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Volumn 107, Issue 3-5, 2007, Pages 220-227

Mass spectrometric analysis of oxygenations in aromatization of androst-4-ene-3,6,17-trione, a suicide substrate of aromatase, by placental microsomes. Isotope effect and stereochemistry

Author keywords

19 Oxygenation; 6 Oxoandrostenedione; Aromatase; Deuterium isotope effect; Mass spectrometry; Stereochemistry; Suicide substrate

Indexed keywords

19 HYDROXY 6 OXOSTEROID; ADRENOSTERONE; ALCOHOL; ANDROST 4 ENE 3,6,7 TRIONE; AROMATASE; DEUTERIUM; ESTRONE DERIVATIVE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG;

EID: 34548508996     PISSN: 09600760     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jsbmb.2007.03.041     Document Type: Article
Times cited : (2)

References (33)
  • 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 P-450
    • Kellis Jr. J.T., and Vickery L.E. Purification and characterization of human placental aromatase P-450. J. Biol. Chem. 262 (1987) 4413-4420
    • (1987) J. Biol. Chem. , vol.262 , pp. 4413-4420
    • Kellis Jr., J.T.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
    • 0016293443 scopus 로고
    • Utilization of oxygen and reduced nicotinamide adenine dinucleotide phosphate by human placental microsomes during aromatization of androstenedione
    • Thompson Jr. E.A., and Siiteri P.K. Utilization of oxygen and reduced nicotinamide adenine dinucleotide phosphate by human placental microsomes during aromatization of androstenedione. J. Biol. Chem. 249 (1974) 5364-5372
    • (1974) J. Biol. Chem. , vol.249 , pp. 5364-5372
    • Thompson Jr., E.A.1    Siiteri, P.K.2
  • 5
    • 0000636448 scopus 로고
    • 4-androstene-3,17-dione to estrone by endocrine tissue
    • 4-androstene-3,17-dione to estrone by endocrine tissue. Biochem. Biophys. Acta 17 (1955) 441-442
    • (1955) Biochem. Biophys. Acta , vol.17 , pp. 441-442
    • Meyer, A.S.1
  • 6
    • 33750023290 scopus 로고
    • 4-androstene-3,17-dione by placental microsomes
    • 4-androstene-3,17-dione by placental microsomes. Endocrinology 71 (1962) 723-728
    • (1962) Endocrinology , vol.71 , pp. 723-728
    • Holland, N.1
  • 7
    • 0014556069 scopus 로고
    • The stereospecific removal of a C-19 hydrogen atom in oestrogen biosynthesis
    • Skinner S.J.M., and Akhtar M. The stereospecific removal of a C-19 hydrogen atom in oestrogen biosynthesis. Biochem. J. 114 (1969) 75-81
    • (1969) Biochem. J. , vol.114 , pp. 75-81
    • Skinner, S.J.M.1    Akhtar, M.2
  • 8
    • 0020073188 scopus 로고
    • Mechanistic studies on C-19 demethylation on oestrogen biosynthesis
    • Akhtar M., Calder M.R., Corina D.L., and Wright J.N. Mechanistic studies on C-19 demethylation on oestrogen biosynthesis. Biochem. J. 201 (1982) 569-580
    • (1982) Biochem. J. , vol.201 , pp. 569-580
    • Akhtar, M.1    Calder, M.R.2    Corina, D.L.3    Wright, J.N.4
  • 9
    • 0027273894 scopus 로고
    • Mechanism of human placental atomatase: a new active site model
    • Oh S.S., and Robinson C.H. Mechanism of human placental atomatase: 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
  • 10
    • 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
  • 11
    • 0016860250 scopus 로고
    • Ressignment of the absolute configuration of estrogen biosynthesis
    • Osawa Y., Shibata K., Rohrer D., Weeks C., and Duax W.L. Ressignment of the absolute configuration of estrogen biosynthesis. J. Am. Chem. Soc. 97 (1975) 4400-4402
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 4400-4402
    • Osawa, Y.1    Shibata, K.2    Rohrer, D.3    Weeks, C.4    Duax, W.L.5
  • 13
    • 0021956401 scopus 로고
