Structure-activity relationship studies of flavonoids as potent inhibitors of human platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 23, 2007, Pages 7408-7425

  Vasquez Martinez, Yesseny ^a   Ohri, Rachana V ^b   Kenyon, Victor ^b   Holman, Theodore R ^b   Sepúlveda Boza, Silvia ^a  

^a Center of Applied Ecology and Sustainability   (Chile)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Flavonoids; IC50; Lipoxygenase; Reductive inhibition

Indexed keywords

3' CHLORO 7,8 DIHYDROXYISOFLAVONE; 4' CHLORO 7,8 DIHYDROXYISOFLAVONE; 4',6,7 TRIHYDROXYISOFLAVAN; 4',6,7 TRIHYDROXYISOFLAVANONE; 4',6,7 TRIHYDROXYISOFLAVONE; 6,7 DIHYDROXY 3' ,4' METHYLENEDIOXYISOFLAVONE; 6,7 DIHYDROXY 3' METHYLISOFLAVAN; 6,7 DIHYDROXY 3',4' METHYLENEDIOXYISOFLAVAN; 6,7 DIHYDROXY 4' METHOXYISOFLAVAN; 6,7 DIHYDROXY 4' METHOXYISOFLAVANONE; 6,7 DIHYDROXY 4' NITROISOFLAVONE; 7,8 DIHYDROXY 3' METHYLISOFLAVONE; 7,8 DIHYDROXY 3' TRIFLUOROMETHYLISOFLAVONE; 7,8 DIHYDROXY 3',4' DIMETHOXYISOFLAVAN; 7,8 DIHYDROXY 4' METHOXYISOFLAVAN; 7,8 DIHYDROXY 4' METHYLISOFLAVAN; 7,8 DIHYDROXY 4'METHYLISOFLAVONE; 7,8 DIHYDROXYISOFLAVONE; FLAVONOID; LIPOXYGENASE INHIBITOR; TEXASIN; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; PROSTATE EPITHELIUM; RETICULOCYTE; STRUCTURE ACTIVITY RELATION; THROMBOCYTE;

ARACHIDONATE 12-LIPOXYGENASE; ARACHIDONATE 15-LIPOXYGENASE; DRUG EVALUATION, PRECLINICAL; EPITHELIAL CELLS; FLAVONOIDS; HUMANS; INHIBITORY CONCENTRATION 50; ISOENZYMES; LIPOXYGENASE INHIBITORS; MALE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROSTATE; RETICULOCYTES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 35148862752     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.07.036     Document Type: Article

References (61)

