Human cytochrome P450-dependent differential metabolism among three 2α-substituted-1α,25-dihydroxyvitamin D3 analogs

Journal of Steroid Biochemistry and Molecular Biology

Volumn 133, Issue 1, 2013, Pages 84-92

  Yasuda, Kaori ^a   Ikushiro, Shinichi ^a   Kamakura, Masaki ^a   Takano, Masashi ^b   Saito, Nozomi ^c   Kittaka, Atsushi ^b   Chen, Tai C ^d   Ohta, Miho ^e   Sakaki, Toshiyuki ^a  

^a TOYAMA PREFECTURAL UNIVERSITY   (Japan)

^b TEIKYO UNIVERSITY   (Japan)

^c HOKKAIDO UNIVERSITY   (Japan)

^d BOSTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^e Soai University   (Japan)

Author keywords

CYP24A1; CYP3A4; Cytochrome P450; Kinetics; Metabolism; Vitamin D analog

Indexed keywords

CALCITRIOL DERIVATIVE; CYTOCHROME P450; CYTOCHROME P450 24A1; CYTOCHROME P450 3A4; KETOCONAZOLE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; HUMAN; HUMAN TISSUE; HYDROXYLATION; LIVER; LIVER MICROSOME; METABOLISM; METABOLITE;

CALCITRIOL; CHOLECALCIFEROL; CYTOCHROME P-450 CYP3A; HUMANS; INTESTINE, SMALL; KINETICS; MICROSOMES; MICROSOMES, LIVER; RECEPTORS, CALCITRIOL; RECOMBINANT PROTEINS; STEROID HYDROXYLASES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84867010817     PISSN: 09600760     EISSN: 18791220     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2012.09.006     Document Type: Article

References (40)

