메뉴 건너뛰기




Volumn 32, Issue 3, 2004, Pages 305-313

Stereo- and regioselectivity account for the diversity of dehydroepiandrosterone (DHEA) metabolites produced by liver microsomal cytochromes P450

Author keywords

[No Author keywords available]

Indexed keywords

ANDROSTENEDIONE; CYTOCHROME P450; CYTOCHROME P450 3A4; CYTOCHROME P450 3A5; PRASTERONE;

EID: 1342281163     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.32.3.305     Document Type: Article
Times cited : (62)

References (34)
  • 1
    • 0344603632 scopus 로고    scopus 로고
    • Endogenous levels of dehydroepiandrosterone sulfate, but not other sex hormones, are associated with depressed mood in older women: The Rancho Bernardo Study
    • Barrett-Connor E, von Muhlen D, Laughlin GA, and Kripke A (1999) Endogenous levels of dehydroepiandrosterone sulfate, but not other sex hormones, are associated with depressed mood in older women: the Rancho Bernardo Study. J Am Geriatr Soc 47:685-691.
    • (1999) J Am Geriatr Soc , vol.47 , pp. 685-691
    • Barrett-Connor, E.1    Von Muhlen, D.2    Laughlin, G.A.3    Kripke, A.4
  • 3
    • 0000155390 scopus 로고
    • 3H-3 beta-hydroxyandrost-5-en-17-one sulfate
    • 3H-3 beta-hydroxyandrost-5-en-17-one sulfate. J Biol Chem 238:1656-1660.
    • (1963) J Biol Chem , vol.238 , pp. 1656-1660
    • Burstein, S.1    Dorfman, R.I.2
  • 4
    • 0030896764 scopus 로고    scopus 로고
    • The role of cytochrome P450 17-alpha-hydroxylase and 3-beta-hydroxysteroid dehydrogenase in the integration of gonadal and adrenal steroidogenesis via the delta 5 and delta 4 pathways of steroidogenesis in mammals
    • Conley AJ and Bird IM (1997) The role of cytochrome P450 17-alpha-hydroxylase and 3-beta-hydroxysteroid dehydrogenase in the integration of gonadal and adrenal steroidogenesis via the delta 5 and delta 4 pathways of steroidogenesis in mammals. Biol. Reprod. 56:789-799.
    • (1997) Biol Reprod , vol.56 , pp. 789-799
    • Conley, A.J.1    Bird, I.M.2
  • 7
    • 0028912205 scopus 로고
    • Expression of cytochrome P450 3A5 in Escherichia coli: Effects of 5′ modification, purification, spectral characterization, reconstitution conditions and catalytic activities
    • Gillam EM, Guo Z, Ueng YF, Yamazaki H, Cock I, Reilly PEB, Hooper WED, and Guengerich FP (1995) Expression of cytochrome P450 3A5 in Escherichia coli: effects of 5′ modification, purification, spectral characterization, reconstitution conditions and catalytic activities. Arch Biochem Biophys 317:374-384.
    • (1995) Arch Biochem Biophys , vol.317 , pp. 374-384
    • Gillam, E.M.1    Guo, Z.2    Ueng, Y.F.3    Yamazaki, H.4    Cock, I.5    Reilly, P.E.B.6    Hooper, W.E.D.7    Guengerich, F.P.8
  • 8
    • 0022577938 scopus 로고
    • 5 on the formation of products in cytochrome P-450-catalyzed reactions
    • 5 on the formation of products in cytochrome P-450-catalyzed reactions. Drug Metab Dispos 14:89-96.
    • (1986) Drug Metab Dispos , vol.14 , pp. 89-96
    • Gorsky, L.D.1    Coon, M.J.2
  • 9
    • 0025860978 scopus 로고
    • Oxidation of dihydropyridine calcium channel blockers and analogues by human liver cytochrome P-450 IIIA4
    • Guengerich FP, Brian WR, Iwasaki M, Sari MA, Baarnhielm C, and Berntsson P (1991) Oxidation of dihydropyridine calcium channel blockers and analogues by human liver cytochrome P-450 IIIA4. J Med Chem 34:1838-1844.
    • (1991) J Med Chem , vol.34 , pp. 1838-1844
    • Guengerich, F.P.1    Brian, W.R.2    Iwasaki, M.3    Sari, M.A.4    Baarnhielm, C.5    Berntsson, P.6
  • 11
    • 0029011908 scopus 로고
    • The age of dehydroepiandrosterone
    • Herbert J (1995) The age of dehydroepiandrosterone. Lancet 345:1193-1194.
    • (1995) Lancet , vol.345 , pp. 1193-1194
