N-p-hydroxypropyl)- methacrylamide copolymers. II. Body distribution and T-cell accumulation of free and polymer bound [125I] daunomycin. J Control Release 10: 37–49

    Article  Google Scholar 

  • Řihová B, Bilej M, Vetvicka V, Ulbrich K, Strohalm J, Kopecek J, Duncan R (1989b) Biocompatibility of A-(2-hydroxypropyl)methacrylamide copolymers containing adriamycin. Biomaterials 10: 335–342

    Article  PubMed  Google Scholar 

  • Řihová B, Krinick NL, Kopecek J (1991) Targetable photoactivatable polymeric drugs. III. Specific in vitro photodestruction of mouse splenocytes or a human hepatoma cell line PLC/PRF/5 by polymer bound chlorin e6 targeted by anti-Thy 1.2 antibodies or galactosamine, respectively. J Control Release (submitted)

    Google Scholar 

  • Řihová B, Strohalm J, Plocova D, Ulbrich K (1990) Selectivity of antibody-targeted anthracycline antibiotics on T lymphocytes. J Bioact Compat Polym 5: 249–266

    Article  Google Scholar 

  • Ringsdorf H (1975) Structures and properties of pharmacologically active polymers. J Polym Sci Polym Symp 51: 135–153

    Article  CAS  Google Scholar 

  • Riordan JR, Ling V (1985) Genetic and biochemical characterization of multidrug resistance. Pharmacol Ther 28: 51–75

    Article  PubMed  CAS  Google Scholar 

  • Roberts JC, Figard SD, Mercer-Smith JA, Svitra ZV, Anderson WL, Lavallee DK (1987) Preparation and characterization of copper-67 porphyrin-antibody conjugates. J Immunol Methods 105: 153–164

    Article  PubMed  CAS  Google Scholar 

  • Roberts JC, Newmyer SL, Mercer-Smith JA, Schreyer SA, Lavellee DK (1989) Labeling antibodies with copper radionuclides using N-4-nitrobenzyl-5-(4- carboxyphenyl)-10,15,20-tris (4-sulfophenyl) porphine. Appl Radiat Isotopes 40: 775–780

    Article  CAS  Google Scholar 

  • Rodwell JD, Alvarez VL, Lee C, Lopes AD, Goers JWF, King HD, Powsner HJ, McKearn TJ (1986) Site-specific covalent modification of monoclonal antibodies: in vitro and in vivo evaluations. Proc Natl Acad Sci USA 83: 2632–2636

    Article  PubMed  CAS  Google Scholar 

  • Rosemeyer H, Sela F (1984) Polymer-linked acycloguanosine. Makromol Chem 185: 687–695

    Article  CAS  Google Scholar 

  • Russell-Jones GJ, de Aizpurua HJ (1988) Vitamin B12: a novel carrier for orally presented antigens. Proc Int Sympcontrol Release Bioact Mater 15: 142–143

    Google Scholar 

  • Rypacek F, Drobnfk J, Chmelar V, Kalal J (1982) The renal excretion and retention of macromolecules: the chemical structure effect. Pflugers Arch 392: 211–217

    Article  PubMed  CAS  Google Scholar 

  • Saffran M, Kumar GS, Savariar C, Burnham JC, Williams F, Neckers DC (1986) A new approach to the oral administration of insulin and other peptide drugs. Science 233: 1081–1084

    Article  PubMed  CAS  Google Scholar 

  • Schacht E (1987a) Polysaccharide macromolecules as drug carriers. In: Ilium L, Davis SS (eds) Polymers in controlled drug delivery. Wright, Bristol, pp 131–151

    Google Scholar 

  • Schacht E (1987b) Modification of dextran and application in prodrug design. In: Yalpani M (ed) Industrial polysaccharides: genetic engineering, structure/ property relations and applications. Elsevier, Amsterdam, pp 389–400

    Google Scholar 

  • Schacht E, Vercauteren R, Vansteenkiste S (1988) Some aspects of the application dextran in prodrug design. J Bioact Compat Polym 3: 72–80

