Steroidal Metabolites Transformed by Marchantia polymorpha Cultures Block Breast Cancer Estrogen Biosynthesis

Cell Biochemistry and Biophysics

Volumn 63, Issue 1, 2012, Pages 85-96

  Hegazy, Mohamed Elamir F ^a,b   Gamal Eldeen, Amira M ^a   El Halawany, Ali M ^c   Mohamed, Abou El Hamd H ^d   Paré, Paul W ^e  

^a NATIONAL RESEARCH CENTRE   (Egypt)

^b KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^c CAIRO UNIVERSITY   (Egypt)

^d ASWAN UNIVERSITY   (Egypt)

^e TEXAS TECH UNIVERSITY   (United States)

Author keywords

Androst 1,4 dien 3,17 dione; Anticancer activity; Aromatase inhibitory activity; Cultured plant cells; Hydrogenation

Indexed keywords

1,4-ANDROSTADIENE-3,17-DIONE; ANDROSTANE DERIVATIVE; AROMATASE; AROMATASE INHIBITOR; BOLDIONE; ESTROGEN;

APOPTOSIS; ARTICLE; BINDING SITE; BIOSYNTHESIS; BREAST TUMOR; CHEMISTRY; COMPUTER SIMULATION; DRUG EFFECT; ENZYME ACTIVE SITE; FEMALE; GENETICS; HUMAN; ISOLATION AND PURIFICATION; KINETICS; MARCHANTIA; METABOLISM; PATHOLOGY; TUMOR CELL LINE;

ANDROSTADIENES; APOPTOSIS; AROMATASE; AROMATASE INHIBITORS; BINDING SITES; BREAST NEOPLASMS; CATALYTIC DOMAIN; CELL LINE, TUMOR; COMPUTER SIMULATION; ESTROGENS; FEMALE; HUMANS; KINETICS; MARCHANTIA;

MARCHANTIA; MARCHANTIA POLYMORPHA;

EID: 84859878159     PISSN: 10859195     EISSN: None     Source Type: Journal    
DOI: 10.1007/s12013-012-9343-4     Document Type: Article

References (50)

