메뉴 건너뛰기




Volumn 73, Issue 12, 2008, Pages 1262-1269

Aromatization of androstenedione and 16α-hydroxyandrostenedione in human placental microsomes. Kinetic analysis of inhibition by the 19-oxygenated and 3-deoxy analogs

Author keywords

16 Hydroxyandrostenedione; Androstenedione; Aromatase; Biochemical aromatization; Substrate binding site

Indexed keywords

16ALPHA BROMANDROST 4 ENE 17,19 DIONE; 16ALPHA BROMO 19 HYDROXYANDROST 4 EN 17 ONE; 16ALPHA BROMOANDROST 4 ENE 17 ONE; 16ALPHA HYDROXYANDROS 4 EN 17 ONE; 16ALPHA HYDROXYANDROST 4 ENE 17,19 DIONE; 16ALPHA HYDROXYANDROSTENEDIONE; 16ALPHA,19 DIHYDROXYANDROST 4 EN 17 ONE; [1BETA 3 H]16ALPHA HYDROXYANDROSTENEDIONE; ANDROST 4 ENE 16ALPHA,17BETA,19 TRIOL; ANDROSTE 4 ENE 16ALPHA,17BETA DIOL; ANDROSTENEDIONE; ANDROSTENEDIONE DERIVATIVE; AROMATASE; AROMATASE INHIBITOR; BROMOKETONE; KETONE DERIVATIVE; UNCLASSIFIED DRUG; 16 HYDROXYANDROST 4 EN 3,17 DIONE; 16-HYDROXYANDROST-4-EN-3,17-DIONE; DRUG DERIVATIVE; OXYGEN;

EID: 50249162480     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2008.06.001     Document Type: Article
Times cited : (4)

