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

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 thiohy...

Full description

Saved in:
Bibliographic Details
Published in:Dalton transactions : an international journal of inorganic chemistry 2018-12, Vol.47 (48), p.17357-17366
Main Authors: Guk, D A, Krasnovskaya, O O, Dashkova, N S, Skvortsov, D A, Rubtsova, M P, Dyadchenko, V P, Yudina, E S, Kosarev, M A, Soldatov, A V, Shapovalov, V V, Semkina, A S, Vlasova, K Y, Pergushov, V I, Shafikov, R R, Andreeva, A A, Melnikov, M Ya, Zyk, N V, Majouga, A G, Beloglazkina, E K
Format: Article
Language:English
Subjects:
Alkynes
Apoptosis
Chemical reactions
Coordination compounds
Copper
Copper compounds
Cycloaddition
Cytotoxicity
Deoxyribonucleic acid
Derivatives
DNA
Electrochemistry
Ferrocenes
NMR
Nuclear magnetic resonance
Redox reactions
Synthesis
Toxicity
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1477-9226
1477-9234
DOI:10.1039/C8DT03164A