Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP)

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 6, 2011, Pages 2090-2102

  Pick, Anne ^a   Müller, Henrik ^a   Mayer, Ralf ^a   Haenisch, Britta ^a   Pajeva, Ilza K ^a,b   Weigt, Mathias ^a   Bönisch, Heinz ^a   Müller, Christa E ^a   Wiese, Michael ^a  

^a UNIVERSITY OF BONN   (Germany)

^b INSTITUTE OF BIOPHYSICS AND BIOMEDICAL ENGINEERING   (Bulgaria)

Author keywords

Breast cancer resistance protein; CoMFA; CoMSIA; Flavonoids; Hoechst 33342 assay; Multidrug resistance; P glycoprotein; QSAR

Indexed keywords

6 METHOXYFLAVANON; APIGENIN; APIGETRIN; AYATIN; BIFLAVONOID; BREAST CANCER RESISTANCE PROTEIN; CALYFLORENON B; CHRYSIN; DIMETHYLPINOCEMBRIN; FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE; FLAVONOID; FLAVONOL DERIVATIVE; GENISTEIN; GLYCOPROTEIN P; GLYCOSIDE; HYPERIN; ISOFLAVONE DERIVATIVE; KAEMPFEROL; MORIN; NEOCALYCOPTERON; NEOCALYCOPTERON 4 METHYLETHER; NOBILETIN; PENDULETIN; PINOSTROMBIN; QUERCETIN; RETUSIN; TANGERETIN; UNCLASSIFIED DRUG; VITEXIN;

ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CANCER CELL CULTURE; CELL VIABILITY; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG STRUCTURE; ENZYME ASSAY; HUMAN; HUMAN CELL; NONHUMAN; PROTEIN EXPRESSION; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANTINEOPLASTIC AGENTS; ATP-BINDING CASSETTE TRANSPORTERS; BREAST NEOPLASMS; CELL LINE, TUMOR; DRUG RESISTANCE, NEOPLASM; FEMALE; FLAVONOIDS; HUMANS; HYDROGEN BONDING; MODELS, MOLECULAR; NEOPLASM PROTEINS; P-GLYCOPROTEIN; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79952455438     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.12.043     Document Type: Article

References (62)

