Activation of human liver 3α-hydroxysteroid dehydrogenase by clofibrate derivatives

Journal of Pharmacology and Experimental Therapeutics

Volumn 285, Issue 3, 1998, Pages 1096-1103

  Matsuura, Kazuya ^a   Hara, Akira ^a   Kato, Makiko ^a   Deyashiki, Yoshihiro ^a   Miyabe, Yoshiyuki ^a   Ishikura, Syuhei ^a   Sugiyama, Tadashi ^b   Katagiri, Yoshihiro ^b  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^b GIFU UNIVERSITY HOSPITAL   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3ALPHA HYDROXYSTEROID DEHYDROGENASE; ALDEHYDE REDUCTASE; ANTILIPEMIC AGENT; BEZAFIBRATE; BILE ACID; BROMSULFOPHTHALEIN; CLINOFIBRATE; CLOFIBRATE DERIVATIVE; CLOFIBRIC ACID; ENZYME ACTIVATOR; FENOFIBRIC ACID; ISOENZYME; PHENOXYACETIC ACID; STEROID HORMONE;

ARTICLE; BINDING SITE; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME BINDING; ENZYME KINETICS; ENZYME MECHANISM; HUMAN; HUMAN TISSUE; LIVER; PH; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ALCOHOL OXIDOREDUCTASES; ANTILIPEMIC AGENTS; BINDING SITES; CLOFIBRATE; CLOFIBRIC ACID; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME ACTIVATION; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROXYSTEROID DEHYDROGENASES; LIVER; PROCETOFEN;

EID: 0031837837     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (43)

