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

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 (androgen-independent) prostate cancer cells. Compound 13 showed the highest act...

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Autores principales: Kim, Sujeong, Ma, Eunsook
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2009
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6255262/
https://www.ncbi.nlm.nih.gov/pubmed/19924093
http://dx.doi.org/10.3390/molecules14114655
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author Kim, Sujeong
Ma, Eunsook
author_facet Kim, Sujeong
Ma, Eunsook
author_sort Kim, Sujeong
collection PubMed
description 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 (androgen-independent) prostate cancer cells. Compound 13 showed the highest activity on both LNCaP (IC(50) 15.17 μM) and PC-3 (IC(50) 11.83 μM) cell lines. Compound 11 showed weak activity on LNCaP cells (IC (50) 71.85 μM) and 8 showed the weak activity on PC-3 cells (IC(50) 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.
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spelling pubmed-62552622018-11-30 Synthesis of Pregnane Derivatives, Their Cytotoxicity on LNCap and PC-3 Cells, and Screening on 5α-Reductase Inhibitory Activity Kim, Sujeong Ma, Eunsook Molecules Article 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 (androgen-independent) prostate cancer cells. Compound 13 showed the highest activity on both LNCaP (IC(50) 15.17 μM) and PC-3 (IC(50) 11.83 μM) cell lines. Compound 11 showed weak activity on LNCaP cells (IC (50) 71.85 μM) and 8 showed the weak activity on PC-3 cells (IC(50) 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. Molecular Diversity Preservation International 2009-11-17 /pmc/articles/PMC6255262/ /pubmed/19924093 http://dx.doi.org/10.3390/molecules14114655 Text en © 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Kim, Sujeong
Ma, Eunsook
Synthesis of Pregnane Derivatives, Their Cytotoxicity on LNCap and PC-3 Cells, and Screening on 5α-Reductase Inhibitory Activity
title Synthesis of Pregnane Derivatives, Their Cytotoxicity on LNCap and PC-3 Cells, and Screening on 5α-Reductase Inhibitory Activity
title_full Synthesis of Pregnane Derivatives, Their Cytotoxicity on LNCap and PC-3 Cells, and Screening on 5α-Reductase Inhibitory Activity
title_fullStr Synthesis of Pregnane Derivatives, Their Cytotoxicity on LNCap and PC-3 Cells, and Screening on 5α-Reductase Inhibitory Activity
title_full_unstemmed Synthesis of Pregnane Derivatives, Their Cytotoxicity on LNCap and PC-3 Cells, and Screening on 5α-Reductase Inhibitory Activity
title_short Synthesis of Pregnane Derivatives, Their Cytotoxicity on LNCap and PC-3 Cells, and Screening on 5α-Reductase Inhibitory Activity
title_sort synthesis of pregnane derivatives, their cytotoxicity on lncap and pc-3 cells, and screening on 5α-reductase inhibitory activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6255262/
https://www.ncbi.nlm.nih.gov/pubmed/19924093
http://dx.doi.org/10.3390/molecules14114655
work_keys_str_mv AT kimsujeong synthesisofpregnanederivativestheircytotoxicityonlncapandpc3cellsandscreeningon5areductaseinhibitoryactivity
AT maeunsook synthesisofpregnanederivativestheircytotoxicityonlncapandpc3cellsandscreeningon5areductaseinhibitoryactivity

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