Immobilization of aminothiols on poly(oxyalkylene phosphates). Formation of poly(oxyethylene phosphates)/cysteamine complexes and their radioprotective efficiency

Journal of Medicinal Chemistry

Volumn 45, Issue 26, 2002, Pages 5797-5801

  Georgieva, Radostina ^a   Tsevi, Raina ^b   Kossev, Krassimir ^b   Kusheva, Rossitsa ^a   Balgjiska, Mariana ^c   Petrova, Radostina ^c   Tenchova, Violeta ^a   Gitsov, Ivan ^d   Troev, Kolio ^b  

^a National Center of Radiobiology and Radiation Protection Bulgaria   (Bulgaria)

^b INSTITUTE OF POLYMERS   (Bulgaria)

^c UNIVERSITY OF SOFIA   (Bulgaria)

^d STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOTHIOL; MERCAPTAMINE; POLY(OXYETHYLENE PHOSPHATE); POLYMER; RADIOPROTECTIVE AGENT; UNCLASSIFIED DRUG;

ACUTE TOXICITY; ANIMAL MODEL; ARTICLE; BIOCOMPATIBILITY; CONTROLLED STUDY; DRUG SYNTHESIS; MAXIMUM TOLERATED DOSE; MOLECULAR WEIGHT; MOUSE; NONHUMAN; POLYMERIZATION; RADIATION PROTECTION; TOXICITY TESTING;

ACUTE TOXICITY TESTS; ANIMALS; CYSTEAMINE; DRUG CARRIERS; ESCHERICHIA COLI; ETHYLENE GLYCOLS; MICE; PHOSPHORIC ACID ESTERS; RADIATION-PROTECTIVE AGENTS; SURVIVAL RATE; WHOLE-BODY IRRADIATION;

EID: 0037137616     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020309o     Document Type: Article

References (32)