1. Amet Y, Simon B, Quemener E, Mangin P, Floch HH and Abalan JH (1992) Partial purification of 3α- and 3β-hydroxysteroid dehydrogenases from human hyperplastic prostate. Comparison between the two enzyme. J Steroid Biochem Mol Biol 41:689-692.
2. Abshagen U, Bablok W, Koch K, Lang PD, Schmidt HAE, Senn M and Stork H (1979) Disposition pharmacokineties of bezafibrate in man. Eur J Clin Pharmacol 16:31-38.
3. +. Biochemistry 35:10702-10711.
4. Cayen MN (1980) Metabolic disposition of antihyperlipidemic agents in man and laboratory animals. Drug Metab Rev 11:291-323.
5. Cayen MN, Ferdinandi ES, Greselin E, Robinson WT and Dvornik D (1977) Clofibrate and clofibric acid: Comparison of the metabolic disposition in rats and dogs. J Pharmacol Exp Ther 200:33-43.
6. Cornish-Bowden A (1995) Fundamentals of Enzyme Kinetics. Portland Press, London.
7. Deyashiki Y, Ogasawara A, Nakayama T, Nakanishi M, Miyabe Y and Hara A (1994) Molecular cloning of two human liver 3α-hydroxysteroid/dihydrodiol dehydrogenase isoenzymes that are identical with chlordecone reductase and bile acid binder. Biochem J 299:545-552.
8. Deyashiki Y, Tamada Y, Miyabe Y, Nakanishi M, Matsuura K and Hara A (1995) Expression and kinetic properties of a recombinant 3α-hydroxysteroid/dihydrodiol dehydrogenase isoenzyme of human liver. J Biochem (Tokyo) 118:285-290.
9. Deyashiki Y, Taniguchi H, Amano T, Nakayama T, Hara A and Sawada H (1992) Structural and functional comparison of two human liver dihydrodiol dehydrogenases associated with 3α-hydroxysteroid dehydrogenase activity. Biochem J 282: 741-746.
10. Elsom LF, Hawkins DR and Chasseaud LF (1976) Identification of a major metabolite of the new hypolipidemic agents, isopropyl 2-[4′(p-chlorobenzoyl)phenoxy]-2-methylpropionate (procetofene) in humans by gas chromatography-mass spectrometry. J Chromatogr 123:463-467.
11. +-dependent 3α-hydroxysteroid dehydrogenase from mouse liver cytosol. J Biochem (Tokyo) 103:1027-1034.
12. Hara A, Matsuura K, Tamada Y, Sato K, Miyabe Y, Deyashiki Y and Ishida N (1996) Relationship of human liver dihydrodiol dehydrogenases to hepatic bile-acid-binding protein and an oxidoreductase of human colon cells. Biochem J 313:373-376.
13. Hara A, Taniguchi H, Nakayama T and Sawada H (1990) Purification and properties of multiple forms of dihydrodiol dehydrogenase from human liver. J Biochem (Tokyo) 108:250-254.
14. Harrison DH, Bohren KM, Ringe D, Petsko GA and Gabbay KH (1994) An Anion binding site in human aldose reductase: Mechanistic implications for the binding of citrate, cacodylate, and glucose-6-phosphate. Biochemistry 33:2011-2020.
15. Isaacs JT, Brenddler CB and Walsh PC (1983) Changes in the metabolism of dihydrotestosterone in the hyperplastic human prostate. J Clin Endocrinol Metabol 56:139-143.
16. Jez JM, Flynn TG and Penning TM (1997) A new nomenclature for the aldo-keto reductase superfamily. Biochem Pharmacol 54:639-647.
17. Jez JM, Schlegel BP and Penning TM (1996) Characterization of the substrate binding site in rat liver 3α-hydroxysteroid/dihydrodiol dehydrogenase. The roles of tryptophans in ligand binding and protein fluorescence. J Biol Chem 271:30190-30198.
18. Khanna M, Qin K-N, Wang RW and Cheng KC (1995) Substrate specificity, gene structure, and tissue-specific distribution of multiple human 3α-hydroxysteroid dehydrogenase. J Biol Chem 270:20162-20168.
19. Kusama H, Nishiyama M, Matsubara Y and Ikeda S (1988) Pharmaceutical investigation of bezafibrate, a hypolipidemic agent (2). Mechanism of the hypolipidemic action of bezafibrate in rats. Folia Pharmacol Jpn 92:181-191.
20. Lombardo ME, Hakky SI, Hall MK and Hudson PB (1992) In vitro studies on the effect of cofactors on the 5α-reductase and 3α- and 3β-hydroxysteroid reductase activities in the hyperplastic human prostate. J Urol 148:1605-1610.
21. Mahendroo MS, Cala KM and Russell DW (1996) 5α-Reduced androgens play a key role in murine parturition. Mol Endocrinol 10:380-392.
22. Majewska MD, Harrison NI, Schwartz RD, Barker JL and Paul SM (1986) Steroid hormone metabolites are barbiturate-like modulators of the GABA receptor. Science 232:1004-1007.
23. Martini L, Melcangi RC and Maggi R (1993) Androgen and progesterone metabolism in the central and peripheral nervous system. J Steroid Biochem Mol Biol 47:195-205.
24. Matsuura K, Tamada Y, Deyashiki Y, Miyabe Y, Nakanishi M, Ohya I and Hara A (1996) Activation of human liver 3α-hydroxysteroid dehydrogenase by sulphobromophthalein. Biochem J 313:179-184.
25. Matsuura K, Tamada Y, Sato K, Iwasa H, Miwa G, Deyashiki Y and Hara A (1997) Involvement of two residues (Lys-270 and Arg-276) of human liver 3α-hydroxysteroid dehydrogenase in NADP(H) binding and activation by sulphobromophthalein: Sitedirected mutagenesis and kinetic analysis. Biochem J 322:89-93.
26. Nakhla AM, Ding VD, Khan MS, Romas NA, Rhodes L, Smith RG and Rosener W (1995) 5α-Androstane-3α,17β-diol is a hormone: stimulation of cAMP accumulation in human and dog prostate. J Clin Endocrinol Metab 80:2259-2262.
27. Nishiyama M, Kusama H, Miyagi M, Ikeda S, Jin Y and Esumi Y (1988) Studies on metabolic fate of bezafibrate in rats and dogs. Iyakuhin Kenkyu 19:788-815.
28. 2 by a human liver 3α-hydroxysteroid dehydrogenase isoenzyme. Biochim Biophys Acta 1215:59-69.
29. Ohara H, Miyabe Y, Deyashiki Y, Matsuura K and Hara A (1995) Reduction of drug ketones by dihydrodiol dehydrogenases, carbonyl reductase and aldehyde reductase of human liver. Biochem Pharmacol 50:221-227.
30. Penning TM, Smithgall TE, Askonas LJ and Sharp RB (1986) Rat liver 3α-hydroxysteroid dehydrogenase. Steroids 47:221-247.
31. Penning TM, Pawlowski JE, Schlegel BP, Jez JM, Lin H-K, Hoog SS, Bennett MJ and Lewis M (1996) Mammalian 3α-hydroxysteroid dehydrogenases. Steroids 61: 508-523.
32. Platt KL and Oesch F (1977) An improved synthesis of trans-5,6-dihydroxy-1,3-cyclohexadiene (trans-1,2-dihydroxy-1,2-dihydrobenzene). Synthesis 7:440-450.
33. Qin K-N, New MI and Cheng K-C (1993) Molecular cloning of multiple cDNA encoding human enzymes structurally related to 3α-hydroxysteroid dehydrogenase. J Steroid Biochem Mol Biol 46:673-679.
34. Segel IH (1975) Enzyme Kinetics. John Wiley & Sons, New York.
35. Stolz A, Hammond L, Lou H, Takikawa H, Ronk M and Shively JE (1993) cDNA cloning and expression of the human hepatic bile acid-binding protein. A member of the monomeric reductase gene family. J Biol Chem 268:10448-10457.
36. Stolz A, Takikawa H, Sugiyama Y, Kuhlenkamp J and Kaplowitz N (1987) 3α-hydroxysteroid dehydrogenase activity of the Y′ bile acid binders in rat liver cytosol. Identification, kinetics and physiological significance. J Clin Invest 79: 427-434.
37. Tomkins G (1956) Enzymatic mechanisms of hormone metabolism 1. Oxidation and reduction of the steroid nucleus. Recent Prog Hormone Res 12:125-133.
38. Takikawa H, Fujimoto M, Nishikawa K and Yamada M (1992) Purification of 3α-hydroxysteroid and 3β-hydroxysteroid dehydrogenases from human liver cytosol. Hepatology 16:365-371.
39. Thorp JM (1962) Experimental evaluation of an orally active combination of androsterone with ethyl chlorophenoxyisobutyrale. Lancet 1:1323-1326.
40. Trapp T, Tunn S and Krieg M (1992) Purification and properties of the 5α-dihydrotestosterone 3α(β)-hydroxysteroid dehydrogenase from human prostatic cytosol. J Steroid Biochem Mol Biol 42:321-327.
41. Usui E and Okuda K (1986) Identification of 7α,12α-dihydroxy-5β-chlestan-3-one 3α-reductase as 3α-hydroxysteroid dehydrogenase. Biochim Biophys Acta 877: 158-166.
42. Winters CJ, Molowa DT and Guzelian PS (1990) Isolation and characterization of cloned cDNAs encoding human liver chlordecone reductase. Biochemistry 29: 1080-1087.
43. Wörner W and Oesch F (1984) Identity of dihydrodiol dehydrogenase and 3α-hydroxysteroid dehydrogenase in rat but not in rabbit liver cytosol. FEBS Lett 170:263-267.