Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds
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AcyclovirMolecular recognitionDFTNon-covalent interactionsH-bonds
Velo-Gala, I.; Barceló-Oliver, M.; Gil, D.M.; González-Pérez, J.M.; Castiñeiras, A.; Domínguez-Martín, A. Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds. Pharmaceuticals 2021, 14, 244. [https://doi.org/10.3390/ph14030244]
SponsorshipAgencia Estatal de Investigacion, Ministerio de Ciencia, Innovacion y Universidades (MICIU) from Spain; European Commission PGC2018-102047-B-I00 CTQ2017-85821-R; Junta de Andalucia FQM-283; University of Granada PPJIA2019-03
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.