Cytostatic and cytotoxic action of Z-1,1-dichloro-2,3-diphenylcyclopropane in three human breast cancer cell lines

Anticancer Research

Volumn 16, Issue 3 A, 1996, Pages 1107-1115

  Ter Haar, Ernst ^a   Day, Billy W ^a,b  

^a UNIVERSITY OF PITTSBURGH CANCER INSTITUTE   (United States)

^b UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

Analog II; Cytostasis; Cytotoxicity; Metabolism; Z chlorochalcone

Indexed keywords

1,1 DICHLORO 2,3 DIPHENYLCYCLOPROPANE; ESTROGEN RECEPTOR;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BACTERIAL MUTATION; BREAST CANCER; CANCER CELL CULTURE; CELL METABOLISM; CELL STRAIN MCF 7; CELL VIABILITY; CLONOGENIC ASSAY; CONTROLLED STUDY; CULTURE MEDIUM; CYTOSTASIS; CYTOTOXICITY; DRUG METABOLISM; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MASS SPECTROMETRY; METABOLIC ACTIVATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SALMONELLA TYPHIMURIUM;

ALKYLATION; ANTINEOPLASTIC AGENTS; BIOTRANSFORMATION; BREAST NEOPLASMS; CELL DIVISION; DRUG SCREENING ASSAYS, ANTITUMOR; DRUG STABILITY; ESTROGENS; HUMANS; HYDROLYSIS; NEOPLASMS, HORMONE-DEPENDENT; OXIDATION-REDUCTION; RECEPTORS, ESTROGEN; TAMOXIFEN; TUMOR CELLS, CULTURED;

EID: 0029980263     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (28)

1. Magarian RA, Benjamin EJ: Syntheses of cyclopropyl analogs of stilhene and stilbenediol as possible antiestrogens. J Pharm Sci 64: 1626-1632, 1975.
2. Day BW, Magarian RA, Pento JT, Jain PT, Mousissian GK, Meyer KL. Synthesis and biological evaluation of 1,1-dichloro-2,2,3-triarylcyclopropanes as pure antiestrogens. J Med Chem 34: 842-851, 1991.
3. Magarian RA, Overacre LB, Singh S, Meyer KL: The medicinal chemistry of nonsteroidal antiestrogens: A review. Curr Med Chem 1: 61-104, 1994.
4. Griffin MT, Magarian RA, Jain PT, Pento JT, Mousissian GK, Graves DC: Synthesis and biological aluation of a series of gemdichlorocyclopropanes as antitumor agents. Anticancer Drug Design 7: 49-66, 1992.
5. Pento JT, Koenig KK, Magadan RA, Kosanke SD, Gilhland D Biological evaluation of novel cyclopropyl analogues of stilbene, stilbenediol. and phenanthrene for estrogenic and antiestrogenic activity. J Pharm Sci 77: 120-125, 1988
6. Bedford GR, Walpole AL, Wright B: Antiestrogenic triarylcyclopropanes. J Med Chem 17: 147-149, 1974.
7. Schneider MR, Schónenberger H: Mammary tumor inhibiting [(1,2-diethyl-1,2-cyclopropanediyl)bis(phenyl)]diacetate. Eur J Med Chem-Chim Ther 17: 491-495, 1982
8. Pento JT, Magarian RA, Wright RJ, King MM, Benjamin EJ: Nonsteroidal estrogens and antiestrogens. Biological activity of cyclopropyl analogs of stilbene and stilbenediol. J Pharm Sci 70: 339-343, 1981.
9. Pento JT, Magarian RA, King MM: A comparison of the efficacy for antitumor activity of the nonsteroidal antiestrogens Analog 11 and tamoxifen in DMBA-induced rat mammary tumors Cancer Lett 15: 261-269, 1982.
10. King MM, Pento JT, Magarian RA, Bnueggemann GL: The interaction of dietary fat and antiestrogen treatment on DMBA-induced mammary tumors in the rat. Nutr Cancer 7: 239-249, 1985.
11. King MM, Magarian RA, Terao J Brueggemann GL: Effects of nonsteroidal antiestrogens. Analog II and tamoxifen, on a metastatic transplantable rat mammary tumor J Natl Cancer Inst 74: 447-451, 1985.
12. Caputo O, Grosa G, Ceruti M, Rocco F, Biglino G: Metabolism of 1,1-dichloro-cisdiphenylcyclopropane by rat liver microsomes. Drug Metab Disp 18: 771-778, 1990.
13. Dehmlow WV Schonefeld J: Umsetzung von olefinen mit dihalogencarbenen. Liebigs Ann Chem 744: 42-50, 1971
14. Edwards MJ, Stemerick DM, Sunkara PS: Chalcones a new class of antimitotic agents. J Med Chem 33: 1948-1954, 1990
15. Abell RD, Siddall W: Haloqen derivatives of phenylstyryl ketone. Part 1 Bromo- and chloroderivatives. J Chem Soc: 2804-2807, 1953.
16. Skopek TR, Liber HL, Krolewski JJ, Thilly WG. Quantitative forward mutation assay in Salmonella iyphimurtum, using 8-azaguanine resistance as a genetic marker. Proc Natl Acad Sci USA 75: 410-414, 1978.
17. Soule HD, Vazquez J, Long A, Albert S, Brennan M: A human cell line from a pleural effusion derived from breast carcinoma. J Natl Cancer Inst 51: 1409-1416, 1973.
18. Engel LW, Young, NA: Human breast carcinoma cells in continuous culture. A review Cancer Res 38: 4327-4339, 1978.
19. Bronzen DA, Greene GL, Lippman ME: Selection and characterization of a breast cancer cell line resistant to the antiestrogen LY 117018. Endocrinology 117: 1409-1417, 1985.
20. Cailleau R, Young R, Olive M, Reeves WJ Jr: Breast tumor cell lines from pleural effusions J Natl Cancer Inst 53: 661-674, 1974.
21. Lail J, Pento JT, Magarian RA: Protein binding characterization of a novel antiestrogen (Analog II) in the rat. Meth Find Exp Clin Pharmacol 9: 441-444, 1987.
22. Griffin MT, Pento JT, Magarian RA, Mousissian GK, Basmadjian GP: Biodistribution of a novel antiestrogen (Analog II) in the mouse and rat. Endocrine Res 16: 269-282, 1990.
23. Jordan VC, Jeng M-H, Jiang S-Y, Yingling J, Stella AL: Hormonal strategies for breast cancer: A new focus on the estrogen receptor as a therapeutic target Sem Oncol 19: 229-307, 1992.
24. Jordan VC: The strategic use of antiestrogens to control the development and growth of breast cancer. Cancer Suppl 70: 977-982, 1992.
25. Woodward RB, Hoffmann R: Stereochemistry of electrocyclic reactions. J Amer Chem Soc 87: 395-397, 1965.
26. Schleyer PvR, Su TM, Saunders M, Rosenfeld JC. Stereochemistry of allyl cations from the isomeric dimetliylcyclopropyl chlorides. The geomutation of allyl cations. J Amer Chem Soc 91: 5174-5175, 1969.
27. 5+ cations Energy relationships among allyl, vinyh and cyclopropyl cations. J Amer Chem Soc 95: 6531-6544, 1973.
28. Leclercq G, Devleeschouwer N, Heuson JC: Guide-lines in the design of new antiestrogens and cytotoxic-linked estrogens for the treatment of breast cancer. J Steroid Biochem 19: 75-85, 1983.