1. Yamamoto S. Biochim. Biophys. Acta 1128 (1992) 117-131
2. Brash A.R. J. Biol. Chem. 274 (1999) 23679-23682
3. Solomon E.I., Zhou J., Neese F., and Pavel E.G. Chem. Biol. 4 (1997) 795-808
4. Prigge S.T., Boyington J.C., Faig M., Doctor K.S., Gaffney B.J., and Amzel L.M. Biochimie 79 (1997) 629-636
5. Kuhn H. Prostaglandins Other Lipid Mediat. 62 (2000) 255-270
6. Yoshimoto T., and Takahashi Y. Prostaglandins Other Lipid Mediat. 68-69 (2002) 245-262
7. Dailey L.A., and Imming P. Curr. Med. Chem. 6 (1999) 389-398
8. Honn K.V., Tang D.G., Gao X., Butovich I.A., Liu B., Timar J., and Hagmann W. Cancer Metastasis Rev. 13 (1994) 365-396
9. Arenberger P., Raap A., Armah B., Kemény L., and Ruzicka T. Skin Pharmacol. 6 (1993) 148-151
10. Zhang Y., Wang H., Li J., Jimenez D.A., Levitan E.S., Aizenman E., and Rosenberg P.A. J. Neurosci. 24 (2004) 10616-10627
11. Kuhn H., Walther M., and Kuban R.J. Prostaglandins Other Lipid Mediat. 68-69 (2002) 263-290
12. Cathcart M.K., and Folcik V.A. Free Radic. Biol. Med. 28 (2000) 1726-1734
13. Neuzil J., Upston J.M., Witting P.K., Scott K.F., and Stocker R. Biochemistry 37 (1998) 9203-9210
14. Schewe T. Biol. Chem. 383 (2002) 365-374
15. Ikawa H., Kamitani H., Calvo B.F., Foley J.F., and Eling T.E. Cancer Res. 59 (1999) 360-366
16. Kelavkar U.P., Glasgow W., Olson S.J., Foster B.A., and Shappell S.B. Neoplasia 6 (2004) 821-830
17. Brash A.R., Boeglin W.E., and Chang M.S. Proc. Natl. Acad. Sci. U.S.A. 94 (1997) 6148-6152
18. Shappell S.B., Boeglin W.E., Olson S.J., Kasper S., and Brash A.R. Am. J. Pathol. 155 (1999) 235-245
19. Tang S., Bhatia B., Maldonado C.J., Yang P., Newman R.A., Liu J., Chandra D., Traag J., Klein R.D., Fischer S.M., Chopra D., Shen J., Zhau H.E., Chung L.W., and Tang D.G. J. Biol. Chem. 277 (2002) 16189-16201
20. Vavrecková C., Gawlik I., and Müller K. Planta Med. 62 (1996) 397-401
21. Suzuki H., Ueda T., Juránek I., Yamamoto S., Katoh T., Node M., and Suzuki T. Biochem. Biophys. Res. Commun. 275 (2000) 885-889
22. Alanko J., Kurahashi Y., Yoshimoto T., Yamamoto S., and Baba K. Biochem. Pharmacol. 48 (1994) 1979-1981
23. Cho H., Ueda M., Tamaoka M., Hamaguchi M., Aisaka K., Kiso Y., Inoue T., Ogino R., Tatsuoka T., Ishihara T., et al. J. Med. Chem. 34 (1991) 1503-1505
24. Müller K., Altmann R., and Prinz H. Eur. J. Med. Chem. 36 (2001) 569-575
25. Segraves E.N., Shah R.R., Segraves N.L., Johnson T.A., Whitman S., Sui J.K., Kenyon V.A., Cichewicz R.H., Crews P., and Holman T.R. J. Med. Chem. 47 (2004) 4060-4065
26. Cichewicz R.H., Kenyon V.A., Whitman S., Morales N.M., Arguello J.F., Holman T.R., and Crews P. J. Am. Chem. Soc. 126 (2004) 14910-14920
27. Amagata T., Whitman S., Johnson T., Stessmann C.C., Carroll J., Loo C., Clardy J., Lobkovsky E., Crews P., and Holman T.R. J. Nat. Prod. 66 (2003) 230-235
28. Whitman S., Gezginci M., Timmermann B.N., and Holman T.R. J. Med. Chem. 45 (2002) 2659-2661
29. Malterud K.E., Farbrot T.L., Huse A.E., and Sund R.B. Pharmacology 47 Suppl 1 (1993) 77-85
