title: Non-covalent interactions: complexes of guanidinium with DNA and RNA nucleobases.
abstract: Considering that guanidine-based derivatives are good DNA minor groove binders, we have theoretically studied, using the Polarizable Continuum model mimicking water solvation, the complexes formed by the biologically relevant guanidinium cation and the DNA and RNA nucleobases (adenine, guanine, cytosine, thymine, and uracil). The interactions established within these complexes both by hydrogen bonds and by cation-π interactions have been analyzed by means of the Atoms in Molecules and Natural Bond Orbital approaches. Moreover, maps of electron density difference have been produced to understand the cation-π complexes. Finally, the NICS and three-dimensional NICS maps of the cation-π complexes have been studied to understand the effect of the guanidinium cation on the aromaticity of the nucleobases.
authors.affiliation: Molecular Design Group, School of Biochemistry and Immunology, Trinity Biomedical Sciences Institute, University of Dublin, Trinity College, Trinity College, 152-160 Pearse Street, Dublin 2, Ireland.
authors.forename: Fernando
authors.initials: F
authors.lastname: Blanco
authors.forename: Brendan
authors.initials: B
authors.lastname: Kelly
authors.forename: Goar
authors.initials: G
authors.lastname: Sánchez-Sanz
authors.forename: Cristina
authors.initials: C
authors.lastname: Trujillo
authors.forename: Ibon
authors.initials: I
authors.lastname: Alkorta
authors.forename: Jose
authors.initials: J
authors.lastname: Elguero
authors.forename: Isabel
authors.initials: I
authors.lastname: Rozas
mesh_terms: D000225:Adenine / Q000737:chemistry*; D002412:Cations / Q000737:chemistry; D003198:Computer Simulation; D003596:Cytosine / Q000737:chemistry*; D004247:DNA / Q000737:chemistry; D004583:Electrons; D019791:Guanidine / Q000737:chemistry*; D006147:Guanine / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D012313:RNA / Q000737:chemistry; D013941:Thymine / Q000737:chemistry*; D014498:Uracil / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D002412:Cations; D014867:Water; D014498:Uracil; D006147:Guanine; D012313:RNA; D003596:Cytosine; D004247:DNA; D000225:Adenine; D019791:Guanidine; D013941:Thymine