Synthesis of monomeric and polymeric conjugates carrying a thrombin inhibitor through an ester bond

Journal of Biomedical Materials Research

Volumn 39, Issue 4, 1998, Pages 621-629

  Noguchi, Hiroshi ^a   Iwata, Hiroo ^a   Ikada, Yoshito ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Antithrombogenic activity; Monomeric conjugate; Polymeric conjugate; Thrombin inhibitor

Indexed keywords

BLOOD; CARBOXYLIC ACIDS; CHEMICAL BONDS; COPOLYMERIZATION; ESTERS; HYDROLYSIS; MONOMERS; POLYAMIDES; PROTEINS; SYNTHESIS (CHEMICAL);

BLOOD CLOTTING TIME; THROMBIN INHIBITORS;

BIOMATERIALS;

ARGATROBAN; MONOMER; POLYMER; THROMBIN;

ANTICOAGULATION; ARTICLE; BLOOD CLOTTING TIME; COMPETITIVE INHIBITION; CONJUGATE; DRUG HYDROLYSIS; DRUG INHIBITION; FIBRINOLYSIS; INHIBITION KINETICS; POLYMERIZATION; PROSTHESIS MATERIAL; STRUCTURE ACTIVITY RELATION; SUSTAINED DRUG RELEASE; THROMBOGENESIS;

ANTITHROMBINS; BLOOD COAGULATION; ESTERS; HUMANS; PIPECOLIC ACIDS; POLYMERS;

EID: 0032520842     PISSN: 00219304     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-4636(19980315)39:4<621::AID-JBM17>3.0.CO;2-9     Document Type: Article

References (18)

1. H. Tanzawa, Y. Mori, N. Harumiya, and H. Miyama, "Preparation and evaluation of a new athrombogenic heparinized hydrophilic polymer for use in cardiovascular system," Trans. Am. Soc. Artif. Intern. Organs, 14, 188-194 (1973).
2. H. Miyama, N. Harumiya, Y. Mori, and H. Tanzawa, "A new antithrombogenic heparinized polymer," J. Biomed. Mater. Res., 11, 251-265 (1977).
3. O. Larm, R. Larsson, and P. Olsson, "A new non-thrombogenic surface prepared by selective covalent binding of heparin via a modified reducing terminal residue," Biomat. Med. Dev. Artif. Organs, 11, 161-173 (1983).
4. V. Videm, L. Nilsson, P. Venge, and J. Svennevig, "Reduced granulocyte activation with heparin coated device in an in vitro model of cardiopulmonary bypass," Artif. Organs, 15, 90-95 (1991).
5. T. Matsuda, H. Iwata, H. Noda, T. Toyosaki, H. Takano, and T. Akutsu, "Antithrombogenic elastomers: Novel anticoagulant/complement inhibitor-controlled release systems," Trans. Am. Soc. Artif. Intern. Organs, 31, 244-249 (1985).
6. T. Matsuda, H. Iwata, T. Toyosaki, H. Noda, T. Nakatani, Y. Fukuda, S. Adachi, H. Takano, and T. Akutsu. "Development of antithrombogenic elastomers with controlled release of anticoagulant," Jpn. J. Artif. Organs, 14, 679-682 (1985).
7. R. Wada, S.-H. Hyon, T. Nakamura, and Y. Ikada. "In vitro evaluation of sustained drug release from biodegradable elastomer," Pharm. Res., 8, 1292-1296 (1991).
8. Y. Ito, L.-S. Liu, R. Matsuo, and Y. Imanishi, "Synthesis and nonthrombogenicity of polymer membrane with surface-graft polymers carrying thrombin inhibitor," J. Biomed. Mater. Res., 26, 1065-1080 (1992).
9. S. Okamoto, A. Hijikata, R. Kikumoto, S. Tonomura, H. Hara, K. Ninomiya, A. Maruyama, M. Sugano, and Y. Tamao, "Potent inhibition of thrombin by the newly synthesized arginine derivative No. 805: The importance of stereo-structure of its hydrophobic carboxyamide portion," Biochem. Biophys. Res. Commun., 101, 440-446 (1981).
10. R. Kikumoto, Y. Tamao, T. Tezuka, S. Tonomura, H. Hara, K. Ninomiya, A. Hijikata, and S. Okamoto, "Selective inhibition of thrombin by (2R,4R)-4-methyl-1-[N2-[(3-methyl-1,2,3,4-tetrahydro-8-quinolinyl)sulfonyl]-L- arginyl)]-2-piperidinecarboxylic acid," Biochemistry, 23, 85-90 (1984).
11. T. Morita, H. Kato, S. Iwanaga, K. Takada, T. Kimura, and S. Sakakibara, "New fluorogenic substrates for α-thrombin, factor Xa, kallikreins, and urokinase," J. Biochem., 82, 1495-1498 (1977).
12. S. Kawabata, T. Miura, T. Morita, H. Kato, K. Fujikawa, S. Iwanaga, K. Takada, T. Kimura, and S. Sakakibara, "Highly sensitive peptide-4-methylcoumaryl-7-amide substrates for blood-clotting proteases and trypsin," Eur. J. Biochem., 172, 17-25 (1988).
13. K. Kobayashi, H. Sumitomo, and Y. Ina, "A carbohydrate-containing synthetic polymer obtained from N-p-vinylbenzyl-D-gluconamide," Polymer J., 15, 667-671 (1983).
14. B. D. Ratner and A. S. Hoffman, "Synthetic hydrogels for biomedical applications," in Hydrogels for Medical and Related Applications, ACS Symposium Series 31, J. D. Andrade (ed.), American Chemical Society, 1976, pp. 1-36.
15. Y. Tamada and Y. Ikada, "Effect of preadsorbed proteins on cell adhesion to polymer surfaces," J. Colloid Interface Sci. 155, 334-339 (1993).
16. Y. Tamada and Y. Ikada, "Cell adhesion to plasma-treated polymer surfaces," Polymer, 34, 2208-2212 (1993).
17. E. Kulik and Y. Ikada. "In vitro platelet adhesion to nonionic and ionic hydrogels with different water contents," J. Biomed. Mater. Res., 30, 295-304 (1996).
18. H. Nagasawa, K. Fukutake, M. Hada, E. Takahashi, Y. Matsubara, T. Samori, S. Ikematsu, T. Kitahara, M. Ukita, M. Fujimaki, and K. Fukutake, "Phase one study of synthetic antithrombin agent (MD-805) single and multiple administration studies," Jpn. J. Clin. Pharmacol. Ther., 12, 359-375 (1981).