Synthesis and biological evaluation of selective aromatase expression regulators in breast cancer cells

Journal of Medicinal Chemistry

Volumn 50, Issue 7, 2007, Pages 1635-1644

  Su, Bin ^a   Landini, Serena ^a   Davis, Danyetta D ^a   Brueggemeier, Robert W ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATASE; CYCLIC AMP DEPENDENT PROTEIN KINASE; CYCLOOXYGENASE 2; N (2 PHENOXY 4 NITROPHENYL)METHANESULFONAMIDE; N METHYL N (2 BENZYLOXY 4 NITROPHENYL)METHANESULFONAMIDE; N METHYL N [2 (2' PHENYLBENZYLOXY) 4 NITROPHENYL]METHANESULFONAMIDE; N METHYL N [2 (4' FLUOROBENZYLOXY) 4 NITROPHENYL]METHANESULFONAMIDE; N METHYL N [2 (4' METHYLBENZYLOXY) 4 NITROPHENYL]METHANESULFONAMIDE; N METHYL N [2 (4' NITROBENZYLOXY) 4 NITROPHENYL]METHANESULFONAMIDE; N METHYL N [2 (BETA NAPHTHYLMETHOXY) 4 NITROPHENYL]METHANESULFONAMIDE; PROSTAGLANDIN E2; PROTEIN KINASE C; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYP19 GENE; ENZYME ACTIVITY; GENE; GENE EXPRESSION REGULATION; HUMAN; HUMAN CELL; IC 50; PROTON NUCLEAR MAGNETIC RESONANCE; SIGNAL TRANSDUCTION;

ANTINEOPLASTIC AGENTS; APOPTOSIS; AROMATASE; AROMATASE INHIBITORS; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL SURVIVAL; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; GENE EXPRESSION REGULATION, ENZYMOLOGIC; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 34147145912     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061133j     Document Type: Article

References (26)