References (34)
  • 1
    • 0016272566 scopus 로고
    • The involvement of human placental microsomal cytochrome P-450 in aromatization
    • Thompson Jr. E.A., and Siiteri P.K. The involvement of human placental microsomal cytochrome P-450 in aromatization. J Biol Chem 249 (1974) 5373-5378
    • (1974) J Biol Chem , vol.249 , pp. 5373-5378
    • Thompson Jr., E.A.1    Siiteri, P.K.2
  • 2
    • 0023180688 scopus 로고
    • Purification and characterization of human placental aromatase cytochrome P-450
    • Kellis Jr. J., and Vickery L.E. Purification and characterization of human placental aromatase cytochrome P-450. J Biol Chem 262 (1987) 4413-4420
    • (1987) J Biol Chem , vol.262 , pp. 4413-4420
    • Kellis Jr., J.1    Vickery, L.E.2
  • 3
    • 0025872595 scopus 로고
    • Purification of human placental aromatase cytochrome P-450 with monoclonal antibody and its characterization
    • Yoshida N., and Osawa Y. Purification of human placental aromatase cytochrome P-450 with monoclonal antibody and its characterization. Biochemistry 30 (1991) 3003-3010
    • (1991) Biochemistry , vol.30 , pp. 3003-3010
    • Yoshida, N.1    Osawa, Y.2
  • 4
    • 0023188890 scopus 로고
    • 13C] 16α-hydroxyandrostenedione and its use for radiometric determination of human placental aromatase activity
    • 13C] 16α-hydroxyandrostenedione and its use for radiometric determination of human placental aromatase activity. Chem Pharm Bull 35 (1987) 2448-2452
    • (1987) Chem Pharm Bull , vol.35 , pp. 2448-2452
    • Numazawa, M.1    Tsuji, M.2    Yarborough, C.3    Osawa, Y.4
  • 5
    • 37049080904 scopus 로고
    • Mechanistic consideration of P-450 dependent enzymic reactions: studies on oestriol biosynthesis
    • Stevenson D.E., Wright J.N., and Akhtar M. Mechanistic consideration of P-450 dependent enzymic reactions: studies on oestriol biosynthesis. J Chem Soc Perkin Trans 1 (1988) 2043-2052
    • (1988) J Chem Soc Perkin Trans , vol.1 , pp. 2043-2052
    • Stevenson, D.E.1    Wright, J.N.2    Akhtar, M.3
  • 6
    • 0001828104 scopus 로고
    • Aromatase inhibitors: specific inhibitors of oestrogen biosynthesis
    • Berg D., and Plemel M. (Eds), Ellis Horwood, Chichester, UK
    • Covey D.F. Aromatase inhibitors: specific inhibitors of oestrogen biosynthesis. In: Berg D., and Plemel M. (Eds). Steroid biosynthesis inhibitors: pharmaceutical and agrochemical aspects (1988), Ellis Horwood, Chichester, UK 534-571
    • (1988) Steroid biosynthesis inhibitors: pharmaceutical and agrochemical aspects , pp. 534-571
    • Covey, D.F.1
  • 7
    • 0027273894 scopus 로고
    • Mechanism of human placental aromatase: a new active site model
    • Cole P.A., and Robinson C.H. Mechanism of human placental aromatase: a new active site model. J Steroid Biochem Mol Biol 44 (1993) 389-397
    • (1993) J Steroid Biochem Mol Biol , vol.44 , pp. 389-397
    • Cole, P.A.1    Robinson, C.H.2
  • 9
    • 0017223888 scopus 로고
    • Cytochrome P-450 and the aromatization of 16α-hydroxy-testosterone and androstenedione by human placental microsomes
    • Canik J.A., and Ryan KJ. Cytochrome P-450 and the aromatization of 16α-hydroxy-testosterone and androstenedione by human placental microsomes. Mol Cell Endocrinol 6 (1976) 105-115
    • (1976) Mol Cell Endocrinol , vol.6 , pp. 105-115
    • Canik, J.A.1    Ryan KJ2
  • 11
    • 0024313829 scopus 로고
    • Evidence for separate sites for aromatization of androstenedione and 16α-hydroxyandrostenedione in human placental microsomes
    • Purohit A., and Oakey R.E. Evidence for separate sites for aromatization of androstenedione and 16α-hydroxyandrostenedione in human placental microsomes. J Steroid Biochem Mol Biol 33 (1989) 439-448
    • (1989) J Steroid Biochem Mol Biol , vol.33 , pp. 439-448
    • Purohit, A.1    Oakey, R.E.2
  • 13
    • 0035984318 scopus 로고    scopus 로고
