New lithocholic and chenodeoxycholic piperazinylcarboxamides with antiproliferative and pro-apoptotic effects on human cancer cell lines

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 18, 2008, Pages 8737-8744

  El Kihel, Laïla ^a   Clément, Monique ^b   Bazin, Marc Antoine ^a   Descamps, Géraldine ^b   Khalid, Mohamed ^c   Rault, Sylvain ^a  

^a CENTRE D ETUDES ET DE RECHERCHE SUR LE MÉDICAMENT DE NORMANDIE   (France)

^b NANTES UNIVERSITY HOSPITAL   (France)

^c HASSAN 1ST UNIVERSITY   (Morocco)

Author keywords

Anticancer; Apoptosis; Bile acid derivatives; Multiple myeloma; Steroid heterocycle

Indexed keywords

17BETA [1 METHYL 3 [1N (4N CINNAMYL)PIPERAZIN 1 YL]CARBOXYPROPYL]ETIOCHOLAN 3ALPHA,7ALPHA DIOL; AMIDE; BILE ACID; CHENODEOXYCHOLIC ACID; HETEROCYCLIC COMPOUND; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; LITHOCHOLIC ACID; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE 1; PIPERAZINE DERIVATIVE; PROTEIN MCL 1; UNCLASSIFIED DRUG;

APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL CYCLE ARREST; CELL PROLIFERATION; COLON CARCINOMA; CONTROLLED STUDY; CYTOTOXICITY; DNA FRAGMENTATION; DRUG STRUCTURE; GLIOBLASTOMA; HUMAN; HUMAN CELL; IMMUNOBLOTTING; LD 50; MULTIPLE MYELOMA; PROTEIN DEGRADATION; SIGNAL TRANSDUCTION; WESTERN BLOTTING;

AMIDES; APOPTOSIS; BLOTTING, WESTERN; CELL LINE, TUMOR; CELL PROLIFERATION; CHENODEOXYCHOLIC ACID; COLONIC NEOPLASMS; DNA FRAGMENTATION; GLIOBLASTOMA; HUMANS; LITHOCHOLIC ACID; MULTIPLE MYELOMA; NEOPLASMS; NF-KAPPA B; PIPERAZINES; SIGNAL TRANSDUCTION;

EID: 51649084472     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.07.046     Document Type: Article

References (41)

