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

Williams, Morwen, Green, Adam I, Fernandez-Cestau, Julio, Hughes, David L, O'Connell, Maria Anne ORCID: https://orcid.org/0000-0002-0267-0951, Searcey, Mark ORCID: https://orcid.org/0000-0003-2273-8949, Bertrand, Benoit and Bochmann, Manfred ORCID: https://orcid.org/0000-0001-7736-5428 (2017) (C^Npz^C)AuIII complexes of acyclic carbene ligands: synthesis and anticancer properties. Dalton Transactions, 46 (39). 13397–13408. ISSN 1477-9226

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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 and the potential of that class of compounds for anticancer applications. Compared to cisplatin, amino ester-containing ACC complexes showed significantly improved selectivity for MCF-7 breast cancer cells over healthy fibroblasts.

Item Type:	Article
Uncontrolled Keywords:	sdg 3 - good health and well-being ,/dk/atira/pure/sustainabledevelopmentgoals/good_health_and_well_being
Faculty \ School:	Faculty of Science > School of Chemistry Faculty of Science > School of Pharmacy
UEA Research Groups:	Faculty of Science > Research Groups > Pharmaceutical Cell Biology (former - to 2017) Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Medicinal Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemical Biology and Medicinal Chemistry (former - to 2021) Faculty of Science > Research Groups > Molecular and Tissue Pharmacology Faculty of Science > Research Groups > Chemistry of Light and Energy Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Depositing User:	Pure Connector
Date Deposited:	13 Sep 2017 05:07
Last Modified:	21 Oct 2022 16:30
URI:	https://ueaeprints.uea.ac.uk/id/eprint/64841
DOI:	10.1039/C7DT02804K

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