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...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Richmond, V., Careaga, V.P., Sacca, P., Calvo, J.C., Maier, M.S.
Formato: JOUR
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: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 todo:paper_0039128X_v84_n_p7_Richmond
record_format dspace
spelling todo:paper_0039128X_v84_n_p7_Richmond2023-10-03T14:49:33Z Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids Richmond, V. Careaga, V.P. Sacca, P. Calvo, J.C. Maier, M.S. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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
Richmond, V.
Careaga, V.P.
Sacca, P.
Calvo, J.C.
Maier, M.S.
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.
format JOUR
author Richmond, V.
Careaga, V.P.
Sacca, P.
Calvo, J.C.
Maier, M.S.
author_facet Richmond, V.
Careaga, V.P.
Sacca, P.
Calvo, J.C.
Maier, M.S.
author_sort Richmond, V.
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
url http://hdl.handle.net/20.500.12110/paper_0039128X_v84_n_p7_Richmond
work_keys_str_mv AT richmondv synthesisandcytotoxicevaluationoffournew6ehydroximinosteroids
AT careagavp synthesisandcytotoxicevaluationoffournew6ehydroximinosteroids
AT saccap synthesisandcytotoxicevaluationoffournew6ehydroximinosteroids
AT calvojc synthesisandcytotoxicevaluationoffournew6ehydroximinosteroids
AT maierms synthesisandcytotoxicevaluationoffournew6ehydroximinosteroids
_version_ 1782024015489007616

Ejemplares similares