Dual-acting agents that possess free radical scavenging and antithrombotic activities: Design, synthesis, and evaluation of phenolic tetrahydro-β-carboline RGD peptide conjugates

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 17, 2006, Pages 4523-4527

  Bi, Wei ^a   Bi, Lanrong ^b   Cai, Jianhui ^a   Liu, Sanguang ^a   Peng, Shiqi ^b   Fischer, Nicholas O ^c   Tok, Jeffrey B H ^c   Wang, Guohua ^a  

^a HEBEI MEDICAL UNIVERSITY   (China)

^b CAPITAL MEDICAL UNIVERSITY   (China)

^c LAWRENCE LIVERMORE NATIONAL LABORATORY   (United States)

Author keywords

Anti thrombotic; Dual action; Free radical

Indexed keywords

ACETYLCHOLINE; ADENOSINE DIPHOSPHATE; ANTICOAGULANT AGENT; ARGINYLGLYCYLASPARTIC ACID; HYDROGEN PEROXIDE; NITRIC OXIDE; SCAVENGER; TETRAHYDRO BETA CARBOLINE ARGINYLGLYCYLASPARTIC ACID CONJUGATE; THROMBOCYTE ACTIVATING FACTOR; TRYPTOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTERY THROMBOSIS; ARTICLE; CELL STRAIN; CELL SURVIVAL; CONJUGATION; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HEART MUSCLE ISCHEMIA; NONHUMAN; RAT; REPERFUSION INJURY; RISK FACTOR; THROMBOCYTE AGGREGATION; THROMBOGENESIS; VASODILATATION;

ADENOSINE DIPHOSPHATE; ANIMALS; CARBOLINES; DRUG DESIGN; FIBRINOLYTIC AGENTS; FREE RADICAL SCAVENGERS; HYDROGEN; MOLECULAR STRUCTURE; OLIGOPEPTIDES; PC12 CELLS; PHENOL; PLATELET ACTIVATING FACTOR; PLATELET AGGREGATION; RABBITS; RATS; THROMBOSIS;

EID: 33746206247     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.06.024     Document Type: Article

References (40)