    • Herbert, J.1
  • 14
    • 0037131879 scopus 로고    scopus 로고
    • Genetic contribution to variable human CYP3A-mediated metabolism
    • Lamba JK, Lin YS, Schuetz EG, and Thummel KE (2002) Genetic contribution to variable human CYP3A-mediated metabolism. Adv Drug Deliv Rev 54:1271-1294.
    • (2002) Adv Drug Deliv Rev , vol.54 , pp. 1271-1294
    • Lamba, J.K.1    Lin, Y.S.2    Schuetz, E.G.3    Thummel, K.E.4
  • 15
    • 0032031874 scopus 로고    scopus 로고
    • Modulation of methylnitrosourea-induced breast cancer in Sprague Dawley rats by dehydroepiandrosterone: Dose-dependent inhibition, effects of limited exposure, effects on peroxisomal enzymes and lack of effects on levels of Ha-Ras mutations
    • Lubet RA, Gordon GB, Prough RA, Lei XD, You M, Wang Y, Grubbs CJ, Steele VE, Kelloff GJ, Thomas CF, and Moon RD (1998) Modulation of methylnitrosourea-induced breast cancer in Sprague Dawley rats by dehydroepiandrosterone: dose-dependent inhibition, effects of limited exposure, effects on peroxisomal enzymes and lack of effects on levels of Ha-Ras mutations. Cancer Res 58:921-926.
    • (1998) Cancer Res , vol.58 , pp. 921-926
    • Lubet, R.A.1    Gordon, G.B.2    Prough, R.A.3    Lei, X.D.4    You, M.5    Wang, Y.6    Grubbs, C.J.7    Steele, V.E.8    Kelloff, G.J.9    Thomas, C.F.10    Moon, R.D.11
  • 16
    • 0036160014 scopus 로고    scopus 로고
    • Ergosteroids. VI. Metabolism of dehydroepiandrosterone by rat liver in vitro: A liquid chromatographic-mass spectrometric study
    • Marwah A, Marwah P, and Lardy H (2002) Ergosteroids. VI. Metabolism of dehydroepiandrosterone by rat liver in vitro: a liquid chromatographic-mass spectrometric study. J Chromatogr 767:285-299.
    • (2002) J Chromatogr , vol.767 , pp. 285-299
    • Marwah, A.1    Marwah, P.2    Lardy, H.3
  • 17
    • 77957003927 scopus 로고
    • The preparation and properties of microsomal TPNH-cytochrome c reductase from pig liver
    • Masters BSS, Willams CH Jr, and Kamin H (1967) The preparation and properties of microsomal TPNH-cytochrome c reductase from pig liver. Methods Enzymol 10:565-573.
    • (1967) Methods Enzymol , vol.10 , pp. 565-573
    • Masters, B.S.S.1    Willams Jr., C.H.2    Kamin, H.3
  • 18
    • 1342275144 scopus 로고    scopus 로고
    • Species differences in metabolism of DHEA
    • Michael KK, Robinzon B, and Prough RA (2002) Species differences in metabolism of DHEA. Drug Metab Rev 34 (Suppl 1):54.
    • (2002) Drug Metab Rev , vol.34 , Issue.SUPPL. 1 , pp. 54
    • Michael, K.K.1    Robinzon, B.2    Prough, R.A.3
  • 20
    • 0003417385 scopus 로고
    • Effect of dehydroepiandrosterone on rodent liver microsomal, mitochondrial and peroxisomal proteins
    • (Kalimi M and Regelson W, eds), Walter de Gruyter, New York
    • Prough RA, Wu HQ, and Milewich L (1990) Effect of dehydroepiandrosterone on rodent liver microsomal, mitochondrial and peroxisomal proteins, in The Biologic Role of Dehydroepiandrosterone (DHEA) (Kalimi M and Regelson W, eds) pp 253-279, Walter de Gruyter, New York.
    • (1990) The Biologic Role of Dehydroepiandrosterone (DHEA) , pp. 253-279
    • Prough, R.A.1    Wu, H.Q.2    Milewich, L.3
  • 22
    • 0026638358 scopus 로고
    • Hepatocarcinogenicity of dehydroepiandrosterone in the rat
    • Rao MS, Subbarao V, Yeldandi AV, and Reddy JK (1992) Hepatocarcinogenicity of dehydroepiandrosterone in the rat. Cancer Res 52:2977-2979.
    • (1992) Cancer Res , vol.52 , pp. 2977-2979
    • Rao, M.S.1    Subbarao, V.2    Yeldandi, A.V.3    Reddy, J.K.4
  • 24
    • 0038198788 scopus 로고    scopus 로고
    • Negative regulation of CYP2C11 by DHEA and peroxisome proliferators: Identification of the negative regulatory region of the gene
