Synthesis and properties of a mitochondrial peripheral benzodiazepine receptor conjugate

ChemMedChem

Volumn 3, Issue 11, 2008, Pages 1687-1695

  El Alaoui, Abdessamad ^a,b   Schmidt, Frédéric ^a,b   Sarr, Marianne ^a,b   Decaudin, Didier ^a   Florent, Jean Claude ^a,b   Johannes, Ludger ^a,b  

^a INSTITUT CURIE   (France)

^b CNRS   (France)

Author keywords

Antitumor agents; Benzodiazepine; Drug delivery; Prodrugs; Shiga toxin

Indexed keywords

4 AMINOBUTYRIC ACID A RECEPTOR; GLOBOTRIAOSYL LYSOSPHINGOLIPID; GLYCOLIPID; SHIGA TOXIN; SPHINGOLIPID;

APOPTOSIS; ARTICLE; CELL MEMBRANE POTENTIAL; CHEMICAL MODEL; CHEMISTRY; DRUG DELIVERY SYSTEM; DRUG DESIGN; ENDOPLASMIC RETICULUM; HUMAN; KINETICS; METABOLISM; METHODOLOGY; MITOCHONDRION; TUMOR CELL LINE;

APOPTOSIS; CELL LINE, TUMOR; CHEMISTRY, PHARMACEUTICAL; DRUG DELIVERY SYSTEMS; DRUG DESIGN; ENDOPLASMIC RETICULUM; GLYCOLIPIDS; HUMANS; KINETICS; MEMBRANE POTENTIALS; MITOCHONDRIA; MODELS, CHEMICAL; RECEPTORS, GABA-A; SHIGA TOXIN; SPHINGOLIPIDS;

EID: 55949093770     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200800249     Document Type: Article

References (40)

