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Título

Synthesis, characterization, and cytotoxic activity of AuI N,S-heterocyclic carbenes derived from peptides containing L-thiazolylalanine

AutorGutiérrez, Alejandro CSIC; Gimeno, M. Concepción CSIC ORCID; Marzo, Isabel CSIC ORCID; Metzler-Nolte, Nils
Palabras clavePeptides
Metal-based drugs
Medicinal chemistry
Gold
Drug design
Carbenes
Antitumor agents
Fecha de publicación2014
EditorWiley-VCH
CitaciónEuropean Journal of Inorganic Chemistry 15: 2512-2519 (2014)
ResumenThiazolium salts 2a-b derived from a dipeptide Boc-Gly-(Thz-Ala)-OMe (1b) containing the nonproteinogenic amino acid L-thiazolylalanine (Thz-Ala) can be used to generate the corresponding N,S-heterocyclic carbene (NSHC) gold(I) (3a-b) and silver(I) (4) complexes. Reaction of the NSHC-gold(I) iodide 3b with Boc-Cys-Gly-OMe gives access to the peptide bioconjugate 5, which contains a NSHC-Au-(S-Cys) unit. Compounds 3-5 constitute the first coin metal NSHC-peptide complexes. All new compounds were comprehensively characterized by 1H, 13C and 2D-NMR spectroscopy, IR spectroscopy, and mass spectrometry. Their cytotoxicity was studied in vitro against three different tumor cell lines (A549, Jurkat T and MiaPaca2) and IC50 values in the low micromolar range (< 25 μM), and as low as 0.4 μM in the best case were observed. All new Au complexes show good stability and promising properties and, as a result, this novel type of gold(I) carbene complex opens possibilities for the design of new metal-based drugs with promising antitumor characteristics. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
URIhttp://hdl.handle.net/10261/111585
DOI10.1002/ejic.201402103
Identificadoresdoi: 10.1002/ejic.201402103
issn: 1434-1948
e-issn: 1099-0682
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