1. Bacq, Z. M.; Dechamps, G.; Fischer, P.; Herve, A.; Lebihan, H.; Lecomte, J.; Pirotte, M.; Rayet, P. Protection against X-rays and therapy of radiation sickness with β-mercaptoethylamine. Science 1953, 117, 633-636.
2. Baldini, G.; Ferri, L. Experimental and clinical research on the radio-protective action of cysteamine and cystamine. 3. Clinical research, Br. J. Radiol. 1957, 30, 271-273.
3. Durkovsky, J.; Siracka-Vasela, E. Klinische applikation von cysteamin bei der strahlungskrankheit. Neoplasma 1958, 5, 417-423.
4. Monig, H.; Messershmidt, O. Streffer, Chemical radioprotection in mammals and in man. Radiation Exposure and Occupational Risks; Springer: Heidelberg, 1990; pp 97-143.
5. (a) Ringsdorf, H. Structure and properties of pharmacologically active polymers. J. Polym. Sci., Polym. Symp. 1975, 51, 135.
6. (b) Ottenbrite, R. M.; Regelson, W.; Kaplan, A.; Carchman, R.; Morahan, P.; Munson, A. Polymeric Drugs; Donaruma, L. G., Vogl, O., Eds.; Academic Press: New York, San Francisco, London, 1978.
7. (c) Duncan, R. Drug-polymer conjugates: potential for improved chemotherapy. Anti-Cancer Drugs 1992, 3, 175.
8. (d) Uhrich, K. Hyperbranched polymers for drug delivery. Trends in Polymer Sci. 1997, 5, 388-393.
9. (e) Tailored Polymeric Materials for Controlled Delivery Systems; McCulloch, I., Shalaby, S. W., Eds.; ACS Symposium Series Vol. 709, American Chemical Society: Washington, DC, 1998.
10. (f) Soppimath, K. S.; Aminabhavi, T. M.; Kulkarni, A. R.; Rudzinski, W. E. Biodegradable polymeric nanoparticles as drug delivery devices. J. Controlled Release 2001, 70, 1-20.
11. (a) Senter, P. D.; Svensson, H. P.; Schreiber, G. J.; Rodriguez, J. L.; Vrudhula, V. M. Poly(ethylene glycol)-doxorubicin conjugates containing beta-lactamase-sensitive linkers. Bioconjugate Chem. 1995, 64, 389-394.
12. (b) Greenwald, R. B.; Pendri, A.; Conover, C.; Gilbert, C.; Yang, R.; Xia, J. Drug delivery systems. 2. Camptothecin 20-O-poly(ethylene glycol)ester transport forms. J. Med. Chem. 1996, 39, 1938-1940.
13. (c) Conover, C. D.; Pendri, A.; Lee, C.; Gilbert, C. W.; Shum, K. L.; Greenwald, R. B. Camptothecin delivery systems: The antitumor activity of a camptothecin 20-0-poly(ethylene glycol) ester transport form. Anticancer Res. 1997, 17 (5A), 3361-3368.
14. (d) Greenwald, R. B.; Pendri, A.; Conover, C. D.; Lee, C.; Choe, Y. H.; Gilbert, C.; Martinez, A.; Xia, J.; Wu, D. C.; Hsue, M. Camptothecin-20-PEG ester transport forms: the effect of spacer groups on antitumor activity. Biorg. Med. Chem. 1998, 65, 551-562.
15. (e) Greenwald, R. B.; Gilbert, C. W.; Pendri, A.; Conover, C. D.; Xia, J.; Martinez, A. Drug delivery systems: Water soluble taxol 2′-poly(ethylene glycol) ester prodrugs - Design and in vivo effectiveness. J. Med. Chem. 1996, 39, 424-431.
16. (a) Penczek, S. Mechanism of ionic polymerization of cyclic esters of phosphoric acid (a new route to models of biopolymers). J. Polym. Sci., Polym. Symp. 1980, 67, 149-168.
17. (b) Petrula, J.; Penczek, S. Poly(ethylene glycol) ionomers with phosphate diesters linkages. Makromol. Chem., Rapid Commun. 1988, 9, 731-737.
18. (c) Brosse, J.; Fontaine, L.; Derouet, D.; Chairatanathavorn, S. Fixation d'amines pharmacologiquement actives sur les polyphosphonates. 1. Etude sur molecule modele. Macromol. Chem. 1989, 190, 2329-2338.
19. (d) Brosse, J.; Fontaine, L.; Derouet, D.; Chairatanathavorn, S. Fixation of pharmacologically active amines on polyphosphonates. 2. Application of benzociane and phenethylamine. Macromol. Chem. 1989, 190, 2339-2345.
20. (e) Petrula, J.; Penczek, S. High-molecular-weight poly(alkylene phosphonate)s by condensation of dialkylphosphonates with diols. Makromol. Chem. 1990, 191, 671-680.
21. (f) Penczek, S.; Petrula J. High-molecular-weight poly(alkylene phosphate)s and preparation of amphiphilic polymers thereof. Macromolecules 1993, 26, 2228-2233.
22. (g) Tsevi, R.; Todorova, G.; Kossev, K.; Troev, K.; Roundhill, D. M. Immobilization of bioactive substances on poly(alkylene phosphate)s. 1. Immobilization of 2-phenythylamine, Makromol Chem. 1993,194, 3261-3269.
23. (h) Tsevi, R.; Novakov, P.; Troev, K.; Roundhill, D. M. Synthesis of poly(oxyethylene phosphonate)s bearing oxirane groups in the side chain. J. Polym. Sci. Part A: Polymer Chem. 1997, 35, 625-630.
24. Nikolov, I.; Rogozkin, V.; Pantev, T.; Chertkov, K.; Dikovenko, E.; Paridova, S. Protection of monkeys against prolonged gamma-irradiation. Strahlenther Oncol. 1986, 162, 200-204.
25. Pantev, T.; Georgieva, R.; Topalova, S. Antiradiation mixture and ionic bond product of AET and adenyl nucleotides. Strahlenther. Oncol. 1991, 167, 422-426.
26. Stefanova, D.; Gatavechia, E.; Ferri, E.; Breccia, A. Depotprotection against γ-irradiation in mice by parenteral glutatione polyvinylpyrrolodone coprecipitates and cellular drug uptake. Drug. Invest. 1990, 2, 219-224.
27. (a) Gitsov, I. Hybrid dendritic capsules. Properties and binding capabilities of amphiphilic copolymers with linear dendritic architecture. Associative Polymers in Aqueous Solutions; Glass, J. E., Ed.; ACS Symposium Series Vol. 765, American Chemical Society: Washington, DC, 2000, pp 72-92.
28. Gitsov, I.; Lambrych, K. R.; Remnant, V. A.; Pracitto, R. Micelles with highly branched nanoporous interior. Solution properties and binding capabilities of amphiphilic copolymers with linear dendritic architecture. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 2711-2727.
29. Finney, D. Probit Analysis, 2nd Ed.; Cambridge University Press: Cambridge, 1962.
30. Doherty, D. G.; Burnelt, W. T.; Shapira, R. Chemical protection against ionizing radiation. II Mercaptoalkylamines and related compounds with protective activity. Radiat. Res. 1957, 7, 13-21.
31. Bacq, Z.; Alexander, P. The role of the oxygen phenomena of chemical protection against ionizing radiation. Oxygen in the Animal Organism; Pergamon Press: Oxford, 1964; pp 509-536.
32. Yarmonenko, S. P. Human and Animal Radiobiology (In Russian); Visshaya Shkola, Moscow, 1984; pp 63-68.