JBIC Journal of Biological Inorganic Chemistry

, Volume 20, Issue 6, pp 1005–1020 | Cite as

Gold(I) NHC-based homo- and heterobimetallic complexes: synthesis, characterization and evaluation as potential anticancer agents

  • Benoît Bertrand
  • Anna Citta
  • Inge L. Franken
  • Michel Picquet
  • Alessandra Folda
  • Valeria Scalcon
  • Maria Pia Rigobello
  • Pierre Le Gendre
  • Angela Casini
  • Ewen Bodio
Original Paper

Abstract

While N-heterocyclic carbenes (NHC) are ubiquitous ligands in catalysis for organic or industrial syntheses, their potential to form transition metal complexes for medicinal applications has still to be exploited. Within this frame, we synthesized new homo- and heterobimetallic complexes based on the Au(I)–NHC scaffold. The compounds were synthesized via a microwave-assisted method developed in our laboratories using Au(I)–NHC complexes carrying a pentafluorophenol ester moiety and another Au(I) phosphane complex or a bipyridine ligand bearing a pendant amine function. Thus, we developed two different methods to prepare homo- and heterobimetallic complexes (Au(I)/Au(I) or Au(I)/Cu(II), Au(I)/Ru(II), respectively). All the compounds were fully characterized by several spectroscopic techniques including far infrared, and were tested for their antiproliferative effects in a series of human cancer cells. They showed moderate anticancer properties. Their toxic effects were also studied ex vivo using the precision-cut tissue slices (PCTS) technique and initial results concerning their reactivity with the seleno-enzyme thioredoxin reductase were obtained.

Keywords

N-heterocyclic carbene Bimetallic complex Gold complex Anticancer drug Thioredoxin reductase 

Supplementary material

775_2015_1283_MOESM1_ESM.pdf (241 kb)
Supplementary material 1 (PDF 240 kb)

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Copyright information

© SBIC 2015

Authors and Affiliations

  • Benoît Bertrand
    • 1
    • 2
  • Anna Citta
    • 3
  • Inge L. Franken
    • 2
  • Michel Picquet
    • 1
  • Alessandra Folda
    • 3
  • Valeria Scalcon
    • 4
  • Maria Pia Rigobello
    • 3
  • Pierre Le Gendre
    • 1
  • Angela Casini
    • 2
  • Ewen Bodio
    • 1
  1. 1.Institut de Chimie Moléculaire, UMR 6302 CNRS Université de Bourgogne Franche ComtéDijonFrance
  2. 2.Department of Pharmacokinetics, Toxicology and Targeting, Research Institute of PharmacyUniversity of GroningenGroningenThe Netherlands
  3. 3.Department of Biomedical SciencesUniversity of PadovaPaduaItaly
  4. 4.Institute of Neuroscience, C.N.R.PaduaItaly

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