Piperazinobenzopyranones and phenalkylaminobenzopyranones: Potent inhibitors of breast cancer resistance protein (ABCG2)

Journal of Medicinal Chemistry

Volumn 48, Issue 23, 2005, Pages 7275-7281

  Boumendjel, Ahcène ^a   Nicolle, Edwige ^a   Moraux, Thomas ^a   Gerby, Bastien ^b   Blanc, Madeleine ^a   Ronot, Xavier ^b   Boutonnat, Jean ^b  

^a Laboratoire de Pharmacochimie   (France)

^b PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 [N (3,4 DIMETHOXYPHENYLETHYLAMINOCARBONYL)] 5 HYDROXYCHROMONE; 2 [N (4 METHOXYPHENYLETHYLAMINOCARBONYL)] 5 HYDROXYCHROMONE; 4 CHROMANONE DERIVATIVE; 5 HYDROXYBENZOFURAN 4 ONE; BREAST CANCER RESISTANCE PROTEIN; BREAST CANCER RESISTANCE PROTEIN INHIBITOR; FUMITREMORGIN C; IMATINIB; MITOXANTRONE; PHENYLALKYLAMINE; PIPERAZINE DERIVATIVE; PIPERAZINOBENZOPYRANONE DERIVATIVE; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BREAST CANCER; CANCER INHIBITION; CELL DEATH; CELLULAR DISTRIBUTION; COLON CANCER; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG PROTEIN BINDING; HUMAN; HUMAN CELL; IN VIVO STUDY; INHIBITION KINETICS; MULTIDRUG RESISTANCE; NONHUMAN; PROTEIN EXPRESSION;

EID: 28544452258     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050705h     Document Type: Article

References (27)

