Ambivalent role of ascorbic acid in the metal-catalyzed oxidation of oligopeptides

Bodnár, Nóra; Várnagy, Katalin; Nagy, Lajos; Csire, Gizella; Kállay, Csilla

doi:10.1016/j.jinorgbio.2021.111510

Cited by 5 publications

(21 citation statements)

References 38 publications

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“…tau (9)(10)(11)(12)(13)(14)(15)(16)). For [CuH-3L] of tau (26)(27)(28)(29)(30)(31)(32)(33) peptide, which also contains a -TXH-sequence, similar λmax value is characteristic (Table 3). In both cases, weak axial coordination of the Thr-OH group may result in a slight red shift of the absorption maximum.…”

Section: Copper(ii) Complexes Of the Peptidesmentioning

confidence: 94%

“…All peptides were prepared in N-and C-terminally protected form and in addition to the histidyl sites only the side chain carboxylate groups of aspartyl or glutamyl and amino group of lysyl residues can take part in protonation equilibria of these molecules. Corresponding pK values are listed in Table 1 and the data published earlier for tau (9)(10)(11)(12)(13)(14)(15)(16) and tau (26)(27)(28)(29)(30)(31)(32)(33) are also involved in this Table for comparison.…”

Section: Acid-base Properties Of the Peptidesmentioning

confidence: 99%

“…In the last few years, we started systematic studies on the metal complexes of various regions of tau protein for the better understanding and comparison of the metal binding ability of the various peptide fragments. Tau (9)(10)(11)(12)(13)(14)(15)(16) and tau (26)(27)(28)(29)(30)(31)(32)(33) containing His14 and His32 residues, respectively, and their mutants were involved in the first study and the results revealed a slight preference for copper(II) binding at His14 over His32 in slightly acidic samples. The stability order, however, changed by the physiological pH range when the amide bonded species are formed [21].…”

Section: Introductionmentioning

confidence: 99%

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Copper(II), Nickel(II) and Zinc(II) Complexes of Peptide Fragments of Tau Protein

Kastal,

Balabán,

Vida

et al. 2024

Preprint

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Copper(II), nickel(II) and zinc(II) complexes of various peptide fragments of tau protein were studied by potentiometric and spectroscopic techniques. All peptides contained one histidyl residue and represented the sequences of tau(91-97) (Ac-AQPHTEI-NH2), tau(385-390) (Ac-KTDHGA-NH2) and tau(404-409) (Ac-SPRHLS-NH2). Imidazole-N donors of histidine were the primary metal binding sites for all peptides and all metal ions but in case of copper(II) and nickel(II) the deprotonated amide groups were also involved in metal binding by increasing pH. The most stable complexes were formed with copper(II) ion but the presence of prolyl residues resulted in significant changes in the thermodynamic stability and speciation of the systems. It was also demonstrated that nickel(II) and especially zinc(II) complexes have relative low thermodynamic stability with these peptides. Copper(II) catalyzed oxidation of the peptides was also studied. In the presence of H2O2 the fragmentation of peptides can be detected in all cases. In the simultaneous presence of of H2O2 and ascorbic acid the extent of the fragmentation of the peptide is less preferred, and the formation of 2-oxo-histidine also occurs.

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Section: Copper(ii) Complexes Of the Peptidesmentioning

confidence: 94%

Section: Acid-base Properties Of the Peptidesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Copper(II), Nickel(II) and Zinc(II) Complexes of Peptide Fragments of Tau Protein

Kastal,

Balabán,

Vida

et al. 2024

Preprint

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“…The authors have cited additional references within the Supporting Information. [99][100][101][102][103][104][105][106][107][108][109][110]…”

Section: Supporting Informationmentioning

confidence: 99%

Unravelling the Mystery of COVID‐19 Pathogenesis: Spike Protein and Cu Can Synergize to Trigger ROS Production

Lesiów

Witwicki

Tan

et al. 2023

Chemistry A European J

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The COVID‐19 pandemic has had a devastating impact on global health, highlighting the need to understand how the SARS‐CoV‐2 virus damages the lungs in order to develop effective treatments. Recent research has shown that patients with COVID‐19 experience severe oxidative damage to various biomolecules. We propose that the overproduction of reactive oxygen species (ROS) in SARS‐CoV‐2 infection involves an interaction between copper ions and the virus's spike protein. We tested two peptide fragments, Ac‐ELDKYFKNH‐NH2 (L1) and Ac‐WSHPQFEK‐NH2 (L2), derived from the spike protein of the Wuhan strain and the β variant, respectively, and found that they bind Cu(II) ions and form a three‐nitrogen complexes at lung pH. Our research demonstrates that these complexes trigger the overproduction of ROS, which can break both DNA strands and transform DNA into its linear form. Using A549 cells, we demonstrated that ROS overproduction occurs in the mitochondria, not in the cytoplasm. Our findings highlight the importance of the interaction between copper ions and the virus's spike protein in the development of lung damage and may aid in the development of therapeutic procedures.

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“…This process catalyses the production of reactive oxygen and nitrogen species (ROS and RNS) which are highly toxic to neurons. [31][32][33] In contrast, Aβ(4-x) form square-planar complexes with Cu(II) ions through its ATCUN (the amino terminal Cu(II)and Ni(II)-binding motif) sequence, that is, by its N-terminal part consisting of Phe-Arg-His (Scheme 1). Because of this, Aβ(4-16)-Cu(II) undergo Cu(II)/Cu(I) reduction at very negative potential values (below -1 V), [34] unattainable for conditions in the human body, which prevents the formation of ROS and RNS.…”

Section: Introductionmentioning

confidence: 99%

Redox behaviour of Cu-Aβ(4-16) complexes related to Alzheimer's Disease

Wiloch,

Linfield,

Baran

et al. 2024

Electrochimica Acta

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Ambivalent role of ascorbic acid in the metal-catalyzed oxidation of oligopeptides

Cited by 5 publications

References 38 publications

Copper(II), Nickel(II) and Zinc(II) Complexes of Peptide Fragments of Tau Protein

Copper(II), Nickel(II) and Zinc(II) Complexes of Peptide Fragments of Tau Protein

Unravelling the Mystery of COVID‐19 Pathogenesis: Spike Protein and Cu Can Synergize to Trigger ROS Production

Redox behaviour of Cu-Aβ(4-16) complexes related to Alzheimer's Disease

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