Cytochrome P450scc-dependent metabolism of 7-dehydrocholesterol in placenta and epidermal keratinocytes

International Journal of Biochemistry and Cell Biology

Volumn 44, Issue 11, 2012, Pages 2003-2018

  Slominski, Andrzej T ^a   Kim, Tae Kang ^a   Chen, Jianjun ^a   Nguyen, Minh N ^b   Li, Wei ^a   Yates, Charles R ^a   Sweatman, Trevor ^a   Janjetovic, Zorica ^a   Tuckey, Robert C ^b  

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

^b UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

Author keywords

7 Dehydrocholesterol; 7 Dehydropregnenolone; CYP11A1; Keratinocytes; Placenta

Indexed keywords

7 DEHYDROCHOLESTEROL; 7 DEHYDROPROGESTERONE; CHOLESTEROL MONOOXYGENASE (SIDE CHAIN CLEAVING); DYDROGESTERONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CELL PROLIFERATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; HUMAN; HUMAN TISSUE; KERATINOCYTE; MASS SPECTROMETRY; MICROSOME; NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY;

ADOLESCENT; ADULT; ANIMALS; CHOLESTEROL SIDE-CHAIN CLEAVAGE ENZYME; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEHYDROCHOLESTEROLS; EPIDERMIS; FEMALE; FORSKOLIN; HUMANS; KERATINOCYTES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; METABOLIC NETWORKS AND PATHWAYS; MICROSOMES; MITOCHONDRIA; PLACENTA; PREGNANCY; PREGNENOLONE; SUS SCROFA; TIME FACTORS; YOUNG ADULT;

EID: 84866432399     PISSN: 13572725     EISSN: 18785875     Source Type: Journal    
DOI: 10.1016/j.biocel.2012.07.027     Document Type: Article

References (52)

