Catanionic systems from conversion of nucleotides into nucleo-lipids.
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-resolved DLS measurements 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.
Angelico
Ruggero
R
Consorzio per lo sviluppo dei Sistemi a Grande Interfase (CSGI) c/o Università del Molise (DISTAAM), v. De Sanctis, I-86100 Campobasso, Italy. angelico@unimol.it
Ceglie
Andrea
A
Cuomo
Francesca
F
Cardellicchio
Cosimo
C
Mascolo
Giuseppe
G
Colafemmina
Giuseppe
G
D002412:Cations / Q000737:chemistry; D000077286:Cetrimonium; D002593:Cetrimonium Compounds / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003102:Colloids / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry; D057927:Hydrophobic and Hydrophilic Interactions; D008055:Lipids / Q000737:chemistry*; D046911:Macromolecular Substances / Q000737:chemistry; D008823:Micelles; D015394:Molecular Structure; D049329:Nanostructures / Q000737:chemistry; D009711:Nucleotides / Q000737:chemistry*; D010316:Particle Size; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D013499:Surface Properties; D013501:Surface-Active Agents / Q000737:chemistry*; D013997:Time Factors; D014867:Water / Q000737:chemistry
D002412:Cations; D002593:Cetrimonium Compounds; D003102:Colloids; D004852:Epoxy Compounds; D008055:Lipids; D046911:Macromolecular Substances; D008823:Micelles; D009711:Nucleotides; D013501:Surface-Active Agents; D014867:Water; D000077286:Cetrimonium