1. J.L. Osborn, G.G. Schwartz, D.C. Smith, R. Bahnson, R. Day, and D.L. Trump Phase II trial of oral 1,25-dihydroxyvitamin D (calcitriol) in hormone refractory prostate cancer Urologic Oncology 1 5 1995 195 198
2. C. Gross, T. Stamey, S. Hancock, and D. Feldman Treatment of early recurrent prostate cancer with 1,25-dihydroxyvitamin D3 (calcitriol) Journal of Urology 159 6 1998 2035 2039 discussion 2039-2040
3. L. Binderup, S. Latini, E. Binderup, C. Bretting, M. Calverley, and K. Hansen 20-epi-Vitamin D3 analogues: a novel class of potent regulators of cell growth and immune responses Biochemical Pharmacology 42 8 1991 1569 1575
4. J.E. Bishop, E.D. Collins, W.H. Okamura, and A.W. Norman Profile of ligand specificity of the vitamin D binding protein for 1 alpha,25- dihydroxyvitamin D3 and its analogs Journal of Bone and Mineral Research 9 8 1994 1277 1288
5. R. Bouillon, W.H. Okamura, and A.W. Norman Structure-function relationships in the vitamin D endocrine system Endocrine Reviews 16 2 1995 200 257
6. S. Yamada, M. Shimizu, and K. Yamamoto Structure-function relationships of vitamin D including ligand recognition by the vitamin D receptor Medicinal Research Reviews 23 1 2003 89 115
7. S. Masuda, and G. Jones Promise of vitamin D analogues in the treatment of hyperproliferative conditions Molecular Cancer Therapeutics 5 4 2006 797 808
8. R.R. Sicinski, P. Rotkiewicz, A. Kolinski, W. Sicinska, J.M. Prahl, C.M. Smith, and F.H. DeLuca 2-Ethyl and 2-ethylidene analogues of 1alpha, 25-dihydroxy-19-norvitamin D(3): synthesis, conformational analysis, biological activities, and docking to the modeled rVDR ligand binding domain Journal of Medicinal Chemistry 45 16 2002 3366 3380
9. H.F. DeLuca Overview of general physiologic features and functions of vitamin D American Journal of Clinical Nutrition 80 6 Suppl. 2004 1689S 1696S
10. A. Kittaka, Y. Suhara, H. Takayanagi, T. Fujishima, M. Kurihara, and H. Takayama A concise and efficient route to 2alpha-(omega-hydroxyalkoxy)-1alpha, 25-dihydroxyvi tam in D3: remarkably high affinity to vitamin D receptor Organic Letters 2 17 2000 2619 2622
11. Y. Suhara, K.I. Nihei, H. Tanigawa, T. Fujishima, K. Konno, K. Nakagawa, T. Okano, and H. Takayama Syntheses and biological evaluation of novel 2alpha-substituted 1alpha,25-dihydroxyvitamin D3 analogues Bioorganic and Medicinal Chemistry Letters 10 10 2000 1129 1132
12. Y. Suhara, K.I. Nihei, M. Kurihara, A. Kittaka, K. Yamaguchi, T. Fujishima, K. Konno, N. Miyata, and H. Takayama Efficient and versatile synthesis of novel 2alpha-substituted 1alpha,25-dihydroxyvitamin D(3) analogues and their docking to vitamin D receptors Journal of Organic Chemistry 66 26 2001 8760 8771
13. N. Saito, Y. Suhara, M. Kurihara, T. Fujishima, S. Honzawa, H. Takayanagi, T. Kozono, M. Matsumoto, M. Ohmori, N. Miyata, H. Takayama, and A. Kittaka Design and efficient synthesis of 2 alpha-(omega-hydroxyalkoxy)-1 alpha,25-dihydroxyvitamin D3 analogues, including 2-epi-ED-71 and their 20-epimers with HL-60 cell differentiation activity Journal of Organic Chemistry 69 22 2004 7463 7471
14. E. Takahashi, K. Nakagawa, Y. Suhara, A. Kittaka, K. Nihei, K. Konno, H. Takayama, K. Ozono, and T. Okano Biological activities of 2alpha-substituted analogues of 1alpha,25-dihydroxyvitamin D3 in transcriptional regulation and human promyelocytic leukemia (HL-60) cell proliferation and differentiation Biological and Pharmaceutical Bulletin 29 11 2006 2246 2250
15. A. Kittaka Structural refinement of seco-steroidal skeleton and the biological activity through nuclear receptors Yakugaku Zasshi 128 9 2008 1235 1250
16. K. Ono, A. Yoshida, N. Saito, T. Fujishima, S. Honzawa, Y. Suhara, S. Kishimoto, T. Sugiura, K. Waku, H. Takayama, and A. Kittaka Efficient synthesis of 2-modified 1alpha,25-dihydroxy-19-norvitamin D3 with Julia olefination: high potency in induction of differentiation on HL-60 cells Journal of Organic Chemistry 68 19 2003 7407 7415
17. M.A. Arai, K. Takeyama, S. Ito, S. Kato, T.C. Chen, and A. Kittaka High-throughput system for analyzing ligand-induced cofactor recruitment by vitamin D receptor Bioconjugate Chemistry 18 3 2007 614 620
18. T.C. Chen, K.S. Persons, S. Zheng, J. Mathieu, M.F. Holick, Y.F. Lee, B. Bao, M.A. Arai, and A. Kittaka Evaluation of C-2-substituted 19-nor-1alpha,25-dihydroxyvitamin D3 analogs as therapeutic agents for prostate cancer Journal of Steroid Biochemistry and Molecular Biology 103 3-5 2007 717 720
19. J.N. Flanagan, S. Zheng, K.C. Chiang, A. Kittaka, T. Sakaki, S. Nakabayashi, X. Zhao, R.A. Spanjaard, K.S. Persons, J.S. Mathieu, M.F. Holick, and T.C. Chen Evaluation of 19-nor-2alpha-(3-hydroxypropyl)-1alpha,25- dihydroxyvitamin D3 as a therapeutic agent for androgen-dependent prostate cancer Anticancer Research 29 9 2009 3547 3553
20. T.C. Chen, and A. Kittaka Novel vitamin d analogs for prostate cancer therapy ISRN Urology 2011 2011 301490
21. Y. Ohyama, K. Ozono, M. Uchida, T. Shinki, S. Kato, T. Suda, O. Yamamoto, M. Noshiro, and Y. Kato Identification of a vitamin D-responsive element in the 5′-flanking region of the rat 25-hydroxyvitamin D3 24-hydroxylase gene Journal of Biological Chemistry 269 14 1994 10545 10550