    Article  CAS  Google Scholar 

  • Schechter I, Berger A (1967) On the size of active site in proteases. I. Papain. Biochem Biophys Res Commun 27: 157–162

    Google Scholar 

  • Schneider YJ (1983) The role of endocytosis and lysosomes in cell physiology. PhD thesis, Catholic University of Louvain

    Google Scholar 

  • Schneider Y-J, Abarca J, Pirak EA, Baurain R, Ceulemans F, Deprez-de Campeneere D, Lesur B, Masquelier M, Otte-Slachmuylder C, Rolin-van Swieten D, Trouet A (1984) Drug targeting in cancer chemotherapy. In: Gregoriadis G, Poste G, Senior J, Trouet A (eds) Receptor-mediated targeting of drugs. Plenum, New York, pp 1–25

    Google Scholar 

  • Segaloff D, Ascoli M (1988) Internalization of peptide hormones and hormone receptors. In: Cooke BA, King RJB, van der Molen HJ (eds) Hormones and their actions, part I. Elsevier, Amsterdam, pp 133–149

    Chapter  Google Scholar 

  • Senter PD (1990) Activation of prodrugs by antibody-enzyme conjugates: a new approach to cancer therapy. FASEB J 4: 188–193

    PubMed  CAS  Google Scholar 

  • Serry TW, Hehre EJ (1956) Degradation of dextrans by enzymes of intestinal bacteria. J Bacteriol 71: 373–380

    Google Scholar 

  • Seymour LW, Duncan R, Strohalm J, Kopecek J (1987) Effect of molecular weight of Ar-(2-hydroxypropyl)methacrylamide copolymers on body distribution and rate of excretion after subcutaneous, intraperitoneal and intravenous administration to rats. J Biomed Mater Res 21: 1341–1358

    Article  PubMed  CAS  Google Scholar 

  • Seymour LW, Ulbrich K, Strohalm J, Kopecek J, Duncan R (1990) The pharmacokinetics of polymer-bound adriamycin. Biochem Pharmacol 39: 1125–1131

    Article  PubMed  CAS  Google Scholar 

  • Sezaki H, Takamura Y, Hashida M (1989) Soluble macromolecular carriers for the delivery of antitumor drugs. Adv Drug Delivery Rev 3: 247–266

    Article  CAS  Google Scholar 

  • Shen W-C, Ryser HJ-P (1981) Cis-aconityl spacer between daunomycin and macromolecular carriers: a model of pH-sensitive linkage releasing drug from a lysosomotropic conjugate. Biochem Biophys Res Commun 102: 1048–1054

    Article  PubMed  CAS  Google Scholar 

  • Shen WC, Ryser HJ-P (1984) Selective killing of Fc-receptor-bearing tumor cells through endocytosis of drug-carrying immune complex. Proc Natl Acad Sci USA 81: 1445–1447

    Article  PubMed  CAS  Google Scholar 

  • Shen W-C, Ryser HJ-P (1986) Disulfide and other spacers for the intracellular release of drugs from polymeric carriers. Polym Prepr (Am Chem Soc Div Polym Chem) 27: 9–10

    CAS  Google Scholar 

  • Shen W-C, Ryser HJ-P, LaManna L (1985) Disulfide spacer between methotrexate and poly(D-lysine). Biol Chem 260: 10905–10908

    CAS  Google Scholar 

  • Shen W-C, Ballou B, Ryser HJ-P, Hakala TR (1986) Targeting, internalization and cytotoxicity of methotrexate-monoclonal anti-stage-specific embryonic antigen-1 antibody conjugates in cultured F-9 teratocarcinoma cells. Cancer Res 46: 3912–3916

    PubMed  CAS  Google Scholar 

  • Shen WC, Du X, Feener EP, Ryser HJ-P (1989) The intracellular release of metho-trexate from a synthetic drug carrier system targeted to Fc receptor-bearing cells. J Control Release 10: 89–96

    Article  CAS  Google Scholar 

  • Shepherd VL (1989) Intracellular pathways and mechanisms of sorting in receptor- mediated endocytosis. Trends Pharmacol Sci 10: 458–462

