Synthesis and Cytotoxicity Studies of Novel NHC*-Gold(I) Complexes Derived from Lepidiline A.

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ID: 95436
2018
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Abstract
Ten novel -heterocyclic carbene gold(I) complexes derived from lepidiline A (1,3-dibenzyl-4,5-dimethylimidazolium chloride) are reported here with full characterisation and biological testing. (1,3-Dibenzyl-4,5-diphenylimidazol-2-ylidene)gold(I) chloride (NHC*-AuCl) () was modified by substituting the chloride for the following: cyanide (), dithiocarbamates (⁻), -mercaptobenzoate derivatives (⁻) and -acetyl-l-cysteine derivatives (⁻). All complexes were synthesised in good yields of 57⁻78%. Complexes , , , and were further characterised by X-ray crystallography. Initial evaluation of the biological activity was conducted on all ten complexes against the multidrug resistant MCF-7 breast cancer, HCT-116, and p53 knockout mutant HCT-116 colon carcinoma cell lines. Across the three cell lines tested, mainly single-digit micromolar IC values were observed. Nanomolar activity was exhibited on the MCF-7 cell line with displaying an IC of 0.28 μM ± 0.03 μM. Complexes incorporating a Au⁻S bond resulted in higher cytotoxic activity when compared to complexes and . Theoretical calculations, carried out at the MN15/6⁻311++G(2df,p) computational level, show that NHC* is the more favourable ligand for Au(I)-Cl when compared to PPh₃.
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curran2018synthesismolecules Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Curran, Danielle;Dada, Oyinlola;Müller-Bunz, Helge;Rothemund, Matthias;Sánchez-Sanz, Goar;Schobert, Rainer;Zhu, Xiangming;Tacke, Matthias;
Journal molecules
Year 2018
DOI
E2031
URL
Keywords
dft calculations n-heterocyclic carbene mtt cytotoxicity assay trxr inhibition gold anticancer drug lepidiline a

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