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A novel dual-functioning ruthenium(II)–arene complex of an anti-microbial ciprofloxacin derivative — anti-proliferative and anti-microbial activity

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Ude, Ziga, Romero-Canelón, Isolda, Twamley, Brendan, Fitzgerald Hughes, Deirdre, Sadler, P. J. and Marmion, Celine J. (2016) A novel dual-functioning ruthenium(II)–arene complex of an anti-microbial ciprofloxacin derivative — anti-proliferative and anti-microbial activity. Journal of Inorganic Biochemistry, 160 . pp. 210-217. doi:10.1016/j.jinorgbio.2016.02.018

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Official URL: http://dx.doi.org/10.1016/j.jinorgbio.2016.02.018

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Abstract

7-(4-(Decanoyl)piperazin-1-yl)-ciprofloxacin, CipA, (1) which is an analogue of the antibiotic ciprofloxacin, and its ruthenium(II) complex [Ru(η6-p-cymene)(CipA-H)Cl], (2) have been synthesised and the x-ray crystal structures of 1·1.3H2O·0.6CH3OH and 2·CH3OH·0.5H2O determined. The complex adopts a typical pseudo-octahedral ‘piano-stool’ geometry, with Ru(II) π-bonded to the p-cymene ring and σ-bonded to a chloride and two oxygen atoms of the chelated fluoroquinolone ligand. The complex is highly cytotoxic in the low μM range and is as potent as the clinical drug cisplatin against the human cancer cell lines A2780, A549, HCT116, and PC3. It is also highly cytotoxic against cisplatin- and oxaliplatin-resistant cell lines suggesting a different mechanism of action. The complex also retained low μM cytotoxicity against the human colon cancer cell line HCT116p53 in which the tumour suppressor p53 had been knocked out, suggesting that the potent anti-proliferative properties associated with this complex are independent of the status of p53 (in contrast to cisplatin). The complex also retained moderate anti-bacterial activity in two Escherichia coli, a laboratory strain and a clinical isolate resistant to first, second and third generation β-lactam antibiotics.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
R Medicine > RC Internal medicine > RC0254 Neoplasms. Tumors. Oncology (including Cancer)
R Medicine > RM Therapeutics. Pharmacology
Divisions: Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH): Ruthenium, Ciprofloxacin, Antineoplastic agents, Anti-infective agents
Journal or Publication Title: Journal of Inorganic Biochemistry
Publisher: Elsevier Science Inc
ISSN: 0162-0134
Official Date: July 2016
Dates:
DateEvent
July 2016Published
11 February 2016Available
10 February 2016Accepted
Volume: 160
Page Range: pp. 210-217
DOI: 10.1016/j.jinorgbio.2016.02.018
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Open Access
Funder: Science Foundation Ireland (SFI), European Research Council (ERC), Engineering and Physical Sciences Research Council (EPSRC)
Grant number: 11/RFP.1/CHS/ 3095, 12/TIDA/B2384 (SFI), 247450 (ERC), EP/F042159/1 (EPSRC)

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