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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 *
Received: 8 September 2009; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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(11):4655-4668.

Chicago/Turabian Style

Kim, Sujeong; Ma, Eunsook. 2009. "Synthesis of Pregnane Derivatives, Their Cytotoxicity on LNCap and PC-3 Cells, and Screening on 5α-Reductase Inhibitory Activity." Molecules 14, no. 11: 4655-4668.


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