Metabolism of 20-epimer of 1α,25-dihydroxyvitamin D3 by CYP24: Species-based difference between humans and rats

Biochemical and Biophysical Research Communications

Volumn 309, Issue 4, 2003, Pages 885-892

  Kusudo, Tatsuya ^a   Sakaki, Toshiyuki ^a   Abe, Daisuke ^a   Fujishima, Toshie ^b   Kittaka, Atsushi ^b   Takayama, Hiroaki ^b   Ohta, Miho ^c   Inouye, Kuniyo ^a  

^a KYOTO UNIVERSITY   (Japan)

^b TEIKYO UNIVERSITY   (Japan)

^c Koshien Junior College   (Japan)

Author keywords

20 Epi vitamin D; CYP24; Cytochrome P450; Metabolism of vitamin D; Species based difference; Vitamin D analog

Indexed keywords

1,24,25 TRIHYDROXYCOLECALCIFEROL; CALCITRIOL; CYTOCHROME P450; DRUG METABOLITE; HYDROXYL GROUP; VITAMIN D RECEPTOR;

ARTICLE; CONTROLLED STUDY; DEMETHYLATION; DRUG RECEPTOR BINDING; EPIMER; ESCHERICHIA COLI; GENE EXPRESSION SYSTEM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAT; SPECIES DIFFERENCE; VITAMIN D METABOLISM;

ESCHERICHIA COLI;

EID: 0141788235     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbrc.2003.08.097     Document Type: Article

References (29)

