| Abstract | This article focuses on reactions performed in nanostructured environments where the pair of complementary
nucleotides, 5¢-AMP and 5¢-UMP, are converted into their amphiphilic derivatives. The synthesis is carried out by
using the hydrophobic reactant dodecyl epoxide (DE) dispersed in a micellar solution based on the cationic surfactant
cetyltrimethylammoniumbromide (CTAB). Novel nucleo-lipids monomers and CTAB molecules give rise to the
spontaneous self-assembly of catanionic supramolecular structures in water, showing typical Maltese crosses in optical
microscopy. In the final colloidal suspensions, mono- and dichained derivatives have been identified in the system
incubated with 5¢-UMP through LC-QqTOF-MS analysis, whereas only mono-alkylated adducts are found in the
analogue reaction with 5¢-AMP. A new di-alkylated 5¢-UMP adduct is obtained from the 1:1 mixture of both
complementary nucleotides, in addition to the nucleo-lipids found in separate systems. Time-resolvedDLSmeasurements
reveal very different kinetic processes for aggregates' formation when 5¢-UMP, 5¢-AMP, or their equimolar combination
are used in the reaction mixture. This system as a whole represents a potential experimental model where the effect
of both intermolecular interactions and self-association processes can be investigated by tuning the type of nucleobases
in the reaction mixtures. |
| Text | 169981 2008 10.1021/la702580j ISI Web of Science WOS 000253941000014 Catanionic Systems from Conversion of Nucleotides into Nucleo Lipids Angelico R., Ceglie A., Cuomo F., Cardellicchio C., Mascolo G., Colafemmina G. Consorzio per lo sViluppo dei Sistemi a Grande Interfase CSGI c/o UniVersita` del Molise DISTAAM , V. De Sanctis, I 86100 Campobasso, Italy, CNR ICCOM , Dipartimento di Chimica, UniVersita` di Bari, Via Orabona 4, I 70126 Bari, Italy, CNR IRSA , Via F. De Blasio 5, I 70123 Bari, Italy, and Dipartimento di Chimica, UniVersita` di Bari, V. Orabona 4, I 70126 Bari, Italy This article focuses on reactions performed in nanostructured environments where the pair of complementary nucleotides, 5¢ AMP and 5¢ UMP, are converted into their amphiphilic derivatives. The synthesis is carried out by using the hydrophobic reactant dodecyl epoxide DE dispersed in a micellar solution based on the cationic surfactant cetyltrimethylammoniumbromide CTAB . Novel nucleo lipids monomers and CTAB molecules give rise to the spontaneous self assembly of catanionic supramolecular structures in water, showing typical Maltese crosses in optical microscopy. In the final colloidal suspensions, mono and dichained derivatives have been identified in the system incubated with 5¢ UMP through LC QqTOF MS analysis, whereas only mono alkylated adducts are found in the analogue reaction with 5¢ AMP. A new di alkylated 5¢ UMP adduct is obtained from the 1 1 mixture of both complementary nucleotides, in addition to the nucleo lipids found in separate systems. Time resolvedDLSmeasurements reveal very different kinetic processes for aggregates formation when 5¢ UMP, 5¢ AMP, or their equimolar combination are used in the reaction mixture. This system as a whole represents a potential experimental model where the effect of both intermolecular interactions and self association processes can be investigated by tuning the type of nucleobases in the reaction mixtures. 24 Catanionic Systems from Conversion of Nucleotides into Nucleo Lipids 2008_Langmuir_2008.pdf Articolo in rivista American Chemical Society, 0743 7463 Langmuir Langmuir Langmuir Langmuir cosimo.cardellicchio CARDELLICCHIO COSIMO giuseppe.mascolo MASCOLO GIUSEPPE PM.P03.011.001 processi e metodologie sostenibili in chimica organica per la sintesi di nuove piattaforme molecolari TA.P07.002.002 Sviluppo di nuovi processi di controllo dell inquinamento idrico. |
