title: Metal ion binding patterns of acyclovir: molecular recognition between this antiviral agent and copper(II) chelates with iminodiacetate or glycylglycinate.
abstract: In order to deepen on metal-binding patterns of acyclovir (acv), {[Cu(IDA)(acv)]·2MeOH}(n) (1) and [Cu(glygly)(acv)]·H(2)O (2) compounds have been synthesized and investigated by X-ray crystallography as well as spectral and thermal methods. These compounds have been chosen upon the assumption that iminodiacetate (IDA) and glycylglycinate (glygly) chelating ligands would bind copper(II) with mer-tridentate conformation, supplying two terminal H-acceptor carboxylate groups (IDA) or one H-acceptor carboxylate and one H-donor primary amino group (glygly). The main aim of this work was to clarify if the amino group of glygly can build an intra-molecular interligand H-bonding interaction to reinforce the Cu-N7(acv) bond. Our results are discussed in the context of an up-to-date critical look regarding the related structural information. From the viewpoint of molecular recognition, the structure of 1 shows that the chelate-nucleoside recognition only involves the Cu-N7(acv) coordination bond. In contrast, the molecular complex of 2 exhibits the Cu-N7(acv) coordination bond reinforced by an intra-molecular (glygly)N-H···O6(acv) interaction (2.961(3)Å, 140.5°).
authors: Department of Inorganic Chemistry, Faculty of Pharmacy, Campus Cartuja, University of Granada, Granada, Spain.
authors: María del Pilar
authors: Mdel P
authors: Brandi-Blanco
authors: Duane
authors: D
authors: Choquesillo-Lazarte
authors: Alicia
authors: A
authors: Domínguez-Martín
authors: Josefa María
authors: JM
authors: González-Pérez
authors: Alfonso
authors: A
authors: Castiñeiras
authors: Juan
authors: J
authors: Niclós-Gutiérrez
mesh_terms: D000212:Acyclovir / Q000737:chemistry* / Q000378:metabolism; D000998:Antiviral Agents / Q000737:chemistry* / Q000378:metabolism; D002614:Chelating Agents / Q000737:chemistry*; D056831:Coordination Complexes / Q000737:chemistry* / Q000378:metabolism; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007098:Imino Acids / Q000737:chemistry* / Q000378:metabolism; D007477:Ions / Q000737:chemistry / Q000378:metabolism; D008024:Ligands; D008670:Metals; D009942:Organometallic Compounds / Q000737:chemistry*; D013754:Tetracyclines / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000998:Antiviral Agents; D002614:Chelating Agents; D056831:Coordination Complexes; D007098:Imino Acids; D007477:Ions; D008024:Ligands; D008670:Metals; D009942:Organometallic Compounds; D013754:Tetracyclines; C087533:CL 331002; D003300:Copper; D000212:Acyclovir; C008109:iminodiacetic acid