A concise method for the preparation of deuterium-labeled cortisone: Synthesis of [6,7-2H]cortisone

Agnieszka Sulima, Thomas E. Prisinzano, Thomas Spande, Jeffrey R. Deschamps, Noel Whittaker, Zeev Hochberg, Arthur E. Jacobson, Kenner C. Rice

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

A method is described for the synthesis of isotopically labeled cortisone from commercially available cortisone acetate through a Δ4,6- dieneone. Direct deuteration of the dienone acetate with various catalysts in different solvent systems failed to give an isolable product. Initial hydrolysis of the side-chain ester of the Δ4,6-dieneone and subsequent derivatization gave the key intermediate, 17α,20;20,21-bismethylenedioxy- pregna-4,6-diene-3,11-dione, which could be satisfactorily deuterated to the desired product. The availability of [6,7-2H]cortisone will provide a tool for the future study of the metabolism of cortisone in human tissues.

Original languageEnglish
Pages (from-to)763-769
Number of pages7
JournalSteroids
Volume70
Issue number11
DOIs
StatePublished - Oct 2005

Bibliographical note

Funding Information:
The authors (at LMC, NIDDK, DHHS) thank the National Institute on Drug Abuse, NIH, DHHS, for partial financial support of our research program, and thank Sonja Hess and Victor Livengood (NIDDK, NIH, DHHS) for mass spectral data and Drs. Martin Garaffo (NIDDK, NIH, DHHS) and Henry Fales (NHLI, NIH, DHHS) for discussions about mass spectrometric analyses of deuterated compounds. The X-ray crystallographic work was supported in part by the National Institute on Drug Abuse, NIH, DHHS, and the Office of Naval Research.

Keywords

  • 11β-HSD
  • Cortisol
  • Cortisone
  • Deuterium-label
  • [6,7-H] Cortisone

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

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