Drug targeting by macromolecules without recognition unit?

Journal of Molecular Recognition

Volumn 16, Issue 5, 2003, Pages 288-298

  Hudecz, Ferenc ^a   Reményi, Judit ^a   Szabó, Rita ^a   Kóczán, György ^a   Mezo, Gábor ^a   Kovács, Péter ^b   Gaál, Dezso ^c  

^a EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^b SEMMELWEIS UNIVERSITY OF MEDICINE   (Hungary)

^c NATIONAL INSTITUTE OF ONCOLOGY   (Hungary)

Author keywords

Daunomycin; Endocytosis; Leishmania donovani; Methotrexate; Peptide carriers of drugs; Uptake without recognition unit

Indexed keywords

ANIMALS; ANTHRACYCLINES; ANTIBIOTICS, ANTINEOPLASTIC; ANTIMETABOLITES, ANTINEOPLASTIC; DAUNORUBICIN; DRUG DELIVERY SYSTEMS; LEISHMANIA DONOVANI; LEISHMANIASIS, VISCERAL; MACROPHAGES; METHOTREXATE;

LEISHMANIA DONOVANI;

EID: 0141942110     PISSN: 09523499     EISSN: None     Source Type: Journal    
DOI: 10.1002/jmr.639     Document Type: Conference Paper

References (97)

