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Volumn 76, Issue 12, 2011, Pages 1232-1240

Synthesis of 3- and 21-monosulfates of [2,2,3β,4,4- 2H 5]-tetrahydrocorticosteroids in the 5β-series as internal standards for mass spectrometry

Author keywords

Electrospray ionization; Hydrogen deuterium exchange; Internal standard; Mass spectrometry; Multiple deuteration; Sodium borodeuteride

Indexed keywords

17,20:20,21 BISMETHYLENEDIOXY 11BETA HYDROXY 4 PREGNEN 3 ONE; 17,20:20,21 BISMETHYLENEDIOXY 11BETA HYDROXY 5BETA PREGNAN 3 ONE; 17,20:20,21 BISMETHYLENEDIOXY 3ALPHA HYDROXY 5BETA PREGNAN 11 ONE; 17,20:20,21 ISMETHYLENEDIOXY 5BETA PREGNAN 3 ONE; 3ALPHA ACETOXY 17,20:20,21 BISMETHYLENEDIOXY 11BETA HYDROXY 5BETA PREGNAN; 3ALPHA ACETOXY 17,20:20,21 BISMETHYLENEDIOXY 5BETA PREGNAN 11 ONE; [2,2,3BETA,4,4 D5] 17,20:20,21 BISMETHYLENDIOXY 3ALPHA HYDROXY 5BETA PREGNAN 11 ONE; [2,2,3BETA,4,4 D5] 17,20:20,21 BISMETHYLENEDIOXY 3ALPHA HYDROXY 5BETA PREGNANE; [2,2,3BETA,4,4 D5] 17,20:20,21 BISMETHYLENEDIOXY 3ALPHA,11BETA DIHYDROXY 5 BETA PREGNAN; [2,2,3BETA,4,4 D5] 3ALPHA ACETOXY 17,20:20,21 BISMETHYLENDIOXY 11BETA HYDROXY 5BETA PREGNAN; [2,2,3BETA,4,4 D5] 3ALPHA ACETOXY 17,20:20,21 TRIHYDROXY 5BETA PREGNAN 20 ONE; [2,2,3BETA,4,4 D5] 3ALPHA ACETOXY 17ALPHA,21 DIHYDROXY 5BETA PREGNAN 11,20 DIONE; [2,2,3BETA,4,4 D5] 3ALPHA ACETOXY 17ALPHA,21 DIHYDROXY 5BETA PREGNAN 20 ONE; CORTODOXONE; HYDROCORTISONE; HYDROFLUORIC ACID; UNCLASSIFIED DRUG;

EID: 80052740224     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2011.05.014     Document Type: Article
Times cited : (7)

