11-Ketodihydrotestosterone
Names
[ CAS No. ]:
32694-37-4
[ Name ]:
11-Ketodihydrotestosterone
[Synonym ]:
Androstane-3,11-dione, 17-hydroxy-, (5α,17β)-
(5α,17β)-17-Hydroxyandrostane-3,11-dione
5α-Androstane-3,11-dione, 17β-hydroxy-
Biological Activity
[Description]:
11-Ketodihydrotestosterone (11-KDHT; 5α-Dihydro-11-keto testosterone) is an endogenous steroid and a metabolite of 11β-Hydroxyandrostenedione. 11-Ketodihydrotestosterone is an active androgen and is also a potent androgen receptor (AR) agonist with a Ki of 20.4 nM and an EC50 of 1.35 nM for human AR. 11-Ketodihydrotestosterone drives gene regulation, protein expression and cell growth in androgen-dependent prostate cancer cells[1][2].
[Related Catalog]:
[Target]
Ki: 20.4 nM (Human androgen receptor)[1] EC50: 1.35 nM (Human androgen receptor)[1]
[In Vitro]
11-Ketodihydrotestosterone (11-KDHT; 1-10 nM; 24 hours; LNCaP and VCaP cells) treatment induces significant cell proliferation[1]. 11-Ketodihydrotestosterone (11-KDHT; 0.1-10 nM; 7-10 days; LNCaP and VCaP cells) treatment results in the significant upregulation of KLK3, TMPRSS2 and FKBP5 in both LNCaP and VCaP cells, with the exception of KLK3 at 1 nM in LNCaP cells[1]. In PNT2 cells, only 20% of 11β-hydroxyandrostenedione (11OHA4) and 11β-hydroxytestosterone (11OHT) are metabolised with the former yielding 11keto-androstenedione (11KA4), 11-Ketodihydrotestosterone (11-KDHT) and 11β-hydroxy-5α-androstanedione (11OH-5αDIONE) and the latter yielding 11OHA4, 11KT and 11-Ketodihydrotestosterone with downstream products <0.03 μM[2]. In prostate cancer tissue, C11-oxy C19 metabolites at significantly higher levels than the C19 steroids are detected, with unconjugated 11-Ketodihydrotestosterone, 11KT and 11OHA4 levels ranging between 13 and 37.5 ng/g. Analyses of total steroid levels in plasma show significant levels of 11OHA4 (≈230-440 nM), 11KT (≈250-390 nM) and 11-Ketodihydrotestosterone (≈19 nM)[2]. Cell Proliferation Assay[1] Cell Line: LNCaP and VCaP cells Concentration: 0.1 nM, 1 nM or 10 nM Incubation Time: 7 days (LNCaP cells) or 10 days (VCaP cells) Result: Induced significant cell proliferation. RT-PCR[1] Cell Line: LNCaP and VCaP cells Concentration: 1 nM, 10 nM Incubation Time: 24 hours Result: Resulted in the significant upregulation of KLK3, TMPRSS2 and FKBP5 in both LNCaP (Fig 3) and VCaP (Fig 4) cells.
[References]
Chemical & Physical Properties
[ Density]:
1.2±0.1 g/cm3
[ Boiling Point ]:
453.4±45.0 °C at 760 mmHg
[ Molecular Formula ]:
C19H28O3
[ Molecular Weight ]:
304.424
[ Flash Point ]:
242.1±25.2 °C
[ Exact Mass ]:
304.203857
[ LogP ]:
1.84
[ Vapour Pressure ]:
0.0±2.5 mmHg at 25°C
[ Index of Refraction ]:
1.546
[ Storage condition ]:
-20°C