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Abstract:

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.

Registro:

Documento: Artículo
Título:Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids
Autor:Richmond, V.; Careaga, V.P.; Sacca, P.; Calvo, J.C.; Maier, M.S.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, 1428 Buenos Aires, Argentina
IBYME (CONICET), Vuelta de Obligado 2490, 1428 Buenos Aires, Argentina
Palabras clave: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
Año:2014
Volumen:84
Página de inicio:7
Página de fin:10
DOI: http://dx.doi.org/10.1016/j.steroids.2014.03.001
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
CAS:6E-hydroximinosteroid; Steroids
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v84_n_p7_Richmond

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Citas:

---------- APA ----------
Richmond, V., Careaga, V.P., Sacca, P., Calvo, J.C. & Maier, M.S. (2014) . Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids. Steroids, 84, 7-10.
http://dx.doi.org/10.1016/j.steroids.2014.03.001
---------- CHICAGO ----------
Richmond, V., Careaga, V.P., Sacca, P., Calvo, J.C., Maier, M.S. "Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids" . Steroids 84 (2014) : 7-10.
http://dx.doi.org/10.1016/j.steroids.2014.03.001
---------- MLA ----------
Richmond, V., Careaga, V.P., Sacca, P., Calvo, J.C., Maier, M.S. "Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids" . Steroids, vol. 84, 2014, pp. 7-10.
http://dx.doi.org/10.1016/j.steroids.2014.03.001
---------- VANCOUVER ----------
Richmond, V., Careaga, V.P., Sacca, P., Calvo, J.C., Maier, M.S. Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids. Steroids. 2014;84:7-10.
http://dx.doi.org/10.1016/j.steroids.2014.03.001