Anticoagulant peptides; synthesis, stability and antithrombin activity of hirudin C-terminal-related peptides and their disulfated analog

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 7, 1996, Pages 1344-1350

  Okayama, Toru ^a   Muramatsu, Ryo ^b   Seki, Sumie ^a   Nukui, Eriko ^a   Hagiwara, Masaki ^a   Hayashi, Hideya ^b   Morikawa, Tadanori ^a  

^a FUJI CHEMICAL INDUSTRIES LTD   (Japan)

^b JAPAN ENERGY CORPORATION   (Japan)

Author keywords

hirudin; hirugen; hirulog 1; MDL28050; NF 22; thrombin inhibitor

Indexed keywords

ANTICOAGULANT AGENT; ANTITHROMBIN; HIRUDIN; HIRUDIN DERIVATIVE; HIRUGEN; HIRULOG; MDL 28050; NF 22; UNCLASSIFIED DRUG;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CONTROLLED STUDY; DRUG POTENCY; DRUG STABILITY; DRUG STRUCTURE; DRUG SULFATION; HEMOSTASIS; HUMAN; NONHUMAN; PROTEIN DOMAIN; RAT; STRUCTURE ACTIVITY RELATION; THROMBIN TIME; THROMBOSIS;

EID: 0030035821     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.1344     Document Type: Article

References (31)