30. Schewe T., Sadik C., Klotz L.O., Yoshimoto T., Kuhn H., and Sies H. Biol. Chem. 382 (2001) 1687-1696
31. Deschamps J.D., Kenyon V.A., and Holman T.R. Bioorg. Med. Chem. 14 (2006) 4295-4301
32. Hsieh R.J., German J.B., and Kinsella J.E. Lipids 23 (1988) 322-326
33. Yamamoto H., Sakakibara J., Nagatsu A., and Sekiya K. J. Agric. Food Chem. 46 (1998) 862-865
34. Gutierrez-Lugo M.T., Deschamps J.D., Holman T.R., Suarez E., and Timmermann B.N. Planta Med. 70 (2004) 263-265
35. Sekiya K., Okuda H., and Arichi S. Biochim. Biophys. Acta 713 (1982) 68-72
36. Sadik C.D., Sies H., and Schewe T. Biochem. Pharmacol. 65 (2003) 773-781
37. Nussbaumer P., Lehr P., and Billich A. J. Med. Chem. 45 (2002) 4310-4320
38. Fougerousse A., Gonzalez E., and Brouillard R. J. Org. Chem. 65 (2000) 583-586
39. Sepúlveda-Boza S., Walizei S.H.G., Rezende M.C., Vásquez Y., Mascayano C., and Meji{dotless}́as L. Synth. Commun. 31 (2001) 1933-1940
40. Waslidge N.B., and Hayes D.J. Anal. Biochem. 231 (1995) 354-358
41. Kenyon V., Chorny I., Carvajal W.J., Holman T.R., and Jacobson M.P. J. Med. Chem. 49 (2006) 1356-1363
42. Amagata T., Whitman S., Johnson T.A., Stessman C.C., Loo C.P., Lobkovsky E., Clardy J., Crews P., and Holman T.R. J. Nat. Prod. 66 (2003) 230-235
43. Kilty I., Logan A., and Vickers P.J. Eur. J. Biochem. 266 (1999) 83-93
44. Nelson M.J. Biochemistry 27 (1988) 4273-4278
45. Nelson M.J., Batt D.G., Thompson J.S., and Wright S.W. J. Biol. Chem. 266 (1991) 8225-8229
46. Kemal C., Louis-Flamberg P., Krupinski-Olsen R., and Shorter A.L. Biochemistry 26 (1987) 7064-7072
47. Voss C., Sepulveda-Boza S., and Zilliken F.W. Biochem. Pharmacol. 44 (1992) 157-162
48. Kostanecki S., and Tambor. J. Chem. Ber. 34 (1901) 1691
49. Holman T.R., Zhou J., and Solomon E. J. Am. Chem. Soc. (1998) 120
50. Lewis E.R., Johansen E., and Holman T.R. J. Am. Chem. Soc. 121 (1999) 1395-1396
51. Gay C., Collins J., and Gebicki J.M. Anal. Biochem. 273 (1999) 149-155
52. Carroll J., Jonsson E.N., Ebel R., Hartman M.S., Holman T.R., and Crews P. J. Org. Chem. 66 (2001) 6847-6851
53. Riendeau D., Falgueyret J.P., Guay J., Ueda N., and Yamamoto S. Biochem. J. 274 (1991) 287-292
54. Falgueyret J.P., Hutchinson J.H., and Riendeau D. Biochem. Pharmacol. 45 (1993) 978-981
55. Hussey H.J., and Tisdale M.J. Br. J. Cancer 74 (1996) 683-687
56. Jacobson M.P., Pincus D.L., Rapp C.S., Day T.J., Honig B., Shaw D.E., and Friesner R.A. Proteins 55 (2004) 351-367
57. Jacobson M.P., Friesner R.A., Xiang Z., and Honig B. J. Mol. Biol. 320 (2002) 597-608
58. Jacobson M.P., Kaminski G.A., Friesner R.A., and Rapp C.S. J. Phys. Chem. B 106 (2002) 11673-11680
59. Friesner R.A., Banks J.L., Murphy R.B., Halgren T.A., Klicic J.J., Mainz D.T., Repasky M.P., Knoll E.H., Shelley M., Perry J.K., Shaw D.E., Francis P., and Shenkin P.S. J. Med. Chem. 47 (2004) 1739-1749
60. Halgren T.A., Murphy R.B., Friesner R.A., Beard H.S., Frye L.L., Pollard W.T., and Banks J.L. J. Med. Chem. 47 (2004) 1750-1759
61. Eldridge M.D., Murray C.W., Auton T.R., Paolini G.V., and Mee R.P. J. Comput. Aided Mol. Des. 11 (1997) 425-445