References (22)
  • 1
    • 0042831855 scopus 로고
    • The adrenal cortex
    • P.K. Bondy, L.E. Rosenberg, 8th ed. W.B. Saunders Company Philadelphia
    • P.K. Bondy The adrenal cortex P.K. Bondy, L.E. Rosenberg, Metabolic control and disease 8th ed. 1980 W.B. Saunders Company Philadelphia 1427 1499
    • (1980) Metabolic Control and Disease , pp. 1427-1499
    • Bondy, P.K.1
  • 2
    • 0041487561 scopus 로고    scopus 로고
    • The adrenal cortex
    • H.M. Kronenberg, S. Melmed, K.S. Polonsky, P.R. Larsen, 11th ed. Saunders Elsevier Philadelphia
    • P.M. Stewart The adrenal cortex H.M. Kronenberg, S. Melmed, K.S. Polonsky, P.R. Larsen, Williams textbook of endocrinology 11th ed. 2008 Saunders Elsevier Philadelphia 445 503
    • (2008) Williams Textbook of Endocrinology , pp. 445-503
    • Stewart, P.M.1
  • 5
    • 0015194270 scopus 로고
    • Studies on steroid conjugates. VII. Isolation and identification of sulfate-conjugated cortisol metabolites from human urine
    • L. Kornel, S. Miyabo, and R. Takeda Studies on steroid conjugates. VII. Isolation and identification of sulfate-conjugated cortisol metabolites from human urine Steroidologia 2 1971 197 236
    • (1971) Steroidologia , vol.2 , pp. 197-236
    • Kornel, L.1    Miyabo, S.2    Takeda, R.3
  • 6
    • 0016696748 scopus 로고
    • Studies on steroid conjugates-VIII: Isolation and characterization of glucuronide-conjugated metabolites of cortisol in human urine
    • L. Kornel, and Z. Saito Studies on steroid conjugates-VIII: isolation and characterization of glucuronide-conjugated metabolites of cortisol in human urine J Steroid Biochem 6 1975 1267 1284
    • (1975) J Steroid Biochem , vol.6 , pp. 1267-1284
    • Kornel, L.1    Saito, Z.2
  • 7
    • 0016762798 scopus 로고
    • Studies on steroid conjugates: IX. Urinary excretion of sulfate conjugated metabolites of cortisol in man
    • L. Kornel, and S. Miyabo Studies on steroid conjugates: IX. Urinary excretion of sulfate conjugated metabolites of cortisol in man Steroids 25 1975 697 706
    • (1975) Steroids , vol.25 , pp. 697-706
    • Kornel, L.1    Miyabo, S.2
  • 8
    • 0018946181 scopus 로고
    • Urinary tetrahydrocortisone and tetrahydrocortisol glucosiduronates in normal newborns, children and adults
    • G. Aranoff, and A. Rösler Urinary tetrahydrocortisone and tetrahydrocortisol glucosiduronates in normal newborns, children and adults Acta Endocrinol 94 1980 371 375 (Pubitemid 10036739)
    • (1980) Acta Endocrinologica , vol.94 , Issue.3 , pp. 371-375
    • Aranoff, G.1    Rosler, A.2
  • 9
    • 57649094408 scopus 로고    scopus 로고
    • Quantitative metabolic profiling of 21 endogenous corticosteroids in urine by liquid chromatography-triple quadrupole-mass spectrometry
    • H.J. Cho, J.D. Kim, W.Y. Lee, B.C. Chung, and M.H. Choi Quantitative metabolic profiling of 21 endogenous corticosteroids in urine by liquid chromatography-triple quadrupole-mass spectrometry Anal Chim Acta 632 2009 101 108
    • (2009) Anal Chim Acta , vol.632 , pp. 101-108
    • Cho, H.J.1    Kim, J.D.2    Lee, W.Y.3    Chung, B.C.4    Choi, M.H.5
  • 10
    • 38649123338 scopus 로고    scopus 로고
    • Development of a liquid chromatography-tandem mass spectrometry method for the determination of 23 endogenous steroids in small quantities of primate urine
    • DOI 10.1016/j.jchromb.2007.11.009, PII S157002320700774X
    • B. Hauser, T. Deschner, and C. Boesch Development of a liquid chromatography-tandem mass spectrometry method for the determination of 23 endogenous steroids in small quantities of primate urine J Chromatogr B 862 2008 100 112 (Pubitemid 351173017)
    • (2008) Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences , vol.862 , Issue.1-2 , pp. 100-112
    • Hauser, B.1    Deschner, T.2    Boesch, C.3
  • 11
    • 65649123439 scopus 로고    scopus 로고
    • Recent advances in the assessment of the ratios of cortisol to cortisone and of some of their metabolites in urine by LC-MS-MS
    • A. Saba, A. Raffaelli, A. Cupisti, A. Petri, C. Marcocci, and P. Salvadori Recent advances in the assessment of the ratios of cortisol to cortisone and of some of their metabolites in urine by LC-MS-MS J Mass Spectrom 44 2009 541 548
    • (2009) J Mass Spectrom , vol.44 , pp. 541-548
    • Saba, A.1    Raffaelli, A.2    Cupisti, A.3    Petri, A.4    Marcocci, C.5    Salvadori, P.6
  • 13
    • 43649108595 scopus 로고    scopus 로고
    • Simultaneous determination of tetrahydrocortisol, allotetrahydrocortisol and tetrahydrocortisone in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry
    • K. Yamashita, R. Nakagawa, M. Okuyama, S. Honma, M. Takahashi, and M. Numazawa Simultaneous determination of tetrahydrocortisol, allotetrahydrocortisol and tetrahydrocortisone in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry Steroids 73 2008 727 737
    • (2008) Steroids , vol.73 , pp. 727-737
    • Yamashita, K.1    Nakagawa, R.2    Okuyama, M.3    Honma, S.4    Takahashi, M.5    Numazawa, M.6
  • 14
    • 72449193070 scopus 로고    scopus 로고
    • Simultaneous determination of twelve tetrahydrocorticosteroid glucuronides in human urine by liquid chromatography/electrospray ionization-linear ion trap mass spectrometry
    • S. Ikegawa, M. Hasegawa, R. Okihara, C. Shimidzu, H. Chiba, T. Iida, and K. Mitamura Simultaneous determination of twelve tetrahydrocorticosteroid glucuronides in human urine by liquid chromatography/electrospray ionization-linear ion trap mass spectrometry Anal Chem 81 2009 10124 10135
    • (2009) Anal Chem , vol.81 , pp. 10124-10135
    • Ikegawa, S.1    Hasegawa, M.2    Okihara, R.3    Shimidzu, C.4    Chiba, H.5    Iida, T.6    Mitamura, K.7
  • 15
    • 77649269512 scopus 로고    scopus 로고
    • Potential corticoid metabolites: Chemical synthesis of 3- and 21-monosulfates and their double-conjugates of tetrahydrocorticosteroids in the 5α- and 5β-series
    • R. Okihara, K. Mitamura, M. Hasegawa, M. Mori, A. Muto, G. Kakiyama, S. Ogawa, T. Iida, M. Shimada, N. Mano, and S. Ikegawa Potential corticoid metabolites: chemical synthesis of 3- and 21-monosulfates and their double-conjugates of tetrahydrocorticosteroids in the 5α- and 5β-series Chem Pharm Bull 58 2010 344 353
    • (2010) Chem Pharm Bull , vol.58 , pp. 344-353
    • Okihara, R.1    Mitamura, K.2    Hasegawa, M.3    Mori, M.4    Muto, A.5    Kakiyama, G.6    Ogawa, S.7    Iida, T.8    Shimada, M.9    Mano, N.10    Ikegawa, S.11
  • 16
    • 28244439965 scopus 로고
    • Steroids and related products. XXVIII. Cardiotonic steroids. III. The synthesis of 3β-hydroxy steroids of the A/B-cis series
    • R. Bouchard, and C.R. Engel Steroids and related products. XXVIII. Cardiotonic steroids. III. The synthesis of 3β-hydroxy steroids of the A/B-cis series Can J Chem 46 1968 2201 2206
    • (1968) Can J Chem , vol.46 , pp. 2201-2206
    • Bouchard, R.1    Engel, C.R.2
  • 17
    • 0020856959 scopus 로고
    • Preparation of haptens for use in immunoassays of tetrahydro-11- deoxycortisol and its glucuronides
    • H. Hosoda, H. Yokohama, K. Ishii, Y. Ito, and T. Nambara Preparation of haptens for use in immunoassays of tetrahydro-11-deoxycortisol and its glucuronides Chem Pharm Bull 31 1983 4001 4007
    • (1983) Chem Pharm Bull , vol.31 , pp. 4001-4007
    • Hosoda, H.1    Yokohama, H.2    Ishii, K.3    Ito, Y.4    Nambara, T.5
  • 18
    • 0014290714 scopus 로고
    • Synthesis of the four pairs of side-chain epoxides epimeric at C-20 derived from 5β-pregnan-3α-ol
    • M.L. Lewbart Synthesis of the four pairs of side-chain epoxides epimeric at C-20 derived from 5β-pregnan-3α-ol J Org Chem 33 1968 1695 1706
    • (1968) J Org Chem , vol.33 , pp. 1695-1706
    • Lewbart, M.L.1
  • 19
    • 33947478220 scopus 로고
    • 17,20;20,21-Bismethylenedioxy steroids. V. A general method for protecting the dihydroxyacetone side chain
    • R.E. Beyler, F. Hoffman, R.M. Moriarty, and L.H. Sarett 17,20;20,21-Bismethylenedioxy steroids. V. A general method for protecting the dihydroxyacetone side chain J Org Chem 26 1961 2421 2425
    • (1961) J Org Chem , vol.26 , pp. 2421-2425
    • Beyler, R.E.1    Hoffman, F.2    Moriarty, R.M.3    Sarett, L.H.4
  • 21
    • 84943930803 scopus 로고
    • Préparation et structure des cortisones et hydrocortisones méthylées en I
    • D. Bertin, and J. Perronnet Préparation et structure des cortisones et hydrocortisones méthylées en I Bull Soc Chim Fr 1964 2782 2791
    • (1964) Bull Soc Chim Fr , pp. 2782-2791
    • Bertin, D.1    Perronnet, J.2
  • 22
    • 0020419324 scopus 로고
    • Synthesis of haptens for use in immunoassay of tetrahydrocortisol, tetrahydrocortisone and their glucuronides
    • H. Hosoda, K. Saito, Y. Ito, H. Yokohama, K. Ishii, and T. Nambara Synthesis of haptens for use in immunoassays of tetrahydrocortisol, tetrahydrocortisone and their glucuronides Chem Pharm Bull 30 1982 2110 2118 (Pubitemid 13231886)
    • (1982) Chemical and Pharmaceutical Bulletin , vol.30 , Issue.6 , pp. 2110-2118
    • Hosoda, H.1    Saito, K.2    Ito, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.