22. T. Sakaki, N. Sawada, Y. Nonaka, Y. Ohyama, and K. Inouye Metabolic studies using recombinant escherichia coli cells producing rat mitochondrial CYP24 CYP24 can convert 1alpha,25-dihydroxyvitamin D3 to calcitroic acid European Journal of Biochemistry 262 1 1999 43 48
23. T. Sakaki, N. Sawada, K. Komai, S. Shiozawa, S. Yamada, K. Yamamoto, Y. Ohyama, and K. Inouye Dual metabolic pathway of 25-hydroxyvitamin D3 catalyzed by human CYP24 European Journal of Biochemistry 267 20 2000 6158 6165
24. N. Sawada, T. Kusudo, T. Sakaki, S. Hatakeyama, M. Hanada, D. Abe, M. Kamao, T. Okano, M. Ohta, and K. Inouye Novel metabolism of 1 alpha,25-dihydroxyvitamin D3 with C24-C25 bond cleavage catalyzed by human CYP24A1 Biochemistry 43 15 2004 4530 4537
25. D. Abe, T. Sakaki, T. Kusudo, A. Kittaka, N. Saito, Y. Suhara, T. Fujishima, H. Takayama, H. Hamamoto, M. Kamakura, M. Ohta, and K. Inouye Metabolism of 2 alpha-propoxy-1 alpha,25-dihydroxyvitamin D3 and 2 alpha-(3-hydroxypropoxy)-1 alpha, 25-dihydroxyvitamin D3 by human CYP27A1 and CYP24A1 Drug Metabolism and Disposition: The Biological Fate of Chemicals 33 6 2005 778 784
26. N. Urushino, S. Nakabayashi, M.A. Arai, A. Kittaka, T.C. Chen, K. Yamamoto, K. Hayashi, S. Kato, M. Ohta, M. Kamakura, S. Ikushiro, and T. Sakaki Kinetic studies of 25-hydroxy-19-nor-vitamin D3 and 1 alpha,25-dihydroxy-19-nor- vitamin D3 hydroxylation by CYP27B1 and CYP24A1 Drug Metabolism and Disposition: The Biological Fate of Chemicals 35 9 2007 1482 1488
27. Y. Ono, H. Watanabe, I. Taira, K. Takahashi, J. Ishihara, S. Hatakeyama, and N. Kubodera Synthesis of putative metabolites of 1alpha,25-dihydroxy-2beta- (3-hydroxypropoxy)vitamin D(3) (ED-71) Steroids 71 7 2006 529 540
28. M. Akiyoshi-Shibata, T. Sakaki, Y. Ohyama, M. Noshiro, K. Okuda, and Y. Yabusaki Further oxidation of hydroxycalcidiol by calcidiol 24-hydroxylase. A study with the mature enzyme expressed in Escherichia coli European Journal of Biochemistry 224 2 1994 335 343
29. T. Kusudo, T. Sakaki, D. Abe, T. Fujishima, A. Kittaka, H. Takayama, S. Hatakeyama, M. Ohta, and K. Inouye Metabolism of A-ring diastereomers of 1alpha,25-dihydroxyvitamin D3 by CYP24A1 Biochemical and Biophysical Research Communications 321 4 2004 774 782
30. Y. Imae, A. Manaka, N. Yoshida, Y. Ishimi, T. Shinki, E. Abe, T. Suda, K. Konno, H. Takayama, and S. Yamada Biological activities of 24-fluoro-1 alpha,25-dihydroxyvitamin D-2 and its 24-epimer Biochimica et Biophysica Acta 1213 3 1994 302 308
31. T. Fujishima, L. Zhaopeng, K. Konno, K. Nakagawa, T. Okano, K. Yamaguchi, and H. Takayama Highly potent cell differentiation-inducing analogues of 1alpha,25-dihydroxyvitamin D3: synthesis and biological activity of 2-methyl-1,25-dihydroxyvitamin D3 with side-chain modifications Bioorganic and Medicinal Chemistry 9 2 2001 525 535
32. T.C. Chen, A.K. Turner, and M.F. Holick A method for the determination of the circulating concentration of 1,25-dihydroxyvitamin D The Journal of Nutritional Biochemistry 1 6 1990 320 327
33. S.J. Collins, F.W. Ruscetti, R.E. Gallagher, and R.C. Gallo Normal functional characteristics of cultured human promyelocytic leukemia cells (HL-60) after induction of differentiation by dimethylsulfoxide Journal of Experimental Medicine 149 4 1979 969 974
34. T. Sakaki, N. Sawada, K. Takeyama, S. Kato, and K. Inouye Enzymatic properties of mouse 25-hydroxyvitamin D3 1 alpha-hydroxylase expressed in Escherichia coli European Journal of Biochemistry 259 3 1999 731 738
35. M. Harmata, and C. Barnes Molecular clefts. 2. An analogue of Kagan's ether as a molecular cleft: synthesis and clathrate formation with ethyl acetate Tetrahedron Letters 31 1990 1825 1828
36. M.G. Soars, B. Burchell, and R.J. Riley In vitro analysis of human drug glucuronidation and prediction of in vivo metabolic clearance Journal of Pharmacology and Experimental Therapeutics 301 1 2002 382 390
37. Y. Xu, T. Hashizume, M.C. Shuhart, C.L. Davis, W.L. Nelson, T. Sakaki, T.F. Kalhorn, P.B. Watkins, E.G. Schuetz, and K.E. Thummel Intestinal and hepatic CYP3A4 catalyze hydroxylation of 1alpha,25-dihydroxyvitamin D(3): implications for drug-induced osteomalacia Molecular Pharmacology 69 1 2006 56 65
38. D. Iglesias-Gato, S. Zheng, J.N. Flanagan, L. Jiang, A. Kittaka, T. Sakaki, K. Yamamoto, T. Itoh, N.K. Lebrasseur, G. Norstedt, and T.C. Chen Substitution at carbon 2 of 19-nor-1alpha,25-dihydroxyvitamin D(3) with 3-hydroxypropyl group generates an analogue with enhanced chemotherapeutic potency in PC-3 prostate cancer cells Journal of Steroid Biochemistry and Molecular Biology 2011
39. T. Okano, N. Tsugawa, S. Masuda, A. Takeuchi, T. Kobayashi, Y. Takita, and Y. Nishii Regulatory activities of 2 beta-(3-hydroxypropoxy)-1 alpha,25-dihydroxyvitamin D3, a novel synthetic vitamin D3 derivative, on calcium metabolism Biochemical and Biophysical Research Communications 163 3 1989 1444 1449
40. N. Kubodera, and S. Hatakeyama Process development for the practical production of eldecalcitol by linear, convergent and biomimetic syntheses Anticancer Research 32 1 2012 303 309