title: Unzipping nucleoside channels by means of alcohol disassembly.
abstract: Gold nanoparticles capped with simple adenosine derivatives can form colloidal aggregates in nonpolar solvents. Theoretical calculations indicate the formation of organic channels by the supramolecular assembly of the nanoparticles by means of hydrogen bonds between the adenine moieties. The aggregates were only negligibly sensitive to nPrOH, iPrOH, and tBuOH, whereas some showed a similar response to MeOH and EtOH, and others showed high selectivity toward MeOH. DNA nucleoside derivatives (1-(2-deoxy-β-D-ribofuranosyl)-5-methyluracil and 2',3'-O-isopropylideneadenosine) as well as thymine and other aromatic compounds such as pyrene derivatives (pyrene, 1-chloropyrene, 1-hydroxypyrene, (1-pyrenyl)methanol, and 2-hydroxynapthalene) did not induce disassembly of the nanoparticle aggregates. Data suggest that the nucleoside channels allow access to alcohols according to their size, and an efficient interaction between the alcohol and the adenine units destabilizes the hydrogen bonds, which eventually leads to nanoparticle disassembly.
authors.affiliation: Instituto de Ciencia Molecular (ICMol), Universidad de Valencia, C/Catedrático José Beltrán 2, 46980 Paterna, Valencia (Spain), Fax: (+34) 963543273.
authors.forename: Julie P
authors.initials: JP
authors.lastname: Vanegas
authors.forename: Lucas E
authors.initials: LE
authors.lastname: Peisino
authors.forename: Salvador
authors.initials: S
authors.lastname: Pocoví-Martínez
authors.forename: Ramón J
authors.initials: RJ
authors.lastname: Zaragozá
authors.forename: Elena
authors.initials: E
authors.lastname: Zaballos-García
authors.forename: Julia
authors.initials: J
authors.lastname: Pérez-Prieto
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D020029:Base Pairing; D004247:DNA / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D006860:Hydrogen Bonding; D053768:Metal Nanoparticles / Q000737:chemistry* / Q000648:ultrastructure; D009705:Nucleosides / Q000737:chemistry*; D012313:RNA / Q000737:chemistry
chemical_list: D000438:Alcohols; D009705:Nucleosides; D012313:RNA; D006046:Gold; D004247:DNA
keywords: alcohols; gold; hydrogen bonds; nanoparticles; nucleosides