Characterization of a novel variant (S145C/L311V) of 3α-hydroxysteroid/dihydrodiol dehydrogenase in human liver

Pharmacogenetics

Volumn 9, Issue 6, 1999, Pages 763-771

  Kume, Toshiyuki ^a,b   Iwasa, Harunori ^c   Shiraishi, Hiroaki ^c   Yokoi, Tsuyoshi ^a   Nagashima, Kazuo ^d   Otsuka, Minezo ^b   Terada, Tomoyuki ^e   Takagi, Tetsuya ^f   Hara, Akira ^c   Kamataki, Tetsuya ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b MITSUBISHI TANABE PHARMA CORPORATION   (Japan)

^c GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^d HOKKAIDO UNIVERSITY HOSPITAL   (Japan)

^e OSAKA UNIVERSITY   (Japan)

^f OSAKA UNIVERSITY   (Japan)

Author keywords

Aldo keto reductase family; Ketone containing xenobiotics; Polymorphism

Indexed keywords

ALDEHYDE; ANDROSTANEDIOL; ANDROSTERONE; BETAMETHASONE; CHOLIC ACID; CYSTEINE; DEXAMETHASONE; DIHYDRODIOL DEHYDROGENASE; ENZYME VARIANT; HEXESTROL; INDOMETACIN; LEUCINE; LIVER ENZYME; MEDROXYPROGESTERONE; NALOXONE; NALTREXONE; NUCLEOTIDE; PHENOLPHTHALEIN; PYRIDINE DERIVATIVE; SERINE; VALINE;

AMINO ACID SUBSTITUTION; ARTICLE; BINDING SITE; DNA POLYMORPHISM; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME MECHANISM; ENZYME SUBSTRATE COMPLEX; GENE MUTATION; HUMAN; HUMAN TISSUE; MOLECULAR GENETICS; PRIORITY JOURNAL; STEROID METABOLISM; XENOBIOTIC METABOLISM;

EID: 0033405547     PISSN: 0960314X     EISSN: None     Source Type: Journal    
DOI: 10.1097/00008571-199912000-00011     Document Type: Article

References (40)