1. Hanson R.F., Szczepanik P.A., Klein P.D., Johnson E.A., and Williams G.C. Biochim. Biophys. Acta 431 (1976) 335
2. Yamanaka K. Gastroenterol. Jpn. 11 (1976) 285
3. Axelson M., Ellis E., Mork B., Garmark K., Abrahamsson A., Bjorkhem I., Ericzon B.-G., and Einarsson C. Hepatology 31 (2000) 1305
4. Anwer M.S., Kroker R., and Hegner D. Biochem. Biophys. Res. Commun. 64 (1975) 603
5. Hofmann A.F. Clin. Gastroenterol. 6 (1977) 3
6. Hylemon P.B. In: Danielsson H., and Sjoevall J. (Eds). New Comprehensive Biochemistry Vol. 12 (1985), Elsevier, Amsterdam 331-345
7. Mahmoud N.N., Dannenberg A.J., Bilinski R.T., Mestre J.R., Chadburn A., Churchill M., Martucci C., and Bertagnolli M.M. Carcinogenesis 20 (1999) 299
8. Fiorucci S., Clerici C., Antonelli E., Orlandi S., Goodwin B., Sadeghpour B.M., Sabatino G., Russo G., Castellani D., Willson T.M., Pruzanski M., Pellicciari R., and Morelli A. J. Pharmacol. Exp. Ther. 313 (2005) 604
9. Pellicciari R., Costantino G., Camaioni E., Sadeghpour B.M., Entrena A., Willson T.M., Fiorucci S., Clerici C., and Gioiello A. J. Med. Chem. 47 (2004) 4559
10. Kato J.-Y., Matsuoka M., Strom D.K., and Sher C.J. Mol. Cell. Biol. 14 (1994) 2713
11. Martinez J.D., Stratagoules E.D., LaRue J.M., Powell A.A., Gause P.R., Craven M.T., Payne C.M., Powell M.B., Gerner E.W., and Earnest D.L. Nutr. Cancer 31 (1998) 111
12. Tatsumura T., Sato H., Yamamoto K., and Ueyama T. Jpn. J. Surg. 11 (1981) 84
13. Alberts D.S., Martinez M.E., Hess L.M., Einspahr J.G., Green S.B., Bhattacharyya A.K., Guillen J., Krutzsch M., Batta A.K., Salen G., Fales L., Koonce K., Parish D., Clouser M., Roe D., and Lance P. J. Natl. Cancer I 97 (2005) 846
14. Lampronti I., Bianchi N., Zuccato C., Medici A., Bergamini P., and Gambari R. Bioorg. Med. Chem. 14 (2006) 5204
15. Park K., Lee G.Y., Kim Y.-S., Yu M., Park R.-W., Kim I.-S., Kim S.Y., and Byun Y. J. Control. Release 114 (2006) 300
16. Wu D., Ji S., Wu Y., Ju Y., and Zhao Y. Bioorg. Med. Chem. Lett. 17 (2007) 2983
17. Patel T., Bronk S.F., and Gores G.J. J. Clin. Invest. 94 (1994) 2183
18. Rust C., Karnitz L.M., Paya C.V., Moscat J., Simari R.D., and Gores G.J. J. Biol. Chem. 275 (2000) 20210
19. Heuman D.M., and Bajaj R. Gastroenterology 106 (1994) 1333
20. Im E.-O., Lee S., Suh H., Kim K.-W., Bae Y.T., and Kim N.D. Pharm. Pharmacol. Commun. 5 (1999) 293
21. Baek J.H., Kim J.-A., Kang C.-M., Lee Y.S., and Kim K.-W. Korean J. Physiol. Pharmacol. 1 (1997) 107
22. Zhang, Y.; Gold, L. C. U.S. Patent 118,612, 2005.
23. Choi Y.H., Im E.-O., Suh H., Jin Y., Yoo Y.H., and Kim N.D. Cancer Lett. 199 (2003) 157
24. Im E.-O., Choi S.-H., Suh H., Choi Y.H., Yoo Y.H., and Kim N.D. Cancer Lett. 229 (2005) 49
25. Park S.E., Choi H.J., Yee S.B., Chung H.Y., Suh H., Choi Y.H., Yoo Y.H., and Kim N.D. Int. J. Oncol. 25 (2004) 231
26. Jeong J.H., Park J.-S., Moon B., Kim M.C., Kim J.-K., Lee S., Suh H., Kim N.D., Kim J.-M., Park Y.C., and Yoo Y.H. Ann. NY Acad. Sci. 1010 (2003) 171
27. Choi Y.H., Im E.-O., Suh H., Jin Y., Lee W.H., Yoo Y.H., Kim K.-W., and Kim N.D. Int. J. Oncol. 18 (2001) 979
28. Im E.-O., Choi Y.H., Paik K.-J., Suh H., Jin Y., Kim K.-W., Yoo Y.H., and Kim N.D. Cancer Lett. 163 (2001) 83
29. Yee S.-B., Yeo W.J., Park B.S., Kim J.Y., Baek S.J., Kim Y.C., Seo S.Y., Lee S.H., Kim J.H., Suh H., Kim N.D., Lim Y.J., and Yoo Y.H. Int. J. Oncol. 27 (2005) 653
30. Gibbons G.F., Mitropoulos K.A., and Myant N.B. In Biochemistry of Cholesterol (1982), Elsevier Biomedical Press, Amsterdam p 189-203
31. Roda A., Cerre C., Manetta A.C., Cainelli G., Ronchi A.U., and Panunzio M. J. Med. Chem. 39 (1996) 2270
32. Cartron P.-F., Juin P., Oliver L., Martin S., Meflah K., and Vallette F.M. Mol. Cell Biol. 23 (2003) 4701
33. Brattain M.G., Fine W.D., Khaled F.M., Thompson J., and Brattain D.E. Cancer Res. 41 (1981) 1751
34. Namba M., Ohtsuki T., Mori M., Togawa A., Wada H., Sugihara T., Yawata Y., and Kimoto T. In Vitro Cell. Dev. Biol. 25 (1989) 723
35. Reed J.C. J. Clin. Oncol. 17 (1999) 2941
36. Nagahara Y., Tanaka M., and Shinomiya T. Cytom. Part A 71 (2007) 232
37. Karin M. Nature 441 (2006) 431
38. Gomez-Bougie P., Oliver L., Le Gouill S., Bataille R., and Amiot M. Oncogene 24 (2005) 8076
39. Podar K., Le Gouill S., Zhang J., Opferman J.T., Zorn E., Tai Y.-T., Hideshima T., Amiot M., Chauhan D., Harousseau J.-L., and Anderson K.C. Oncogene 27 (2008) 721
40. Khong T., Sharkey J., and Spencer A. Haematologica 93 (2008) 860
41. Nahar L., and Turnere A.B. J. Chem. Res 5 (2004) 329