1. Abraham A, Nair MG, Kisliuk RL, Gaumont Y, Galivan J. 1990. Folate analogues. 33. Synthesis of folate and antifolate poly-γ-glutamates by [(9-fluorenylmethoxy)oxylcarbonyl chemistry and biological evaluation of certain methotrexate polyglutamate polylysine conjugates as inhibitors of the growth of H35 hepatoma cells. J. Med. Chem. 33: 711-717.
2. Al-Shamkhani A, Duncan R. 1995. Synthesis, controlled release properties and antitumour activity of alginate-cis-aconityldaunomycin conjugates. Int. J. Pharm. 122: 107-119.
3. Arnold LJ Jr. 1985. Polylysine-drug conjugates. Meth. Enzymol. 112: 270-285.
4. Ben-Yedidia T, Arnon R. 1997. Design of peptide and polypeptide vaccines. Curr. Opin. Biotechnol. 8: 442-448.
5. Bernstein A, Hurwitz E, Maron R, Arnon R, Sela M, Wilchek M. 1978. Higher antitumor efficacy of daunomycin when linked to dextran: in vivo and in vitro studies. J. Natl Cancer Inst. 60: 379-384.
6. Bleyer WA, Drake JC, Chabner BA. 1973. Neurotoxicity and elevated cerebrospinal-fluid methotrexate concentration in meningeal leukemia. New Engl. J. Med. 289: 770-773.
7. Bryceson ADM. 1996. Manson's Tropical Diseases, Cook GC (ed.). W.B. Saunders: London; 1213-1245.
8. Bures L, Lichy A, Bostik, J, Spundova M. 1990. The use of protein as a carrier of methotrexate for experimental cancer chemotherapy. Alternative method for preparation of serum albumin-methotrexate derivative. Neoplasma 37: 225-231.
9. Cassidy J, Duncan R, Morrison GJ, Strohalm J, Kopecek J, Kaze SB. 1989. Activity of N-(2-hydroxypropyl)methacrylamide copolymers containing daunomycin against a rat tumor model. Biochem. Pharmac. 38: 785-879.
10. Cerottini JC, Isliker H. 1966. Studies of the possibilities of the use of serum albumin as a transporter of antitumoral agents. Helv Physiol. Pharmac. Acta 24: 13-16.
11. Chakraborty P, Bhaduri AN, Das PK. 1990a. Neoglycoproteins as carriers for receptor-mediated drug targeting in the treatment of experimental visceral leishmaniasis. J. Protozool. 37: 358-364.
12. Chakraborty P, Bhaduri AN, Das PK. 1990b. Sugar receptor mediated drug delivery to macrophages in the therapy of experimental visceral leishmaniasis. Biochem. Biophys. Res. Commun. 166: 404-410.
13. Chaudhuri G, Mukhopadhyay A, Basu SK. 1989. Selective delivery of drugs to macrophages through a highly specific receptor. An efficient chemotherapeutic approach against leishmaniasis. Biochem. Pharmac. 38: 2995-3002.
14. Clegg JA, Hudecz F, Mezo G, Pimm MV, Szekerke M, Baldwin RW. 1990. Carrier design: biodistribution of branched polypeptides with poly-(L-lysine) backbone. Bioconjugate Chem. 2: 425-430.
15. Daussin F, Boschetti E, Delmotte F, Monsigny M. 1988. p-Benzylthiocarbamoyl-aspartyl-daunorubicin-substituated polytrisacryl. A new drug acid-labile arm-carrier conjugate. Eur. J. Biochem. 176: 625-628.
16. De Duve C, Trouet A, Campeneere DD, Baurian R. 1978. Liposomes as lysosomotropic carriers. Ann. NY Acad. Sci. 308: 226-234.
17. Duncan R. 1992. Drug-polymer conjugates; potential for improved chemotherepy. Anti-Cancer Drugs 3: 153-156.
18. Duncan R, Kopeková-Rejmanová P, Strohalm J, Hume I, Cable HC, Pohl J, Lloyd JB, Kopeek J. 1987. Anticancer agents coupled to N-(2-hydroxypropyl)methacrylamide copolymers. I. Evaluation of daunomycin and puromycin conjugates in vitro. Br. J. Cancer 55: 165-174.
19. Duncan R, Seymour LW, Ohare KB, Flanagan PA, Wedge S, Hume IC, Ulbrich K, Strohalm J, Subr V, Spreafico F, Grandi M, Ripamonti M, Farao M, Saurato P. 1992. Preclinical evaluation of polymer bound doxorubicin. J. Controlled Release 19: 331-346.
