Issue 35, 2022

Synthesis, chemical characterization, and biological evaluation of a novel auranofin derivative as an anticancer agent

Abstract

A novel gold(I) complex inspired by the known medicinal inorganic compounds auranofin and thimerosal, namely ethylthiosalicylate(triethylphosphine)gold(I) (AFETT hereafter), was synthesized and characterised and its structure was resolved through X-ray diffraction. The solution behavior of AFETT and its interactions with two biologically relevant proteins (i.e. human serum albumin and haemoglobin) and with a synthetic dodecapeptide reproducing the C-terminal portion of thioredoxin reductase were comparatively analyzed through 31P NMR and ESI-MS. Remarkable binding properties toward these biomolecules were disclosed. Moreover, the cytotoxic effects produced by AFETT on two ovarian cancer cell lines (A2780 and A2780 R) and one colorectal cancer cell line (HCT116) were analyzed and found to be strong and nearly superimposable to those of auranofin. Interestingly, for both compounds, the ability to induce downregulation of vimentin expression in A2780 R cells was evidenced. Despite its close similarity to auranofin, AFETT is reported to exhibit some peculiar and distinctive features such as a lower lipophilicity, an increased water solubility and a faster reactivity towards the selected target biomolecules. These differences might confer to AFETT significant pharmaceutical and therapeutic advantages over auranofin itself.

Graphical abstract: Synthesis, chemical characterization, and biological evaluation of a novel auranofin derivative as an anticancer agent

Supplementary files

Article information

Article type
Paper
Submitted
17 Mar 2022
Accepted
05 Aug 2022
First published
08 Aug 2022

Dalton Trans., 2022,51, 13527-13539

Synthesis, chemical characterization, and biological evaluation of a novel auranofin derivative as an anticancer agent

D. Cirri, L. Massai, C. Giacomelli, M. L. Trincavelli, A. Guerri, C. Gabbiani, L. Messori and A. Pratesi, Dalton Trans., 2022, 51, 13527 DOI: 10.1039/D2DT00836J

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