    • Aromatization of 16α-hydroxyandrostenedione by human placental microsomes: effect of preincubation with suicide substrates of androstenedione aromatization
    • Numazawa M., Tachibana M., Mutsumi A., Yoshimura A., and Osawa Y. Aromatization of 16α-hydroxyandrostenedione by human placental microsomes: effect of preincubation with suicide substrates of androstenedione aromatization. J Steroid Biochem Mol Biol 81 (2002) 165-172
    • (2002) J Steroid Biochem Mol Biol , vol.81 , pp. 165-172
    • Numazawa, M.1    Tachibana, M.2    Mutsumi, A.3    Yoshimura, A.4    Osawa, Y.5
  • 14
    • 10644239093 scopus 로고    scopus 로고
    • Kinetic analysis of reversible inhibition of 16α-hydroxyandrostenedione aromatization in human placental microsomes by suicide substrates of androstenedione aromatization
    • Numazawa M., Mutsumi A., Tachibana M., and Yoshimura A. Kinetic analysis of reversible inhibition of 16α-hydroxyandrostenedione aromatization in human placental microsomes by suicide substrates of androstenedione aromatization. Biol Pharm Bull 26 (2003) 890-892
    • (2003) Biol Pharm Bull , vol.26 , pp. 890-892
    • Numazawa, M.1    Mutsumi, A.2    Tachibana, M.3    Yoshimura, A.4
  • 15
    • 0006656956 scopus 로고
    • Isolation of a full-length cDNA insert encoding human aromatase cytochrome P-450 and its expression in nonsteroidogenic cells
    • Corbin C.J., Graham-Lorence S., McPhaul M., Mason J.I., Mendelson C.R., and Simpson E.R. Isolation of a full-length cDNA insert encoding human aromatase cytochrome P-450 and its expression in nonsteroidogenic cells. Proc Natl Acad Sci USA 85 (1988) 8948-8953
    • (1988) Proc Natl Acad Sci USA , vol.85 , pp. 8948-8953
    • Corbin, C.J.1    Graham-Lorence, S.2    McPhaul, M.3    Mason, J.I.4    Mendelson, C.R.5    Simpson, E.R.6
  • 18
    • 0000064019 scopus 로고
    • Stereospecific synthesis of 16α-hydroxy-17-oxo steroids by controlled alkaline hydrolysis of corresponding 16-bromo-17-ketones and its reaction mechanism
    • Numazawa M., Nagaoka M., and Osawa Y. Stereospecific synthesis of 16α-hydroxy-17-oxo steroids by controlled alkaline hydrolysis of corresponding 16-bromo-17-ketones and its reaction mechanism. J Org Chem 47 (1982) 4024-4029
    • (1982) J Org Chem , vol.47 , pp. 4024-4029
    • Numazawa, M.1    Nagaoka, M.2    Osawa, Y.3
  • 19
    • 0023624207 scopus 로고
    • Synthesis of 16α,19-dihydroxy-4-androstene-3,17-dione and 3β,16α, 19-trihydroxy-5-androsten-17-one and their 17β-hydroxy-16-keto isomers
    • Numazawa M., Mutsumi A., Ogata M., and Osawa Y. Synthesis of 16α,19-dihydroxy-4-androstene-3,17-dione and 3β,16α, 19-trihydroxy-5-androsten-17-one and their 17β-hydroxy-16-keto isomers. Steroids 49 (1987) 247-257
    • (1987) Steroids , vol.49 , pp. 247-257
    • Numazawa, M.1    Mutsumi, A.2    Ogata, M.3    Osawa, Y.4
  • 20
    • 0025024561 scopus 로고
    • Synthesis of 16α-hydroxyandrost-4-ene-3,17,19-trione and 3β,16α-dihydroxyandrost-5-ene-17, 19-dione: potential intermediates of estriol biosynthesis
    • Numazawa M., Hoshi K., Konnno T., and Nagaoka M. Synthesis of 16α-hydroxyandrost-4-ene-3,17,19-trione and 3β,16α-dihydroxyandrost-5-ene-17, 19-dione: potential intermediates of estriol biosynthesis. Chem Pharm Bull 38 (1990) 2040-2042
    • (1990) Chem Pharm Bull , vol.38 , pp. 2040-2042
    • Numazawa, M.1    Hoshi, K.2    Konnno, T.3    Nagaoka, M.4
  • 21
    • 0024396307 scopus 로고
    • 19-Hydroxy-4-androsten-17-one: potential competitive inhibitor of estrogen biosynthesis
    • Numazawa M., Mutsumi A., Hoshi K., and Koike R. 19-Hydroxy-4-androsten-17-one: potential competitive inhibitor of estrogen biosynthesis. Biochem Biophys Res Commun 160 (1989) 1009-1014
    • (1989) Biochem Biophys Res Commun , vol.160 , pp. 1009-1014
    • Numazawa, M.1    Mutsumi, A.2    Hoshi, K.3    Koike, R.4
  • 22
    • 0028321927 scopus 로고