1. Bouillon R., Okamura W.H., Norman A.W. Structure-function relationships in the vitamin D endocrine system. Endocr. Rev. 16:1995;200-257.
2. 3 and its analogs. J. Bone Miner. Res. 9:1994;1277-1288.
3. Yamada S., Shimizu M., Yamamoto K. Structure-function relationships of vitamin D including ligand recognition by the vitamin D receptor. Med. Res. Rev. 23:2003;89-115.
4. 3 analogues: a novel class of potent regulators of cell growth and immune responses. Biochem. Pharmacol. 42:1991;1569-1575.
5. 3. Biochem. Pharmacol. 49:1995;621-624.
6. 3 and its 20-epi analogues (MC 1288, MV 1301, KH 1060), on clonal keratinocyte growth: evidence for differentiation of keratinocyte stem cells and analysis of the modulatory effects of cytokines. Br. J. Pharmacol. 120:1997;1119-1127.
7. 3, is in part due to its metabolism into stable intermediary metabolites with significant biological activity. J. Steroid Biochem. Mol. Biol. 71:1999;111-121.
8. Konno K., Fujishima T., Maki S., Liu Z., Miura D., Chokki M., Ishizuka S., Yamaguchi K., Kan Y., Kurihara M., Miyata N., Smith C., DeLuca H.F., Takayama H. Synthesis, biological evaluation, and conformational analysis of A-ring diastereomers of 2-methyl-1,25-dihydroxyvitamin D(3) and their 20-epimers: unique activity profiles depending on the stereochemistry of the A-ring and at C-20. J. Med. Chem. 43:2000;4247-4265.
9. 3 and its 20-epimer. Bioorg. Med. Chem. 8:2000;123-134.
10. Fujishima T., Konno K., Nakagawa K., Tanaka M., Okano T., Kurihara M., Miyata N., Takayama H. Synthesis and biological evaluation of all A-ring stereoisomers of 5,6-trans-2-methyl-1,25-dihydroxyvitamin D(3) and their 20-epimers: possible binding modes of potent A-ring analogues to vitamin D receptor. Chem. Biol. 8:2001;1011-1024.
11. 3. Steroids. 66:2001;277-285.
12. Liu Y.Y., Nguyen C., Ali Gardezi S.A., Schnirer I., Peleg S., Ali Gradezi S. Differential regulation of heterodimerization by 1alpha,25-dihydroxyvitamin D(3) and its 20-epi analog. Steroids. 66:2001;203-212.
13. Yamamoto K., Masuno H., Choi M., Nakashima K., Taga T., Ooizumi H., Umesono K., Sicinska W., VanHooke J., DeLuca H.F., Yamada S. Three-dimensional modeling of and ligand docking to vitamin D receptor ligand binding domain. Proc. Natl. Acad. Sci. USA. 97:2000;1467-1472.
14. 3-24-hydroxylase, a multicatalytic enzyme. Biochemistry. 35:1996;8465-8472.
15. 3 catalyzed by human CYP24. Eur. J. Biochem. 267:2000;6158-6165.
16. Akiyoshi-Shibata M., Sakaki T., Ohyama Y., Noshiro M., Okuda K., Yabusaki Y. Further oxidation of hydroxycalcidiol by calcidiol 24-hydroxylase. Eur. J. Biochem. 224:1994;335-343.
17. Sakaki T., Sawada N., Nonaka Y., Ohyama Y., Inouye K. Metabolic studies using recombinant Escherichia coli cells producing rat mitochondrial CYP24. Eur. J. Biochem. 262:1999;43-48.
18. 3-23-hydroxylase, a renal enzyme in several animal species. Arch. Biochem. Biophys. 250:1986;86-93.
19. Hayashi K., Akiyoshi-Shibata M., Sakaki T., Yabusaki Y. Rat CYP24 catalyses 23S-hydroxylation of 26,26,26,27,27,27-hexafluorocalcitriol in vitro. Xenobiotica. 28:1998;457-463.
20. 3 by CYP24: Species-based difference between humans and rats. Biochem. Pharmacol. 65:2003;1957-1965.
21. Blattner F.R., Plunkett III G., Bloch C.A., Perna N.T., Burland V., Rilley M., Vides C., Glasner J.D., Rode C.K., Mayhew G.F., Gregor J., Davis N.W., Kirkpatrick H.A., Goeden M.A., Rose D.J., Mau B., Shao Y. The complete genomesequence of Escherichia coli K-12. Science. 277:1997;1453-1462.
22. Omura T., Sato T.R. The carbon monoxide-binding pigment of liver microsomes, II. Solubilization, purification, and properties. J. Biol. Chem. 239:1964;2379-2385.
23. 3 analogs and their 3-epimers on human promyelocytic leukemia (HL-60) cell differentiation and apoptosis. Steroids. 66:2001;327-337.
24. 3-1α-hydroxylase) of bovine kidney mitochondria. Biochem. Biophys. Res. Commun. 105:1982;320-327.
25. Lowry O.H., Rosebrough N.J., Farr A.L., Randall R.J. Protein measurement with the folin phenol reagent. J. Biol. Chem. 193:1951;265-275.
26. 3 into new metabolites with significant biological activity: studies in rat osteosarcoma cells (UMR 106and ROS17/2.8). J. Cell. Biochem. 82:2001;599-609.
27. Shyadehi A.Z., Lamb D.C., Kelly S.L., Kelly D.E., Schunck W.H., Wright J.N., Corina D., Akhtar M. The mechanism of the acyl-carbon bond cleavage reaction catalyzed by recombinant sterol 14 alpha-demethylase of Candida albicans (other names are: lanosterol 14alpha-demethylase, P-45014DM, and CYP51). J. Biol. Chem. 271:1996;12445-12450.
28. Rochel N., Wurtz J.M., Mitschler A., Klaholz B., Moras D. The crystal structure of the nuclear receptor for vitamin D bound to its natural ligand. Mol. Cell. 5:2000;173-179.
29. Tocchini-Valentini G., Rochel N., Wurtz J.M., Mitschler A., Moras D. Crystal structures of the vitamin D receptor complexed to superagonist 20-epi ligands. Proc. Natl. Acad. Sci. USA. 98:2001;5491-5496.