1. Cannon R.O. Nat. Clin. Pract. Cardiovasc. Med. 2 (2005) 88
2. Neuzil J., Rayner B.S., Lowe H.C., and Witting P.K. Redox Rep. 10 (2005) 187
3. Saeed S.A., Waqar M.A., Zubairi A.J., Bhurgri H., Khan A., Gowani S.A., Waqar S.N., Choudary M.I., Jalil S., Zaidi A.H., and Ara I. J. Coll. Physician Surg. Pak. 15 (2005) 507
4. Parlakpinar H., Sahna E., Acet A., Mizrak B., and Polat A. Toxicology 209 (2005) 1
5. Parlakpinar H., Ozer M.K., and Acet A. Mol. Cell. Biochem. 277 (2005) 137
6. Esrefoglu M., Gul M., Parlakpinar H., and Acet A. Fundam. Clin. Pharmacol. 19 (2005) 365
7. Jin Z.Q., Zhou H.Z., Cecchini G., Gray M.O., and Karliner J.S. Am. J. Physiol. Heart Circ. Physiol. 288 (2005) 2986
8. Sahna E., Acet A., Ozer M.K., and Olmez E. J. Pineal. Res. 33 (2002) 234
9. Lee Y.M., Chen H.R., Sheu J.R., Wang J.J., and Yen M.H. J. Pineal. Res. 33 (2002) 72
10. Sahna E., Olmez E., and Acete A. J. Pineal. Res. 32 (2002) 194
11. Herraiz T., and Galisteo J. J. Agric. Food Chem. 51 (2003) 7156
12. Ichikawa M., Ryu K., Yoshida J., Ide N., Yoshida S., Sasaoka T., and Sumi S. Biofactors 16 (2002) 57
13. Herraiz T., Galisteo J., and Chamorro C. J. Agric. Food Chem. 51 (2003) 2168
14. Herraiz T., and Galisteo J. Free Radic. Res. 36 (2002) 923
15. Pless G., Frederiksen T.J., Garcia J.J., and Reiter R.J. J. Pineal Res. 26 (1999) 236
16. Hsu L.Y., Lin C.F., Hsu W.C., Hsu W.L., and Chang T.C. Biol. Pharm. Bull. 28 (2005) 1211
17. Yilmaz Y., and Toledo R.T. Trends Food Sci. Technol. 15 (2004) 422
18. Nicholson N.S., Abood N.A., Panzer-Knodle S.G., Frederick L.G., Page J.D., Salyers A.K., Suleymanov O.D., Szalony J.A., Taite B.B., and Anders R.J. Med. Res. Rev. 21 (2001) 211
19. Scarborough R.M., and Gretler D.D. J. Med. Chem. 43 (2000) 3453
20. Zablocki J.A., Rico J.G., Garland R.B., Rogers T.E., Williams K., Schretzman L.A., Rao S.A., Bovy P.R., Tjoeng F.S., Lindmark R.J., et al. J. Med. Chem. 38 (1995) 2378
21. Ruoslahti E. Integrins as Receptors for Extracellular Matrix. In: Hay E.D. (Ed). Cell Biology of Extracellular Matrix (1991), Plenum Press, New York, NY
22. Cheng S., Craig W.S., Mullen D., Tschopp J.F., Dixon D., and Pierschbacher M.D. J. Med. Chem. 37 (1994) 1
23. Batchelor W.B., Tolleson T.R., Huang Y., Larsen R.L., Mantell R.M., Dillard P., Davidian M., Zhang D., Cantor W.J., Sketch Jr. M.H., Ohman E.M., Zidar J.P., Gretler D., DiBattiste P.M., Tcheng J.E., Califf R.M., and Harrington R.A. Circulation 106 (2002) 1470
24. Zhao M., and Peng S. J. Prakt. Chem. 341 (1999) 668
25. Zhao M., Wang C., Yang J., and Peng S. Prep. Biochem. Biotechnol. 30 (2000) 247
26. Lin N., Zhao M., Wang C., and Peng S. Bioorg. Med. Chem. Lett. 12 (2002) 585
27. Desole M.S., Sciola L., Sircana S., Godani C., Migheli R., Delogu M.R., Piras G., De N.G., and Miele E. Neurosci. Lett. 247 (1998) 1
28. Mosmann T. J. Immunol. Methods 65 (1983) 55
29. Wu, Y.; Bi, L.; Bi, W.; Zhao, M.; Li, Z.; Ju, J.; Peng, S. Bioorg. Med. Chem., in press.
30. Cowart M., Kowaluk E.A., Daanen J.F., Kohlhaas K.L., Alexander K.M., Wagenaar F.L., and Kerwin J.F. J. Med. Chem. 41 (1998) 2636
31. Komori K., and Vanhoutte P.M. Blood Vessels 27 (1990) 238-245
32. Moncada S., Palmer R.M.J., and Higgs E.A. Pharmacol. Rev. 43 (1991) 109
33. Calles-Escandon J., and Cippola M. Endocr. Rev. 22 (2001) 36
34. Chalupsky K., Lobysheva I., Nepveu F., Gadea I., Beranova P., Entlicher G., Stoclet J., and Muller B. Biochem. Pharmacol. 67 (2004) 1203
35. Beranova P., chalupsky K., Kleschyov A., Schott C., Boucher J., Mansuy D., Munzel T., Muller B., and Stoclet J. Eur. J. Pharmacol. 516 (2005) 260
36. Nakae I., Matsumoto T., Omura T., Takashima H., Ohira N., Tarutani Y., Yasuda Y., Matsuo S., Koh T., Nakamura Y., Kinoshitaa M., and Horie M. Life Sci. 73 (2003) 3083
37. Zhao M., Bi L., Bi W., Wang C., Yang Z., Ju J., and Peng S. Bioorg. Med. Chem. 14 (2006) 4761
38. Liu J., Zhao M., Wang C., and Peng S. Bioorg. Med. Chem. Lett. 13 (2003) 4065
39. + 369, (M+H-73) 296.
40. +.