Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids

Four new 6E-hydroximinosteroids (1, 2a, 3 and 4) have been synthesized from the corresponding ketones, 2β,3β-dihydroxy-5α-cholestan-6-one (5), 2α,3α-dihydroxy-5α-cholestan-6-one (6), 2β,3α-dihydroxy-5α-cholestan-6-one (7) and 2β,3α- dihydroxy-5α-cholestan-6-one-disulfate (8). The cytotoxic activity...

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Autores principales:	Careaga Quiroga, Valeria P., Sacca, Paula Alejandra, Calvo, Juan Carlos, Maier, Marta Silvia
Publicado:	2014
Materias:	Hydroximinosteroids Prostate cancer Sulfated steroids Synthesis 6e hydroximinosteroid corticosteroid derivative unclassified drug 6E-hydroximinosteroid steroid article cytotoxicity drug synthesis human human cell male nonhuman prostate carcinoma drug screening electrospray mass spectrometry infrared spectroscopy proton nuclear magnetic resonance synthesis tumor cell line Cell Line, Tumor Drug Screening Assays, Antitumor Humans Male Proton Magnetic Resonance Spectroscopy Spectrometry, Mass, Electrospray Ionization Spectroscopy, Fourier Transform Infrared Steroids
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v84_n_p7_Richmond http://hdl.handle.net/20.500.12110/paper_0039128X_v84_n_p7_Richmond
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_0039128X_v84_n_p7_Richmond
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spelling	paper:paper_0039128X_v84_n_p7_Richmond2023-06-08T15:03:23Z Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids Careaga Quiroga, Valeria P. Sacca, Paula Alejandra Calvo, Juan Carlos Maier, Marta Silvia Hydroximinosteroids Prostate cancer Sulfated steroids Synthesis 6e hydroximinosteroid corticosteroid derivative unclassified drug 6E-hydroximinosteroid steroid article cytotoxicity drug synthesis human human cell male nonhuman prostate carcinoma drug screening electrospray mass spectrometry infrared spectroscopy proton nuclear magnetic resonance synthesis tumor cell line Cell Line, Tumor Drug Screening Assays, Antitumor Humans Male Proton Magnetic Resonance Spectroscopy Spectrometry, Mass, Electrospray Ionization Spectroscopy, Fourier Transform Infrared Steroids Four new 6E-hydroximinosteroids (1, 2a, 3 and 4) have been synthesized from the corresponding ketones, 2β,3β-dihydroxy-5α-cholestan-6-one (5), 2α,3α-dihydroxy-5α-cholestan-6-one (6), 2β,3α-dihydroxy-5α-cholestan-6-one (7) and 2β,3α- dihydroxy-5α-cholestan-6-one-disulfate (8). The cytotoxic activity of the steroidal oximes was evaluated against two prostate carcinoma cell lines (PC-3 and LNCaP) and compared with that of five polyhydroxylated sulfated analogs (8-12). Oxime 3 and trisulfated analog 11 were the most active compounds with IC50 values of 10.8 μM (PC-3) and 7.9 μM (LNCaP), respectively. © 2014 Elsevier Inc. All rights reserved. Fil:Careaga, V.P. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Sacca, P. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Calvo, J.C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Maier, M.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2014 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v84_n_p7_Richmond http://hdl.handle.net/20.500.12110/paper_0039128X_v84_n_p7_Richmond
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Hydroximinosteroids Prostate cancer Sulfated steroids Synthesis 6e hydroximinosteroid corticosteroid derivative unclassified drug 6E-hydroximinosteroid steroid article cytotoxicity drug synthesis human human cell male nonhuman prostate carcinoma drug screening electrospray mass spectrometry infrared spectroscopy proton nuclear magnetic resonance synthesis tumor cell line Cell Line, Tumor Drug Screening Assays, Antitumor Humans Male Proton Magnetic Resonance Spectroscopy Spectrometry, Mass, Electrospray Ionization Spectroscopy, Fourier Transform Infrared Steroids
spellingShingle	Hydroximinosteroids Prostate cancer Sulfated steroids Synthesis 6e hydroximinosteroid corticosteroid derivative unclassified drug 6E-hydroximinosteroid steroid article cytotoxicity drug synthesis human human cell male nonhuman prostate carcinoma drug screening electrospray mass spectrometry infrared spectroscopy proton nuclear magnetic resonance synthesis tumor cell line Cell Line, Tumor Drug Screening Assays, Antitumor Humans Male Proton Magnetic Resonance Spectroscopy Spectrometry, Mass, Electrospray Ionization Spectroscopy, Fourier Transform Infrared Steroids Careaga Quiroga, Valeria P. Sacca, Paula Alejandra Calvo, Juan Carlos Maier, Marta Silvia Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids
topic_facet	Hydroximinosteroids Prostate cancer Sulfated steroids Synthesis 6e hydroximinosteroid corticosteroid derivative unclassified drug 6E-hydroximinosteroid steroid article cytotoxicity drug synthesis human human cell male nonhuman prostate carcinoma drug screening electrospray mass spectrometry infrared spectroscopy proton nuclear magnetic resonance synthesis tumor cell line Cell Line, Tumor Drug Screening Assays, Antitumor Humans Male Proton Magnetic Resonance Spectroscopy Spectrometry, Mass, Electrospray Ionization Spectroscopy, Fourier Transform Infrared Steroids
description	Four new 6E-hydroximinosteroids (1, 2a, 3 and 4) have been synthesized from the corresponding ketones, 2β,3β-dihydroxy-5α-cholestan-6-one (5), 2α,3α-dihydroxy-5α-cholestan-6-one (6), 2β,3α-dihydroxy-5α-cholestan-6-one (7) and 2β,3α- dihydroxy-5α-cholestan-6-one-disulfate (8). The cytotoxic activity of the steroidal oximes was evaluated against two prostate carcinoma cell lines (PC-3 and LNCaP) and compared with that of five polyhydroxylated sulfated analogs (8-12). Oxime 3 and trisulfated analog 11 were the most active compounds with IC50 values of 10.8 μM (PC-3) and 7.9 μM (LNCaP), respectively. © 2014 Elsevier Inc. All rights reserved.
author	Careaga Quiroga, Valeria P. Sacca, Paula Alejandra Calvo, Juan Carlos Maier, Marta Silvia
author_facet	Careaga Quiroga, Valeria P. Sacca, Paula Alejandra Calvo, Juan Carlos Maier, Marta Silvia
author_sort	Careaga Quiroga, Valeria P.
title	Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids
title_short	Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids
title_full	Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids
title_fullStr	Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids
title_full_unstemmed	Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids
title_sort	synthesis and cytotoxic evaluation of four new 6e-hydroximinosteroids
publishDate	2014
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v84_n_p7_Richmond http://hdl.handle.net/20.500.12110/paper_0039128X_v84_n_p7_Richmond
work_keys_str_mv	AT careagaquirogavaleriap synthesisandcytotoxicevaluationoffournew6ehydroximinosteroids AT saccapaulaalejandra synthesisandcytotoxicevaluationoffournew6ehydroximinosteroids AT calvojuancarlos synthesisandcytotoxicevaluationoffournew6ehydroximinosteroids AT maiermartasilvia synthesisandcytotoxicevaluationoffournew6ehydroximinosteroids
_version_	1768543836265512960

Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids

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