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Transfer hydrogenation and antiproliferative activity of tethered half-sandwich organoruthenium catalysts
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Chen, Feng, Romero-Canelón, Isolda, Soldevila-Barreda, Joan J., Song, Ji-Inn, Coverdale, James P. C., Clarkson, Guy J., Kasparkova, Jana, Habtemariam, Abraha, Wills, Martin, Brabec, Viktor and Sadler, P. J. (2018) Transfer hydrogenation and antiproliferative activity of tethered half-sandwich organoruthenium catalysts. Organometallics, 37 (10). pp. 1555-1566. doi:10.1021/acs.organomet.8b00132
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Official URL: http://dx.doi.org/10.1021/acs.organomet.8b00132
Abstract
We report the synthesis and characterization of four neutral organometallic tethered complexes, [Ru(η6-Ph(CH2)3-ethylenediamine-N-R)Cl], where R = methanesulfonyl (Ms, 1), toluenesulfonyl (Ts, 2), 4-trifluoromethylbenzenesulfonyl (Tf, 3), and 4-nitrobenzenesulfonyl (Nb, 4), including their X-ray crystal structures. These complexes exhibit moderate antiproliferative activity toward human ovarian, lung, hepatocellular, and breast cancer cell lines. Complex 2 in particular exhibits a low cross-resistance with cisplatin. The complexes show potent catalytic activity in the transfer hydrogenation of NAD+ to NADH with formate as hydride donor in aqueous solution (310 K, pH 7). Substituents on the chelated ligand decreased the turnover frequency in the order Nb > Tf > Ts > Ms. An enhancement of antiproliferative activity (up to 22%) was observed on coadministration with nontoxic concentrations of sodium formate (0.5–2 mM). Complex 2 binds to nucleobase guanine (9-EtG), but DNA appears not to be the target, as little binding to calf thymus DNA or bacterial plasmid DNA was observed. In addition, complex 2 reacts rapidly with glutathione (GSH), which might hamper transfer hydrogenation reactions in cells. Complex 2 induced a dose-dependent G1 cell cycle arrest after 24 h exposure in A2780 human ovarian cancer cells while promoting an increase in reactive oxygen species (ROS), which is likely to contribute to its antiproliferative activity.
| Item Type: | Journal Article | |||||||||||||||||||||
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| Subjects: | Q Science > QD Chemistry | |||||||||||||||||||||
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||||||||||||||
| Library of Congress Subject Headings (LCSH): | Organoruthenium compounds, Catalysts, Catalysis, Hydrogenation | |||||||||||||||||||||
| Journal or Publication Title: | Organometallics | |||||||||||||||||||||
| Publisher: | American Chemical Society | |||||||||||||||||||||
| ISSN: | 0276-7333 | |||||||||||||||||||||
| Official Date: | 23 April 2018 | |||||||||||||||||||||
| Dates: |
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| Volume: | 37 | |||||||||||||||||||||
| Number: | 10 | |||||||||||||||||||||
| Page Range: | pp. 1555-1566 | |||||||||||||||||||||
| DOI: | 10.1021/acs.organomet.8b00132 | |||||||||||||||||||||
| Status: | Peer Reviewed | |||||||||||||||||||||
| Publication Status: | Published | |||||||||||||||||||||
| Access rights to Published version: | Open Access | |||||||||||||||||||||
| RIOXX Funder/Project Grant: |
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