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Molecules 2009, 14(11), 4655-4668; doi:10.3390/molecules14114655
Article

Synthesis of Pregnane Derivatives, Their Cytotoxicity on LNCap and PC-3 Cells, and Screening on 5α-Reductase Inhibitory Activity

 and *
College of Pharmacy, Catholic University of Daegu, Hayang, 712-702, Korea
* Author to whom correspondence should be addressed.
Received: 8 September 2009 / Revised: 4 November 2009 / Accepted: 8 November 2009 / Published: 17 November 2009
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Abstract

A series of epoxy- and/or 20-oxime pregnanes were synthesized from commercially available pregnenolone. Compounds 1, 3, 7, 8 and 11-13 were evaluated for cytotoxicity activity towards LNCaP (androgen-dependent) and PC-3 (androgenindependent) prostate cancer cells. Compound 13 showed the highest activity on both LNCaP (IC50 15.17 μM) and PC-3 (IC50 11.83 μM) cell lines. Compound 11 showed weak activity on LNCaP cells (IC50 71.85 μM) and 8 showed the weak activity on PC-3 cells (IC50 68.95 μM), respectively. The 5α-reductase II (5AR2) inhibitory effects of compounds 1-3, 5 and 7-13 were investigated in a convenient screening model, in which compounds 5, 8, 11 and 12 were observed to be potential inhibitors of 5α-reductase, in particular, the 4-azasteroid 11, that also inhibited cell proliferation of androgen-dependent cells and 8, that in addition inhibited PC-3 cells more potently than LNCaP cells.
Keywords: 5α-reductase inhibitor; LNCaP; PC-3; epoxypregnanes; 20-oxime pregnanes 5α-reductase inhibitor; LNCaP; PC-3; epoxypregnanes; 20-oxime pregnanes
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Kim, S.; Ma, E. Synthesis of Pregnane Derivatives, Their Cytotoxicity on LNCap and PC-3 Cells, and Screening on 5α-Reductase Inhibitory Activity. Molecules 2009, 14, 4655-4668.

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