1. Ayengar PK, Hayaishi O, Nakajima M, Tomida I. Enzymatic aromatization of 3,5-cyclohexadiene-1,2-diol. Biochim Biophys Acta 1959; 33:111-119.
2. + bound to 3α-hydroxysteroid/ dihydrodiol dehydrogenase. Structure 1997; 5:799-812.
3. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976; 72:248-254.
4. Deyashiki Y, Taniguchi H, Amano T, Nakayama T, Hara A, Sawada H. Structural and functional comparison of two human liver dihydrodiol dehydrogenases associated with 3α-hydroxysteroid dehydrogenase activity. Biochem J 1992; 282:741-746.
5. Deyashiki Y, Ogasawara A, Nakayama T, Nakanishi M, Miyabe Y, Sato K, Hara A. Molecular cloning of two human liver 3α-hydroxysteroid/dihydrodiol dehydrogenase isoenzymes that are identical with chlordecone reductase and bile-acid binder. Biochem J 1994; 299:545-552.
6. Deyashiki Y, Tamada Y, Miyabe Y, Nakanishi M, Matsuura K, Hara A. Expression and kinetic properties of a recombinant 3α-hydroxysteroid/dihydrodiol dehydrogenase isoenzyme of human liver. J Biochem 1995; 118:285-290.
7. Flowers L, Bleczinski WF, Burczynski ME, Harvey RG, Penning TM. Disposition and biological activity of benzo[a]pyrene-7,8-dione. A genotoxic metabolite generated by dihydrodiol dehydrogenase. Biochemistry 1996; 35:13664-13672.
8. Flowers-Geary L, Bleczinski WF, Harvey RG, Penning TM. Cytotoxicity and mutagenicity of polycyclic aromatic hydrocarbon ortho-quinones produced by dihydrodiol dehydrogenase. Chem Biol Interact 1996; 99:55-72.
9. Goldstein JA, Faletto MB, Romkes Sparks M, Sullivan T, Kitareewan S, et al. Evidence that CYP2C19 is the major (S)-mephenytoin 4′-hydroxylase in humans. Biochemistry 1994; 33:1743-1752 .
10. Hara A, Deyashiki Y, Nakagawa M, Nakayama T, Sawada H. Isolation of proteins with carbonyl reductase activity and prostaglandin-9-ketoreductase activity from chicken kidney. J Biochem 1982; 92:1753-1762.
11. Hara A, Taniguchi H, Nakayama T, Sawada H. Purification and properties of multiple forms of dihydrodiol dehydrogenase from human liver. J Biochem 1990; 108:250-254.
12. Hara A, Matsuura K, Tamada Y, Sato K, Miyabe Y, Deyashiki Y, Ishida N. Relationship of human liver dihydrodiol dehydrogenases to hepatic bile-acid-binding protein and an oxidoreductase of human colon cells. Biochem J 1996; 313:373-376.
13. Jez JM, Flynn TG, Penning TM. A new nomenclature for the aldo-keto reductase superfamily. Biochem Pharmacol 1997a; 54:639-647.
14. Jez JM, Bennett MJ, Schlegel BP, Lewis M, Penning TM. Comparative anatomy of the aldo-keto reductase superfamily. Biochem J 1997b; 326:625-656.
15. Khanna M, Qin KN, Wang RW, Cheng KC. Substrate specificity, gene structure, and tissue distribution of multiple human 3α-hydroxysteroid dehydrogenase. J Biol Chem 1995; 270:20162-20168.
16. Kimura S, Umeno M, Skoda RC, Meyer UA, Gonzalez FJ. The human debrisoquine 4-hydroxylase (CYP2D) locus; sequence and identification of the polymorphic CYP2D6 gene, a related gene, and a pseudogene. Am J Hum Genet 1989; 45:889-904.
17. Klein J, Thomas H, Post K, Wörner W, Oesch F. Dihydrodiol dehydrogenase activities of rabbit liver are associated with hydroxysteroid dehydrogenases and aldo-keto reductases. Eur J Biochem 1992; 205:1155-1162.
18. 4. Nature 1970; 227:680-685.
19. Matsuura K, Tamada Y, Deyashiki Y, Miyabe Y, Nakanishi M, Ohya I, Hara A. Activation of human liver 3α-hydroxysteroid dehydrogenase by sulphobromophthalein. Biochem J 1996; 313:179-184.
20. Matsuura K, Hara A, Deyashiki Y, Iwasa H, Kume T, Ishikura S, et al. Roles of the C-terminal domains of human dihydrodiol dehydrogenase isoforms in the binding of substrates and modulators: probing with chimeric enzymes. Biochem J 1998; 336:429-436.
21. Miyabe Y, Matsuura K, Nakayama T, Ohya I, Hara A. A sensitive fluorometric assay for dihydrodiol dehydrogenase. Yakugaku Zasshi 1997; 117:167-177.
22. Mizoguchi T, Nanjo H, Umemura T, Nishinaka T, Iwata C, Imanishi T, et al. A novel dihydrodiol dehydrogenase in bovine liver cytosol: purification and characterization of multiple forms of dihydrodiol dehydrogenase. J Biochem 1992; 112:523-529.
23. Molowa DT, Shayne AG, Guzelain PS. Purification and characterization of chlordecone reductase from human liver. J Biol Chem 1986; 261:12624-12627.
24. Oesch F, Glatt HR, Vogel K, Siedel A, Pltrovic P, Platt KL, Dihydrodiol dehydrogenase: a new level of control by both sequestration of proximate and inactivation of ultimate carcinogens. In: Greim H, Jung R, Kramer M, Marquardt H, Oesch F, editors. Biochemical basis of carcinogenesis. New York: Raven Press; 1984, pp, 23-31.
25. 2 by a human liver 3α-hydroxysteroid/dihydrodiol dehydrogenase isozyme. Biochim Biophys Acta 1994; 1215:59-65.
26. Ohara H, Miyabe Y, Deyashiki Y, Matsuura K, Hara A. Reduction of drug ketones by dihydrodiol dehydrogenases, carbonyl reductase and aldehyde reductase of human liver. Biochem Pharmacol 1995; 50:221-227.
27. Penning TM, Simithgall TE, Askonas LJ, Sharp RB. Rat liver 3α-hydroxysteroid dehydrogenase. Steroids 1986; 47:221-247.
28. Penning TM, Sharp RB. Characterization of dihydrodiol dehydrogenase in human liver and lung. Carcinogenesis 1990; 11:1203-1208.
29. Sambrook J, Fritsch EF, Maniatis T. Molecular cloning: a laboratory manual, 2nd edn. Cold Spring Harbor: Cold Spring Harbor Laboratory Press; 1989.
30. Sanger F, Nicklen S, Coulson AR. DNA sequencing with chain-terminating inhibitors. Proc Natl Acad Sci USA 1977; 74:5463-5467.
31. Sawada H, Hara A, Nakayama T, Nakagawa M, Inoue Y, Hasebe K, Zhang YP. Mouse liver dihydrodiol dehydrogenases. Identity of the predominant and a minor form with 17β-hydroxysteroid dehydrogenase and aldehyde reductase. Biochem Pharmacol 1988; 37:453-458.
32. Shiraishi H, Ishikura S, Matsuura K, Deyashiki Y, Ninomiya M, Sakai S, Hara A. Sequence of human dihydrodiol dehydrogenase isoform (AKR1C2) cDNA and tissue distribution of its mRNA. Biochem J 1998; 334:399-405.
33. Smithgall TE, Harvey RG, Penning TM. Regio-and stereospecificity of homogeneous 3α-hydroxysteroid-dihydrodiol dehydrogenase for trans-dihydrodiol metabolites of polycylic aromatic hydrocarbons. J Biol Chem 1986; 261:6184-6191.
34. 359 allelic variant in the tolbutamide polymorphism. Pharmacogenetics 1996; 6:341-349.
35. Towbin H, Staehelin T, Gordon J. Electrophoretic transfer of proteins from polyacrylamide gels to ntirocellulose sheets: procedures and some applications. Proc Natl Acad Sci USA 1979; 76:4350-4355.
36. Vogel K, Bentley P, Platt KL, Oesch F. Rat liver cytoplasmic dihydrodiol dehydrogenase: purification to apparent homogeneity and properties. J Biol Chem 1980; 255:9621-9625.
37. Wilson DK, Tarle I, Petrash JM, Quiocho FA. Refined 1.8 Å structure of human aldose reductase complexed with the potent inhibitor zopolrestat. Proc Natl Acad Sci USA 1993; 90:9847-9851.
38. Wilson DK, Nakano T, Petrash JM, Quiocho FA. 1.7 Å structure of FR-1, a fibroblast growth factor-induced member of the aldo-keto reductase family, complexed with coenzyme and inhibitor. Biochemistry 1995; 34:14323-14330.
39. Winters CJ, Molowa DT, Guzelian PS. Isolation and characterization of cloned cDNAs encoding human liver chlordecone reductase. Biochemistry 1990; 29:1080-1087.
40. Wörner W, Oesch F. Identity of dihydrodiol dehydrogenase and 3α-hydroxysteroid dehydrogenase in rat but not in rabbit liver cytosol. FEBS Lett 1984; 170:263-267.