Synthesis and structure of [(η6-p-cymene)Ru(2-anthracen-9- ylmethylene-N-ethylhydrazinecarbothioamide)Cl]Cl; Biological evaluation, topoisomerase II inhibition and reaction with DNA and human serum albumin

Abstract

We have synthesized and evaluated the biological properties of a compound of the type [η6-p-cymene)Ru(EtATSC)Cl]Cl (1) where EtATSC = 2-anthracen-9-ylmethylene-N-ethylhydrazinecarbothioamide, a thiosemicarbazone. The complex has been characterized by elemental analysis, spectroscopically (NMR, UV-Vis, and IR) and structurally by XRD. The in vitro anticancer activity of 1 has been evaluated against two human colon cancer cell lines. The IC 50 value for activity against HCT-116 was 224 ± 7 μM and 205 ± 5 μM against the Caco-2 cell line. The proficiency of 1 as an antibacterial agent was also evaluated against six bacterial strains. The minimum inhibitory concentration for Bacillus cereus was determined to be 5 μM and for Enterococcus faecalis it was 20 μM. At the maximum concentration tested the complex showed no activity against the Gram-negative strains. The complex binds strongly to human serum albumin with a binding constant of 1.37 ± 0.02 M-1 at 308 K on a single binding site. It is also a strong binder to DNA with an apparent binding constant of 2.82 × 105 M-1 at 308 K. 1 shows very good activity as a catalytic inhibitor of human topoisomerase II at concentrations as low as 20 μM.

Department(s)

Chemistry and Biochemistry

Document Type

Article

DOI

https://doi.org/10.1039/c1mt00003a

Publication Date

5-1-2011

Journal Title

Metallomics

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