1. S. A. Susin, N. Zamzami, M. Castedo, E. Daugas, H. G. Wang, S. Geley, F. Fassy, J. C. Reed, G. Kroemer, J. Exp. Med. 1997, 186, 25.
2. R. R. Anholt, P. L. Pedersen, E. B. De Souza, S. H. Snyder, J. Biol. Chem. 1986, 261, 576.
3. D. Decaudin, Anticancer Drugs 2004, 15, 737.
4. A. Beinlich, R. Strohmeier, M. Kaufmann, H. Kuhl, Biochem. Pharmacol. 2000, 60, 397-402.
5. W. Li, M. Hardwick, D. Rosenthal, M. Culty, V. Papadopoulos, Biochemical Pharmacology 2007, 73, 491-503.
6. Y. Katz, G. Ben-Baruch, Y. Klog, J. Menczert, M. Gavish, Clin. Sci. 1990, 78, 155-158.
7. K. Maaser, P. Grabowski, A. P. Sutter, M. Höpfner, H. D. Foss, H. Stein, G. Berger, M. Gavish, M. Zeitz, H. Scherübl, Clin. Cancer Res. 2002, 8, 3205-3209.
8. M. Corda, M. Ferrari, A. Guidotti, D. Konkel, Neurosci. Lett. 1984, 47, 310-324.
9. C. Mantione, M. Goldman, B. Martin, G. Bolger, H. Lueddens, S. Paul, Biochem. Pharmacol. 1988, 37, 339-347.
10. A. Verma, J. Nye, S. Snyder, Proc. Natl. Acad. Sci. USA 1987, 84, 2256-2260.
11. G. Wendler, P. Lindemann, J. Lacapere, Biochem. Biophys. Res. Commun. 2003, 311, 847-852.
12. G. Le Fur, F. Guilloux, P. Rufat, J. Benavides, A. Uzan, C. Renault, M. Dubroeucq, C. Gueremy, Life Sci. 1983, 32, 1849-1856.
13. E. Romeo, J. Auta, A. Kozikowski, D. Ma, V. Papadopoulos, G. Puia, E. Costa, J. Pharmacol. Exp. Ther. 1992, 262, 971-978.
14. A. Kozikowski, D. Ma, J. Brewer, S. Sun, E. Costa, E. Romeo, A. Guidotti, J. Med. Chem. 1993, 36, 2908-2920.
15. S. Langer, S. Arbilla, S. Tan, K. Lloyd, P. George, J. Allen, A. Wick, Pharmacopsychiatry 1990, 23, 103-107.
16. T. Okubo, R. Yoshikawa, S. Chaki, S. Okuyama, A. Nakazato, Bioorg. Med. Chem. 2004, 12, 423-438.
17. G. Primofiore, F. Da Settimo, S. Taliani, F. Simorini, M. Patrizi, E. Novellino, G. Greco, E. Abignente, B. Costa, B. Chelli, C. Martini, Med. Chem. 2004, 47, 1852-1855.
18. F. Bono, I. Lamarche, V. Prabonnnaud, G. Le Fur, J. M. Herbert, Biochem. Biophys. Res. Commun. 1999, 265, 457-461.
19. D. Decaudin, M. Castedo, F. Nemati, A. Beurdely-Thomas, G. De Pinieux, A. Caron, P. Pouillard, J. Wijdenes, D. Rouillard, G. Kroemer, M.-F. Poupon, Cancer Res. 2002, 62, 1388-1393.
20. K. Hirai, T. Ishiba, H. Sugimoto, K. Sasakura, T. Fujishita, T. Toyoda, Y. Tsukinoki, H. Joyama, H. Hatakeyama, K. Hirose, J. Med. Chem. 1980, 23, 764-773.
21. K. Hirai K, T. Ishiba, H. Sugimoto, T. Fujishita, Y. Tsukinoki, K. Hirose, J. Med. Chem. 1981, 24, 20-27.
22. H. Bundgaard, Adv. Drug Delivery Rev. 1989, 3, 39-65.
23. L. Johannes, D. Decaudin, Gene Ther. 2005, 18, 1360-1368.
24. K.-P. Janssen, D. Vignjevic, R. Boisgard, T. Falguires, G. Bousquet, D. Decaudin, F. Dolle, D. Louvard, B. Tavitian, S. Robine, L. Johannes, Cancer Res. 2006, 14, 7230-7236.
25. A. El Alaoui, F. Schmidt, M. Amessou, M. Sarr, D. Decaudin, J.-C. Florent, L. Johannes, Angew. Chem. 2007, 119, 6589-6592;
26. Angew. Chem. Int. Ed. 2007, 46, 6469-6472.
27. T. Falguières, M. Maak, C. von Weyhern, M. Sarr, X. Sastre, M. F. Poupon, S. Robine, L. Johannes, K. P. Janssen, Mol. Cancer Ther. 2008, 7, 2498-2508.
28. C. L. Morton, M. Wierdl, L. Oliver, M. K. Ma, M. K. Danks, C. F. Stewart, J. L. Eiseman, P. M. Potter, Cancer Res. 2000, 60, 4206-4210.
29. T. L. Huang, A. Szekacs, T. Uematsu, E. Kuwano, A. Parkinson, B. D. Hammock, Pharm. Res. 1993, 10, 639-648.
30. R. B. Greenwald, A. Pendri, C. D. Conover, H. Zhao, Y. H. Choe, A. Martinez, K. Shum, S. Guan, J. Med. Chem. 1999, 42, 3657-3667.
31. R. B. Greenwald, Y. H. Choe, C. D. Conover, K. Shum, D. Wu, M. Royzen, J. Med. Chem. 2000, 43, 475-487.
32. J. Muchowski, M. Venuti, J. Org. Chem. 1980, 45, 4789-4801.
33. G. Mouzin, H. Cousse, J.-M. Autin, Synthesis 1981, 448-449.
34. T. Sugasawa, T. Toyada, M. Adachi, K. Sasakura, J. Am. Chem. Soc. 1978, 100, 4842-4852.
35. D. Walsh, Synthesis 1980, 677-688.
36. I. Houpis, A. Molina, A. Douglas, L. Xavier, J. Lynch, R. Volante, P. Reider, Tetrahedron Lett. 1994, 35, 6811-6814.
37. A. Abe, J. Inokuchi, M. Jimbo, H. Shimeno, A. Nagamatsu, J. A. Shayman, G. S. Shukla, N. S. Radin, J. Biochem. 1992, 111, 191.
38. Z. Vejdelek, Z. Polivka, M. Protiva, Collect. Czech. Chem. Commun. 1985, 50, 1064-1069.
39. S. Smiley, M. Reers, C. Mottola-Hartshorn, M. Lin, A. Chen, T. Smith, G. Steele, L. Chen, Proc. Natl. Acad. Sci. USA 1991, 88, 3671-3675.
40. E. Bligh, W. Dyer, Can. J. Biochem. Physiol. 1959, 37, 911-917.