Au(III)-complexes of the alanyl-containing peptides glycylalanine and glycylalanylalanine – Synthesis, spectroscopic and structural characterization

Synthesis, spectroscopic analysis and structure deduction of gold(III), palladium(II) and platinum(II) complexes with the tripeptide glycyl-l-phenylalanyl-glycine

“…The absorption maximum at 1,680 cm -1 is assigned to d as (NH 3 + ) and that at 1,398 cm -1 to m s (COO -). These data correlate well with those previously reported for glycyl-and phenylalanyl containing di-and tripeptides [25][26][27][28].…”

“…Peptides are another appropriate class of ligands for development of new anticancer medications both with Pt(II) and Au(III). In a series of papers the coordination ability of the above-mentioned metal ions with small peptides has been investigated [22][23][24][25][26][27][28]. Up to now, only three crystal structures of Au(III) peptide complexes have been reported [22,23]: two with the dipeptide glycylhistidine, namely ([Au(H-Gly-His-OH)H -1 )Cl]Cl 9 3H 2 O) and [Au(H-Gly-His-OH)H -3 )] 4 9 10H 2 O, and one with the tripeptide glycylglycylhistidine, [Au(H-Gly-GlyHis-OH)H -2 )]Cl 9 H 2 O, obtained in strongly acid medium.…”

Gold Ion–Angiotensin Peptide Interaction by Mass Spectrometry

“…The bidentate/tridentate complexes have been proposed to be the possible structures in previous studies on Cu-and Zn-angiotensin complexes [34,48]. In addition, many NMR and X-ray studies on simple Au-peptide complexes have proposed multidentate structures involving the amide nitrogen and the N-terminal NH 2 group in addition to the amino acid residues [21][22][23][24][25][26][27]. The angiotensin I solution containing gold ion is digested with trypsin to produce gold ion-VYIHPFHL complex.…”

“…A number of gold(III) complexes with ligands such as bipyridyls, dithiocarbamato, porphyrins, and quinolines, which display in vitro and in vivo potent anticancer activities and reduced systemic toxicity compared with the cisplatin, have been synthesized [4][5][6][7][8][9][10][11][12][13][14][15][16][17]. Small peptides such as S-phenylalanine-S-phenylalanine, glycyl-alaline, glycyl-histidine, alanyl-phenylalanine, glycyl-S-serine, glycyl-alanyl-alanine, glycyl-glycyl-histidine, and glycyl-glycyl-methyonyl-glycyl-glycine are another class of ligands of gold(III) ion that have been investigated for development of potential anticancer drugs [18][19][20][21][22][23][24]. Although evidence [10,11,28] suggests that gold-based chemotherapy agents seem to induce antiproliferative activities against tumor cells, the main biological targets and mechanisms responsible for gold-induced cytotoxicity are still largely unknown.…”

“…Collision induced dissociation (CID), a well established tandem mass spectrometry experiment, which produces the information of the sequence and metal ion binding sites of a peptide, of Zn ionand Cu ion-angiotensin peptide complexes [34,41,48] indicate that zinc and copper interaction sites are in the neighborhood of the His and Arg residues, respectively. In addition, there are some MS studies on the gold-protein complexes [14,28,33,[49][50][51][52], disulfide bridge cleavage of gold(I) cationized peptides [53,54], and characterization of synthetic pure gold-peptide complexes [21][22][23][24][25][26][27]. Data from gold-attached glutathione reductase or thioredoxin reductase probed by MALDI-TOF MS speculates that Cys residue is critical to their biological functions [14,50].…”