2013
DOI: 10.1002/chem.201302550
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Insights into the Reactivity of Gold–Dithiocarbamato Anticancer Agents toward Model Biomolecules by Using Multinuclear NMR Spectroscopy

Abstract: Some gold(III)-dithiocarbamato derivatives of either single amino acids or oligopeptides have shown promise as potential anticancer agents, but their capability to interact with biologically relevant macromolecules is still poorly understood. We investigated the affinity of the representative complex [Au(III)Br2(dtc-Sar-OCH3)] (dtc: dithiocarbamate; Sar: sarcosine (N-methylglycine)) with selected model molecules for histidine-, methionine-, and cysteine-rich proteins (that is, 1-methylimidazole, dimethylsulfid… Show more

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Cited by 21 publications
(15 citation statements)
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“…[13,14] This phenomenonw as recently explained by the presence of two differenti soformso ft he compounds (in dynamic equilibrium in solution). [56] Crystal structures Complex IT05, racemate IT03/IT04, and the urethane-protected precursor of ap eptide ligand,n amely Z-l-Pro-Aib-OtBu, were characterized by single crystal X-ray diffraction analysis. The molecular structure of IT05i sr eported in Figure2.T he metal exhibits asquare planar geometry achieved by the (S,S)chelate dithiocarbamato( dtc) ligand and by two bromide ions.…”
Section: Characterizationmentioning
confidence: 99%
“…[13,14] This phenomenonw as recently explained by the presence of two differenti soformso ft he compounds (in dynamic equilibrium in solution). [56] Crystal structures Complex IT05, racemate IT03/IT04, and the urethane-protected precursor of ap eptide ligand,n amely Z-l-Pro-Aib-OtBu, were characterized by single crystal X-ray diffraction analysis. The molecular structure of IT05i sr eported in Figure2.T he metal exhibits asquare planar geometry achieved by the (S,S)chelate dithiocarbamato( dtc) ligand and by two bromide ions.…”
Section: Characterizationmentioning
confidence: 99%
“…7,8 This compound consists of a square planar gold(III) centre with a bidentate dithiocarbamato ligand and two bromide ligands. 9 Notably, AuL12 has been shown to behave as a prodrug by releasing its bromide ligands. Significant oxidizing properties of the compound were also documented.…”
mentioning
confidence: 99%
“…In fact, the [AuCl 2 (pipeDTC)] complex was poorly soluble in DMSO, while chloroform was not chosen because its volatility did not allow analyses at 37 °C. The molar ratio between the complex and the model molecule was 1:1 for DMS, and 1:2 for PrSH and 1-MeIm [ 26 ]. This study highlighted that all the three compounds are inert toward dimethyl sulfide and 1-methylimidazole, but underwent reduction in the presence of the thiol moiety ( Figures S3–S11 ).…”
Section: Resultsmentioning
confidence: 99%