20. Duncan R, Gac-Breton S, Keane R, Musila R, Sat YN, Satchi R, Searle F. 2001. Polymer-drug conjugates, PDEPT and PELT: basic principles for design and transfer from the laboratory to clinic. J. Controlled Release 74: 135-146.
21. Farber S, Diamond LK, Mercer RD, Sylvester RF, Wolff JA. 1948. Temporary remissions in acute leukemia in children produced by folic acid antagonists, 4-aminopteroylglutamic acid, (aminopterin). New Engl. J. Med. 238: 787-793.
22. Friend DR, Pangburn S. 1987. Site-specific drug delivery. Med. Res. Rev. 7: 53-106.
23. Furst DE, Kremer JM. 1988. Methotrexate in rheumatoid arthritis. Arthritis Rheum. 31: 305-314.
24. Gaál D, Hudecz F. 1998. Low toxicity and high antitumour activity of daunomycin by conjugation to immunpotential amphoteric branched polypeptide. Eur. J. Cancer 34: 155-161.
25. Galivan J, Balinska M, Whiteley JM. 1982. Interaction of methotrexate-poly(L-Lys) with transformed hepatic cells in culture. Arch. Biochem. Biophys. 216: 544-550.
26. Gardner-Medwin JM, Powell RJ. 1996. One patient, two unusual conditions and three basic lessons. Ann. Rheum. Dis. 55: 350-352.
27. Golightly L, Brown JE, Mitchell JB, Brown JR. 1988. Trypanocidal activity of free and carrier bound daunomycin. Cell. Biol. Int. Rep. 12: 77-83.
28. Halbert GW, Florence AT, Stuart JFB. 1987. Characterization of in-vivo drug release and biological activity of methotrexatebovine serum albumin conjugates. J. Pharm. Pharmac. 39: 871-876.
29. Harding NGL. 1971. Amethopterin linked covalently to water-soluble macromolecules. Ann. NY Acad. Sci. 186: 270-283.
30. Hirano T, Ohashi S, Morimoto S, Tsukada K, Kobayashi T, Tsukagoshi S. 1986. Synthesis of antitumor-active conjugates of adriamycin or daunomycin with the copolymer of divinyl ether and maleic anhydride. Macromol. Chem. 187: 2815-2824.
31. Hoes CJT, Potman W, Van Heeswijk WA. 1985. Optimisation of macromolecular produgs of antitumor antibiotic adriamycin. J. Controlled Release 2: 205-218.
32. Hoes CJT, Grootoonk J, Duncan R, Hume Bhakoo M, Bouma JMW, Feijen J. 1993. Biological properties of adriamycin bound to biodegradable polymer carriers. J. Controlled Release 23: 37-53.
33. Hudecz F. 1995. Design of synthetic branched-chain polypeptides as carriers for bioactive molecules. Anti-Cancer Drugs 6: 171-193.
34. Hudecz F. 2001. Self-assembling Peptide Systems in Biology, Medicine and Engineering, Agelli A, Boden N, Zhang S (eds). Kluwer Academic: Dordrecht; 139-160.
35. Hudecz F, Tóth GK. 1994. Synthetic peptide constructs to increase the immunogenicity of B-cell epitopes. In Synthetic Peptides in the Search for B- and T-cell Epitopes, Rajnavölgyi É (ed.). R.G. Landes: Austin, TX; 97-119.
36. Hudecz F, Votavova H, Gaál D, Sponar J, Kajtár J, Blaha K, Szekerke M. 1985. Branched polypeptides with a poly(L-lysine) backbone: synthesis, conformation and immunomodulation. In Polymeric Materials in Medication, Gebelein ChG, Carraher ChE (eds). Plenum Press: New York; 265-289.
37. Hudecz F, Clegg JA, Kajtár J, Embleton MJ, Szekerke M, Baldwin RW. 1992. Synthesis, conformation, biodistribution and in vitro cytotoxicity of daunomycin-branched polypeptide conjugates. Bioconjugate Chem. 3: 49-57.
38. Hudecz F, Clegg JA, Kajtár J, Embleton MJ, Pimm MV, Szekerke M, Baldwin RW. 1993. Influence of carrier on biodistribution and in vitro cytotoxicity of methotrexate-branched polypeptide conjugates. Bioconjugate Chem. 4: 25-33.
