Structure-activity relationships of new inhibitors of breast cancer resistance protein (ABCG2)

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 17, 2008, Pages 8224-8236

  Pick, Anne ^a   Müller, Henrik ^a   Wiese, Michael ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

3rd generation modulators; Breast cancer resistance protein; CoMFA; CoMSIA; Hoechst 33342 assay; Multidrug resistance; P glycoprotein; Quantitative structure activity relationships; XR9576 (tariquidar)

Indexed keywords

BREAST CANCER RESISTANCE PROTEIN; CYCLOSPORIN; DILTIAZEM; DOXORUBICIN; ELACRIDAR; GEFITINIB; GENISTEIN; HOE 33342; IMATINIB; IRINOTECAN; MITOXANTRONE; NICARDIPINE; NOVOBIOCIN; PODOPHYLLOTOXIN DERIVATIVE; PROGESTERONE; PROTEIN INHIBITOR; RESERPINE; TARIQUIDAR; TOPOTECAN; VERAPAMIL;

ARTICLE; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG BINDING SITE; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; GENE EXPRESSION; HUMAN; HUMAN CELL; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION;

ATP-BINDING CASSETTE TRANSPORTERS; BREAST NEOPLASMS; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; FEMALE; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NEOPLASM PROTEINS; P-GLYCOPROTEINS; PHTHALIC ACIDS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUINOLINES; REPRODUCIBILITY OF RESULTS; STEREOISOMERISM; TIME FACTORS; TUMOR CELLS, CULTURED;

EID: 50349103259     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.07.034     Document Type: Article

References (68)