    • Radiometric analysis of oxidative reactions in aromatization by placental microsomes
    • Miyairi S., and Fishman J. Radiometric analysis of oxidative reactions in aromatization by placental microsomes. J. Biol. Chem. 260 (1985) 320-325
    • (1985) J. Biol. Chem. , vol.260 , pp. 320-325
    • Miyairi, S.1    Fishman, J.2
  • 14
    • 0001689527 scopus 로고
    • 1H]-3β-hydroxyandrost-5-en-17-ones by human placental aromatase
    • 1H]-3β-hydroxyandrost-5-en-17-ones by human placental aromatase. J. Am. Chem. Soc. 108 (1986) 1847-1852
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 1847-1852
    • Caspi, E.1    Arunachalam, T.2    Nelson, P.A.3
  • 15
    • 0022450438 scopus 로고
    • Role of substrate conformational features in the stereospecificity of aromatase
    • Beucen D.D., Kalman B.L., and Covey D.F. Role of substrate conformational features in the stereospecificity of aromatase. Biochemistry 25 (1986) 662-667
    • (1986) Biochemistry , vol.25 , pp. 662-667
    • Beucen, D.D.1    Kalman, B.L.2    Covey, D.F.3
  • 16
    • 0026050836 scopus 로고
    • Synthesis and biochemical studies of 16- or 19-substituted androst-4-enes as aromatase inhibitors
    • Numazawa M., Mutsumi A., Hoshi K., Oshibe M., and Ishikawa E. Synthesis and biochemical studies of 16- or 19-substituted androst-4-enes as aromatase inhibitors. J. Med. Chem. 34 (1991) 2496-2504
    • (1991) J. Med. Chem. , vol.34 , pp. 2496-2504
    • Numazawa, M.1    Mutsumi, A.2    Hoshi, K.3    Oshibe, M.4    Ishikawa, E.5
  • 17
    • 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) 2188-2205
    • (1994) J. Med. Chem. , vol.37 , pp. 2188-2205
    • Numazawa, M.1    Mutsumi, A.2    Tachibana, M.3    Hoshi, K.4
  • 18
    • 0033490365 scopus 로고    scopus 로고
    • 19-Oxygenation of 3-deoxy androgens, potent competitive inhibitors of estrogen biosynthesis, with human placental aromatase
    • Numazawa M., Nagaoka M., Morio M., and Kamiyama T. 19-Oxygenation of 3-deoxy androgens, potent competitive inhibitors of estrogen biosynthesis, with human placental aromatase. J. Steroid Biochem. Mol. Biol. 71 (1999) 173-179
    • (1999) J. Steroid Biochem. Mol. Biol. , vol.71 , pp. 173-179
    • Numazawa, M.1    Nagaoka, M.2    Morio, M.3    Kamiyama, T.4
  • 19
    • 23844448080 scopus 로고    scopus 로고
    • 2] 19-hydroxy androgens by placental aromatase. Absence of a deuterium-isotope effect
    • 2] 19-hydroxy androgens by placental aromatase. Absence of a deuterium-isotope effect. Steroids 70 (2005) 831-839
    • (2005) Steroids , vol.70 , pp. 831-839
    • Nagaoka, M.1    Numazawa, M.2
  • 21
    • 0015594143 scopus 로고
    • Studies on the mechanism of estrogen biosynthesis. VIII. The development of inhibitors of the enzyme system in human placenta
    • Schwarzel W.C., Kruggel W., and Brodie H.J. Studies on the mechanism of estrogen biosynthesis. VIII. The development of inhibitors of the enzyme system in human placenta. Endocrinology 92 (1973) 866-880
    • (1973) Endocrinology , vol.92 , pp. 866-880
    • Schwarzel, W.C.1    Kruggel, W.2    Brodie, H.J.3
  • 22
    • 0019449456 scopus 로고
    • Enzyme-generated intermediates derived from 4-androstene-3,6,17-trione and 1,4,6-androstatrione cause a time-dependent decrease in human placental aromatase activity
    • Covey D.F., and Hood W.F. Enzyme-generated intermediates derived from 4-androstene-3,6,17-trione and 1,4,6-androstatrione cause a time-dependent decrease in human placental aromatase activity. Endocrinology 108 (1981) 1589-1599
    • (1981) Endocrinology , vol.108 , pp. 1589-1599
    • Covey, D.F.1    Hood, W.F.2
  • 23
    • 0028326629 scopus 로고
