Syntheses of stable isotope-labeled 6β-hydroxycortisol, 6β-hydroxycortisone, and 6β-hydroxytestosterone

Steroids

Volumn 68, Issue 7-8, 2003, Pages 693-703

  Furuta, Takashi ^a   Suzuki, Atsushi ^a   Matsuzawa, Mitsuhiro ^a   Shibasaki, Hiromi ^a   Kasuya, Yasuji ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

6 Hydroxytestosterone; 6 Hydroxycortisol; 6 Hydroxycortisone; 13C Label; Deuterium label; Mass spectrometry

Indexed keywords

11 OXOINDANYLPROPIONIC ACID; 6BETA HYDROXYHYDROCORTISONE; 6BETA HYDROXYTESTOSTERONE; ACETONE; ANION; CARBENE; CARBON; CORTISONE DERIVATIVE; DEUTERIUM; ETHER DERIVATIVE; ETHYLENE DERIVATIVE; HYDROGEN; HYDROXYCORTISONE; ISOPROPENYL ANION; ISOTOPE; KETONE; METHYL GROUP; PROPIONIC ACID; TESTOSTERONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC PARTICLE; AUTOOXIDATION; CATALYSIS; CHEMICAL REACTION; COMMERCIAL PHENOMENA; EPIMER; GAS CHROMATOGRAPHY; HYDROLYSIS; MASS SPECTROMETRY; OPTICAL ROTATION; SEPARATION TECHNIQUE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; ULTRAVIOLET IRRADIATION;

EID: 0042737832     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(03)00102-8     Document Type: Article

References (26)

1. Frantz A.G., Katz F.H., Jailer J.M. 6β-Hydroxycortisol and other polar corticosteroids: measurement and significance in human urine. J. Clin. Endocrinol. Metab. 21:1961;1290-1303.
2. Ged C., Rouillon J.M., Pichard L., Combalbert J., Bressot N., Bories P. et al. The increase in urinary excretion of 6β-hydroxycortisol as a marker of human hepatic cytochrome P450IIIA induction. Br. J. Clin. Pharmacol. 28:1989;373-387.
3. Wrighton S.A., Ring B.J., Watkins P.B., Vandenbranden M. Identification of a polymorphically expressed member of the human cytochrome P-450III family. Mol. Pharmacol. 36:1989;97-105.
4. Watanabe N., Goda R., Ochiai H., Yamashita K. Quantitative method for hydroxytestosterone by GC/MS and its application for measurement of P450 enzyme activity. J. Mass Spectrom. Soc. Jpn. 45:1997;367-375.
5. Watkins P.B. Noninvasive tests of CYP3A enzymes. Pharmacogenetics. 4:1994;171-184.
6. Wilkinson G.R. Cytochrome P4503A (CYP3A) metabolism: prediction of in vivo activity in humans. J. Pharmacokinet. Biopharm. 24:1996;475-490.
7. Streetman D.S., Bertino J.S. Jr., Nafziger A.N. Phenotyping of drug-metabolizing enzymes in adults: a review of in-vivo cytochrome P450 phenotyping probes. Pharmacogenetics. 10:2000;187-216.
8. Ghosh S., Grogan W.M., Basu A., Watlington C. Renal corticosterone 6β-hydroxylase in the spontaneously hypertensive rat. Biochim. Biophys. Acta. 1182:1993;152-156.
9. Ghosh S.S., Basu A.K., Ghosh S., Hagley R., Kramer L., Schuetz J.et al. Renal and hepatic family 3A cytochromes P450 (CYP3A) in spontaneously hypertensive rats. Biochem. Pharmacol. 50:1995;49-54.
10. Morris D.J., Latif S.A., Rokaw M.D., Watlington C.O., Johnson J.P. A second enzyme protecting mineralocorticoid receptors from glucocorticoid occupancy. Am. J. Physiol. 274:1998;C1245-C1252.
11. Shackleton C.H.L., Chai W. Mass spectrometry: application to steroid and peptide research. Endocr. Rev. 6:1985;441-486.
12. Palermo M., Gomez-Sanchez C., Roitman E., Shackleton C.H.L. Quantitation of cortisol and related 3-oxo-4-ene steroids in urine using gas chromatography/mass spectrometry with stable isotope-labeled internal standards. Steroids. 61:1996;583-589.
13. Minagawa K, Furuta T, Kasuya Y, Fujino A, Avery MA, Tanabe M. Total synthesis of cortisol: application to selective deuteriation at C-1 and C-19. J Chem Soc Perkin Trans 1 1988;587-91.
14. 13C for study of cortisol metabolism in humans Steroids. 65:2000;180-189.
15. Furuta T., Matsuzawa M., Shibasaki H., Kasuya Y. Simultaneous determination of 6β- and 6α-hydroxycortisols and 6β -hydroxycortisone in human urine by stable isotope dilution mass spectrometry. J. Chromatogr. B. 738:2000;367-376.
16. 4-3-ketones. J. Org. Chem. 32:1967;2647-2649.
17. 3 ]-testosterone, -epitestosterone and their glucuronides and sulfates J. Steroid Biochem. Mol. Biol. 58:1996;225-234.
18. Kraan G.P.B., van Wee K.T., Wolthers B.G., van der Molen J.C., Nagel G.T., Drayer N.M.et al. Synthesis and characterization of the 6α- and 6β-hydroxylated derivatives of corticosterone, 11-dehydrocorticosterone, and 11-deoxycortisol. Steroids. 58:1993;495-503.
19. Djerassi C., Gutzwiller J. Selective reduction of steroids by homogeneous catalytic hydrogenation. J. Am. Chem. Soc. 88:1966;4537-4538.
20. Brodie H.J., Hayano M., Gut M. The stereochemical course of the catalytic hydrogenation of ring A unsaturated steroids. J. Am. Chem. Soc. 84:1962;3766-3767.
21. Ringold H.J., Hayano M., Stefanovic V. Concerning the stereochemistry and mechanism of the bacterial C-1,2 dehydrogenation of steroids. J. Biol. Chem. 238:1963;1960-1965.
22. 4-cholestenone. J. Org. Chem. 30:1965;2052-2053.
23. 4-3-Keto steroidal enol ethers. Paradoxical dependency of their effectiveness on the administration route. J. Am. Chem. Soc. 82:1960;746-748.
24. Furuta T, Suzuki A, Shibasaki H, Yokokawa A, Kasuya Y. Urinary 6β-hydroxycortisol/cortisol ratio does not reflect in vivo CYP3A activity in human. In: 16th Annual Meeting of the Japanese Society for the Study of Xenobiotics, Kobe, Japan; October 17, 2001. Xenobiol Metabol Dispos 2001;16(Suppl):s98-9.
25. Furuta T, Suzuki A, Mori C, Shibasaki H, Yokokawa A, Kasuya Y. Evidence for the validity of cortisol 6β-hydroxylation clearance as a new index for in vivo cytochrome P450 3A phenotyping in humans. Drug Metab Dispos, in press.
26. Suzuki A, Shibasaki H, Kasuya Y, Furuta T. Simultaneous determination of endogenous and stable isotope-labelled 6β-hydroxycortisols in human urine by stable isotope dilution mass spectrometry. J Chromatogr B, in press.