Reactions and structural characterization of gold(iii) complexes with amino acids, peptides and proteins

Glišić, Biljana Đ.; Rychłewska, Urszula; Djuran, Miloš I.

doi:10.1039/c2dt30169e

Cited by 84 publications

(53 citation statements)

References 94 publications

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“…Nevertheless, investigation on the oxidation state of gold suggested that Au I and Au 0 could be both present in the clusters [14][15][16]18], which implicates that different residues are involved in the process. It has been demonstrated that cysteine is not the only amino acid by which Au I species can be formed: methionine can also reduce gold salts in a similar manner [27,28]. Tryptophan, having a similar redox character to that of tyrosine at high pH values [29], has been found to be the strongest reducing amino acid for Au III in its free form and also as a peptide residue for gold nanoparticle synthesis [26].…”

Section: Introductionmentioning

confidence: 99%

On the selection and design of proteins and peptide derivatives for the production of photoluminescent, red-emitting gold quantum clusters

et al. 2013

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Novel pathways of the synthesis of photoluminescent gold quantum clusters (AuQCs) using biomolecules as reactants provide biocompatible products for biological imaging techniques. In order to rationalize the rules for the preparation of red-emitting AuQCs in aqueous phase using proteins or peptides, the role of different organic structural units was investigated. Three systems were studied: proteins, peptides, and amino acid mixtures, respectively. We have found that cysteine and tyrosine are indispensable residues. The SH/S-S ratio in a single molecule is not a critical factor in the synthesis, but on the other hand, the stoichiometry of cysteine residues and the gold precursor is crucial. These observations indicate the importance of proper chemical behavior of all species in a wide size range extending from the atomic distances (in the Au I -S semi ring) to nanometer distances covering the larger sizes of proteins assuring the hierarchical structure of the whole self-assembled system.

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Section: Introductionmentioning

confidence: 99%

On the selection and design of proteins and peptide derivatives for the production of photoluminescent, red-emitting gold quantum clusters

et al. 2013

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“…During the recent years, a large number of gold(III) complexes, in which the reduction potential of the Au(III) was lowered by the use of polydentate ligands, have been reported to be appreciably stable under physiologically relevant conditions and to manifest relevant cytotoxic activity against different human tumor cell lines [4][5][6][7][8][9][10][11][12][13][14][15][16]. The possible involvement of gold(III) complexes in cancer treatment initiated an interest in the area of gold(III) interactions with different biologically important ligands, such as amino acids and peptides [17]. It was shown that the amino acid L-histidine and L-histidine-containing peptides with N3 anchoring site of the imidazole ring are good chelating ligands for Au(III) ion [18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Oxidation of methionine residue in Gly-Met dipeptide induced by [Au(en)Cl2]+ and influence of the chelated ligand on the rate of this redox process

et al. 2013

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“…It is known that cysteine residues reduce Au 3+ to form Au + species [6,7], which is a critical step in the formation of photoluminescent products [8,9]. Recently, the chemistry of gold and biogenic thiols (including Cys) has been investigated at the molecular level.…”

Section: Introductionmentioning

confidence: 99%

The supramolecular chemistry of gold and l -cysteine: Formation of photoluminescent, orange-emitting assemblies with multilayer structure

Söptei

Mihály

Szigyártó

et al. 2015

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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The protein mediated approach is a common method for the synthesis of photoluminescent gold quantum clusters (GQCs), where proteins, acting as reducing and stabilizing agents, react with gold salts through cysteine residues. For the better understanding of the phenomenon, the aqueous phase reaction of HAuCl4 and L-cysteine has been investigated at the supramolecular level by various experimental techniques and molecular mechanics simulations. We have observed the formation of a novel photoluminescent product, (AuCys)n β , which shows emission in the orange region of the spectrum. Small-and wide-angle X-ray scattering (SWAXS) measurements have revealed the presence of nanosized lamellae, which have an internal multilayer superlattice structure with a characteristic periodic distance of 1.3 nm. Based on the results, the layers are built up by zigzag shaped (AuCys)n polymer chains connected through aurophilic bonds. The aurophilic network is stabilized via salt bridges and hydrogen bonds, which are also responsible for the interlayer interactions. Here, the evolution of the multilayer structure has been monitored by the combined application of photoluminescence spectroscopy and time-resolved SAXS. It has been concluded that there is a strong correlation between the emission and the scattering intensity, which suggests that the two-and three-dimensional aggregation of the building blocks to form sheets and multilayers are simultaneous processes. Furthermore, we have revealed that the formation and behavior of (AuCys)n β show significant differences to that of Au-L-glutathione compounds desrcibed earlier despite the similarity of L-cysteine and L-glutathione. These results evidence that L-cysteine and gold species form building blocks that can be applied expansively in supramolecular and cluster chemistry.

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Reactions and structural characterization of gold(iii) complexes with amino acids, peptides and proteins

Cited by 84 publications

References 94 publications

On the selection and design of proteins and peptide derivatives for the production of photoluminescent, red-emitting gold quantum clusters

On the selection and design of proteins and peptide derivatives for the production of photoluminescent, red-emitting gold quantum clusters

Oxidation of methionine residue in Gly-Met dipeptide induced by [Au(en)Cl2]+ and influence of the chelated ligand on the rate of this redox process

The supramolecular chemistry of gold and l -cysteine: Formation of photoluminescent, orange-emitting assemblies with multilayer structure

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