11β-Hydroxydihydrotestosterone and 11-ketodihydrotestosterone, novel C19 steroids with androgenic activity: a

Karl-Heinz Storbeck1, Liezl M Bloem, Donita Africander

  • 1Department of Biochemistry, University of Stellenbosch, Stellenbosch 7600, South Africa.

Insights

New adrenal steroid metabolism in castration-resistant prostate cancer (CRPC) produces potent androgens. These metabolites, including 11keto-dihydrotestosterone (11KDHT), may drive CRPC when testosterone is absent.

Area of Science:

  • Endocrinology
  • Oncology
  • Steroid Metabolism

Background:

  • Adrenal C19 steroids like dehydroepiandrostenedione (DHEA(S)) and androstenedione (A4) are crucial in castration-resistant prostate cancer (CRPC).
  • These steroids are metabolized to dihydrotestosterone (DHT), driving CRPC progression.
  • The metabolic fate of 11-hydroxyandrostenedione (11OHA4) in CRPC remains largely unknown.

Purpose of the Study:

  • To elucidate the novel metabolic pathway of 11OHA4 in CRPC.
  • To identify the metabolites of 11OHA4 and assess their androgenic activity.
  • To determine the role of these metabolites in driving CRPC progression.

Main Methods:

  • Investigated 11OHA4 metabolism in CRPC.
  • Identified novel 5α-reduced C19 steroids using mass spectrometry.
  • Validated the metabolic pathway in the LNCaP prostate cancer cell line.
  • Performed androgen receptor (AR) transactivation studies.

Main Results:

  • A novel pathway for 11OHA4 metabolism in CRPC was identified.
  • Metabolites include 11ketoT (11KT), 11keto-5α-androstanedione, 11OHDHT, and 11ketoDHT (11KDHT).
  • 11KT and 11OHDHT are partial AR agonists; 11KDHT is a full AR agonist, comparable to DHT.
  • 11OHA4 itself has negligible androgenic activity.

Conclusions:

  • Metabolism of 11OHA4 generates potent androgens (11KT, 11KDHT) in CRPC.
  • These metabolites may contribute to CRPC progression in the absence of testicular androgens.
  • Understanding this pathway offers potential therapeutic targets for CRPC.

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