1. J.R. Arthur, and G.S. Boyd The effect of inhibitors of protein synthesis on cholesterol side-chain cleavage in the mitochondria of luteinized rat ovaries European Journal of Biochemistry 49 1974 117 127
2. D.D. Bikle Vitamin D: an ancient hormone Experimental Dermatology 20 2011 7 13
3. H.S. Bose, M.A. Baldwin, and W.L. Miller Evidence that StAR and MLN64 act on the outer mitochondrial membrane as molten globules Endocrine Research 26 2000 629 637
4. J. Chen, C.M. Li, J. Wang, S. Ahn, Z. Wang, and Y. Lu Synthesis and antiproliferative activity of novel 2-aryl-4-benzoyl-imidazole derivatives targeting tubulin polymerization Bioorganic and Medicinal Chemistry 19 2011 4782 4795
5. J. Chen, Z. Wang, C.M. Li, Y. Lu, P.K. Vaddady, and B. Meibohm Discovery of novel 2-aryl-4-benzoyl-imidazoles targeting the colchicines binding site in tubulin as potential anticancer agents Journal of Medicinal Chemistry 53 2010 7414 7427
6. C. Djerassi, J. Romo, and G. Rosenkranz Steroidal sapogenins. VIII. Steroids. XVIII. Synthesis of Δ7,9(11)-allopregnadien-3β-ol-20-one from diosgenin and from Δ5-pregnen-3β-ol-20-one Journal of Organic Chemistry 16 1951 754 760
7. L. Dorfman Ultraviolet absorption of steroids Chemical Reviews 53 1953 47 144
8. O. Guryev, R.A. Carvalho, S. Usanov, A. Gilep, and R.W. Estabrook A pathway for the metabolism of vitamin D3: unique hydroxylated metabolites formed during catalysis with cytochrome P450scc (CYP11A1) Proceedings of the National Academy of Sciences of the United States of America 100 2003 14754 14759
9. M.F. Holick Vitamin D: a millenium perspective Journal of Cellular Biochemistry 88 2003 296 307
10. R. Hume, R.W. Kelly, P.L. Taylor, and G.S. Boyd The catalytic cycle of cytochrome P-450scc and intermediates in the conversion of cholesterol to pregnenolone European Journal of Biochemistry 140 1984 583 591
11. Z. Janjetovic, A.A. Brozyna, R.C. Tuckey, T.K. Kim, M.N. Nguyen, and W. Jozwicki High basal NF-kappaB activity in nonpigmented melanoma cells is associated with an enhanced sensitivity to vitamin D3 derivatives British Journal of Cancer 105 2011 1874 1884
12. Z. Janjetovic, R.C. Tuckey, M.N. Nguyen, E.M. Thorpe Jr., and A.T. Slominski 20,23-Dihydroxyvitamin D3, novel P450scc product, stimulates differentiation and inhibits proliferation and NF-kappaB activity in human keratinocytes Journal of Cellular Physiology 223 2010 36 48
13. Z. Janjetovic, M.A. Zmijewski, R.C. Tuckey, D.A. DeLeon, M.N. Nguyen, and L.M. Pfeffer 20-Hydroxycholecalciferol, product of vitamin D3 hydroxylation by P450scc, decreases NF-kappaB activity by increasing IkappaB alpha levels in human keratinocytes PLoS One 4 2009 e5988
14. B.A. Janowski, P.J. Willy, T.R. Devi, J.R. Falck, and D.J. Mangelsdorf An oxysterol signalling pathway mediated by the nuclear receptor LXR alpha Nature 383 1996 728 731
15. T.K. Kim, J. Chen, W. Li, J. Zjawiony, D. Miller, and Z. Janjetovic A new steroidal 5,7-diene derivative, 3beta-hydroxyandrosta-5,7-diene-17beta- carboxylic acid, shows potent anti-proliferative activity Steroids 75 2010 230 239
16. H. Ma, and T.M. Penning Conversion of mammalian 3alpha-hydroxysteroid dehydrogenase to 20alpha-hydroxysteroid dehydrogenase using loop chimeras: changing specificity from androgens to progestins Proceedings of the National Academy of Sciences of the United States of America 96 1999 11161 11166
17. J. Marcos, L.W. Guo, W.K. Wilson, F.D. Porter, and C. Shackleton The implications of 7-dehydrosterol-7-reductase deficiency (Smith-Lemli-Opitz syndrome) to neurosteroid production Steroids 69 2004 51 60
18. W.L. Miller, and R.J. Auchus The molecular biology, biochemistry, and physiology of human steroidogenesis and its disorders Endocrine Reviews 32 2011 81 151
