Abstract
According to different studies, the interaction between amyloid β-peptide (Aβ) and copper ions could yield radical oxygen species production, in particular the highly toxic hydroxyl radical OH· that is suspected to contribute to Alzheimer’s disease pathogenesis. Despite intensive experimental and computational studies, the nature of the interaction between copper and Aβ peptide, as well as the redox reactivity of the system, are still matter of debate. It was proposed that in Cu(II) → Cu(I) reduction the complex Cu(II)–Aβ could follow a multi-step conformational change with redox active intermediates that may be responsible for OH· radical production from H2O2 through a Fenton-like process. The purpose of this work is to evaluate, using ab initio Density Functional Theory computations, the reactivity of different Cu(I)–Aβ coordination modes proposed in the literature, in terms of OH· production. For each coordination model, we considered the corresponding H2O2 adduct and performed a potential energy surface scan along the reaction coordinate of O–O bond dissociation of the peroxide, resulting in the production of OH· radical, obtaining reaction profiles for the evaluation of the energetic of the process. This procedure allowed us to confirm the hypothesis according to which the most populated Cu(I)–Aβ two-histidine coordination is not able to perform efficiently H2O2 reduction, while a less populated three-coordinated form would be responsible for the OH· production. We show that coordination modes featuring a third nitrogen containing electron-donor ligand (an imidazole ring of an histidine residue is slightly favored over the N-terminal amine group) are more active towards H2O2 reduction.
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Acknowledgments
This research was supported by a PRIN project 2010M2ARJ_010 of the Italian MIUR.
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775_2015_1322_MOESM1_ESM.pdf
In the SI are reported i) details of the electronic structure of 2H 2 O model (QTAIM analysis, MO diagrams); ii) details of the computational method adopted iii) pictures of the van der Waals adducts, of the His 2 -H 2 O model and of the His 2 -NH 2 PES scan; iv) the atomic coordinates of all S = 0 η1 adduct and η2 S = 0 products (PDF 1069 kb)
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Prosdocimi, T., De Gioia, L., Zampella, G. et al. On the generation of OH· radical species from H2O2 by Cu(I) amyloid beta peptide model complexes: a DFT investigation. J Biol Inorg Chem 21, 197–212 (2016). https://doi.org/10.1007/s00775-015-1322-y
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DOI: https://doi.org/10.1007/s00775-015-1322-y