A multi-approach study of the interaction of the Cu(II) and Ni(II) ions with alanylglycylhistamine, a mimicking pseudopeptide of the serum albumine N-terminal residue

The role of terminal amino group and histidine at the fourth position in the metal ion binding of oligopeptides revisited: Copper(II) and nickel(II) complexes of glycyl-glycyl-glycyl-histamine and its N-Boc protected derivative

“…the proton release from the N 1 nitrogen of the histamine moiety. Similar process have been proposed at very basic pH in the Ac-His-His-Gly-His- [42], GlyGly-Histamine- [32] and Ala-Gly-Histamine-copper(II) [43] systems, with spectroscopic features suggesting also the predominance of the {3 × N amide ,N im } [42] or {NH 2 ,2 × N amide ,N im } [32,43] coordination environments, respectively.…”

“…8, recorded at pH = 12.3. Such important upfield shift of the imidazole ring protons have been assigned to the deprotonation of the pyrrolic nitrogen of the N 3 -coordinated imidazole ring, without metal ion coordination to the N 1 -site [32,40,43]. The same phenomenon takes place also in the BGGGHa-nickel(II) system, which is an essential difference compared to the high-pH NiH − 3 L complex of the nonprotected GGGHa ligand (when N 3 is not coordinated to nickel(II), the pyrrolic nitrogen deprotonates only above pH 14).…”

The role of albumin receptors in regulation of albumin homeostasis: Implications for drug delivery

“…For instance, Wilsons disease, caused by mutations in copper-transporter genes, gives rise to high levels of Cu (II) in the blood that result in hepatic and neural deficits [193]. Strategies have been taken to develop albumin mimicking peptides that can sequester metals [194][195][196][197], and such peptides may potentially be used to ease the symptoms, as binding of Cu (II) to the peptides would result in rapid clearance via the kidneys due to their low molecular weights. However, this will also require large doses and frequent injections to maintain a therapeutic effect.…”

Copper chelating anti-inflammatory agents; N1-(2-aminoethyl)-N2-(pyridin-2-ylmethyl)-ethane-1,2-diamine and N-(2-(2-aminoethylamino)ethyl)picolinamide: An in vitro and in vivo study

“…6c(i)). The 100 nm blue shift in k max for Cu[H(555)-N]H À1 suggests coordination of two amino, a pyridyl and one deprotonated amide nitrogen groups in a tetragonally distorted arrangement [44,46,47].…”