Unzipping Nucleoside Channels by Means of Alcohol Disassembly |
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Authors: | Julie P. Vanegas Lucas E. Peisino Dr. Salvador Pocoví‐Martínez Dr. Ramón J. Zaragozá Dr. Elena Zaballos‐García Dr. Julia Pérez‐Prieto |
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Affiliation: | 1. Instituto de Ciencia Molecular (ICMol), Universidad de Valencia, C/Catedrático José Beltrán 2, 46980 Paterna, Valencia (Spain), Fax: (+34)?963543273;2. Current address: INFIQC, Departamento Química Orgánica, Universidad Nacional de Córdoba, Ciudad Universitaria, 5000 Córdoba (Argentina);3. Departamento Química Orgánica, Facultad de Quimica, Universidad de Valencia, Dr. Moliner, 50, 46100 Burjassot (Spain);4. Departamento Química Orgánica, Facultad de Farmacia, Universidad de Valencia, C/Vicent Andrés Estellés s/n, 46100 Burjassot (Spain) |
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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. |
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Keywords: | alcohols gold hydrogen bonds nanoparticles nucleosides |
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