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New ferrocene-based 2-thio-imidazol-4-ones and their copper complexes. Synthesis and cytotoxicity

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Abstract

Synthesis, characterization (HRMS, NMR, EPR, XANES, UV-Vis spectroscopy, and electrochemistry), DNA and BSA binding and in vitro biological screening of two new ferrocene-incorporated thiohydantoin derivatives (5 and 6) and their copper coordination compounds are reported. The ferrocene-based thiohydantoin derivatives were prepared by copper-catalyzed azide alkyne cycloaddition reactions between alkynyl ferrocenes and 5-(Z)-3-(2-azidoethyl)-2-(methylthio)-5-(pyridin-2-ylmethylene)-1H-imidazol-4H-one. Alkynyl ferrocenes necessary for these syntheses were prepared by new procedures. Intermolecular redox reactions between the ferrocene fragment and copper(+2) coordinated ions were studied by different methods to determine the mechanism and kinetic constants of redox processes. Ferrocene-containing imidazolones (5 and 6) and their copper complexes were also tested for their in vitro cytotoxic activity against MCF-7 and A-549 carcinoma cells, and also against the noncancerous cell line Hek-293. The results showed modest cytotoxicity against the subjected cancer cell line compared with cisplatin. The ability of the obtained compounds to cause DNA degradation and cell apoptosis was investigated, and the distribution of cytosol/pellets was studied by AAS.

Graphical abstract: New ferrocene-based 2-thio-imidazol-4-ones and their copper complexes. Synthesis and cytotoxicity

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Publication details

The article was received on 03 Aug 2018, accepted on 13 Nov 2018 and first published on 15 Nov 2018


Article type: Paper
DOI: 10.1039/C8DT03164A
Citation: Dalton Trans., 2018, Advance Article
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    New ferrocene-based 2-thio-imidazol-4-ones and their copper complexes. Synthesis and cytotoxicity

    D. A. Guk, O. O. Krasnovskaya, N. S. Dashkova, D. A. Skvortsov, M. P. Rubtsova, V. P. Dyadchenko, E. S. Yudina, M. A. Kosarev, A. V. Soldatov, V. V. Shapovalov, A. S. Semkina, K. Y. Vlasova, V. I. Pergushov, R. R. Shafikov, A. A. Andreeva, M. Ya. Melnikov, N. V. Zyk, A. G. Majouga and E. K. Beloglazkina, Dalton Trans., 2018, Advance Article , DOI: 10.1039/C8DT03164A

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