title: Synthesis and cytotoxic evaluation of four new 6E-hydroximinosteroids.
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 10.8μM (PC-3) and 7.9μM (LNCaP), respectively.
authors.affiliation: UMYMFOR (CONICET-UBA) and Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina.
authors.forename: Victoria
authors.initials: V
authors.lastname: Richmond
authors.affiliation: UMYMFOR (CONICET-UBA) and Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina; IBYME (CONICET), Vuelta de Obligado 2490, 1428 Buenos Aires, Argentina.
authors.forename: Valeria P
authors.initials: VP
authors.lastname: Careaga
authors.affiliation: IBYME (CONICET), Vuelta de Obligado 2490, 1428 Buenos Aires, Argentina.
authors.forename: Paula
authors.initials: P
authors.lastname: Sacca
authors.affiliation: IBYME (CONICET), Vuelta de Obligado 2490, 1428 Buenos Aires, Argentina.
authors.forename: Juan C
authors.initials: JC
authors.lastname: Calvo
authors.affiliation: UMYMFOR (CONICET-UBA) and Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina. Electronic address: maier@qo.fcen.uba.ar.
authors.forename: Marta S
authors.initials: MS
authors.lastname: Maier
mesh_terms: D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008297:Male; D066244:Proton Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared; D013256:Steroids / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: C525525:6E-hydroximinosteroid; D013256:Steroids
keywords: Hydroximinosteroids; Prostate cancer; Sulfated steroids; Synthesis