39. Hudecz F, Pimm MV, Rajnavölgyi É, Mezo G, Fabra A, Gaál D, Kovács AL, Horváth A, Szekerke M. 1999. Carrier design: new generation of polycationic branched polypeptides containing OH groups with prolonged blood survival and diminished in vitro cytotoxicity. Bioconjugate Chem. 10: 781-790.
40. Hudecz F, Nagy IB, Kóczán Gy, Alsina MA, Reig F. 2001. Biomedical Polymers and Polymer Therapeutics, Chiellini E, Sunamoto J, Migliaresi C, Ottenbrite RM, Cohn D (eds). Kluwer Academic/Plenum: New York; 103-120.
41. 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.
42. Kitao T, Hattori K. 1977. Concanavalin A as a carrier of daunomycin. Nature 265: 81-82.
43. Kóczán Gy, Hudecz F. 2002. Novel RP-HPLC approach for the purification and analysis of methotrexate-branched polymeric polypeptide conjugates. Chromatographia 55: 163-170.
44. Kóczán Gy, Ghose AC, Mookerjee A, Hudecz F. 2002. Methotrexate conjugate with branched polypeptide influences Leishmania donovani infection in vitro and in experimental animals. Bioconjugate Chem. 13: 518-524.
45. Kratz F, Beyer U, Roth T, Tarasova N, Collery P, Lechenault F, Cazabat A, Schumacher P, Unger C, Falken U. 1998. Transferrin conjugates of doxorubicin: synthesis, characterization, cellular uptake, and in vitro efficacy. J. Pharm. Sci. 87: 338-346.
46. Kratz F, Beyer U, Schütte MT. 1999. Drug-polymer conjugates containing acid-cleavable bonds. Crit. Rev. Ther. Drug Carrier Systems 16: 245-288.
47. Lagueux J, Pagė M, Delorme F. 1984. Daunorubicin-albumin copolymer targeting to leukemic cells in vitro and in vivo. Semin. Oncol. 11: 59-63.
48. Lemieux P, Page M, Noel C. 1992. In vivo cytotoxicity and antineoplastic activity of a transferrin-daunorubicin conjugate. In Vivo 6: 621-627.
49. Levi-Schaffer F, Bernstein A, Meshorer A, Arnon R. 1992. Reduced toxicity of daunorubicin by conjugation to dextran. Cancer Treat. Rep. 66: 107-114.
50. Lothstein L, Israel M, Sweatman TW. 2001. Anthracycline drug targeting: cytoplasmic versus nuclear - a fork in the road. Drug Resist. Update : 169-177.
51. Mann JS, Huang JC, Keana JFW. 1992. Molecular amplifiers: synthesis and functionalization of a poly(aminopropyl)dextran bearng a uniquely reactive terminus for univalent attachment to biomolecules. Bioconjugate Chem. 3: 154-159.
52. Mathe G, Loc TB, Bernard J. 1958. Effet sur la leucemie 1210 de la souris d'un combinaison par diazotation d'Amethopterine et de gamma-globulines de hamsters porteurs de cette leucemie par hetirogreffe. C. R Acad. Sci (D) Paris 246: 1626-1632.
53. McGuire JJ, Russell CA. 1990. A human leukemia cell culture system for testing new antifols: differential sensitivity of lymphoid and non-lymohoid cell lines to unconjugated and methotrexate conjugated polymers of basic amino acids. Leukemia 4: 48-52.
54. m) substituted poly[L-lysine]. Biopolymers 33: 873-883.
55. Mezo G, Mezo I, Seprodi A, Teplán I, Kovȧcs M, Vincze B, Pályi I, Kajtár J, Szekerke M, Hudecz F. 1996a. Synthesis, conformation, biodistribution and hormon related in vitro anti-tumor effect of a GnRH antagonist-branched polypeptide conjugate. Bioconjugate Chem. 7: 642-650.
56. Mezo G, Sármay G, Hudecz F, Kajtár J, Nagy Zs, Gergely J, Szekerke M. 1996b. Synthesis and characterization of p-borono-Phe-branched polypeptide-monoclonal antibody ternary systems for potential use in boron neutron capture therapy (BNCT). J. Bioactive Compatible Polym. 11: 263-285.
57. Mezo G, Kajtár J, Nagy I, Majer Zs, Szekerke M, Hudecz F. 1997. Carrier design: synthesis and conformational studies of poly[L-lysine] based branched polypeptides with hydroxyl groups. Biopolymers 42: 719-730.