1. Sarkadi B., Ozvegy-Laczka C., Nemet K., and Varadi A. FEBS Lett. 567 (2004) 116-120
2. Fojo T., and Bates S. Oncogene 22 (2003) 7512-7523
3. Bodo A., Bakos E., Szeri F., Varadi A., and Sarkadi B. Toxicol. Lett. 140 (2003) 133-143
4. Borst P., Evers R., Kool M., and Wijnholds J. J. Natl. Cancer Inst. 92 (2000) 1295-1302
5. Rao V.V., Dahlheimer J.L., Bardgett M.E., Snyder A.Z., Finch R.A., Sartorelli A.C., and Piwnica-Worms D. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 3900-3905
6. Doyle L.A., and Ross D.D. Oncogene 22 (2003) 7340-7358
7. Sarkadi B., Homolya L., Szakacs G., and Varadi A. Physiol. Rev. 86 (2006) 1179-1236
8. Ling R.L., and Juliano V. Biochim. Biophys. Acta 455 (1976) 152-162
9. Ling V.P. Am. J. Med. 99 (1995) 31-34
10. Schinkel A.H., and Jonker J.W. Adv. Drug Deliv. Rev. 55 (2003) 3-29
11. Hoffmann U., and Kroemer H.K. Drug Metab. Rev. 36 (2004) 669-701
12. Wiese M., and Pajeva I.K. Curr. Med. Chem. 8 (2001) 685-713
13. Chen C.J., Chin J.E., Ueda K., Clark D.P., Pastan I., Gottesman M.M., and Roninson I.B. Cell 47 (1986) 381-389
14. Ambudkar S.V., Dey S., Hrycyna C.A., Ramachandra M., Pastan I., and Gottesman M.M. Annu. Rev. Pharmacol. Toxicol. 39 (1999) 361-398
15. Litman T., Brangi M., Hudson E., Fetsch P., Abati A., Ross D.D., Miyake K., Resau J.H., and Bates S.E. J. Cell Sci. 113 (2000) 2011-2021
16. Kusuhara H., and Sugiyama Y. Pflugers Arch. 453 (2007) 735-744
17. Doyle L.A., Yang W.D., Abruzzo L.V., Krogmann T., Gao Y.M., Rishi A.K., and Ross D.D. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 15665-15670
18. Robey R.W., Polgar O., Deeken J., To K.W., and Bates S.E. Cancer Metastasis Rev. 26 (2007) 39-57
19. Bailey-Dell K.J., Hassel B., Doyle L.A., and Ross D.D. Biochim. Biophys. Acta 1520 (2001) 234-241
20. Diop N.K., and Hrycyna C.A. Biochemistry 44 (2005) 5420-5429
21. Mohrmann K., van Eijndhoven M.A.J., Schinkel A.H., and Schellens J.H.M. Cancer Chemother. Pharmacol. 56 (2005) 344-350
22. Takada T., Suzuki H., and Sugiyama Y. Pharm. Res. 22 (2005) 458-464
23. Saito H., Hirano H., Nakagawa H., Fukami T., Oosumi K., Murakami K., Kimura H., Kouchi T., Konomi M., Tao E., Tsujikawa N., Tarui S., Nagakura M., Osumi M., and Ishikawa T. J. Pharmacol. Exp. Ther. 317 (2006) 1114-1124
24. Staud F., and Pavek P. Int. J. Biochem. Cell Biol. 37 (2005) 720-725
25. Chen C.J., Chin J.E., Ueda K., Clark D.P., Pastan I., Gottesman M.M., and Roninson I.B. Cell 47 (1986) 381-389
26. Suzuki M., Suzuki H., Sugimoto Y., and Sugiyama Y. J. Biol. Chem. 278 (2003) 22644-22649
27. Volk E.L., and Schneider E. Cancer Res. 63 (2003) 5538-5543
28. Bates S.E., Robey R., Miyake K., Rao K., Ross D.D., and Litman T. J. Bioenerg. Biomembr. 33 (2001) 503-511
29. Robey R.W., Medina-Perez W.Y., Nishiyama K., Lahusen T., Miyake K., Litman T., Senderowicz A.M., Ross D.D., and Bates S.E. Clin. Cancer Res. 7 (2001) 145-152
30. Shiozawa K., Oka M., Soda H., Yoshikawa M., Ikegami Y., Tsurutani J., Nakatomi K., Nakamura Y., Doi S., Kitazaki T., Mizuta Y., Murase K., Yoshida H., Ross D.D., and Kohno S. Int. J. Cancer 108 (2004) 146-151
31. Allen J.D., van Loevezijn A., Lakhai J.M., van der Valk M., van Tellingen O., Reid G., Schellens J.H.M., Koomen G.J., and Schinkel A.H. Mol. Cancer Ther. 1 (2002) 417-425
32. Ahmed-Belkacem A., Pozza A., Muñoz-Marti{dotless}́nez F., Bates S.E., Castanys S., Gamarro F., Di Pietro A., and Pérez-Victoria J.M. Cancer Res. 65 (2005) 4852-4860
33. Imai Y., Tsukahara S., Asada S., and Sugimoto Y. Cancer Res. 64 (2004) 4346-4352
34. Maliepaard M., van Gastelen M.A., Tohgo A., Hausheer F.H., van Waardenburg R.C.A.M., de Jong L.A., Pluim D., Beijnen J.H., and Schellens J.H.M. Clin. Cancer Res. 7 (2001) 935-941
35. Qadir M., O'Loughlin K.L., Fricke S.M., Williamson N.A., Greco W.R., Minderman H., and Baer M.R. Clin. Cancer Res. 11 (2005) 2320-2326
