The in vitro antiproliferative activity of the title compound on five tumor cell lines shows preference for the colon−rectal tumor HCT116, IC50 = 13.98 μM, followed by breast MCF7 (19.58 μM) and ovarian A2780 (23.38 μM) cell lines; human glioblastoma U-87 and lung carcinoma A549 are less sensitive. A commercial curcumin reagent, also containing demethoxy and bis-demethoxy curcumin, was used to synthesize the title compound, and so (p-cymene)Ru(demethoxycurcuminato) chloro was also isolated and chemically characterized. The crystal structure of the title compound shows (1) the chlorine atom linking two neighboring complexes through H-bonds with two O- (hydroxyl), forming an infinite two-step network; (2) significant twist in the curcuminato, 20° between the planes of the two phenyl rings. This was also seen in the docking of the Ru-complex onto a rich guanine B-DNA decamer, where a Ru−N7(guanine) interaction is detected. This Ru−N7(guanine) interaction is also seen with ESI-MS on a Rucomplex- guanosine derivative.
Ruthenium-arene complexes of curcumin: X-ray and DFT structure, synthesis and spectroscopic (NMR, ESI-MS) characterization, in vitro antitumor activity and DNA docking studies of (p-cymene)Ru(curcuminato)chloro
MARCHETTI, Fabio;PETTINARI, Riccardo;PETTINARI, Claudio
2012-01-01
Abstract
The in vitro antiproliferative activity of the title compound on five tumor cell lines shows preference for the colon−rectal tumor HCT116, IC50 = 13.98 μM, followed by breast MCF7 (19.58 μM) and ovarian A2780 (23.38 μM) cell lines; human glioblastoma U-87 and lung carcinoma A549 are less sensitive. A commercial curcumin reagent, also containing demethoxy and bis-demethoxy curcumin, was used to synthesize the title compound, and so (p-cymene)Ru(demethoxycurcuminato) chloro was also isolated and chemically characterized. The crystal structure of the title compound shows (1) the chlorine atom linking two neighboring complexes through H-bonds with two O- (hydroxyl), forming an infinite two-step network; (2) significant twist in the curcuminato, 20° between the planes of the two phenyl rings. This was also seen in the docking of the Ru-complex onto a rich guanine B-DNA decamer, where a Ru−N7(guanine) interaction is detected. This Ru−N7(guanine) interaction is also seen with ESI-MS on a Rucomplex- guanosine derivative.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
