Affiliation:
1. Faculty of Chemistry University of Gdańsk Gdańsk Poland
2. Faculty of Chemistry University of Wroclaw Wroclaw Poland
3. Faculty of Biology, Department of Medical Biology and Genetics University of Gdańsk Gdańsk Poland
4. Interdepartmental Research Unit of Peptide and Protein Chemistry and Biology, Department of Neurofarba University of Florence Sesto Fiorentino Italy
5. Interdepartmental Research Unit of Peptide and Protein Chemistry and Biology, Department of Chemistry “Ugo Schiff” University of Florence Sesto Fiorentino Italy
Abstract
Argireline (Ac‐EEMQRR‐NH2), a well‐known neurotransmitter peptide with a potency similar to botulinum neurotoxins, reveals a proven affinity toward Cu(II) ions. We report herein Cu(II) chelating properties of three new Argireline derivatives, namely, AN4 (Ac‐EAHRR‐NH2), AN5 (Ac‐EEHQRR‐NH2), and AN6 (Ac‐EAHQRK‐NH2). Two complementary experimental techniques, i.e., potentiometric titration (PT) and isothermal titration calorimetry (ITC), have been employed to describe the acid–base properties of the investigated peptides as well as the thermodynamic parameters of the Cu(II) complex formation. Additionally, based on density functional theory (DFT) calculations, we propose the most likely structures of the resulting Cu‐peptide complexes. Finally, the cytotoxicity of the free peptides and the corresponding Cu(II) complexes was estimated in human skin cells for their possible future cosmetic application. The biological results were subsequently compared with free Argireline, its Cu(II)‐complexes, and the previously studied AN2 derivative (EAHQRR).
Subject
Organic Chemistry,Drug Discovery,Pharmacology,Molecular Biology,Molecular Medicine,General Medicine,Biochemistry,Structural Biology
Cited by
1 articles.
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