1. Sedlaczek, L. (1988). Biotransformation of steroids. CRC Critical Reviews in Biotechnology, 7, 187-236.
2. Zhi, F. W., Yu, L. H., James, R. F., & Shang-Tian, Y. (2002). Lecithin-enhanced biotransformation of cholesterol to androst-1, 4-diene-3, 17-dione and androst-4-ene-3, 17-dione. Journal of Chemical Technology and Biotechnology, 77, 1349-1357.
3. Hirata, T., Takarada, A., Hegazy, M., Sato, Y., et al. (2005). Hydrogenation of the C-C double bond of maleimides with cultured plant cells. Journal of Molecular Catalysis B, 32, 131-134.
4. Hegazy, M.-E. F., Hirata, T., Abdel-Lateff, A., et al. (2008). Ketoisophorone transformation by Marchantia polymorpha and Nicotiana tabacum cultured cells. Zeitschrift fuer Naturforschung, C, 63c, 403-408.
5. Hesselink, P. G. M., van Vliet, S., de Vries, H., & Witholt, B. (1989). Optimization of steroid side chain cleavage by Mycobacterium sp. in the presence of cyclodextrins. Enzyme and Microbial Technology, 11, 398-404.
6. Hu, S.-h., & Azerad, G. R. (1995). Microbial transformation of steroids: Contribution to 14α-hydroxylations. Steroids, 60, 337-352.
7. Wang, Z., Zhao, F., Hao, X., Chen, D., & Li, D. (2004). Microbial transformation of hydrophobic compound in cloud point system. Journal of Molecular Catalysis B, 27, 147-153.
8. Dutta, T. K., & Samanta, B. (1997). Novel catalytic activity of immobilized spores under reduced water activity. Bioorganic and Medicinal Chemistry Letters, 7, 629-632.
9. Faramarzi, M. A., Yazdi, M. T., Jahandar, H., Amini, M., & Monsef-Esfahani, H. R. (2006). Studies on the microbial transformation of androst-1, 4-dien-3, 17-dione with Acremonium strictum. Journal of Industrial Microbiology and Biotechnology, 33, 725-733.
10. Labrie, F., Luu-The, V., Lin, S. X., Simard, J., Labrie, C., El-Alfy, M., et al. (2000). Intracrinology: Role of the family of 17 betahydroxysteroid dehydrogenases in human physiology and disease. Journal of Molecular Endocrinology, 25, 1-16.
11. Zhu, B. T., & Conney, A. H. (1998). Functional role of estrogen metabolism in target cells: Review and perspectives. Carcinogenesis, 19, 1-27.
12. Bagchi, S. (2007). Men with breast cancer have high risk of second cancer. The Lancet Oncology, 8, 198.
13. Ju, Y. H., Doerge, D. R., Woodling, K. A., Hartman, J. A., Kwak, J., & Helferich, W. G. (2008). Dietary genistein negates the inhibitory effect of letrozole on the growth of aromatase-expressing estrogen-dependent human breast cancer cells (MCF-7Ca) in vivo. Carcinogenesis, 29, 2162-2168.
14. Harlan, L. C., Abrams, J., Warren, J. L., Clegg, L., Stevens, J., & Ballard-Barbash, R. (2002). Adjuvant therapy for breast cancer: Practice patterns of community physicians. Journal of Clinical Oncology, 20, 1809-1817.
15. Howell, A., & Locker, G. Y. (2005). Defining the roles of aromatase inhibitors in the adjuvant treatment of early-stage breast cancer. Clinical Breast Cancer, 6, 302-309.
16. Simpson, E. R. (2000). Biology of aromatase in the mammary gland. Journal of Mammary Gland Biology and Neoplasia, 5, 251-258.
17. Parker, C. R. J., Slayden, S. M., Azziz, R., Crabbe, S. L., Hines, G. A., Boots, L. R., et al. (2000). Effects of aging on adrenal function in the human: Responsiveness and sensitivity of adrenal androgens and cortisol to adrenocorticotropin in premenopausal and postmenopausal women. The Journal of Clinical Endocrinology and Metabolism, 85, 48-54.
18. Bulun, S. E., Zeitoun, K., Sasano, H., & Simpson, E. R. (1999). Aromatase in aging women. Seminars in Reproductive Endocrinology, 17, 349-358.
19. James, V. H., McNeill, J. M., Lai, L. C., Newton, C. J., Ghilchik, M. W., & Reed, M. J. (1987). Aromatase activity in normal breast and breast tumor tissues: In vivo and in vitro studies. Steroids, 50, 269-279.
20. Lu, Q., Nakmura, J., Savinov, A., Yue, W., Weisz, J., Dabbs, D. J., et al. (1996). Expression of aromatase protein and messenger ribonucleic acid in tumor epithelial cells and evidence of functional significance of locally produced estrogen in human breast cancers. Endocrinology, 137, 3061-3068.
21. Bhatnagar, A. S., Brodie, A. M., Long, B. J., Evans, D. B., & Miller, W. R. (2001). Intracellular aromatase and its relevance to the pharmacological efficacy of aromatase inhibitors. The Journal of Steroid Biochemistry and Molecular Biology, 76, 199-202.
22. Cuzick, J. (2003). Aromatase inhibitors in prevention-data from the ATAC (arimidex, tamoxifen alone or in combination) trial and the design of IBIS-II (the second International Breast Cancer Intervention Study). Recent Results in Cancer Research, 163, 96-103.
23. Coombes, R. C., Hall, E., Gibson, L. J., et al. (2004). A randomized trial of exemestane after two to three years of tamoxifen therapy in postmenopausal women with primary breast cancer. The New England Journal of Medicine, 350, 1081-1092.
24. Howell, A., Cuzick, J., Baum, M., et al. (2005). ATAC Trialists' Group, results of the ATAC (arimidex, tamoxifen, alone or in combination) trial after completion of 5 years' adjuvant treatment for breast cancer. Lancet, 365, 60-62.
25. Herold, C. I., & Blackwell, K. L. (2008). Aromatase inhibitors for breast cancer: Proven efficacy across the spectrum of disease. Clinical Breast Cancer, 8, 50-64.