    • Synthesis of androst-5-en-7-ones and androsta-3,5-dien-7-ones and their related 7-deoxy analogs as conformational and catalytic probes for the active site of aromatase
    • Numazawa M., Mutsumi A., Tachibana M., and Hoshi K. Synthesis of androst-5-en-7-ones and androsta-3,5-dien-7-ones and their related 7-deoxy analogs as conformational and catalytic probes for the active site of aromatase. J Med Chem 37 (1994) 2198-2205
    • (1994) J Med Chem , vol.37 , pp. 2198-2205
    • Numazawa, M.1    Mutsumi, A.2    Tachibana, M.3    Hoshi, K.4
  • 23
    • 0027273894 scopus 로고
    • Mechanism of human placental aromatase: a new active site model
    • Oh S.S., and Robinson C.H. Mechanism of human placental aromatase: a new active site model. J Steroid Biochem Mol Biol 44 (1993) 389-397
    • (1993) J Steroid Biochem Mol Biol , vol.44 , pp. 389-397
    • Oh, S.S.1    Robinson, C.H.2
  • 24
    • 0022396732 scopus 로고
    • Stereoselective hydrolysis of 16α-halo-17-keto steroids and long-range substitution effects of the hydrolysis of 16α-bromo-17-ketones and 2α-bromo-3-ketones
    • Numazawa M., Ogata M., Abiko K., and Nagaoka M. Stereoselective hydrolysis of 16α-halo-17-keto steroids and long-range substitution effects of the hydrolysis of 16α-bromo-17-ketones and 2α-bromo-3-ketones. Steroids 45 (1985) 403-410
    • (1985) Steroids , vol.45 , pp. 403-410
    • Numazawa, M.1    Ogata, M.2    Abiko, K.3    Nagaoka, M.4
  • 26
    • 0142216815 scopus 로고
    • Biological aromatization of steroids
    • Ryan K.J. Biological aromatization of steroids. J Biol Chem 234 (1959) 268-272
    • (1959) J Biol Chem , vol.234 , pp. 268-272
    • Ryan, K.J.1
  • 28
    • 0030199503 scopus 로고    scopus 로고
    • 4-Oxygenated androst-5-en-17-ones and their 7-oxo derivatives as aromatase inhibitors
    • Numazawa M., Tachibana M., and Tateda Y. 4-Oxygenated androst-5-en-17-ones and their 7-oxo derivatives as aromatase inhibitors. J Steroid Biochem Mol Biol 58 (1996) 431-438
    • (1996) J Steroid Biochem Mol Biol , vol.58 , pp. 431-438
    • Numazawa, M.1    Tachibana, M.2    Tateda, Y.3
  • 29
    • 50249101293 scopus 로고    scopus 로고
    • GraFit Version 5.0.3, Erithacus Software Limited, Surrey, UK, 2001.
    • GraFit Version 5.0.3, Erithacus Software Limited, Surrey, UK, 2001.
  • 32
    • 0019314572 scopus 로고
    • Steroid structure and function. VI. The molecular conformation of 19-hydroxy-4-androstene-3,17-dione, as an intermediate for estrogen synthetase
    • Duax W.L., and Osawa Y. Steroid structure and function. VI. The molecular conformation of 19-hydroxy-4-androstene-3,17-dione, as an intermediate for estrogen synthetase. J Steroid Biochem 13 (1980) 383-386
    • (1980) J Steroid Biochem , vol.13 , pp. 383-386
    • Duax, W.L.1    Osawa, Y.2
  • 33
    • 0029974579 scopus 로고    scopus 로고
    • Why so much estriol? A comparison of the aromatization of androstenedione and 16α-hydroxyandrostenedione when incubated alone or together with human placental microsomes
    • Othman Y.S.H., and Oakey R.E. Why so much estriol? A comparison of the aromatization of androstenedione and 16α-hydroxyandrostenedione when incubated alone or together with human placental microsomes. J Endocrinol 148 (1996) 399-407
    • (1996) J Endocrinol , vol.148 , pp. 399-407
    • Othman, Y.S.H.1    Oakey, R.E.2
  • 34
    • 0021922417 scopus 로고
    • High-performance liquid chromatographic determination of aromatization of 16α-hydroxylated androgens with human placental microsomes
    • Numazawa M., Osada R., Tsuji M., and Osawa Y. High-performance liquid chromatographic determination of aromatization of 16α-hydroxylated androgens with human placental microsomes. Anal Biochem 146 (1985) 75-81
    • (1985) Anal Biochem , vol.146 , pp. 75-81
    • Numazawa, M.1    Osada, R.2    Tsuji, M.3    Osawa, Y.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.