58. Mukherjee S, Grosh RN, Maxfield FR. 1997. Endocytosis. Physiol. Rev. 77: 759-803.
59. Mukhopadhyay A, Chaudhuri G, Arora SK, Sehgal S, Basu SK. 1989. Receptor mediated drug delivery to macrophages in chemotherapy of leishmaniasis. Science 244: 705-707.
60. Mukhopadhyay A, Mukhopadhyay B, Srivastava RK, Basu SK. 1992. Scavenger receptor-mediated delivery of daunomycin elicits selective toxicity towards neoplastic cells of macrophage lineage. Biochem. J. 284: 237-241.
61. Mukhopadhyay B, Mukhopadhyay A, Basu SK. 1993. Enhancement of tumouricidal activity of daunomycin by receptor-mediated delivery. In vivo studies. Biochem. Pharm. 46: 912-924.
62. Mukhopadhyay A, Mukhopadhyay B, Basu SK. 1995. Circumvention of multidrug resistance in neoplastic cells through scavenger receptor mediated drug delivery. FEBS Lett. 376: 95-98.
63. Nagy IB, Majer Zs, Hudecz F. 2001. Effect of phospholipid bilayers on solution conformation of branched polymeric polypeptides and peptide-polymer conjugates. Biopolymers 58: 152-164.
64. Ohkawa K, Hatano T, Tsukuda Y, Matsuda M. 1993a. Chemotherapeutic efficacy of the protein-doxorubicin conjugates on multidrug resistant rat hepatoma cell line in vitro. Br. J. Cancer 67: 274-278.
65. Ohkawa K, Hatano T, Yamada K, Joh K, Takada K, Tsukuda Y, Matsuda M. 1993b. Bovine serum albumin-doxorubicin conjugate overcomes multidrug resistance in a rat hepatoma. Cancer Res. 53: 4238-4242.
66. Pató J, Ulbrich K, Baker P, Mezo G, Hudecz F. 1999. Synthesis of macromolecular conjugates of a urokinase inhibitor. J. Bioactive Compatible Polym. 14: 99-121.
67. 99mTc-branched chain polypeptide (BCP): a potential synthetic radiopharmaceutical. J. Labelled Compounds 41: 631-638.
68. 51Cr) for biodistribution studies and radiopharmaceutical development. J. Labelled Compounds 36: 157-172.
69. Poznansky MJ, Cleland LG. 1980. Biological macromolecules as carriers of drugs and enzymes. In Drug Delivery Systems, Juliano RL (ed.). Oxford University Press: Oxford; 253-315.
70. 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.
71. Przybylski M, Fell E, Ringsdorf H, Zaharko DS. 1978. Synthesis and characterization of polymeric derivatives of the antitumour agent methotrexate. Makromol. Chem. 179: 1719-1733.
72. Reményi J, Hegedus T, Sarkadi B, Tóth S, Falus A, Gaál D, Hudecz F. 2001. Daunomycin-polypetide conjugates: in vitro antitumour effect in sensitive and multidrug resistant cell lines. Eur. J. Cancer 37: S66.
73. Ryser HJP, Shen WC. 1978. Conjugation of methotrexate to poly(l-lysine) increases drug transport and overcomes drug resistance. Proc. Natl Acad. Sci. USA 75: 3867-3870.
74. Sanzgiri Y, Blaton CD, Gallo JM. 1990. Synthesis, characterization and in vitro stability of chitosan-methotrexate conjugates. Pharm. Res. 7: 418-421.
75. Sett R, Sarkar K, Das PK. 1993a. Macrophage-directed delivery of doxorubicin conjugated to neoglycoprotein using leishmaniasis as the model disease. J. Infect. Dis. 168: 994-999.
76. Sett R, Sarkar HS, Das PK. 1993b. Pharmacokinetics and biodistribution of methotrexate conjugated to mannosyl human serum albumin. J. Antimicrob. Chemother. 31: 151-159.
77. Seymour LW, Ulbrich K, Strohalm J, Kopecek J, Duncan R. 1990. The pharmacokinetics of polymer-bound adriamycin. Biochem. Pharm. 39: 1125-1131.
78. Shen WC, Ryser HJP. 1979. Poly(L-Lysine) and poly(D-Lysine) conjugates of methotrexate: different inhibitory effect on drug resistant cells. Mol. Pharmac. 16: 614-622.
