A new steroidal 5,7-diene derivative, 3β-hydroxyandrosta-5,7-diene-17β-carboxylic acid, shows potent anti-proliferative activity

Steroids

Volumn 75, Issue 3, 2010, Pages 230-239

  Kim, Tae Kang ^a   Chen, Jianjun ^b   Li, Wei ^b   Zjawiony, Jordan ^c,d   Miller, Duane ^b   Janjetovic, Zorica ^a   Tuckey, Robert C ^e   Slominski, Andrzej ^a  

^a Center for Cancer Research   (United States)

^b UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

^c UNIVERSITY OF MISSISSIPPI   (United States)

^d UNIVERSITY OF MISSISSIPPI   (United States)

^e UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

3 Hydroxyandrosta 5,7 diene 17 carboxylic acid; 5,7 Dienes; Keratinocytes; Melanocytes; Melanoma; Skin

Indexed keywords

3BETA HYDROXYANDROST 5 ENE 17BETA CARBOXYLIC ACID; 3BETA HYDROXYANDROSTA 5,7 DIENE 17BETA CARBOXYLIC ACID; ALKADIENE; ANTINEOPLASTIC AGENT; CALCITRIOL; CYCLIN E; EPIDERMAL GROWTH FACTOR RECEPTOR; MESSENGER RNA; METHYL 3BETA HYDROANDROSTA 5,7 DIENE 17BETA CARBOXYLATE; OXYGEN; PREGNENOLONE DERIVATIVE; PROTEIN BCL 2; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CHEMOTHERAPY; CANCER INHIBITION; CANCER INVASION; CELL CULTURE; CELL CYCLE G0 PHASE; CELL CYCLE G1 PHASE; CELL PROLIFERATION; CELL STRAIN HL 60; CONTROLLED STUDY; CULTURE MEDIUM; DNA SYNTHESIS INHIBITION; DRUG POTENCY; DRUG SPECIFICITY; DRUG STRUCTURE; DRUG SYNTHESIS; EPIDERMIS; GENE EXPRESSION REGULATION; GROWTH INHIBITION; HUMAN; HUMAN CELL; KERATINOCYTE; LEUKEMIA CELL; MELANOCYTE; MELANOMA CELL; NONHUMAN; OXIDATION; PROTEIN EXPRESSION; SKIN FIBROBLAST;

ANDROSTADIENES; ANIMALS; ANTINEOPLASTIC AGENTS; CARBOXYLIC ACIDS; CELL PROLIFERATION; CELLS, CULTURED; CRICETINAE; CRICETULUS; CYCLIN E; HL-60 CELLS; HUMANS; KERATINOCYTES; MELANOCYTES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; ONCOGENE PROTEINS; PROTEIN PRECURSORS; PROTO-ONCOGENE PROTEINS C-BCL-2; RECEPTOR, EPIDERMAL GROWTH FACTOR; STEROIDS;

CRICETINAE;

EID: 76349100272     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2009.12.004     Document Type: Article

References (35)

