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(C^Npz^C)AuIII complexes of acyclic carbene ligands: synthesis and anticancer properties

Abstract

A series of cyclometallated gold(III) complexes supported by pyrazine-based (C^Npz^C)-type pincer ligands were synthesized via two different pathways. Nucleophilic attack on the isocyanide complex [(C^Npz^C)Au(C≡NC6H3Me2-2,6)]SbF6 (2) gave [(C^Npz^C)Au(ACC)]SbF6 complexes with aniline (4·SbF6), adamantylamine (5), glycine ethyl ester (6), alanine methyl ester (7), valine methyl ester (8), phenylglycine methyl ester (9) and methionine methyl ester (10) substituents (ACC = acyclic carbene). The pathway via isocyanide insertion into gold-amide bonds was also investigated; e.g. the reaction of xylyl isocyanide with (C^Npz^C)AuNHPh followed by protonation with HBF4·OEt2 gave the acyclic carbene complex 4·BF4. To the best of our knowledge compounds 6 - 10 represent the first examples of gold(III) acyclic carbene complexes bearing amino acid functions. The compounds provide a versatile platform for the study of anti-proliferative properties of gold(III) complexes. Tests against human adenoma-type lung cancer cells identified 5, 6, 7 and 10 as particularly promising and demonstrate the synthetic flexibility of acyclic carbene complexes for anticancer applications.

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Publication details

The article was received on 31 Jul 2017, accepted on 08 Sep 2017 and first published on 11 Sep 2017


Article type: Paper
DOI: 10.1039/C7DT02804K
Citation: Dalton Trans., 2017, Accepted Manuscript
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    (C^Npz^C)AuIII complexes of acyclic carbene ligands: synthesis and anticancer properties

    M. Williams, A. I. Green, J. Fernandez-Cestau, D. L. Hughes, M. A. O'Connell, M. Searcey, B. Bertrand and M. Bochmann, Dalton Trans., 2017, Accepted Manuscript , DOI: 10.1039/C7DT02804K

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