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Synthesis, Characterization and Biological Activity of Bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(I) Complexes

Abstract

Bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(I) complexes (8a-h) with methoxy, methyl and fluorine substituents in different positions at the 4-aryl residue were synthesized and characterized. The relevance of the 2-methoxypyridin-5-yl residue and the substituents at the 4-aryl ring on the activity against a series of cell lines was evaluated. Especially against the Cisplatin-resistant ovarian cancer cell line A2780cis, the most active bromido[3-ethyl-4-(4-methoxy-phenyl)-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(I) complex 8c was more active than Auranofin. It also inhibited the thioredoxin reductase more effectively and induced high amounts of reactive oxygen species in A2780cis cells. Furthermore, the influence on non-cancerous SV80 lung fibroblasts is lower than that of Auranofin. This fact, together with a high accumulation rate in tumor cells, determined on the example of MCF-7 cells, makes this complex to an interesting candidate for further extensive studies.

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Article information


Submitted
20 Dec 2019
Accepted
05 Mar 2020
First published
06 Mar 2020

Dalton Trans., 2020, Accepted Manuscript
Article type
Paper

Synthesis, Characterization and Biological Activity of Bromido[3-ethyl-4-aryl-5-(2-methoxypyridin-5-yl)-1-propyl-1,3-dihydro-2H-imidazol-2-ylidene]gold(I) Complexes

C. M. Gallati, S. Götzfried, M. Ausserer, J. Sagasser, M. Plangger, K. Wurst, M. Hermann, D. Bäcker, B. Kircher and R. Gust, Dalton Trans., 2020, Accepted Manuscript , DOI: 10.1039/C9DT04824C

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