26. Ono, K., Ohyama, K., & Gamborg, O. L. (1979). Regeneration of the liverwort Marchantia polymorpha L. from protoplasts isolated from cell suspension culture. Plant Science Letters, 14, 225-229.
27. Katoh, K., Ishikawa, M., Miyake, K., Ohta, Y., Hirose, Y., & Iwamura, T. (1980). Nutrient utilization and requirement under photoheterotrophic growth of Marchantiapolymorpha: Improvement of the culture medium. Physiologia Plantarum, 49, 241-247.
28. Hansen, M. B., Nielsen, S. E., & Berg, K. (1989). Re-examination and further development of a precise and rapid dye method for measuring cell growth/cell kill. Journal of Immunological Methods, 119, 203-210.
29. Sun, X.-Z., Zhou, D., & Chen, S. (1997). Autocrine and paracrine actions of breast aromatase. A three-dimensional cell culture study involving aromatase transfected MCF-7 and T-47D cells. The Journal of Steroid Biochemistry and Molecular Biology, 63, 29-36.
30. Smith, P. K., Krohn, R. I., Hermanson, G. T., Mallia, A. K., Gartner, F. H., et al. (1985). Measurement of protein using bicinchoninic acid. Analytical Biochemistry, 150, 76-85.
31. Grube, B. J., Eng, E. T., Kao, Y.-C., Kwon, A., & Chen, S. (2001). White button mushroom phytochemicals inhibit aromatase activity and breast cancer cell proliferation. Journal of Nutrition, 131, 3288-3293.
32. Giuliett, A., Overbergh, L., Valckx, D., Decallonne, B., Bouillon, R., & Mathieu, C. (2001). An overview of real-time quantitative PCR: Applications to quantify cytokine gene expression. Methods, 25, 386-401.
33. Wang, Y., Chan, F. L., Chen, S., & Leung, L. K. (2005). The plant polyphenol butein inhibits testosterone-induced proliferation in breast cancer cells expressing aromatase. Life Sciences, 77, 39-51.
34. 13C-NMR spectra of steroids-a survey and commentary. Organic Magnetic Resonance, 9, 439-464.
35. Shimoda, K., & Hirata, T. (2000). Biotransformation of enones with biocatalysts-two enone reductases from Astasia longa. Journal of Molecular Catalysis B, 8, 255-264.
36. Means, G. D., Mahendroo, M. S., Corbin, C. J., Mathis, J. M., Powell, F. E., Mendelson, C. R., et al. (1989). Structural analysis of the gene encoding human aromatase cytochrome P-450, the enzyme responsible for estrogen biosynthesis. The Journal of Biological Chemistry, 264, 19385-19391.
37. Toda, K., Fukata, J., Onishi, S., Hashimoto, K., Sagara, Y., & Shizuta, Y. (1997). Cooperative regulation of the human aromatase cytochrome P450 gene transcription by placenta-specific cis-acting elements. The Journal of Steroid Biochemistry and Molecular Biology, 61, 211-217.
38. Simpson, E. R., Michael, M. D., Agarwal, V. R., Hinshelwood, M. M., Bulun, S. E., & Zhao, Y. (1997). Cytochromes P450 11: Expression of the CYP19 (aromatase) gene: An unusual case of alternative promoter usage. The FASEB Journal, 11, 29-36.
39. Ciolino, H. P., Wang, T. T. Y., & Sathyamoorthy, N. (2000). Inhibition of aromatase activity and expression in MCF-7 cells by the chemopreventive retinoid N-(4-hydroxy-phenyl)-retinamide. British Journal of Cancer, 83, 333-337.
40. Brodie, A., Lu, Q., & Long, B. (1999). Aromatase and its inhibitors. The Journal of Steroid Biochemistry and Molecular Biology, 69, 205-210.
41. Santner, S. J., Pauley, R. J., Tait, L., Kaseta, J., & Santen, R. J. (1997). Aromatase activity and expression in breast cancer and benign breast tissue stromal cells. The Journal of Clinical Endocrinology and Metabolism, 82, 200-208.
42. Prall, O. W., Rogan, E. M., & Sutherland, R. L. (1998). Oestrogen regulation of cell cycle progression in breast cancer cells. The Journal of Steroid Biochemistry and Molecular Biology, 65, 169-174.
43. De Cupis, A., & Favoni, R. E. (1997). Oestrogen/growth factor cross-talk in breast carcinoma: A specific target for novel antiestrogens. Trends in Pharmacological Sciences, 18, 245-251.
44. Brueggemeier, R. W., Hackett, J. C., & Diaz-Cruz, E. S. (2005). Aromatase inhibitors in the treatment of breast cancer. Endocrine Reviews, 26, 331-345.
45. Carmichael, P. L. (1998). Mechanisms of action of antiestrogens: Relevance to clinical benefits and risks. Cancer Investigation, 16, 604-611.
46. Jordan, V. C. (1995). Tamoxifen: Toxicities and drug resistance during the treatment and prevention of breast cancer. Annual Review of Pharmacology and Toxicology, 35, 195-211.
47. Covey, D. F., & Hood, W. F. (1981). Enzyme-generated intermediates derived from 4-androstene-3, 6, 17-trione and 1, 4, 6-androstatriene- 3, 17-dione cause a time-dependent decrease in human placental aromatase activity. Endocrinology, 108, 1597-1599.
48. Covey, D. F., & Hood, W. F. (1982). Aromatase enzyme catalysis is involved in the potent inhibition of estrogen biosynthesis caused by 4-ace. Molecular Pharmacology, 21, 173-180.
49. Brueggemeier, R. W., Li, P. K., Chen, H. H., Moh, P. P., & Katlic, N. E. (1990). Biochemical and pharmacological development of steroidal inhibitors of aromatase. The Journal of Steroid Biochemistry and Molecular Biology, 37, 379-385.
50. Ghosh, D., Griswold, J., Erman, M., & Pangborn, W. (2009). Structural basis for androgen specificity and oestrogen synthesis in human aromatase. Nature, 457, 219-223.