    • Ripp SL, Falkner KC, Pendleton ML, Tamasi V, and Prough RA (2003) Negative regulation of CYP2C11 by DHEA and peroxisome proliferators: identification of the negative regulatory region of the gene. Mol Pharmacol 64:113-122.
    • (2003) Mol Pharmacol , vol.64 , pp. 113-122
    • Ripp, S.L.1    Falkner, K.C.2    Pendleton, M.L.3    Tamasi, V.4    Prough, R.A.5
  • 25
    • 0036236065 scopus 로고    scopus 로고
    • Induction of CYP3A expression by DHEA: Involvement of the pregnane X receptor
    • Ripp SL, Fitzpatrick JL, Peterson JM, and Prough RA (2002) Induction of CYP3A expression by DHEA: involvement of the pregnane X receptor. Drug Metab Dispos 30:570-575.
    • (2002) Drug Metab Dispos , vol.30 , pp. 570-575
    • Ripp, S.L.1    Fitzpatrick, J.L.2    Peterson, J.M.3    Prough, R.A.4
  • 26
    • 0037445848 scopus 로고    scopus 로고
    • Glucocorticoids inhibit interconversion of 7-hydroxy and 7-oxo metabolites of dehydroepiandrosterone: A role for 11β-hydroxysteroid dehydrogenases?
    • Robinzon B, Michael KK, Ripp SL, Winters SJ, and Prough RA (2003) Glucocorticoids inhibit interconversion of 7-hydroxy and 7-oxo metabolites of dehydroepiandrosterone: a role for 11β-hydroxysteroid dehydrogenases? Arch Biochem Biophys 412:251-258.
    • (2003) Arch Biochem Biophys , vol.412 , pp. 251-258
    • Robinzon, B.1    Michael, K.K.2    Ripp, S.L.3    Winters, S.J.4    Prough, R.A.5
  • 27
    • 0034044068 scopus 로고    scopus 로고
    • Bioreactor systems in drug metabolism: Synthesis of cytochrome P450-generated metabolites
    • Rushmore TH, Reider PJ, Slaughter D, Assang C, and Shou M (2000) Bioreactor systems in drug metabolism: synthesis of cytochrome P450-generated metabolites. Metab Engin 2:115-125.
    • (2000) Metab Engin , vol.2 , pp. 115-125
    • Rushmore, T.H.1    Reider, P.J.2    Slaughter, D.3    Assang, C.4    Shou, M.5
  • 30
    • 0022578632 scopus 로고
    • Hormonal regulation of P450scc (20,22-desmolase) and P450c17 (17-hydroxylase/17,20-lyase) in cultured human granulosa cells
    • Voutilainen R, Tapanainen J, Chung BC, Matteson KJ, and Miller WL (1986) Hormonal regulation of P450scc (20,22-desmolase) and P450c17 (17-hydroxylase/17,20-lyase) in cultured human granulosa cells. J Clin Endocrinol Metab 63:202-207.
    • (1986) J Clin Endocrinol Metab , vol.63 , pp. 202-207
    • Voutilainen, R.1    Tapanainen, J.2    Chung, B.C.3    Matteson, K.J.4    Miller, W.L.5
  • 32
    • 0017088267 scopus 로고
    • Some properties of a detergent-solubilized NADPH-cytochrome (cytochrome P450) reductase purified by biospecific affinity chromatography
    • Yasukochi Y and Masters BSS (1976) Some properties of a detergent-solubilized NADPH-cytochrome (cytochrome P450) reductase purified by biospecific affinity chromatography. J Biol Chem 251:5337-5344.
    • (1976) J Biol Chem , vol.251 , pp. 5337-5344
    • Yasukochi, Y.1    Masters, B.S.S.2
  • 33
    • 0031557110 scopus 로고    scopus 로고
    • Effects of Dehydroepiandrosterone on proliferation of human aortic smooth muscle cells
    • Yoneyama A, Kamiya Y, Kawaguchi M, and Fujiinami T (1997) Effects of Dehydroepiandrosterone on proliferation of human aortic smooth muscle cells. Life Sci 60:833-838.
    • (1997) Life Sci , vol.60 , pp. 833-838
    • Yoneyama, A.1    Kamiya, Y.2    Kawaguchi, M.3    Fujiinami, T.4
  • 34
    • 0036886841 scopus 로고    scopus 로고
    • Effects of prohormone supplementation in humans: A review
    • Ziegenfuss TN, Beradi JM, and Lowery LM (2002) Effects of prohormone supplementation in humans: a review. Can J Appl Physiol 27:628-646.
    • (2002) Can J Appl Physiol , vol.27 , pp. 628-646
    • Ziegenfuss, T.N.1    Beradi, J.M.2    Lowery, L.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.