Study of the anticancer properties of optically active titanocene oximato compounds

Publication date: Available online 17 December 2018Source: Journal of Organometallic ChemistryAuthor(s): Isabel de la Cueva-Alique, Sara Sierra, Adrián Pérez-Redondo, Isabel Marzo, Lourdes Gude, Tomás Cuenc, Eva RoyoAbstractNew water soluble and optically active cyclopentadienyl titanium derivatives [(η5-C5H5)2Ti{(1R,4S)-ĸON,(R)NH}Cl] (R = Bn (Benzyl) 1a’, 2-pic (2-picolylamine) 1b’) have been synthesized. The novel compounds along with those previously described [(η5-C5H5)2Ti{(1S,4R)-ĸON,(R)NH}Cl] (R = Bn 1a, 2-pic 1b) were evaluated by polarimetry, ultra-violet and circular dichroism spectroscopy. The structure of 1b was determined by single crystal X-ray crystallography and showed a unique terminal monohapto Ti-O disposition of the oximato ligand. All enantiomers have been tested against several cancer cell lines in vitro: prostate PC-3 and DU-145, lung A-549, pancreas MiaPaca-2, colorectal HCT-116, leukemia Jurkat and cervical HeLa. In addition, 1a, 1b and 1b’ were tested against non-tumorigenic prostate RWPE-1 cell line. After 24 h of incubation, 1b and 1b’ were moderately active against Jurkat and A-549 cells. The anti-proliferative effect of titanium compounds on prostate PC-3, DU-145 and RWPE-1 cell lines was also assessed after 72 h of drug exposure. The cytotoxic profile of the enantiomers was similar, exception made for the PC-3 cells, with S,R-isomers exhibiting cytotoxicities 2 to 3 times higher than R,S-compounds. Under these c...
Source: Journal of Organometallic Chemistry - Category: Chemistry Source Type: research