Iodination of verapamil for a stronger induction of death, through GSH efflux, of cancer cells overexpressing MRP1

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 17, 2010, Pages 6265-6274

  Barattin, Régis ^b   Perrotton, Thomas ^a   Trompier, Doriane ^a   Lorendeau, Doriane ^a   Pietro, Attilio Di ^a   D'Hardemare, Amaury Du Moulinet ^b   Baubichon Cortay, Hélne ^a  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

Apoptosis; GSH efflux; MRP1; Verapamil iodination

Indexed keywords

2 (3,4 DIMETHOXYPHENYL) 2 ISOPROPYL 5 [[2 (4 METHOXYPHENYL)ETHYL]METHYL AMINO]PENTANENITRILE; 2 (3,4 DIMETHOXYPHENYL) 5 [(4 HYDROXY 3 IODOBENZYL) METHYL AMINO] 2 ISOPROPYL PENTANENITRILE; 2 (3,4 DIMETHOXYPHENYL) 5 [(4 HYDROXY 3,5 DIIODOBENZYL) METHYL AMINO] 2 ISOPROPYL PENTANENITRILE; 2 (3,4 DIMETHOXYPHENYL) 5 [(4 HYDROXYBENZYL)METHYL AMINO] 2 ISOPROPYL PENTANENITRILE; 2 (3,4 DIMETHOXYPHENYL) 5 [2 (4 HYDROXY 3 IODOPHENYL)ETHYLAMINO] 2 ISOPROPYL PENTANENITRILE; 2 (3,4 DIMETHOXYPHENYL) 5 [2 (4 HYDROXY 3,5 DIIODOPHENYL) ETHYLAMINO] 2 ISOPROPYL PENTANENITRILE; 2 (3,4 DIMETHOXYPHENYL) 5 [2 (4 HYDROXYPHENYL)ETHYLAMINO] 2 ISOPROPYL PENTANENITRILE; 2 (3,4 DIMETHOXYPHENYL) 5 [[2 (3 IODO 4 METHOXYPHENYL) ETHYL]METHYL AMINO] 2 ISOPROPYL PENTANENITRILE; 2 (3,4 DIMETHOXYPHENYL) 5 [[2 (4 HYDROXY 3 IODOPHENYL)ETHYL]METHYL AMINO] 2 ISOPROPYL PENTANENITRILE; 2 (3,4 DIMETHOXYPHENYL) 5 [[2 (4 HYDROXY 3,5 DIIODOPHENYL)ETHYL]METHYL AMINO] 2 ISOPROPYL PENTANENITRILE; 2 (3,4 DIMETHOXYPHENYL) 5 [[2 (4 HYDROXYPHENYL) ETHYL]METHYL AMINO] 2 ISOPROPYL PENTANENITRILE; 2 (3,4 DIMETHOXYPHENYL) 5 [[3 (4 HYDROXY 3 IODOPHENYL)PROPYL]METHYL AMINO] 2 ISOPROPYL PENTANENITRILE; 2 (3,4 DIMETHOXYPHENYL) 5 [[3 (4 HYDROXY 3,5 DIIODOPHENYL)PROPYL]METHYL AMINO] 2 ISOPROPYL PENTANENITRILE; 2 (3,4 DIMETHOXYPHENYL) 5 [[3 (4 HYDROXYPHENYL)PROPYL]METHYL AMINO] 2 ISOPROPYL PENTANENITRILE; 5 [[2 (3,5 DIIODO 4 METHOXYPHENYL)ETHYL]METHYLAMINO] 2 (3,4 DIMETHOXYPHENYL) 2 ISOPROPYL PENTANENITRILE; ANTINEOPLASTIC AGENT; GLUTATHIONE; MULTIDRUG RESISTANCE PROTEIN 1; UNCLASSIFIED DRUG; VERAPAMIL; VERAPAMIL DERIVATIVE;

ANIMAL CELL; ARTICLE; CANCER CELL; CANCER RESISTANCE; CARDIOTOXICITY; CELL DEATH; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; GENE OVEREXPRESSION; IODINATION; NONHUMAN; STIMULATION; STRUCTURE ACTIVITY RELATION;

EID: 77955980791     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.07.031     Document Type: Article

References (28)