1. Tint G.S., Irons M., Elias E.R., Batta A.K., Frieden R., Chen T.S., et al. Defective cholesterol biosynthesis associated with the Smith-Lemli-Opitz syndrome. N Engl J Med 330 (1994) 107-113
2. Shackleton C.H., Roitman E., and Kelley R. Neonatal urinary steroids in Smith-Lemli-Opitz syndrome associated with 7-dehydrocholesterol reductase deficiency. Steroids 64 (1999) 481-490
3. Shackleton C., Roitman E., Guo L.W., Wilson W.K., and Porter F.D. Identification of 7(8) and 8(9) unsaturated adrenal steroid metabolites produced by patients with 7-dehydrosterol-delta7-reductase deficiency (Smith-Lemli-Opitz syndrome). J Steroid Biochem Mol Biol 82 (2002) 225-232
4. Slominski A., Zjawiony J., Wortsman J., Semak I., Stewart J., Pisarchik A., et al. A novel pathway for sequential transformation of 7-dehydrocholesterol and expression of the P450scc system in mammalian skin. Eur J Biochem 271 (2004) 4178-4188
5. Guryev O., Carvalho R.A., Usanov S., Gilep A., and Estabrook R.W. A pathway for the metabolism of vitamin D3: unique hydroxylated metabolites formed during catalysis with cytochrome P450scc (CYP11A1). Proc Natl Acad Sci U S A 100 (2003) 14754-14759
6. Slominski A.T., Zmijewski M.A., Semak I., Sweatman T., Janjetovic Z., Li W., et al. Sequential metabolism of 7-dehydrocholesterol to steroidal 5,7-dienes in adrenal glands and its biological implication in the skin. PLoS One 4 (2009) e4309
7. Holick M.F. Vitamin D: a millennium perspective. J Cell Biochem 88 (2003) 296-307
8. Holick M.F. McCollum award lecture, Vitamin D-new horizons for the 21st century. Am J Clin Nutr 60 (1994) 619-630
9. Tian X.Q., and Holick M.F. A liposomal model that mimics the cutaneous production of vitamin D3. Studies of the mechanism of the membrane-enhanced thermal isomerization of previtamin D3 to vitamin D3. J Biol Chem 274 (1999) 4174-4179
10. Kamradt J., Rafi L., Mitschele T., Meineke V., Gartner B.C., Wolfgang T., et al. Analysis of the vitamin D system in cutaneous malignancies. Recent Results Cancer Res 164 (2003) 259-269
11. Bikle D.D. Vitamin D regulated keratinocyte differentiation. J Cell Biochem 92 (2004) 436-444
12. Wiseman H. Vitamin D is a membrane antioxidant. Ability to inhibit iron-dependent lipid peroxidation in liposomes compared to cholesterol, ergosterol and tamoxifen and relevance to anticancer action. FEBS Lett 326 (1993) 285-288
13. Chen T.C., Holick M.F., Lokeshwar B.L., Burnstein K.L., and Schwartz G.G. Evaluation of vitamin D analogs as therapeutic agents for prostate cancer. Recent Results Cancer Res 164 (2003) 273-288
14. Anderson C.M., Buzaid A.C., and Legha S.S. Systemic treatments for advanced cutaneous melanoma. Oncology (Williston Park) 9 (1995) 1149-1158
15. Serrone L., Zeuli M., Sega F.M., and Cognetti F. Dacarbazine-based chemotherapy for metastatic melanoma: thirty-year experience overview. J Exp Clin Cancer Res 19 (2000) 21-34
16. Gray-Schopfer V., Wellbrock C., and Marais R. Melanoma biology and new targeted therapy. Nature 445 (2007) 851-857
17. Zmijewski M.A., Li W., Zjawiony J.K., Sweatman T.W., Chen J., Miller D.D., et al. Synthesis and photo-conversion of androsta- and pregna-5,7-dienes to vitamin D3-like derivatives. Photochem Photobiol Sci 7 (2008) 1570-1576
18. Zmijewski M.A., Li W., Zjawiony J.K., Sweatman T.W., Chen J., Miller D.D., et al. Photo-conversion of two epimers (20R and 20S) of pregna-5,7-diene-3beta, 17alpha, 20-triol and their bioactivity in melanoma cells. Steroids 74 (2009) 218-228
19. Marwah P., Marwah A., and Lardy H.A. Microwave induced selective enolization of steroidal ketones efficient acetylation of sterols in semisolid state. Tetrahedron 59 (2003) 2273-2287
20. Guo L.W., Wilson W.K., Pang J., and Shackleton C.H. Chemical synthesis of 7- and 8-dehydro derivatives of pregnane-3,17alpha,20-triols, potential steroid metabolites in Smith-Lemli-Opitz syndrome. Steroids 68 (2003) 31-42
21. Antonucci R., Bernstein S., Giancola D., and Sax K.J. Δ5,7-steroids. VI. The preparation of Δ5,7-steroidal hormones. J Org Chem 16 (1951) 1126-1133
22. Dey S., and Mal D. Total synthesis of BE-23254, a chlorinated angucycline antibiotic. Tetrahedron Lett 46 (2005) 5483-5486
23. Slominski A., Zbytek B., Pisarchik A., Slominski R.M., Zmijewski M.A., and Wortsman J. CRH functions as a growth factor/cytokine in the skin. J Cell Physiol 206 (2006) 780-791
24. Zbytek B., Janjetovic Z., Tuckey R.C., Zmijewski M.A., Sweatman T.W., Jones E., et al. 20-Hydroxyvitamin D3, a product of vitamin D3 hydroxylation by cytochrome P450scc, stimulates keratinocyte differentiation. J Invest Dermatol 128 (2008) 2271-2280
25. Fischer T.W., Zmijewski M.A., Zbytek B., Sweatman T.W., Slominski R.M., Wortsman J., et al. Oncostatic effects of the indole melatonin and expression of its cytosolic and nuclear receptors in cultured human melanoma cell lines. Int J Oncol 29 (2006) 665-672
26. Mahdavi M., and Yazdanparast R. Gnidilatimonoein from Daphne mucronata induces differentiation and apoptosis in leukemia cell lines. Arch Pharm Res 30 (2007) 177-181
27. Li M., Chen B., Monteiro S., and Rustum A.M. Mechanism of base-catalyzed autooxidation of corticosteroids containing 20-keto-21-hydroxyl side chain. Tetrahedron Lett 50 (2009) 4575-4581
28. Velluz L., Petit A., Pesez M., and Berret R. Saponification of the acetate of desoxycorticosterone. Bull. Soc. Chim. France (1947) 123-125
29. Herzig P.T., and Ehrenstein M. Investigations on steroids. XIV. Studies in the series of the adrenal cortical hormones: dehydration of 6,21-diacetoxyallopregnane-5-ol-3,20-dione. J. Org. Chem 16 (1951) 1050-1063
30. Spina C.S., Tangpricha V., Uskokovic M., Adorinic L., Maehr H., and Holick M.F. Vitamin D and cancer. Anticancer Res 26 (2006) 2515-2524
31. Holick M.F. Vitamin D deficiency. N Engl J Med 357 (2007) 266-281
32. Bikle D.D., Oda Y., and Xie Z. Vitamin D and skin cancer: a problem in gene regulation. J Steroid Biochem Mol Biol 97 (2005) 83-91
33. Bikle D.D. What is new in vitamin D: 2006-2007. Curr Opin Rheumatol 19 (2007) 383-388
34. Tait A.D., Hodge L.C., and Allen W.R. The biosynthesis of 3 beta-hydroxy-5,7-androstadien-17-one by the horse fetal gonad. FEBS Lett 182 (1985) 107-110
35. Marcos J., Guo L.W., Wilson W.K., Porter F.D., and Shackleton C. The implications of 7-dehydrosterol-7-reductase deficiency (Smith-Lemli-Opitz syndrome) to neurosteroid production. Steroids 69 (2004) 51-60