1. B. Sarkadi, C. Ozvegy-Laczka, K. Nemet, and A. Varadi FEBS Lett. 567 2004 116 120
2. T. Fojo, and S. Bates Oncogene 22 2003 7512 7523
3. A. Bodo, E. Bakos, F. Szeri, A. Varadi, and B. Sarkadi Toxicol. Lett. 140 2003 133 143
4. P. Borst, R. Evers, M. Kool, and J. Wijnholds J. Natl. Cancer Inst. 92 2000 1295 1302
5. L.A. Doyle, and D.D. Ross Oncogene 22 2003 7340 7358
6. V.V. Rao, J.L. Dahlheimer, M.E. Bardgett, A.Z. Snyder, R.A. Finch, A.C. Sartorelli, and D. Piwnica-Worms Proc. Natl. Acad. Sci. U.S.A. 96 1999 3900 3905
7. B. Sarkadi, L. Homolya, G. Szakacs, and A. Varadi Physiol. Rev. 86 2006 1179 1236
8. S. Shukla, C.P. Wu, and S.V. Ambudkar Expert Opin. Drug Metab. Toxicol. 4 2008 205 223
9. R.W. Robey, O. Polgar, J. Deeken, K.W. To, and S.E. Bates Cancer Metastasis Rev. 26 2007 39 57
10. F.J. Sharom Pharmacogenomics 9 2008 105 127
11. A. van Loevezijn, J.D. Allen, A.H. Schinkel, and G.J. Koomen Bioorg. Med. Chem. Lett. 11 2001 29 32
12. J.D. Allen, and A.H. Schinkel Mol. Cancer Ther. 1 2002 427 434
13. J.D. Allen, A. van Loevezijn, J.M. Lakhai, M. van der Valk, O. van Tellingen, G. Reid, J.H.M. Schellens, G.J. Koomen, and A.H. Schinkel Mol. Cancer Ther. 1 2002 417 425
14. K. Shiozawa, M. Oka, H. Soda, M. Yoshikawa, Y. Ikegami, J. Tsurutani, K. Nakatomi, Y. Nakamura, S. Doi, T. Kitazaki, Y. Mizuta, K. Murase, H. Yoshida, D.D. Ross, and S. Kohno Int. J. Cancer 108 2004 146 151
15. C.J. Henrich, H.R. Bokesch, M. Dean, S.E. Bates, R.W. Robey, E.I. Goncharova, J.A. Wilson, and J.B. McMahon J. Biomol. Screening 11 2006 176 183
16. R.W. Robey, K. Steadman, O. Polgar, K. Morisaki, M. Blayney, P. Mistry, and S.E. Bates Cancer Res. 64 2004 1242 1246
17. M. Maliepaard, M.A. van Gastelen, A. Tohgo, F.H. Hausheer, R.C.A.M. van Waardenburg, L.A. de Jong, D. Pluim, J.H. Beijnen, and J.H.M. Schellens Clin. Cancer Res. 7 2001 935 941
18. A. Pick, H. Mueller, and M. Wiese Bioorg. Med. Chem. 16 2008 8224 8236
19. M. de Bruin, K. Miyake, T. Litman, R. Robey, and S.E. Bates Cancer Lett. 146 1999 117 126
20. M. Kuhnle, M. Egger, C. Muller, A. Mahringer, G. Bernhardt, G. Fricker, B. Konig, and A. Buschauer J. Med. Chem. 52 2009 1190
21. C. Lemos, G. Jansen, and G.J. Peters Br. J. Cancer 98 2008 857 862
22. F. Teillet, A. Boumendjel, J. Boutonnat, and X. Ronot Med. Res. Rev. 28 2008 715 745
23. J. Kuhnau World Rev. Nutr. Diet. 24 1976 117 191
24. J.P. Spencer Proc. Nutr. Soc. 67 2008 238 252
25. C. Manach, G. Williamson, C. Morand, A. Scalbert, and C. Remesy Am. J. Clin. Nutr. 81 2005 230S 242S
26. B.H. Havsteen Pharmacol. Ther. 96 2002 67 202
27. M. Wang Toxicol. Sci. 96 2007 203 205
28. H. Kohno, T. Tanaka, K. Kawabata, Y. Hirose, S. Sugie, H. Tsuda, and H. Mori Int. J. Cancer 101 2002 461 468
29. H.C. Cooray, T. Janvilisri, H.W. van Veen, S.B. Hladky, and M.A. Barrand Biochem. Biophys. Res. Commun. 317 2004 269 275
30. S. Zhang, X. Yang, and M.E. Morris Mol. Pharmacol. 65 2004 1208 1216
31. A. Ahmed-Belkacem, A. Pozza, F. Munoz-Martinez, S.E. Bates, S. Castanys, F. Gamarro, A. Di Pietro, and J.M. Perez-Victoria Cancer Res. 65 2005 4852 4860
