Design, synthesis, and biological evaluation of dibromotyrosine analogues inspired by marine natural products as inhibitors of human prostate cancer proliferation, invasion, and migration

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 21, 2010, Pages 7446-7457

  Sallam, Asmaa A ^a   Ramasahayam, Sindhura ^a   Meyer, Sharon A ^a   Sayed, Khalid A El ^a  

^a UNIVERSITY OF LOUISIANA AT MONROE   (United States)

Author keywords

Aeroplysinin 1; Angiogenesis; Dibromotyrosine; Invasion; Marine natural products; Migration; Proliferation; Prostate cancer; Verongiaquinol

Indexed keywords

3,5 DIBROMO 1 HYDROXY 4 OXOCYCLOHEXA 2,5 DIENE 1 ACETAMIDE; AEROPLYSININ 1; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG; VERONGIAQUINOL;

ANIMAL CELL; ANTIANGIOGENIC ACTIVITY; ARTICLE; CANCER INHIBITION; CANCER INVASION; CELL MIGRATION; CELL PROLIFERATION; CHORIOALLANTOIS; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG SYNTHESIS; MOLECULAR DOCKING; NONHUMAN; PROSTATE CANCER; RAT; SPONGE (PORIFERA); WOUND HEALING;

ANGIOGENESIS INHIBITORS; ANIMALS; BINDING SITES; BIOLOGICAL PRODUCTS; CELL LINE, TUMOR; CELL MOVEMENT; CELL PROLIFERATION; COMPUTER SIMULATION; DRUG DESIGN; HUMANS; MALE; NEOVASCULARIZATION, PATHOLOGIC; PORIFERA; PROSTATIC NEOPLASMS; TYROSINE; VASCULAR ENDOTHELIAL GROWTH FACTOR RECEPTOR-2;

APLYSINA;

EID: 77957991639     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.08.057     Document Type: Article

References (42)