1. 2Bzl=2,6-dichlorobenzyl, DCC=dicyclohexylcarbodiimide, DIEA=diisopropylethylamine, DMF=N,N-dimethylformamide, Fmoc=9-fluorenylmethoxycarobnyl, HOBt=1-hydroxybenzotriazole, NMM =N-methylmorpholine, ODS=octadecylated silica gel, Pac=phenacyl, RP-HPLC=reverse-phase high-performance liquid chromatography, suc=succinyl, Tee= 2,2,2-trichloroethyl, TFA=trifluoroacetic acid, WSCI=water-soluble carbodiimide [1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride]. Numbering of hirudin analogs is based on that for hirudin variant-1: Bagdy D., Barabas E., Graf L., Petersen T. E., Magnussen S., Methods Enzymol., 45, 669-678 (1976).
2. 2Bzl=2,6-dichlorobenzyl, DCC=dicyclohexylcarbodiimide, DIEA=diisopropylethylamine, DMF=N,N-dimethylformamide, Fmoc=9-fluorenylmethoxycarobnyl, HOBt=1-hydroxybenzotriazole, NMM =N-methylmorpholine, ODS=octadecylated silica gel, Pac=phenacyl, RP-HPLC=reverse-phase high-performance liquid chromatography, suc=succinyl, Tee= 2,2,2-trichloroethyl, TFA=trifluoroacetic acid, WSCI=water-soluble carbodiimide [1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride]. Numbering of hirudin analogs is based on that for hirudin variant-1: Bagdy D., Barabas E., Graf L., Petersen T. E., Magnussen S., Methods Enzymol., 45, 669-678 (1976).
3. Tapparelli C., Metternich R., Ehrhardt C., Cook N. S., Trends Pharmacol. Sci., 14, 366-376 (1993).
4. Rydel T. J, Ravichandran K. G., Tulinsky A., Bode W., Huber R., Roitsch C., Fenton J. W., II, Science, 249, 277-280 (1990).
5. a) Kaiser B., Markwardt F., Folia Haematot., 115, 41-46 (1988)
6. b) Kelly A. B., Maraganore J. M., Bourdon P., Hanson S. R., Harker L. A., Proc. Natl. Acad. Sci. U.S.A., 89, 6040-6044 (1992).
7. Rosenberg R. D., "The Chemistry and Physiology of the Human Plasma Proteins," ed. by Bing D. H., Pergamon Press, New York, 1979, pp. 353-368.
8. Kaiser B., Markwardt F., Thromb. Res., 43, 613-620 (1986).
9. a) Topol E. J., Fuster V., Harrington R. A., Califf R. M., Kleiman N. S., Kereiakes D. J., Cohen M., Chapekis A., Gold H. K., Tannenbaum M. A., Rao A. K., Debowey D., Schwartz D., Henis M., Chesebro J., Circulation, 89, 1557-1566 (1994)
10. b) Zeymer U., Von Essen R., Tebbe U., Niederer W., Maeurer W., Vogt A., Neuhaus K.-L., Am. J. Cardiol., 76, 997-1001 (1995)
11. c) Bittl J. A., Strony J., Brinker J. A., Ahmed W. H., Meckel C. R., Chaitman B. R., Maraganore J., Deutsch E., N. Engl. J. Med., 333, 764-769 (1995).
12. Schmilz T., Rothe M., Dodt J., Eur. J. Biochem., 195, 251-256 (1991).
13. Muramatsu R., Komatsu Y., Nukui E., Okayama T., Morikawa T., Kobashi K., Hayashi H., "Peptide Chemistry 1994," ed. by Ohno M., Protein Research Foundation, Osaka, 1995, pp. 297-300.
14. Owen T. J., Krstenansky J. L., Yates M. T., Mao S. J. T., J. Med. Chem., 31, 1009-1011 (1988).
15. Krstenansky J. L., Owen T. J., Yates M. T., Mao S. J. T., J. Med. Chem., 30, 1688-1691 (1987).
16. Jakubowski J. A., Maraganore J. M., Blood, 75, 399-406 (1990).
17. Krstenansky J. L. Broersma R. J., Owen T. J., Payne M. H., Yates M. T., Mao S. J. T., Thromb. Haemostasis, 63, 208-214 (1990).
18. Maraganore J. M., Bourdon P., Jablonski J., Ramachandran K. L., Fenton J. W., II, Biochemistry, 29, 7095-7101 (1990).
19. Hoekstra W. J., Sunder S. S., Cregge R. J., Ashton L. A., Stewart K. T., King C.-H. R., Tetrahedron, 48, 307-318 (1992).
20. Kuroda H., Kubo S., China N., Kimura T., Sakakibara S., "Peptide Chemistry 1990," ed. by Shimonishi Y., Protein Research Foundation, Osaka, 1991, pp. 15-18.
21. Fujii N., Futaki S., Morimoto H., Inoue K., Doi R., Tobe T., Yajima H. J., Chem. Soc., Chem. Commun., 1988, 324-325.
22. Okayama T., Hongo T., Nukui E., Muramatsu R., Hayashi H., Morikawa, T., "Peptide Chemistry 1995," ed. by Nishi N., Protein Research Foundation, Osaka, 1996, pp. 129-132.
23. Thurieau C., Simonet J., Paladino J.-F. P., Verbeuren T., Fauchère J.-L., J. Med. Chem., 37, 625-629 (1994).
24. Mao S. J. T., Yates M. T., Owen T. J., Krstenansky J. L., Biochemistry, 27, 8170-8173 (1988).
25. Bode W., Huber R., Eur. J. Biochem., 204, 433-451 (1992).
26. Stone S. R., Hofsteenge J., Biochemistry, 25, 4622-4628 (1986).
27. a) Maraganore J., Chao B., Joseph M. L., Jablonsky J., Ramachandra K. L., J. Biol. Chem., 264, 8692-8698 (1989)
28. b) Payne M. H., Krstenansky J. L., Yates M. T., Mao S. J. T., J. Med. Chem., 34, 1184-1187 (1991).
29. Bernard H. E. J., Höfften H. W., Hornverger W., Rübsamen K., Schmied B., "Peptides: Chemistry and Biology," (Proceedings of the Thirteenth American Peptide Symposium), ed. by Hodges R. S., Smith J. A., Escom, Leiden, The Netherlands, 1994, pp. 592-594.
30. Wang S.-S., Gisin B. F., Winter D. P., Makofske R., Kulesha I. D., Tzougraki C., Meienhofer J., J. Org. Chem., 42, 1286-1290 (1977).
31. Carson J. F., Synthesis, 1979, 24-25.