    Article  PubMed  CAS  Google Scholar 

  • Shepherd VL, Lee YC, Schlesinger PH, Stahl PD (1981) L-fucose-terminated glycoconjugates are recognized by pinocytosis receptors on macrophages. Proc Natl Acad Sci USA 78: 1019–1022

    Article  PubMed  CAS  Google Scholar 

  • Simeckova J, Ftfhova B, Plocova D, Kopecek J (1986) The activity of complement in the presence of A-(2-hydroxypropyl)methacrylamide copolymers. J Bioact Compat Polym 1: 20–31

    Article  CAS  Google Scholar 

  • Sinkula A A (1987) Drug delivery systems research from an industrial perspective. In: Roche EB (ed) Bioreversible carriers in drug design. Theory and application. Pergamon, Oxford, pp 262–280

    Google Scholar 

  • Snider MD, Rogers OC (1986) Membrane traffick in animal cells: cellular glyco¬proteins return to the site of Golgi mannosidase. J Cell Biol 103: 265–275

    Article  PubMed  CAS  Google Scholar 

  • Spikes JD (1988) Photosensitization. In: Smith KC (ed) The science of photobiology, 2nd edn. Plenum, New York, pp 79–110

    Google Scholar 

  • Spikes JD (1990) Chlorins as photosensitizers in biology and medicine. J Photochem Photobiol B6: 259–274

    Article  CAS  Google Scholar 

  • Spikes JD, Bommer JC (1986) Zinc tetrasulphophthalocyanine as a photodynamic sensitizer for biomolecules. Int J Radiat Biol 50: 41–45

    Article  CAS  Google Scholar 

  • Spikes JD, Bommer JC (1991) Chlorophyll and related pigments as photosensitizers in biology and medicine. In: Sheer H (ed) The chlorophylls. CRC, Boca Raton pp 1181–1204

    Google Scholar 

  • Spikes JD, Straight RC (1985) Photodynamic behavior of porphyrins in model cell, tissue and tumor systems. In: Jori G, Perria C (eds) Photodynamic therapy of tumors and other diseases. Progetto, Padova, pp 46–53

    Google Scholar 

  • Stahl PD, Rodman JS, Miller MJ, Schlesinger PH (1978) Evidence for receptor- mediated binding of glycoproteins, glycoconjugates, and lysosomal glycosidases by alveolar macrophages. Proc Natl Acad Sci USA 75: 1399–1403

    Article  PubMed  CAS  Google Scholar 

  • Steele JK, Liu D, Stammers AT, Whitney S, Levy JG (1988) Suppressor deletion therapy: selective elimination of T suppressor cells in vivo using a hematopor- phyrin conjugated monoclonal antibody permits animals to reject syngeneic tumor cells. Cancer Immunol Immunother 26: 125–131

    Article  PubMed  CAS  Google Scholar 

  • Steele KJ, Liu D, Davis N, Deal H, Levy JG (1989) The preparation and application of porphyrin-monoclonal antibodies for cancer therapy. Proc SPIE 1065: 73–79

    CAS  Google Scholar 

  • Straight RC (1990) Photodynamic laser therapy. In: Keye WR (ed) Laser surgery in gynecology and obstetrics. Year Book Medical Publishers, Chicago (in press)

    Google Scholar 

  • Subr V (1986) 7V-(2-hydroxypropyl)methacrylamide copolymers containing enzymatically degradable sequences as carriers of biologically active molecules (in Czech), (PhD thesis). Institute of Macromolecular Chemistry, Czechoslovak Academy of Sciences, Prague

    Google Scholar 

  • Subr V, Rejmanova P, Pohl J, Baudys M, Kostka V, Kopecek J (1984) Degradation of oligopeptide-poly[Af-(2-hydroxypropyl)methacrylamide] conjugates by cathepsins L and H (Abstr 69). 26th Microsymposium Polymers in Medicine and Biology, Prague

    Google Scholar 

  • Subr V, Kopecek J, Pohl J, Baudys M, Kostka V (1988) Cleavage of oligopeptide side- chains in 7V-(2-hydroxypropyl)methacrylamide copolymers by mixture of lysosomal enzymes. J Control Release 8: 133–140