36. Zhou S., Schuetz J.D., Bunting K.D., Colapietro A.M., Sampath J., Morris J.J., Lagutina I., Grosveld G.C., Osawa M., Nakauchi H., and Sorrentino B.P. Nat. Med. 7 (2001) 1028-1034
37. Robey R.W., Steadman K., Polgar O., Morisaki K., Blayney M., Mistry P., and Bates S.E. Cancer Res. 64 (2004) 1242-1246
38. Mistry P., Stewart A.J., Dangerfield W., Okiji S., Liddle C., Bootle D., Plumb J.A., Templeton D., and Charlton P. Cancer Res. 61 (2001) 749-758
39. Müller H., Klinkhammer W., Globisch C., Kassack M.U., Pajeva I.K., and Wiese M. Bioorg. Med. Chem 15 (2007) 7470-7479
40. Müller H., Pajeva I.K., Globisch C., and Wiese M. Bioorg. Med. Chem. 16 (2008) 2448-2462
41. van Hattum A.H., Schluper H.M.M., Hausheer F.H., Pinedo H.M., and Boven E. Int. J. Cancer 100 (2002) 22-29
42. van Hattum A.H., Hoogsteen I.J., Schluper H.M.M., Maliepaard M., Scheffer G.L., Scheper R.J., Kohlhagen G., Pommier Y., Pinedo H.M., and Boven E. Br. J. Cancer 87 (2002) 665-672
43. Volk E.L., Farley K.M., Wu Y., Li F., Robey R.W., and Schneider E. Cancer Res. 62 (2002) 5035-5040
44. Volk E.L., Rohde K., Rhee M., McGuire J.J., Doyle L.A., Ross D.D., and Schneider E. Cancer Res. 60 (2000) 3514-3521
45. Minderman H., Suvannasankha A., O'Loughlin K.L., Scheffer G.L., Scheper R.J., Robey R.W., and Baer M.R. Cytometry 48 (2002) 59-65
46. Raaijmakers M.H.G.P., de Grouw E.P.L.M., Heuver L.H.H., van der Reijden B.A., Jansen J.H., Scheper R.J., Scheffer G.L., de Witte T.J.M., and Raymakers R.A.P. Clin. Cancer Res. 11 (2005) 2436-2444
47. Maliepaard M., Scheffer G.L., Faneyte I.F., van Gastelen M.A., Pijnenborg A.C.L.M., Schinkel A.H., van de Vijver M.J., Scheper R.J., and Schellens J.H.M. Cancer Res. 61 (2001) 3458-3464
48. Okochi E., Iwahashi T., and Tsuruo T. Leukemia 11 (1997) 1119-1123
49. Aihara M., Aihara Y., Schmidtwolf G., Schmidtwolf I., Sikic B.I., Blume K.G., and Chao N.J. Blood 77 (1991) 2079-2084
50. Tawar U., Jain A.K., Dwarakanath B.S., Chandra R., Singh Y., Chaudhury N.K., Khaitan D., and Tandon V. J. Med. Chem. 46 (2003) 3785-3792
51. Tawar U., Jain A.K., Chandra R., Singh Y., Dwarakanath B.S., Chaudhury N.K., Good L., and Tandon V. Biochem. 42 (2003) 13339-13346
52. Shapiro A.B., and Ling V. J. Biol. Chem. 270 (1995) 16167-16175
53. Shapiro A.B., and Ling V. J. Bioenerg. Biomembr. 27 (1995) 7-13
54. Jekerle V., Klinkhammer W., Scollard D.A., Breitbach K., Reilly R.M., Piquette-Miller M., and Wiese M. Int. J. Cancer 119 (2006) 414-422
55. Ifergan I., Shafran A., Jansen G., Hooijberg J.H., Scheffer G.L., and Assaraf Y.G. J. Biol. Chem. 279 (2004) 25527-25534
56. Doyle L.A., and Ross D.D. Oncogene 22 (2003) 7340-7358
57. Clark R., Kerr I.D., and Callaghan R.Br. J. Pharmacol. 149 (2006) 506-515
58. Free S.M., and Wilson J.W. J. Med. Chem. 7 (1964) 395-399
59. SYBYL 6.9-7.3 versions; Tripos Inc., 1699 South Hanley Road, St. Louis, MO 63114-2917.
60. Tropsha A., Gramatica P., and Gombar V.K. QSAR Comb. Sci. 22 (2003) 69-77
61. Höltje H.-D., Sippl W., Rognan D., and Folkers G. Molecular Modeling (2008), Wiley-VCH, Weinheim
62. Matsson P., Englund G., Ahlin G., Bergstrom C.A.S., Norinder U., and Artursson P. J. Pharmacol. Exp. Ther. 323 (2007) 19-30
63. Segel I.H. Enzyme Kinetics (1976), Wiley, New York
64. Su Y., Hu P., Lee S.-H., and Sinko P.J. J. Pharm. Sci. 10 (2007) 519-536
65. Ozvegy-Laczka C., Hegedus T., Varady G., Ujhelly O., Schuetz J.D., Varadi A., Keri G., Orfi L., Nemet K., and Sarkadi B. Mol. Pharmacol. 65 (2004) 1485-1495
66. Klinkhammer, W.; Design, Synthese und 3D-QSAR neuartiger P-gp-Modulatoren, Ph.D. Thesis, University of Bonn, 2006; http://deposit.ddb.de/cgi-bin/dokserv?idn=981124488&dok_var=d1&dok_ext=pdf&filename=981124488.pdf.
67. ACD/Labs, version 5.09, ACD pKa DB, Advanced Chemistry Development, Inc., Toronto, ON, Canada.
68. SPSS, version 14, SPSS, Chicago, IL, USA.