19. M.N. Nguyen, A. Slominski, W. Li, Y.R. Ng, and R.C. Tuckey Metabolism of vitamin d2 to 17,20,24-trihydroxyvitamin d2 by cytochrome p450scc (CYP11A1) Drug Metabolism and Disposition: The Biological Fate of Chemicals 37 2009 761 767
20. M.J. Nowaczyk, and J.S. Waye The Smith-Lemli-Opitz syndrome: a novel metabolic way of understanding developmental biology, embryogenesis, and dysmorphology Clinical Genetics 59 2001 375 386
21. B. Ruan, W.K. Wilson, and G.J. Schroepfer Jr. An improved synthesis of (20R,22R)-cholest-5-ene-3beta, 20,22-triol, an intermediate in steroid hormone formation and an activator of nuclear orphan receptor LXR alpha Steroids 64 1999 385 395
22. C. Shackleton, E. Roitman, L.W. Guo, W.K. Wilson, and F.D. Porter Identification of 7(8) and 8(9) unsaturated adrenal steroid metabolites produced by patients with 7-dehydrosterol-delta7-reductase deficiency (Smith-Lemli-Opitz syndrome) Journal of Steroid Biochemistry and Molecular Biology 82 2002 225 232
23. C.H. Shackleton, E. Roitman, and R. Kelley Neonatal urinary steroids in Smith-Lemli-Opitz syndrome associated with 7-dehydrocholesterol reductase deficiency Steroids 64 1999 481 490
24. A. Slominski, G. Ermak, and M. Mihm ACTH receptor, CYP11A1, CYP17 and CYP21A2 genes are expressed in skin Journal of Clinical Endocrinology and Metabolism 81 1996 2746 2749
25. A. Slominski, I. Semak, J. Wortsman, J. Zjawiony, W. Li, and B. Zbytek An alternative pathway of vitamin D metabolism. Cytochrome P450scc (CYP11A1)-mediated conversion to 20-hydroxyvitamin D2 and 17,20-dihydroxyvitamin D2 FEBS Journal 273 2006 2891 2901
26. A. Slominski, I. Semak, J. Zjawiony, J. Wortsman, M.N. Gandy, and J. Li Enzymatic metabolism of ergosterol by cytochrome p450scc to biologically active 17alpha, 24-dihydroxyergosterol Chemistry and Biology 12 2005 931 939
27. A. Slominski, I. Semak, J. Zjawiony, J. Wortsman, W. Li, and A. Szczesniewski The cytochrome P450scc system opens an alternate pathway of vitamin D3 metabolism FEBS Journal 272 2005 4080 4090
28. A. Slominski, J. Wortsman, R. Paus, P.M. Elias, D.J. Tobin, and K.R. Feingold Skin as an endocrine organ: implications for its function Drug Discovery Today: Disease Mechanisms 5 2008 137 144
29. A. Slominski, J. Zjawiony, J. Wortsman, I. Semak, J. Stewart, and A. Pisarchik A novel pathway for sequential transformation of 7-dehydrocholesterol and expression of the P450scc system in mammalian skin European Journal of Biochemistry 271 2004 4178 4188
30. A.T. Slominski, Z. Janjetovic, B.E. Fuller, M.A. Zmijewski, R.C. Tuckey, and M.N. Nguyen Products of vitamin D3 or 7-dehydrocholesterol metabolism by cytochrome P450scc show anti-leukemia effects, having low or absent calcemic activity PLoS One 5 2010 e9907
31. A.T. Slominski, T.-K. Kim, H.Z. Shehabi, I. Semak, E.K.Y. Tang, and M.N. Nguyen In vivo evidence for a novel pathway of vitamin D3 metabolism initiated by P450scc and modified by CYP27B1 FASEB Journal 2012 10.1096/fj.12-208975
32. A.T. Slominski, T.K. Kim, Z. Janjetovic, R.C. Tuckey, R. Bieniek, and J. Yue 20-Hydroxyvitamin D2 is a noncalcemic analog of vitamin D with potent antiproliferative and prodifferentiation activities in normal and malignant cells American Journal of Physiology-Cell Physiology 300 2011 C526 C541
33. A.T. Slominski, W. Li, S.K. Bhattacharya, R.A. Smith, P.L. Johnson, and J. Chen Vitamin D analogs 17,20S(OH)2pD and 17,20R(OH)2pD are noncalcemic and exhibit antifibrotic activity Journal of Investigative Dermatology 131 2011 1167 1169
34. A.T. Slominski, M.A. Zmijewski, I. Semak, T. Sweatman, Z. Janjetovic, and W. Li 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