    Article  CAS  Google Scholar 

  • Tartakoff AM (1987) The secretory and endocytic paths. Wiley, New York Tomlinson E (1987) Theory and practice of site-specific drug delivery. Adv Drug Delivery Rev 1: 87–198

    Google Scholar 

  • Trouet A, Jolles G (1984) Targeting of daunorubicin by association with DNA or proteins: a review. Semin Oncol (4)[Suppl 3] 11: 64–72

    CAS  Google Scholar 

  • Trouet A, Masquelier M, Baurain R, Deprez-de Campaneere D (1982a) A covalent linkage between daunorubicin and proteins that is stable in serum and reversible by lysosomal hydrolases, as required for a lysosomotropic drug-carrier conjugate. In vitro and in vivo studies. Proc Natl Acad Sci USA 79: 626–629

    Google Scholar 

  • Tsukada Y, Bischof WK-D, Hibi N, Hirai H, Hurwitz E, Sela M (1982) Effect of a conjugate of daunomycin and antibodies to rat a-fetoprotein on the growth of a- fetoprotein-producing tumor cells. Proc Natl Acad Sci USA 79: 621–625

    Article  PubMed  CAS  Google Scholar 

  • Tsukada Y, Ohkawa K, Hibi N (1987) Therapeutic effect of treatment with polyclonal or monoclonal antibodies to a-fetoprotein that have been conjugated to daunomycin via a dextran bridge: studies with a-fetoprotein producing rat hepa-toma tumor model. Cancer Res 47: 4293–4295

    PubMed  CAS  Google Scholar 

  • Tycko B, Maxfield FR (1982) Rapid acidification of endocytic vesicles containing alpha2-macroglobulin. Cell 28: 643–651

    Article  PubMed  CAS  Google Scholar 

  • Ulbrich K, Konak C, Tuzar Z, Kopecek J (1987) Solution properties of drug carriers based on poly[A-(2-hydroxypropyl)methacrylamide] containing biodegradable bonds. Makromol Chem 188: 1261–1272

    Article  CAS  Google Scholar 

  • Van Heeswijk WAR, Stoffer T, Eenink MJD, Potman W, van der Vijgh WJF, van der Poort J, Pinedo HM, Lelieveld P, Feijen J (1984) Synthesis, characterization and antitumor activity of macromolecular prodrugs of adriamycin. In: Anderson JM, Kim SW (eds) Recent advances in drug delivery systems. Plenum, New York, pp 77–100

    Chapter  Google Scholar 

  • Varga JM (1985) Hormone-drug conjugates. Methods Enzymol 112: 259–269

    Article  PubMed  CAS  Google Scholar 

  • Varga JM, Asato N (1983) Hormones as drug carriers. Polym Biol Med 2: 73–88

    CAS  Google Scholar 

  • Varga JM, Asato N, Lande S, Lerner AB (1977) Melanotropin-daunomycin conjugate shows receptor-mediated cytotoxicity in cultured murine melanoma cells. Nature 267: 56–58

    Article  PubMed  CAS  Google Scholar 

  • Vercauteren R, Bruneel D, Schacht E, Duncan R (1990) Effect of the chemical modification of dextran on the degradation by dextranase. J Bioact Compat Polym 5: 4–15

    Article  CAS  Google Scholar 

  • Vitetta ES, Fulton RJ, Uhr JW (1986) Immunotoxins: the development of new strategies for treating B cell tumours. In: Tomlinson E, Davis SS (eds) Site specific drug delivery. Wiley, New York, pp 69–80

    Google Scholar 

  • Von Figura K, Hasilik A, Steckel F (1984) Lysosomal storage disorders caused by instability of the missing enzymes. In: Barranger JA, Brady RO (eds) Molecular basis of lysosomal storage disorders. Academic, New York, pp 133–143

    Google Scholar 

  • Waley SG, Watson J (1953) The action of trypsin on polylysine. Biochem J 55: 328–337

    PubMed  CAS  Google Scholar 

  • Wileman T, Boshans RL, Schlesinger P, Stahl P (1984) Monesin inhibits recycling of macrophage mannose-glycoprotein receptors and ligand delivery to lysosomes. Biochem J 220: 665–675

