Quantum chemistry study of interaction of Cu2+ cation and aqua-copper [Cu(H2O)1-4]2+ complexes with resveratrol stereoisomers, phospholipid and deoxythymidine 5′-monophosphate

The accurate quantum-chemical computations based on DFT, Hartree-Fock and second-order Møller-Plesset (MP2) methods have been performed for the first time to study the interaction of the Cu2+ ion and [Cu(H2O)1-4]2+ complexes with trans-resveratrol, its cis-stereoisomer, phospholipid and deoxythymidine 5′-monophosphate in vacuum and water medium. On the basis of the interaction energies we have demonstrated that O3 and O5 oxygen atoms of the stereoisomers of resveratrol form the most stable chelate complexes with Cu2+. It has been shown that the capacity of trans-resveratrol to chelate Cu2+ is higher than that of cis-resveratrol. The trans-resveratrol-Cu2+-phospholipid [trans-resveratrol-Cu(H2O)4-phospholipid]2+, trans-resveratrol-Cu2+-deoxythymidine 5′-monophosphate and [trans-resveratrol-Cu(H2O)4-deoxythymidine 5′-monophosphate]2+ systems in which Cu2+ and [Cu(H2O)4]2+ aqua complex coordinate to the negatively charged oxygen atoms of 5′-monophosphate group of deoxythymidine 5′-monophosphate and phospholipid are characterised by the lowest interaction energy. We have proved that the hydration of the Cu(II) ion by four water molecules contributes to the dramatic reduction of the energetical stability of all the complexes studied. It was pointed out that in aqueous medium the stability of all complexes is significantly higher than in vacuum. The result suggests that trans-resveratrol-Cu(II) and [trans-resveratrol-Cu(H2O)4]2+ complexes can bind with negatively charged oxygen atoms of 5′-monophosphate anion of phospholipids which form a polar shell surrounding LDL particles. Furthermore, it has been found that trans-resveratrol-3-O-Cu(II) and trans-resveratrol-5-O-Cu(II) complexes are capable of forming the most stable complexes with deoxythymidine 5′-monophosphate and phospholipid. The findings obtained satisfactorily explain the experimental data and give insight into understanding of therapeutical and biological activity of trans-resveratrol-Cu2+ complexes.