1. C. Debitus, G. Guella, I. Mancini, J. Waikedre, J.P. Guemas, J.L. Nicolas, and F. Pietra J. Mar. Biotechnol. 6 1998 136
2. A. Koulman, P. Proksch, R. Eberl, A.C. Beekman, W. Uden, A.W.T. Konings, J.A. Pedersen, N. Pras, and H.J. Woerdenbag J. Nat. Prod. 59 1996 591
3. F.J. Ankudey, P. Kiprof, E.R. Stromquist, and L.C. Chang Planta Med. 74 2008 555
4. R. Teeyapant, P. Kreis, V. Wray, L. Witte, and P. Proksch Z. Naturforsch. 48c 1993 640
5. M. D'Ambrosio, A. Guerriero, and F. Pietra Helv. Chim. Acta 67 1984 1484
6. R. Cordoba, N. Salvador Tormo, A. Fernandez Medarde, and J. Plumet Bioorg. Med. Chem. 15 2007 5300
7. M.H. Kreuter, R.E. Leake, F. Rinaldi, W. Müller-Klieser, A. Maidhof, W.E.G. Müller, and H.C. Schröder Comp. Biochem. Physiol. 97B 1990 151
8. S. Rodríguez-Nieto, M. González-Iriarte, R. Carmona, R. Muńoz-Chápuli, M.A. Medina, and A.R. Quesada FASEB J. 16 2002 261
9. P.W. Manley, P. Furet, G. Bold, J. Brüggen, J. Mestan, T. Meyer, C.R. Schnell, and J. Wood J. Med. Chem. 45 2002 5687
10. R.S. Kerbel Carcinogenesis 21 2000 505
11. C.O. McDonnell, A.D. Hill, D.A. McNamara, T.N. Walsh, and D.J. Bouchier Hayes Eur. J. Surg. Oncol. 26 2000 105
12. Y. Liang, R.A. Brekken, and S.M. Hyder Endocr. Relat. Cancer 13 2006 905
13. F.M. Uckun, I. Dibirdik, S. Qazi, A. Vassilev, H. Ma, C. Mao, A. Benyumov, and K.H. Emami Bioorg. Med. Chem. 15 2007 800
14. L. Calcul, R. Chow, A.G. Oliver, K. Tenney, K.N. White, A.W. Wood, C. Fiorilla, and P. Crews J. Nat. Prod. 72 2009 443
15. K.A. El Sayed, M. Yousaf, M.T. Hamann, M.A. Avery, M. Kelly, and P. Wipf J. Nat. Prod. 65 2002 1547
16. A. Miller, and P.H. Solomon Writing Reaction Mechanisms in Organic Chemistry 1999 Harcourt Academic Press California, USA
17. A. Kijjoa, R. Watanadilok, P. Sonchaeng, P. Sawangwong, M. Pedro, M.S.J. Nascimento, A.M.S. Silva, G. Eaton, and W. Herz Z. Naturforsch., C: J. Biosci. 57 2002 732
18. B.C. Pearce, R.A. Parker, M.E. Deason, A.A. Qureshi, and J.J.K. Wright J. Med. Chem. 35 1992 3595
19. M. Hoshi, A. Takashima, K. Noguchi, M. Murayama, M. Sato, S. Kondo, Y. Saitoh, K. Ishiguro, T. Hoshino, and K. Imahori Proc. Natl. Acad. Sci. U.S.A. 93 1996 2719
20. K. MacAulay, and J.R. Woodgett Expert Opin. Ther. Targets 12 2008 1265
21. S. Liu, and Z. Shen Yaoxue Xuebao 42 2007 1227
22. P. Harris, A. Boloor, M. Cheung, R. Kumar, R.M. Crosby, R.G. Davis-Ward, A.H. Epperly, K.W. Hinkle, R.N. Hunter, J.H. Johnson, V.B. Knick, C.P. Laudeman, D.K. Luttrell, R.A. Mook, R.T. Nolte, S.K. Rudolph, J.R. Szewczyk, A.T. Truesdale, J.M. Veal, L. Wang, and J.A. Stafford J. Med. Chem. 51 2008 4632
23. P. Harris, M. Cheung, R.N. Hunter, M.L. Brown, J.M. Veal, R.T. Nolte, L. Wang, W. Liu, R.M. Crosby, J.H. Johnson, A.H. Epperly, R. Kumar, D.K. Luttrell, and J.A. Stafford J. Med. Chem. 48 2005 1610
24. F. Hilberg, G.J. Roth, M. Krssak, S. Kautschitsch, W. Sommergruber, U. Tontsch-Grunt, P. Garin-Chesa, G. Bader, A. Zoephel, J. Quant, A. Heckel, and W.J. Rettig Cancer Res. 68 2008 4774
25. C. Peifer, and G. Dannhardt Anticancer Res. 24 2004 1545
26. D. Ribatti, A. Cruz, B. Nico, J. Favier, A. Vacca, P. Corsi, L. Roncali, and F. Dammacco Cytokine 17 2002 262
27. D. Ribatti, A. Vacca, L. Roncali, and F. Dammacco Curr. Pharm. Biotech. 1 2000 73
28. TACS™ MTT Cell Proliferation Assays Protocol, TREVIGEN® (www.trevigen.com, accessed on 05/27/2010).
29. T. Mosmann J. Immunol. Methods 65 1983 55
30. M.C. Alley, D.A. Saudiero, A. Monks, M.L. Hursey, M.J. Czerwinski, D.L. Fine, B.J. Abbott, J.G. Mayo, R.H. Shoemaker, and M.R. Boyd Cancer Res. 48 1988 589
31. L.G. Rodriguez, X. Wu, and J.L. Guan Methods Mol. Biol. 294 2005 23
32. M. Mudit, M. Khanfar, A. Muralidharan, S. Thomas, G. Van Shah, R.W.M. Soest, and K.A. El Sayed Bioorg. Med. Chem. 17 2009 1731
33. Cultrex® BME Cell Invasion Assay Protocol; www.trevigen.com, accessed on 05/27/2010.
34. M.A. Khanfar, D.T.A. Youssef, and K.A. El Sayed ChemMedChem 5 2010 274
35. M.A. Khanfar, B. Abu Asal, M. Mudit, A. Kaddoumi, and K.A. El Sayed Bioorg. Med. Chem. 17 2009 6032
36. M. Clark, R.D. Cramer III, and N. van Opdenbosch J. Comput. Chem. 10 1989 982
37. J.J. Stewart J. Comput. Aided Mol. Des. 4 1990 1
38. Tripos Associates. SYBYL Molecular Modeling Software, version 8.0; Tripos Associates: St. Louis, MO, 2007; http://www.tripos.com, accessed on 05/27/2010.
39. W. Welch, J. Ruppert, and A.N. Jain Chem. Biol. 3 1996 449
40. J. Ruppert, W. Welch, and A.N. Jain Protein Sci. 6 1997 524
41. J.C. Murray Methods in Molecular Medicine Angiogenesis Protocols Vol. 46 2001 Humana Press Inc Totowa, New Jersey, USA
42. S. Jain, A. Shirode, Yacoub, Shenouda, A. Barbo, P.W. Sylvester, E. Huntimer, F. Halaweish, and K.A. El Sayed Planta Med. 73 2007 591