1. H. Glavinas, P. Krajcsi, J. Cserepes, and B. Sarkadi Curr. Drug Deliv. 1 2004 27
2. R.G. Deeley, and S.P. Cole FEBS Lett. 580 2006 1103
3. V. Gekeler, W. Ise, K.H. Sanders, W.R. Ulrich, and J. Beck Biochem. Biophys. Res. Commun. 208 1995 345
4. S. Aoki, Z.S. Chen, K. Higasiyama, A. Setiawan, S. Akiyama, and M. Kobayashi Jpn. J. Cancer Res. 92 2001 886
5. T. Tsuruo, H. Iida, M. Nojiri, S. Tsukagoshi, and Y. Sakurai Cancer Res. 43 1983 2905
6. T. Tsuruo, H. Iida, S. Tsukagoshi, and Y. Sakurai Cancer Res. 43 1983 2267
7. T. Tsuruo, H. Iida, S. Tsukagoshi, and Y. Sakurai Cancer Res. 41 1981 1967
8. S. Huet, and J. Robert Int. J. Cancer 41 1988 283
9. S.P. Cole, K.E. Sparks, K. Fraser, D.W. Loe, C.E. Grant, G.M. Wilson, and R.G. Deeley Cancer Res. 54 1994 5902
10. R.A. Davey, T.J. Longhurst, M.W. Davey, L. Belov, R.M. Harvie, D. Hancox, and H. Wheeler Leuk. Res. 19 1995 275
11. D.W. Loe, R.G. Deeley, and S.P. Cole J. Pharmacol. Exp. Ther. 293 2000 530
12. D.W. Loe, K.C. Almquist, R.G. Deeley, and S.P. Cole J. Biol. Chem. 271 1996 9675
13. K.V. Cullen, R.A. Davey, and M.W. Davey Biochem. Pharmacol. 62 2001 417
14. D. Trompier, X.B. Chang, R. Barattin, A. du Moulinet D'Hardemare, A. Di Pietro, and H. Baubichon-Cortay Cancer Res. 64 2004 4950
15. C.L. Hammond, R. Marchan, S.M. Krance, and N. Ballatori J. Biol. Chem. 282 2007 14337
16. R.M. Laberge, J. Karwatsky, M.C. Lincoln, M.L. Leimanis, and E. Georges Biochem. Pharmacol. 73 2007 1727
17. E. Teodori, S. Dei, P. Quidu, R. Budriesi, A. Chiarini, A. Garnier-Suillerot, F. Gualtieri, D. Manetti, M.N. Romanelli, and S. Scapecchi J. Med. Chem. 42 1999 1687
18. G. Toffoli, F. Simone, G. Corona, M. Raschack, B. Cappelletto, M. Gigante, and M. Boiocchi Biochem. Pharmacol. 50 1995 1245
19. F. Bois, C. Beney, A. Boumendjel, A.M. Mariotte, G. Conseil, and A. Di Pietro J. Med. Chem. 41 1998 4161
20. The synthesis of mesylate 1 and amine 2 was performed according to the previously reported procedure: Teodori, E.; Dei, S.; Quidu, P.; Budriesi, R.; Chiarini, A.; Garnier-Suillerot, A.; Gualtieri, F.; Manetti, D.; Novella Romanelli, M.; Scapecchi, S. J. Med. Chem. 1999, 42, 1687. For convenient reasons, phase transfer catalysis was chosen to achieve the successive alkylations of homoveratronitrile with 2-bromopropane, and bromopropyl tetrahydropyranyl. T. Gajda, A. Koziara, S. Zawadzki, and A. Zwierzak Synth. Commun. 79 1979 549
21. G.D. Yadav, and Y.B. Jadhav Org. Proc. Res. Dev. 7 2003 588
22. T.W. Kometani, D.S. Watt, and T. Ji Tetrahedron Lett. 26 1985 2043
23. J.H. Flanagan Jr., C.V. Owens, S.E. Romero, E. Waddell, S.H. Kahn, R.P. Hammer, and S.A. Soper Anal. Chem. 70 1998 2676
24. D. Berger, R. Citarella, M. Dutia, L. Greenberger, W. Hallett, R. Paul, and D. Powell J. Med. Chem. 42 1999 2145
25. E. Pereira, E. Teodori, S. Dei, F. Gualtieri, and A. Garnier-Suillerot Biochem. Pharmacol. 50 1995 451
26. W. Berger, U. Setinek, P. Hollaus, T. Zidek, E. Steiner, L. Elbling, H. Cantonati, J. Attems, A. Gsur, and M. Micksche J. Cancer Res. Clin. Oncol. 131 2005 355
27. D.W. Loe, C.J. Oleschuk, R.G. Deeley, and S.P. Cole Biochem. Biophys. Res. Commun. 275 2000 795
28. T. Perrotton, D. Trompier, X.B. Chang, A. Di Pietro, and H. Baubichon-Cortay J. Biol. Chem. 282 2007 31542