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Molecules 2015, 20(11), 19699-19718;

Anticancer and Antibacterial Activity Studies of Gold(I)-Alkynyl Chromones

Department of Thermobiology, Faculty of Biology and Environmental Protection, University of Łód´z, Pomorska 141/143, Łód´z PL-90236, Poland
Department of Organic Chemistry, Faculty of Chemistry, University of Łód´z, Tamka 12, Łód´z PL-91403, Poland
Laboratory of Biologically Active Compounds, National Institute of Public Health-National Institute of Hygiene, Chocimska 24, Warsaw PL-00791, Poland
Institute of Medicinal and Pharmaceutical Chemistry, Technische Universität Braunschweig, Beethovenstr. 55, Braunschweig D-38106, Germany
Institute of Chemistry, Faculty of Science, University of Neuchatel, Avenue de Bellevaux 51, Neuchatel CH-2000, Switzerland
Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 8 September 2015 / Revised: 18 October 2015 / Accepted: 23 October 2015 / Published: 30 October 2015
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Three gold(I) complexes of alkynyl chromones were synthesized and characterized. The single-crystal X-ray structure analysis of a dinuclear compound and of a flavone derivative exhibit a typical d10 gold(I)-alkynyl linear arrangement. All complexes were evaluated as anticancer and antibacterial agents against four human cancer cell lines and four pathogenic bacterial strains. All compounds show antiproliferative activity at lower micromolar range concentrations. Complex 4 showed a broad activity profile, being more active than the reference drug auranofin against HepG2, MCF-7 and CCRF-CEM cancer cells. The cellular uptake into MCF-7 cells of the investigated complexes was measured by atomic absorption spectroscopy (AAS). These measurements showed a positive correlation between an increased cellular gold content and the incubation time of the complexes. Unexpectedly an opposite effect was observed for the most active compound. Biological assays revealed various molecular mechanisms for these compounds, comprising: (i) thioredoxin reductase (TrxR) inhibition, (ii) caspases-9 and -3 activation; (iii) DNA damaging activity and (iv) cell cycle disturbance. The gold(I) complexes were also bactericidal against Gram-positive methicillin-sensitive Staphylococcus aureus (MSSA) and methicillin-resistant S. aureus (MRSA) bacterial strains, while showing no activity against the Gram-negative Escherichia coli bacterial strain. View Full-Text
Keywords: anticancer activity; gold(I) complexes; ferrocene; TrxR; caspases; antibacterial activity anticancer activity; gold(I) complexes; ferrocene; TrxR; caspases; antibacterial activity

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Hikisz, P.; Szczupak, Ł.; Koceva-Chyła, A.; Guśpiel, A.; Oehninger, L.; Ott, I.; Therrien, B.; Solecka, J.; Kowalski, K. Anticancer and Antibacterial Activity Studies of Gold(I)-Alkynyl Chromones. Molecules 2015, 20, 19699-19718.

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