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• W2016339623 abstract "Metformin (Metf), the most commonly used type 2 diabetes drug, is known to affect the cellular housekeeping of copper. Recently, we discovered that the structurally closely related propanediimidamide (PDI) shows a cellular behavior different from that of Metf. Here we investigate the binding of these compounds to copper, to compare their binding strength. Furthermore, we take a closer look at the electronic properties of these compounds and their copper complexes such as molecular orbital interactions and electrostatic potential surfaces. Our results clearly show that the copper binding energies cannot alone be the cause of the biochemical differentiation between Metf and PDI. We conclude that other factors such as pKa values and hydrophilicity of the compounds play a crucial role in their cellular activity. Metf in contrast to PDI can occur as an anion in aqueous medium at moderate pH, forming much stronger complexes particularly with CuII ions, suggesting that biguanides but not PDI may induce easy oxidation of CuI ions extracted from proteins. The higher hydrophobicity and the lack of planarity of PDI may further differentiate it from biguanides in terms of their molecular recognition characteristics. These different properties could hold the key to metformin’s mitochondrial activity because they suggest that the drug could act at least in part as a pro-oxidant of accessible protein-bound CuI ions." @default.
• W2016339623 created "2016-06-24" @default.
• W2016339623 creator A5026911623 @default.
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• W2016339623 date "2014-01-24" @default.
• W2016339623 modified "2023-09-27" @default.
• W2016339623 title "Biomolecular Mode of Action of Metformin in Relation to Its Copper Binding Properties" @default.
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• W2016339623 doi "https://doi.org/10.1021/bi401444n" @default.
• W2016339623 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/24433134" @default.
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