35. A.T. Slominski, M.A. Zmijewski, C. Skobowiat, B. Zbytek, R.M. Slominski, and J.D. Steketee Sensing the environment: regulation of local and global homeostasis by the skin's neuroendocrine system Advances in Anatomy, Embryology and Cell Biology 212 2012 1 115
36. D.W. Smith, L. Lemli, and J.M. Opitz A newly recognized syndrome of multiple congenital anomalies Journal of Pediatrics 64 1964 210 217
37. N. Strushkevich, F. MacKenzie, T. Cherkesova, I. Grabovec, S. Usanov, and H.W. Park Structural basis for pregnenolone biosynthesis by the mitochondrial monooxygenase system Proceedings of the National Academy of Sciences of the United States of America 108 2011 10139 10143
38. A.D. Tait, L.C. Hodge, and W.R. Allen Biosynthesis of 3 beta-hydroxy-5,7-pregnadien-20-one by the horse fetal gonad FEBS Letters 153 1983 161 164
39. G.S. Tint, M. Irons, E.R. Elias, A.K. Batta, R. Frieden, and T.S. Chen Defective cholesterol biosynthesis associated with the Smith-Lemli-Opitz syndrome New England Journal of Medicine 330 1994 107 113
40. R.C. Tuckey Progesterone synthesis by the human placenta Placenta 26 2005 273 281
41. R.C. Tuckey, H.S. Bose, I. Czerwionka, and W.L. Miller Molten globule structure and steroidogenic activity of N-218 MLN64 in human placental mitochondria Endocrinology 145 2004 1700 1707
42. R.C. Tuckey, and K.J. Cameron Catalytic properties of cytochrome P-450scc purified from the human placenta: comparison to bovine cytochrome P-450scc Biochimica et Biophysica Acta 1163 1993 185 194
43. R.C. Tuckey, and K.J. Cameron Human placental cholesterol side-chain cleavage: enzymatic synthesis of (22R)-20 alpha, 22-dihydroxycholesterol Steroids 58 1993 230 233
44. R.C. Tuckey, W. Li, J.K. Zjawiony, M.A. Zmijewski, M.N. Nguyen, and T. Sweatman Pathways and products for the metabolism of vitamin D3 by cytochrome P450scc FEBS Journal 275 2008 2585 2596
45. R.C. Tuckey, M.N. Nguyen, and A. Slominski Kinetics of vitamin D3 metabolism by cytochrome P450scc (CYP11A1) in phospholipid vesicles and cyclodextrin International Journal of Biochemistry and Cell Biology 40 2008 2619 2626
46. R.C. Tuckey, W. Li, H.Z. Shehabi, Z. Janjetovic, M.N. Nguyen, and T.K. Kim Production of 22-hydroxy-metabolites of vitamin D3 by cytochrome P450scc (CYP11A1) and analysis of their biological activities on skin cells Drug Metabolism and Disposition 39 2011 1577 1588
47. R.C. Tuckey, S.T. Woods, and M. Tajbakhsh Electron transfer to cytochrome P-450scc limits cholesterol-side-chain-cleavage activity in the human placenta European Journal of Biochemistry 244 1997 835 839
48. S.T. Woods, J. Sadleir, T. Downs, T. Triantopoulos, M.J. Headlam, and R.C. Tuckey Expression of catalytically active human cytochrome p450scc in Escherichia coli and mutagenesis of isoleucine-462 Archives of Biochemistry and Biophysics 353 1998 109 115
49. B. Zbytek, Z. Janjetovic, R.C. Tuckey, M.A. Zmijewski, T.W. Sweatman, and E. Jones 20-Hydroxyvitamin D3, a product of vitamin D3 hydroxylation by cytochrome P450scc, stimulates keratinocyte differentiation Journal of Investigative Dermatology 128 2008 2271 2280
50. M.A. Zmijewski, W. Li, J. Chen, T.K. Kim, J.K. Zjawiony, and T.W. Sweatman Synthesis and photochemical transformation of 3beta, 21-dihydroxypregna-5,7-dien-20-one to novel secosteroids that show anti-melanoma activity Steroids 76 2011 193 203
51. M.A. Zmijewski, W. Li, J.K. Zjawiony, T.W. Sweatman, J. Chen, and D.D. Miller Synthesis and photo-conversion of androsta- and pregna-5,7-dienes to vitamin D3-like derivatives Photochemical & Photobiological Sciences 7 2008 1570 1576
52. M.A. Zmijewski, W. Li, J.K. Zjawiony, T.W. Sweatman, J. Chen, and D.D. Miller 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