Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds.
Inmaculada Velo-GalaMiquel Barceló-OliverDiego M GilJosefa María González-PérezAlfonso CastiñeirasAlicia Dominguez-MartinPublished in: Pharmaceuticals (Basel, Switzerland) (2021)
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.
Keyphrases
- single molecule
- high resolution
- molecular dynamics
- mental health
- density functional theory
- molecular dynamics simulations
- herpes simplex virus
- physical activity
- magnetic resonance imaging
- minimally invasive
- computed tomography
- electron microscopy
- mass spectrometry
- aqueous solution
- energy transfer
- metal organic framework
- dual energy