Antiproliferative activity of some 1,4-dimethylcarbazoles on cells that express estrogen receptors: Part i

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 27, Issue 4, 2012, Pages 609-613

  Caruso, Anna ^a   Chimento, Adele ^a   El Kashef, Hussein ^b   Lancelot, Jean Charles ^c   Panno, Antonella ^a   Pezzi, Vincenzo ^a   Saturnino, Carmela ^d   Sinicropi, Maria Stefania ^a   Sirianni, Rosa ^a   Rault, Sylvain ^c  

^a UNIVERSITY OF CALABRIA   (Italy)

^b Assiut University   (Egypt)

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

^d UNIVERSITY OF SALERNO   (Italy)

Author keywords

Anticancer; Carbazoles; Ishikawa cell line; MCF 7 cell line

Indexed keywords

1,4 DIMETHYLCARBAZOLE DERIVATIVE; 9H CARBAZOLE DERIVATIVE; ANTINEOPLASTIC AGENT; CARBAZOLE DERIVATIVE; ESTROGEN RECEPTOR; UNCLASSIFIED DRUG;

ADULT; ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CELL STRAIN MCF 7; CONTROLLED STUDY; CYTOTOXICITY; FEMALE; HUMAN; HUMAN CELL; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ADULT; AGED; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CARBAZOLES; CARCINOMA, ENDOMETRIOID; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; ENDOMETRIAL NEOPLASMS; FEMALE; HUMANS; MOLECULAR STRUCTURE; RECEPTORS, ESTROGEN; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84864038889     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2011.603132     Document Type: Article

References (31)