1. Sheps, J. A.; Ralph, S.; Zhao, Z.; Baillie, D. L.; Ling, V. The ABC transporter gene family of Caenorhabditis elegans has implications for the evolutionary dynamics of multidrug resistance in eukaryotes. Genome Biol. 2004, 5, R15. |
2. Cole, S. P.; Bhardwaj, G.; Gerlach, J. H.; Mackie, J. E.; Grant, C. E.; Almquist, K. C.; Stewart, A. J.; Kurz, E. U.; Duncan, A. M.; Deeley, R. G. Overexpression of a transporter gene in a multidrug-resistant human lung cancer cell line. Science 1992, 258, 1650-1654.
3. Benderra, Z.; Faussat, A. M.; Sayada, L.; Perrot, J. Y.; Chaoui, D.; Marie, J. P.; Legrand, O. Breast cancer resistance protein and P-glycoprotein in 149 adult acute myeloid leukaemias. Clin. Cancer Res. 2004, 10, 7896-7902.
4. Cisternino, S.; Mercier, C.; Bourasset, F.; Roux, F.; Schermann, J. M. Expression, up regulation and transport activity of the multidrug resistance protein ABCG2 at the blood brain barrier. Cancer Res. 2004, 64, 3296-3301.
5. Litman, T.; Druley, T. E.; Stein, W. D.; Bates, S. E. From MDR to MXR; new understanding of multidrug resistance systems, their properties and clinical significance. Cell. Mol. Life Sci. 2001, 58, 931-959.
6. Doyle, L. A.; Yang, W.; Abruzzo, L. V.; Krogmann, T.; Gao, Y.; Roshi, A. K.; Ross, D. D. A multidrug resistance transporter from human MCF-7 breast cancer cells. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 15665-15670.
7. Maliepaard, M.; van Gastelen, M. A.; Jong, L. A.; Pluim, D.; van Waardenburg, R. C.; Ruevekamp-Helmers, M. C.; Floot, B. G.; Schellens, J. H. Overexpression of the BCRP,/MXR/ABCP gene in a topotecan-selected ovarian tumor cell line. Cancer Res. 1999, 61, 3458-3464.
8. Robey, R. W.; Medina-Perez, W. Y.; Nishiyama, K.; Lahusen, T.; Miyake, K.; Litman, T.; Senderowicz, A. M.; Ross, D. D.; Bates, S. E2001 Overexpression of the ATP binding cassette half-transporter, ABCG2 (Mxr, BCRP, ABCP1) in flavopiridol resistant human breast cancer cells. Clin. Cancer Res. 2001, 7, 145-152.
9. Volk, E. L.; Parley, K. M.; Wu, Y.; Li, F.; Robey, R. W.; Schneider, E. Overexpression of wild-type breast cancer resistant protein-mediated methotrexate resistance. Cancer Res. 2002, 62, 5035-5040.
10. Wang, X.; Furukawa, T.; Nitanda, T.; Okamoto, M.; Sugimoto, Y.; Akiyama, S.; Baba, M. Breast cancer resistant protein (BCRP/ABCG2) induces cellular resistance to HIV-1 nucleoside reverse transcriptase inhibitors. Mol. Pharmacol. 2003, 63, 65-72.
11. Schinkel, A. H.; Jonker, J. W. Mammalian drug efflux transporters of the ATP binding cassette (ABC) family: an overview. Adv. Drug Delivery Rev. 2003, 55, 3-29.
12. Rabindran, S. K.; He, H.; Singh, M.; Brown, E.; Collins, K. I.; Annable, T.; Greenberger, L. M. Reversal of a novel multidrug resistance mechanism in human colon carcinoma cells by fumitremorgine C. Cancer Res. 1998, 58, 5850-5858.
13. Rabindran, S. K.; Ross, D. D.; Doyle, L. A.; Yang, W.; Greenberger, L. M. Fumitremorgin C reverses multidrug resistance in cells transfected with the breast cancer resistance protein. Cancer Res. 2000, 60, 47-50.
14. Ojima, I.; Borella, C. P.; Wu, X.; Bounaud, P.-Y.; Oderda, C. F.; Sturm, M.; Miller, M. L.; Chakravarty, S.; Chen, J.; Huang, Q.; Pera, P.; Brooks, T. A.; Baer, M. R.; Bernacki, R. J. Design, synthesis and structure-activity relationships of novel taxane-based multidrug resistance reversal agents. J. Med. Chem. 2005, 48, 2218-2228.
15. Sugimoto, Y.; Tsukahara, S.; Imai, Y.; Sugimoto, Y.; Ueda, K.; Tsuruo, T. Reversal of breast cancer resistance protein-mediated drug resistance by estrogen antagonists and agonists. Mol. Cancer Ther. 2003, 2, 105-112.
16. Houghton, P. J.; Germain, G. S.; Harwood, F. C.; Schuetz, J. D.; Stewart, C. F.; Buchdunger, E.; Traxler, P. Imatinib mesylate is a potent inhibitor of the ABCG2 (BCRP) transporter and reverses resistance to topotecan and SN-38 in vitro. Cancer Res. 2004, 64, 2333-2337.
17. Burger, H.; Tol, H. V.; Boersma, A. W. M.; Brok, M.; Wiemer, E. A. C.; Stoter, G.; Nooter, K. Imatinib mesylate (STI571) is a substrate for the breast cancer resistance protein (BCRP)/ABCG2 drug pump. Blood 2004, 104, 2940-2942.
18. Shuzhong, Z.; Xinning, Y.; Marilyn, E. M. Flavonoids are inhibitors of breast cancer resistance protein (ABCG2)-mediated transport. Mol. Pharmacol. 2004, 65, 1208-1216.
19. Zhang, S.; Wang, X.; Sagawa, K.; Morris, M. E. Flavonoids: chrysin and benzoflavone, potent breast cancer resistance protein inhibitors, have no significant effect on topotecan pharmacokinetics in rats or mdr1A/1B (-/-) mice. Drug Metab. Dispos. 2005, 33, 341-348.
20. Ahmed-Belkacem, A.; Pozza, A.; Muñoz-Martinez, F.; Bates, S. E.; Castanys, S.; Gamarro, F.; Di Pietro, A.; Pérez-Victoria, J. M. Flavonoid structure-activity studies identify 6-prenylchrysin and tectochrysin as potent and specific inhibitors of breast cancer resistance protein ABCG2. Cancer Res. 2005, 65, 4852-4860.
21. Boumendjel, A.; DiPietro, A.; Dumontet, C.; Barron, D. Recent advances in the discovery of flavonoids and analogs with high-affinity binding to P-glycoprotein responsible for cancer cell multidrug resistance. Med. Res. Rev. 2002, 22, 512-529.
22. Boumendjel, A.; Conseil, G.; Baubichon-Cortay, H.; Di Pietro, A. Anticancer multidrug resistance mediated by MRP1: recent advances in the discovery of reversal agents. Med. Res. Rev. 2005, 25, 453-472.
23. Hadjeri, M.; Barbier, M.; Ronot, X.; Mariotte, A.-M.; Boumendjel, A.; Boutonnat, J. Modulation of P-glycoprotein mediated multidrug resistance by flavonoid derivatives. J. Med. Chem. 2003, 46, 2125-2131.
24. Allen, J. D.; Van Loevezjin, V.; Lakhai, J. M.; van der Valk, M.; van Tellingen, O.; Reid, G.; Schellens, J. H. M.; Koomen, G. J.; Schinkel, A. H. Potent and specific inhibition of the breast cancer resistance protein multidrug transporter in vitro and in mouse intestine by a novel analogue of fumitremorgin C. Mol. Cancer Ther. 2002, 1, 417-425.
25. Allen, J. D.; Brinkhuis, R. F.; Wijnholds, J.; Schinkel, A. H. The mouse Bcrp1/Mxr/Abcp gene: amplification and overexpression in cell lines selected for resistance to topotecan, mitoxantrone, or doxorubicin. Cancer Res. 1999, 59, 4237-4241.
26. Ross, D. D.; Yang, W.; Abruzzo, L. V.; Dalton, W. S.; Schneider, E.; Lage, H.; Dietel, M.; Greenberger, L.; Cole, S. P.; Doyle, L. A. Atypical multidrug resistance: breast cancer resistance protein messenger RNA expression in mitoxantrone-selected cell lines. J. Natl. Cancer. Inst. 1999, 91, 429-343.
27. Candeil, L.; Gourdier, I.; Peyron, D.; Vezzio, N.; Copois, V.; Bibeau, F.; Orsetti, B.; Scheffer, G. L.; Ychou, M.; Khan, Q. A.; Pommier, Y.; Pau, B.; Martineau, P.; Del Rio, M. ABCG2 overexpression in colon cancer cells resistant to SN38 and in irinotecan-treated metastases. Int. J. Cancer. 2004, 109, 848-854.