    • Metabolic aspects of the 1β-proton and the 19-methyl group of androst-4-ene-3,6,17-trione during aromatization by placental microsomes and inactivation of aromatase
    • Numazawa M., Midzuhashi K., and Nagaoka M. Metabolic aspects of the 1β-proton and the 19-methyl group of androst-4-ene-3,6,17-trione during aromatization by placental microsomes and inactivation of aromatase. Biochem. Pharmacol. 47 (1994) 717-726
    • (1994) Biochem. Pharmacol. , vol.47 , pp. 717-726
    • Numazawa, M.1    Midzuhashi, K.2    Nagaoka, M.3
  • 24
    • 0030601838 scopus 로고    scopus 로고
    • Mechanism for aromatase inactivation by a suicide substrate, androst-4-ene-3,6,17-trione as binding to the active site
    • Numazawa M., Mutsumi A., and Tachibana M. Mechanism for aromatase inactivation by a suicide substrate, androst-4-ene-3,6,17-trione as binding to the active site. Biochem. Pharmacol. 52 (1996) 1253-1259
    • (1996) Biochem. Pharmacol. , vol.52 , pp. 1253-1259
    • Numazawa, M.1    Mutsumi, A.2    Tachibana, M.3
  • 25
    • 0029070375 scopus 로고
    • Conformational analysis of 19-oxygenated steroids with a 4-ene or 2,4-diene structure, potential intermediates of aromatase reaction, with semiempirical molecular orbital PM 3 calculations
    • Numazawa M., and Oshibe M. Conformational analysis of 19-oxygenated steroids with a 4-ene or 2,4-diene structure, potential intermediates of aromatase reaction, with semiempirical molecular orbital PM 3 calculations. Biol. Pharm. Bull. 18 (1995) 782-784
    • (1995) Biol. Pharm. Bull. , vol.18 , pp. 782-784
    • Numazawa, M.1    Oshibe, M.2
  • 28
    • 0026331103 scopus 로고
    • A time-dependent inactivation of aromatase by 19-oxygenated androst-4-ene-3,6,17-triones
    • Numazawa M., Mutsumi A., Hoshi K., and Kigawa H. A time-dependent inactivation of aromatase by 19-oxygenated androst-4-ene-3,6,17-triones. J. Steroid Biochem. Mol. Biol. 39 (1991) 959-966
    • (1991) J. Steroid Biochem. Mol. Biol. , vol.39 , pp. 959-966
    • Numazawa, M.1    Mutsumi, A.2    Hoshi, K.3    Kigawa, H.4
  • 29
    • 0032942888 scopus 로고    scopus 로고
    • Synthesis of deuterium-labeled androst-5-ene-17β,19-diol and its 4-ene isomer as internal standards for the determination of the 19-oxygenation of aromatase inhibitors using GC-MS
    • Nagaoka M., Morio M., and Numazawa M. Synthesis of deuterium-labeled androst-5-ene-17β,19-diol and its 4-ene isomer as internal standards for the determination of the 19-oxygenation of aromatase inhibitors using GC-MS. Chem. Pharm. Bull. 47 (1999) 263-266
    • (1999) Chem. Pharm. Bull. , vol.47 , pp. 263-266
    • Nagaoka, M.1    Morio, M.2    Numazawa, M.3
  • 31
    • 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
  • 32
    • 0033770029 scopus 로고    scopus 로고
    • Synthesis and biochemical studies of 19-oxygenated derivatives of 6α- and 6β-methylandrostenediones as catalytic probes for the active site of aromatase
    • Numazawa M., and Yoshimura A. Synthesis and biochemical studies of 19-oxygenated derivatives of 6α- and 6β-methylandrostenediones as catalytic probes for the active site of aromatase. Biol. Pharm. Bull. 23 (2000) 1059-1065
    • (2000) Biol. Pharm. Bull. , vol.23 , pp. 1059-1065
    • Numazawa, M.1    Yoshimura, A.2
  • 33
    • 0005979490 scopus 로고
    • Placental synthesis of steroid hormone
    • Tulchinsky D., and Ryan K.J. (Eds), W.B. Sanders, Philadelphia
    • Ryan K.J. Placental synthesis of steroid hormone. In: Tulchinsky D., and Ryan K.J. (Eds). Material-fetal endocrinology (1980), W.B. Sanders, Philadelphia 3-16
    • (1980) Material-fetal endocrinology , pp. 3-16
    • Ryan, K.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.