Halogen Bonding in Nucleic Acid Complexes

0482693 - ÚOCHB 2018 RIV US eng J - Journal Article
Kolář, Michal H. - Tabarrini, O.
Halogen Bonding in Nucleic Acid Complexes.
Journal of Medicinal Chemistry. Roč. 60, č. 21 (2017), s. 8681-8690. ISSN 0022-2623. E-ISSN 1520-4804
Institutional support: RVO:61388963
Keywords : aldose reductase inhibition * minor groove binders * medicinal chemistry
OECD category: Physical chemistry
Impact factor: 6.253, year: 2017

Halogen bonding (X-bonding) has attracted notable attention among noncovalent interactions. This highly directional attraction between a halogen atom and an electron donor has been exploited in knowledge-based drug design. A great deal of information has been gathered about X-bonds in protein ligand complexes, as opposed to nucleic acid complexes. Here we provide a thorough analysis of nucleic acid complexes containing either halogenated building blocks or halogenated ligands. We analyzed close contacts between halogens and electron-rich moieties. The phosphate backbone oxygen is clearly the most common halogen acceptor. We identified 21 X-bonds within known structures of nucleic acid complexes. A vast majority of the X-bonds is formed by halogenated nucleobases, such as bromouridine, and feature excellent geometries. Noncovalent ligands have been found to form only interactions with suboptimal interaction geometries. Hence, the first X-bonded nucleic acid binder remains to be discovered.
Permanent Link: http://hdl.handle.net/11104/0278100