    PubMed  CAS  Google Scholar 

  • Wileman, T, Harding C, Stahl P (1985) Receptor-mediated endocytosis. Biochem J 232: 1–14

    PubMed  CAS  Google Scholar 

  • Willingham M, Pastan I (1982) The transit of epidermal growth factor through coated pits of the golgi system. J Cell Biol 94: 207–212

    Article  PubMed  CAS  Google Scholar 

  • Willingham MC, Hanover JA, Dickson RB, Pastan I (1984) Morphologic character¬ization of the pathway of transferrin endocytosis and recycling in KB cells. Proc Natl Acad Sci USA 81: 175–179

    Article  PubMed  CAS  Google Scholar 

  • Woodman PG, Warren G (1988) Fusion between vesicles from the pathway of receptor-mediated endocytosis in a cell-free system. Eur J Biochem 173: 101–108

    Article  PubMed  CAS  Google Scholar 

  • Woods JW, Doriaux M, Farquhar MG (1986) Transferrin receptors recycle to cis and middle as well as trans Golgi cisternae in lg-secreting myeloma cells. J Cell Biol 103: 277–286

    Article  PubMed  CAS  Google Scholar 

  • Worrell NR, Cumber AJ, Parnell GD, Mirza A, Forrester JA, Ross WCJ (1986) Effect of linkage variation on pharmacokinetics of ricin A chain-antibody conjugates in normal rats. Anticancer Drug Design 1: 179–188

    CAS  Google Scholar 

  • Yaacobi Y, Sideman S, Lotan N (1985) A mechanistic model for the enzymic degradation of synthetic biopolymers. Life Support Syst 3: 313–326

    PubMed  CAS  Google Scholar 

  • Yamamoto I, Izumiya N (1966) Action of chy mo trypsin on synthetic substrates. VI. The action of a-chymotrypsin on glycyl-amino-acyl-L-tyrosine ethyl esters. Arch Biochem Biophys 114: 459–464

    Google Scholar 

  • Yokoyama M, Maeda M, Inoue S, Kataoka K, Yui N, Sakurai Y (1988) Molecular design of missile drug: synthesis of poly(ethylene glycol)-poly(aspartic acid) block copolymer binding adriamycin. Proc The Third World Biomat Cong 4D - 14: 229

    Google Scholar 

  • Yokoyama M, Inoue S, Kataoka K, Yui N, Okano T, Sakurai Y (1989) Molecular design for missile drug: Synthesis of adriamycin conjugated with immunoglobulin G using poly (ethylene glycol)-block-poly(aspartic acid) as intermediate carrier. Makromol Chem 190: 2041–2054

    Google Scholar 

  • Yokoyama M, Miyauchi M, Yamada N, Okano T, Sakurai Y, Kataoka K, Inoue S (1990) Characterization and anticancer activity of the micelle-forming polymeric anticancer drug adriamycin conjugated poly (ethylene glycol)-poly(aspartic acid) block copolymer. Cancer Res 50: 1693–1700

    PubMed  CAS  Google Scholar 

  • Young RC, Ozols RF, Myers CE (1981) Medical progress. The anthracycline antineoplastic drugs. N Engl J Med 305: 139–153

    Google Scholar 

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Authors
  1. N. L. Krinick
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  2. J. Kopeček
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Editors and Affiliations

  1. Department of Pharmacology, University of North Carolina School of Medicine, CB#7365, Faculty Laboratory Office Building, 27599-7365, Chapel Hill, NC, USA

    Rudolph L. Juliano Prof., Ph.D. (Professor and Chairman) (Professor and Chairman)

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© 1991 Springer-Verlag Berlin Heidelberg

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Krinick, N.L., Kopeček, J. (1991). Soluble Polymers as Targetable Drug Carriers. In: Juliano, R.L. (eds) Targeted Drug Delivery. Handbook of Experimental Pharmacology, vol 100. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-75862-1_5

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  • DOI: https://doi.org/10.1007/978-3-642-75862-1_5

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-75864-5

  • Online ISBN: 978-3-642-75862-1

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