1. American Cancer Society. Cancer Facts and Figures 2006; American Cancer Society. Atlanta, Jan 1, 2006.
2. Chen, S.; Zhou, D.; Okubo, T.; Kao, Y. C.; Eng, E. T.; Grube, B.; Kwon, A.; Yang, C.; Yu, B. Prevention and treatment of breast cancer by suppressing aromatase activity and expression. Ann. N. Y. Acad. Sci. 2002, 963, 229-238.
3. Leygue, E.; Dotzlaw, H.; Watson, P. H.; Murphy, L. C. Altered estrogen receptor alpha and beta messenger RNA expression during human breast tumorigenesis. Cancer Res. 1998, 58, 3197-3201.
4. Brueggemeier, R. W.; Hackett, J. C.; Diaz-Cruz, E. S. Aromatase inhibitors in the treatment of breast cancer. Endocr. Rev. 2005, 26, 331-345.
5. Riggs, B. L.; Hartmann, L. C. Selective estrogen-receptor modulators - mechanisms of action and application to clinical practice. N. Engl. J. Med. 2003, 348, 618-629.
6. Fisher, B.; Costantino, J. P.; Redmond, C. K.; Fisher, E. R.; Wickerham, D. L.; Cronin, W. M. Endometrial cancer in tamoxifen-treated breast cancer patients: findings from the National Surgical Adjuvant Breast and Bowel Project (NSABP) B-14. J. Natl. Cancer Inst. 1994, 86, 527-537.
7. Seralini, G.; Moslemi, S. Aromatase inhibitors: past, present and future. Mol. Cell Endocrinol. 2001, 178, 117-131.
8. Brueggemeier, R. W. Aromatase inhibitors: new endocrine treatment of breast cancer. Semin. Reprod. Med 2004, 22, 31-43.
9. Choueiri, T. K.; Alemany, C. A.; Abou-Jawde, R. M.; Budd, G. T. Role of aromatase inhibitors in the treatment of breast cancer. Clin. Ther. 2004, 26, 1199-1214.
10. Heshmati, H. M.; Khosla, S.; Robins, S. P.; O'Fallon, W. M.; Melton, L. J. III; Riggs, B. L. Role of low levels of endogenous estrogen in regulation of bone resorption in late postmenopausal women. J. Bone Miner. Res. 2002, 17, 172-178.
11. Bulun, S. E.; Sebastian, S.; Takayama, K.; Suzuki, T.; Sasano, H.; Shozu, M. The human CYP19 (aromatase P450) gene: update on physiologic roles and genomic organization of promoters. J. Steroid Biochem. Mol. Biol. 2003, 86, 219-224.
12. Simpson, E. R.; Mahendroo, M. S.; Means, G. D.; Kilgore, M. W.; Hinshelwood, M. M.; Graham-Lorence, S.; Amarneh, B.; Ito, Y.; Fisher, C. R.; Michael, M. D. Aromatase cytochrome P450, the enzyme responsible for estrogen biosynthesis. Endocr. Rev. 1994, 15, 342-355.
13. Simpson, E. R. Aromatase: biologic relevance of tissue-specific expression. Semin. Reprod. Med. 2004, 22, 11-23.
14. Chen, S. Aromatase and breast cancer. Front Biosci. 1998, 3, d922-d933.
15. Zhou, C.; Zhou, D.; Esteban, J.; Murai, J.; Siiteri, P. K.; Wilczynski, S.; Chen, S. Aromatase gene expression and its exon 1 usage in human breast tumors. Detection of aromatase messenger RNA by reverse transcription-polymerase chain reaction. J. Steroid Biochem. Mol. Biol. 1996, 59, 163-171.
16. Zhou, D.; Clarke, P.; Wang, J.; Chen, S. Identification of a promoter that controls aromatase expression in human breast cancer and adipose stromal cells. J. Biol. Chem. 1996, 271, 15194-15202.
17. Zhou, D.; Zhou, C.; Chen, S. Gene regulation studies of aromatase expression in breast cancer and adipose stromal cells. J Steroid Biochem. Mol. Biol. 1997, 61, 273-280.
18. Zhao, Y.; Agarwal, V. R.; Mendelson, C. R.; Simpson, E. R. Estrogen biosynthesis proximal to a breast tumor is stimulated by PGE2 via cyclic AMP, leading to activation of promoter II of the CYP19 (aromatase) gene. Endocrinology 1996, 137, 5739-5742.
19. Yoshikawa, Y.; Ochi, Y.; Sekiuchi, K.; Saito, H.; Hatayama, K. Preparation of sulfonanilide derivatives as antiinflammatory agents. Taisho Pharmaceutical Co., Ltd. Japan. JP 88-17244.0[02022260], 11-19900.125. 1990, Jul 11, 1988.
20. Yoshikawa, K.; Ohuchi, Y.; Sekiuchi, K.; Saito, S.; Hatayama, K.; Sota, K. Preparation of sulfonanilide compounds as antiinflammatory agents. Taisho Pharmaceutical Co., Ltd. Japan. EP 88-31089.9-[317332], 15-19890.524. 1989, Nov 18, 1988.
21. Diaz-Cruz, E. S.; Shapiro, C. L.; Brueggemeier, R. W. Cyclooxygenase inhibitors suppress aromatase expression and activity in breast cancer cells. J. Clin. Endocrinol. Metab. 2005, 90, 2563-2570.
22. Su, B.; Diaz-Cruz, E. S.; Landini, S.; Brueggemeier, R. W. Novel sulfonanilide analogues suppress aromatase expression and activity in breast cancer cells independent of COX-2 inhibition. J. Med. Chem. 2006, 49, 1413-1419.
23. Hiroya, K.; Matsumoto, S.; Sakamoto, T. New synthetic method for indole-2-carboxylate and its application to the total synthesis of duocarmycin SA. Org. Lett. 2004, 6, 2953-2956.
24. Toda, K.; Nomoto, S.; Shizuta, Y. Identification and characterization of transcriptional regulatory elements of the human aromatase cytochrome P450 gene (CYP19). J. Steroid Biochem. Mol. Biol. 1996, 56, 151-159.
25. Yue, W.; Wang, J. P.; Conaway, M. R.; Li, Y.; Santen, R. J. Adaptive hypersensitivity following long-term estrogen deprivation: involvement of multiple signal pathways. J. Steroid Biochem. Mol. Biol. 2003, 86, 265-274.
26. Balthazart, J.; Baillien, M.; Ball, G. F. Phosphorylation processes mediate rapid changes of brain aromatase activity. J Steroid Biochem. Mol. Biol. 2001, 79, 261-277.