32. C. Ozvegy-Laczka, G. Varady, G. Koblos, O. Ujhelly, J. Cervenak, J.D. Schuetz, B.P. Sorrentino, G.J. Koomen, A. Varadi, K. Nemet, and B. Sarkadi J. Biol. Chem. 280 2005 4219 4227
33. C. Ozvegy-Laczka, R. Laczko, C. Hegedus, T. Litman, G. Varady, K. Goda, T. Hegedus, N.V. Dokholyan, B.P. Sorrentino, A. Varadi, and B. Sarkadi J. Biol. Chem. 283 2008 26059 26070
34. A.H. van Hattum, I.J. Hoogsteen, H.M.M. Schluper, M. Maliepaard, G.L. Scheffer, R.J. Scheper, G. Kohlhagen, Y. Pommier, H.M. Pinedo, and E. Boven Br. J. Cancer 87 2002 665 672
35. A.H. van Hattum, H.M.M. Schluper, F.H. Hausheer, H.M. Pinedo, and E. Boven Int. J. Cancer 100 2002 22 29
36. E.L. Volk, K.M. Farley, Y. Wu, F. Li, R.W. Robey, and E. Schneider Cancer Res. 62 2002 5035 5040
37. E.L. Volk, K. Rohde, M. Rhee, J.J. McGuire, L.A. Doyle, D.D. Ross, and E. Schneider Cancer Res. 60 2000 3514 3521
38. E. Okochi, T. Iwahashi, and T. Tsuruo Leukemia 11 1997 1119 1123
39. M. Aihara, Y. Aihara, G. Schmidtwolf, I. Schmidtwolf, B.I. Sikic, K.G. Blume, and N.J. Chao Blood 77 1991 2079 2084
40. R. Clark, I.D. Kerr, and R. Callaghan Br. J. Pharmacol. 149 2006 506 515
41. I. Ifergan, A. Shafran, G. Jansen, J.H. Hooijberg, G.L. Scheffer, and Y.G.F. Assaraf J. Biol. Chem. 279 2004 25527 25534
42. H. Mueller, M.U. Kassack, and M. Wiese J. Biomol. Screen. 9 2004 506 515
43. E. Nicolle, A. Boumendjel, S. Macalou, E. Genoux, A. Ahmed-Belkacem, P.-A. Carrupt, and A. Di Pietro Adv. Drug Deliv. Rev. 61 2009 34 46
44. A. Tropsha, P. Gramatica, and V.K. Gombar QSAR Comb. Sci. 22 2003 69 77
45. H.-D. Höltje, W. Sippl, D. Rognan, and G. Folkers Molecular Modeling. Basic Principles and Applications 3rd ed. 2008 Wiley-VCH Weinheim pp 9-91
46. S. Zhang, X. Yang, R.A. Coburn, and M.E. Morris Biochem. Pharmacol. 70 2005 627 639
47. K. Katayama, K. Masuyama, S. Yoshioka, H. Hasegawa, J. Mitsuhashi, and Y. Sugimoto Cancer Chemother. Pharmacol. 60 2007 789 797
48. A. Scalbert, and G. Williamson J. Nutr. 130 2000 2073S 2085S
49. E. Malan, and D.G. Roux J. Chem. Soc., Perkin Trans. 1 1979 2696 2703
50. M. Kaulich, F. Streicher, R. Mayer, I. Müller, and C.E. Müller Drug Dev. Res. 59 2003 72 82
51. E. Tripoli, M. La Guardia, S. Giammanco, D. Di Majo, and M. Giammanco Food Chem. 104 2007 466 479
52. R. Mayer Phytochemistry 29 1990 1340 1342
53. R. Mayer Planta Med. 59 1993 269 271
54. R. Mayer J. Nat. Prod. 62 1999 1274 1278
55. R. Mayer Phytochemistry 65 2004 593 601
56. J.A. Manthey, N. Guthrie, and K. Grohmann Curr. Med. Chem. 8 2001 135 153
57. G. Merino, J.W. Jonker, E. Wagenaar, A.E. van Heraarden, and A.H. Schinkel Mol. Pharmacol. 67 2005 1758 1764
58. B. Haenisch, R. Gilsbach, and H. Bönisch J. Neural. Trans. 115 2008 973 982
59. M.W. Pfaffl Nucleic Acids Res. 29 9 2001 e45
60. a DB, Advanced Chemistry Development, Toronto ON, Canada.
61. SPSS, version 14, SPSS, Chicago, IL, USA.
62. SYBYL 6.9-7.3 versions; Tripos Inc., 1699 South Hanley Road, St. Louis, MO 63114-2917.