1. De Koning CB, Michael JP, Rousseau AL. A versatile and convenient method for the synthesis of substituted benzo[a] carbazoles and pyrido[2,3-a] carbazoles. J Chem Soc Perkin Trans 2000;1:1705-1713.
2. Caruso A, Lancelot JC, El-Kashef H, Sinicropi MS, Legay R, Lesnard A, Rault S. A rapid and versatile synthesis of novel pyrimido[5,4-b] carbazoles. Tetrahedron 2009;65:10400-10405.
3. Caruso A, Voisin-Chiret AS, Lancelot JC, Sinicropi MS, Garofalo A, Rault S. Efficient and simple synthesis of 6-aryl-1,4-dimethyl-9Hcarbazoles. Molecules 2008;13:1312-1320.
4. Waldau D, Mikolasch A, Lalk M, Schauer F. Derivatization of bioactive carbazoles by the biphenyl-degrading bacterium Ralstonia sp. strain SBUG 290. Appl Microbiol Biotechnol 2009;83:67-75.
5. Auclair C. Multimodal action of antitumor agents on DNA: The ellipticine series. Arch Biochem Biophys 1987;259:1-14.
6. Stiborova M, Rupertova M, Schmeiser HH, Frei E. Molecular mechanisms of antineoplastic action of an anticancer drug ellipticine. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub 2006;150:13-23.
7. Soule HD, Vazguez J, Long A, Albert S, Brennan M. A human cell line from a pleural effusion derived from a breast carcinoma. J Natl Cancer Inst 1973;51:1409-1416.
8. Bullinger D, Neubauer H, Fehm T, Laufer S, Gleiter CH, Kammerer B. Metabolic signature of breast cancer cell line MCF-7: Profiling of modified nucleosides via LC-IT MS coupling. BMC Biochem 2007;8-25.
9. Matthews J, Gustafsson JA. Estrogen signaling: A subtle balance between ER α and ER β. Mol Interv 2003;3:281-292.
10. Nishida M, Kasahara K, Kaneko M, Iwasaki H, Hayashi K. Establishment of a new human endometrial adenocarcinoma cell line, Ishikawa cells, containing estrogen and progesterone receptors. Nippon Sanka Fujinka Gakkai Zasshi 1985;37:1103-1111.
11. Holinka CF, Hata H, Kuramoto H, Gurpide E. Responses to estradiol in a human endometrial adenocarcinoma cell line (Ishikawa). J Steroid Biochem 1986;24:85-89.
12. Lessey BA, Ilesanmi AO, Castelbaum AJ, Yuan L, Somkuti SG, Chwalisz K et al. Characterization of the functional progesterone receptor in an endometrial adenocarcinoma cell line (Ishikawa): Progesterone-induced expression of the α1 integrin. J Steroid Biochem Mol Biol 1996;59:31-39.
13. Lovely LP, Appa Rao KB, Gui Y, Lessey BA. Characterization of androgen receptors in a well-differentiated endometrial adenocarcinoma cell line (Ishikawa). J Steroid Biochem Mol Biol 2000;74:235-241.
14. Wormke M, Castro-Rivera E, Chen I, Safe S. Estrogen and aryl hydrocarbon receptor expression and crosstalk in human Ishikawa endometrial cancer cells. J Steroid Biochem Mol Biol 2000;72:197-207.
15. Vollmer G. Endometrial cancer: Experimental models useful for studies on molecular aspects of endometrial cancer and carcinogenesis. Endocr Relat Cancer 2003;10:23-42.
16. Labrie F, Labrie C, Bélanger A, Simard J, Giguère V, Tremblay A et al. EM-652 (SCH57068), a pure SERM having complete antiestrogenic activity in the mammary gland and endometrium. Steroid Biochem Mol Biol 2001;79:213-225.
17. Holinka CF, Anzai Y, Hata H, Kimmel N, Kuramoto H, Gurpide E. Proliferation and responsiveness to estrogen of human endometrial cancer cells under serum-free culture conditions. Cancer Res 1989;49:3297-3301.
18. Apparao KB, Murray MJ, Fritz MA, Meyer WR, Chambers AF, Truong PR et al. Osteopontin and its receptor αvβ(3) integrin are coexpressed in the human endometrium during the menstrual cycle but regulated differentially. J Clin Endocrinol Metab 2001;86:4991-5000.
19. Frigo DE, Duong BN, Melnik LI, Schief LS, Collins-Burow BM, Pace DK et al. Flavonoid phytochemicals regulate activator protein-1 signal transduction pathways in endometrial and kidney stable cell lines. J Nutr 2002;132:1848-1853.
20. Bergeron RM, Thompson TB, Leonard LS, Pluta L, Gaido KW. Estrogenicity of bisphenol A in a human endometrial carcinoma cell line. Mol Cell Endocrinol 1999;150:179-187.
21. Arnold JT, Lessey BA, Seppälä M, Kaufman DG. Effect of normal endometrial stroma on growth and differentiation in Ishikawa endometrial adenocarcinoma cells. Cancer Res 2002;62:79-88.
22. Kanishi Y, Kobayashi Y, Noda S, Ishizuka B, Saito K. Differential growth inhibitory effect of melatonin on two endometrial cancer cell lines. J Pineal Res 2000;28:227-233.
23. Nishida M, Kasahara K, Tsuji T, Kaneko M, Iwasaki H. Mechanisms of the antitumor action of gestagens on endometrial cancer. Nippon Sanka Fujinka Gakkai Zasshi 1986;38:2214-2222.
24. Cranwell A, Saxton JE. A synthesis of ellipticine. J Chem Soc 1962;3482-3487;
25. Lancelot JC, Rault S, Robba M, Nguyen HD. Efficient synthesis of 6H-pyrido[3,2-b]carbazole derivatives from 3-amino-1,4-dimethylcarbazole. Chem Pharm Bull 1987;35:425-428.
26. Tabka T, Letois B, Lancelot JC, Gauduchon P, Heron JF, Le Talaer JY, Rault S, Robba M. Etude de la cytotoxicité in vitro de dérivés du carbazole II. Nitro et amino halogéno-6 diméthyl-1,4 9H-carbazoles. Eur J Med Chem, 1989;24:605-610
27. Testard A, Picot L, Fruitier-Arnaudin I, Piot JM, Chabane H, Domon L, Thiery V, Besson T. Microwave-assisted synthesis of novel thiazolocarbazoles and evaluation as potential anticancer agents. Part III. J Enzym Inhib Med Chem, 2004;19:467-473.
28. Moinet-Hedin V, Tabka T, Sichel F, Gauduchon P, Le Talaer JY,Saturnino C, Letois B, Lancelot JC, Robba M. In vitro cytotoxicity of carbazole derivatives. V. 9-Halogeno-substituted 5,11- dimethyl-6H-pyrido[3,2-b]carbazoles. Eur J Med Chem 1997;32: 113-122.
29. Caruso A, Voisin-Chiret AS, Lancelot JC, Sinicropi MS, Garofalo A, Rault S. Novel and efficient synthesis of 5,8-dimethyl-9Hcarbazol- 3-ol via a hydroxydeboronation reaction. Heterocycles 2007;71(10):2203-2210.
30. Caruso A. Ph.D. Thesis. Synthesis of novel dimethylcarbazole, dimethylpyrimidocarbazole, benzofuro quinazolinone, benzothienoquinazolinone derivatives with potential anticancer activity. University of Calabria-Italy, 17.12. 2008.
31. Sylvester PW. Optimization of the tetrazolium dye (MTT) colorimetric assay for cellular growth and viability. Methods Mol Biol 2011;716:157-168.