Structure-based design of residue 1 analogs of the direct thrombin inhibitor pentapeptide FM 19

Chemical Biology and Drug Design

Volumn 75, Issue 1, 2010, Pages 35-39

  Girnys, Elizabeth A ^a   Sobczyk Kojiro, Katarzyna ^a   Mosberg, Henry I ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Antithrombotic therapy; Peptide synthesis; Protease activated receptor; Structure based design; Thrombin

Indexed keywords

AMINE; FIBRIN; FIBRINOGEN; FM 19; G PROTEIN COUPLED RECEPTOR; PENTAPEPTIDE; PROTEINASE ACTIVATED RECEPTOR 1; PROTEINASE ACTIVATED RECEPTOR 4; THROMBIN INHIBITOR; UNCLASSIFIED DRUG;

ACUTE CORONARY SYNDROME; AMINO TERMINAL SEQUENCE; ANTICOAGULANT THERAPY; ARTICLE; CORONARY ARTERY ATHEROSCLEROSIS; DRUG CONFORMATION; DRUG DESIGN; DRUG POTENCY; DRUG STRUCTURE; ELECTRICITY; HEART MUSCLE ISCHEMIA; IC 50; PRIORITY JOURNAL; RECEPTOR UPREGULATION; THROMBOCYTE AGGREGATION; THROMBOSIS;

AMINO ACID SEQUENCE; ANTICOAGULANTS; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; DIPEPTIDES; DRUG DESIGN; FIBRINOLYTIC AGENTS; MOLECULAR STRUCTURE; OLIGOPEPTIDES; PLATELET AGGREGATION; PLATELET AGGREGATION INHIBITORS; PROTEIN CONFORMATION; SERINE PROTEASES; STRUCTURE-ACTIVITY RELATIONSHIP; THROMBIN;

EID: 71449097054     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2009.00915.x     Document Type: Article

References (15)

1. Rauch U., Osende J.I., Fuster V., Badimon J.J., Fayad Z., Chesebro J.H. (2001) Thrombus formation on atherosclerotic plaques: pathogenesis and clinical consequences. Ann Intern Med 134 : 224 238.
2. Grech E.D., Ramsdale D.R. (2003) Acute coronary syndrome: unstable angina and non-ST segment elevation myocardial infarction. Br Med J 326 : 1259 1261.
3. Hamilton J.R. (2009) Protease-activated receptors as targets for antiplatelet therapy. Blood Rev 23 : 61 65.
4. Hasan A.A., Warnock M., Nieman M., Srikanth S., Mahdi F., Krishnan R., Tulinsky A., Schmaier A.H. (2003) Mechanisms of Arg-Pro-Pro-Gly-Phe inhibition of thrombin. Am J Physiol Heart Circ Physiol 285 : H183 H193.
5. Paoli G., Merlini P.A., Ardissino D. (2005) Direct thrombin inhibitors for the treatment of acute coronary syndromes and during percutaneous coronary interventions. Curr Pharm Des 11 : 3919 3929.
6. Schmaier A.H. (2002) The plasma kallikrein-kinin system counterbalances the renin-angiotensin system. J Clin Invest 109 : 1007 1009.
7. Hasan A.A., Amenta S., Schmaier A.H. (1996) Bradykinin and its metabolite, Arg-Pro-Pro-Gly-Phe, are selective inhibitors of a-thrombin-induced platelet activation. Circulation 94 : 517 528.
8. Kuoppala A., Lindstedt K.A., Saarinen J., Kovanen P.T., Kokkonen J.O. (2000) Inactivation of bradykinin by angiotensin-converting enzyme and by carboxypeptidase N in human plasma. Am J Physiol Heart Circ Physiol 278 : H1069 H1074.
9. Burke F., Warnock M., Schmaier H., Mosberg H. (2006) Synthesis of novel peptide inhibitors of thrombin-induced platelet activation. Chem Biol Drug Des 68 : 235 238.
10. Nieman M.T., Burke F., Warnock M., Zhou Y., Sweigart J., Chen A., Ricketts D., Lucchesi B.R., Chen Z., DiCera E., Hilfinger J., Kim J.S., Mosberg H.I., Schmaier A.H., (2008) Thrombostatin FM compounds: direct thrombin inhibitors - mechanism of action in vitro and in vivo. J Thromb Haemost 6 : 837 845.
11. Hruby V.J., Toth G., Gehrig C.A., Kao L.-F., Knapp R., Liu G.K., Yamamura H.I., Kramer T.H., Davis P., Burks T.F. (1991) Topographically designed analogs of [D-Pen,D-Pen5]enkephalin. J Med Chem 34 : 1823 1830.
12. Feichtinger K., Zapf C., Sings H.L., Goodman M. (1998) Diprotected triflylguanidines: a new class of guanidinylation reagents. J Org Chem 63 : 3804 3805 supporting information.
13. Przydzial M.J., Pogozheva I.D., Bosse K.E., Andrews S.M., Tharp T.A., Traynor J.R., Mosberg H.I. (2005) Roles of residues 3 and 4 in cyclic tetrapeptide ligand recognition by the κ-opioid receptor. Pept Res 65 : 333 342.
14. Nieman M.T., Warnock M., Hasan A.A., Mahdi F., Lucchesi B.R., Brown N.J., Murphey L.J., Schmaier A.H. (2004) The preparation and characterization of novel peptide antagonists to thrombin and Factor VIIa and activation of protease-activated receptor 1. J Pharmacol Exp Ther 311 : 492 501.
15. Masic L.P. (2006) Arginine mimetic structures in biologically active antagonists and inhibitors. Curr Med Chem 13 : 3627 3648.