79. Shen WC, Ryser HJP. 1981. Cis-aconityl spacer between daunomycin and macromolecular carriers. Biochem. Biophys. Res. Commun. 102: 1048-1054.
80. Shen WC, Ryser HJ, LaManna L. 1985. Disulfide spacer between methotrexate and poly(D-lysine). A probe for exploring the reductive process in endocytosis. J. Biol. Chem. 260: 10905-10908.
81. Taatjes DJ, Koch TH. 2001. Nuclear targeting and retention of anthracycline antitumour drugs in sensitve and resistant tumor cells. Curr. Med. Chem. 8: 15-29.
82. Takakura Y, Hashida M. 1995. Macromolecular drug carrier Systems in cancer chemotherapy: macromolecular prodrugs. Crit. Rev. Oncol./Haematol. 18: 207-231.
83. Trouet A, Jolles G. 1984. Targeting of daunorubicin by association with DNA or proteins: a review. Semin. Oncol. 11: 64-72.
84. Trouet A, Masquelier M, Baurain R, Deprez-De Campeneere D. 1982. 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.
85. Tsou H-R, Wallace R, Citarella RV, Upeslacis J. 1991. Methotrexate/gamma/hydrazide and divinyl ethet-maleic anhydride conjugate. In Polymeric Drugs and Drug Delivery Systems, Dunn RL, Ottenbrite RM (eds). ACS Symposium Series 469: 84-90.
86. Tsukada Y, Bischof WK, Hibi N, Hirai H, Hurwitz E, Sela M. 1982. Effect of a conjugate of daunomycin and antibodies to rat α-fetoprotein on the growth of alpha-fetoprotein-producing tumor cells. Proc. Natl Acad. Sci. USA 79: 621-625.
87. Umemoto N, Kato Y, Hara T. 1989a. Cytotoxicities of two disulfide-bond-linked conjugates of methotrexate with monoclonal anti-MM46 antibody. Cancer Immunol. Immunother, 28: 9-16.
88. Umemoto N, Kato Y, Endo N, Takeda Y, Hara T. 1989b. Preparation and in vitro toxicity of a MTX-anti-MM46 monoclonal antibody conjugate via an oligopeptide spacer. Int. J. Cancer 43: 677-684.
89. Upeslacis J, Hinman L. 1988. Chemical modification of antibodies for cancer chemotherapy In Annual Reports in Medicinal Chemistry, Saltzman N (ed.). Academic Press: New York; 151-160.
90. Van Regenmortel HMV. 2001. Pitfalls of reductionism in the design of peptide-based vaccines. Vaccine 19: 2369-2374.
91. Vasey PA, Kaye SB, Morrison R, Twelves C, Wilson P, Duncan R, Thomson AH, Murray LS, Hilditch TE, Murray T, Burtles S, Fraier D, Frigerio E, Cassidy J. 1999. Phase I clinical and pharmacokinetic study of PK1 [N-(2-hydroxypropyl)methacrylamide copolymer doxorubicin]: first member of a new class of chemotherapeutic agents - drug-polymer conjugates. Clin. Cancer Res. 5: 83-94.
92. Vincze B, Pályi I, Daubner D, Kálnay A, Mezo G, Hudecz F, Szekerke M, Teplán I, Mezo I. 1994. Antitumor effect of a GnRH antagonist and its conjugate on human breast cancer cells and their xenografts. J. Cancer Res. Clin. Oncol. 120: 578-584.
93. Whiteley JM, Nimec Z, Galivan J. 1981. Treatment of Reuber H35 hepatoma cells with carrier-bound methotrexate. Mol. Pharmac. 19: 503-508.
94. Williamson J, Scott-Finningan TJ, Hardman MA, Brown JR. 1981. Trypanocidal activity of daunorubicin and related compounds. Nature 292: 466-467.
95. Zunino F, Giuliani F, Savi G, Dasdia T, Gambetta R. 1982. Antitumor activity of daunorubicin linked to poly-L-aspartic acid. Int. J. Cancer 30: 465-470.
96. Zunino F, Savi G, Giuliani F, Gambetta R, Supino R, Tinelli S, Pezzoni G. 1984. Comparison of antitumor effects of daunorubicin covalently linked to poly-L-amino acid carriers. Eur. J. Cancer Clin. Oncol. 20: 421-425.
97. Zunino F, Pratesi G, Pezzoni G. 1987. Increased therapeutic efficacy and reduced toxicity of doxorubicin linked to pyran copolymer via side chain of the drug. Cancer Treat. Rep. 71: 367-373.