Abstract
The synthetic nucleoside acyclovir is considered an outstanding model of the natural nucleoside guanosine. With the purpose of deepening on the influence and nature of non-covalent interactions regarding molecular recognition patterns, three novel Cu(II) complexes, involving acyclovir (acv) and the ligand receptor N-(2-hydroxyethyl)ethylenediamine (hen), have been synthesized and thoroughly characterized. The three novel compounds introduce none, one or two acyclovir molecules, respectively. Molecular recognition has been evaluated using single crystal X-ray diffraction. Furthermore, theoretical calculations and other physical methods such as thermogravimetric analysis, infrared and UV-Vis spectroscopy, electron paramagnetic resonance and magnetic measurements have been used. Theoretical calculations are in line with experimental results, supporting the relevance of the [metal-N7(acv) + H-bond] molecular recognition pattern. It was also shown that (hen)O-H group is used as preferred H-donor when it is found within the basal coordination plane, since the higher polarity of the terminal (hen)O-H versus the N-H group favours its implication. Otherwise, when (hen)O-H occupies the distal coordination site, (hen)N-H groups can take over.
Highlights
Synthetic nucleoside analogues have been widely used as suitable models for the study of nucleic acids and its applications along different research fields [1,2,3,4,5]
Molecular electrostatic potential (MEP) surfaces have been computed at the same level of theory and represented using the 0.001 a.u. isosurface
O6 atom of the guanosine moiety as H-acceptor. This molecular recognition pattern has been described for the binding of cis-platinum drugs to DNA
Summary
Synthetic nucleoside analogues have been widely used as suitable models for the study of nucleic acids and its applications along different research fields [1,2,3,4,5]. In contrast to the furanose ring of natural nucleosides, which undergoes opening-cyclization equilibrium, the presence of an acyclic side-chain in some synthetic nucleosides offers a remarkable chemical stability. This fact can be conveniently harnessed by structural studies, especially those involving metal binding and ligand interaction. In this context, the similarities between acyclic and natural nucleosides are worth noting, despite the different chemical nature of the O-ether group and the furanosic oxygen in acyclic and natural nucleosides, respectively. Acyclovir is phosphorylated by viral thymidine kinase into acyclovir triphosphate, which
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