Supramolecular Assemblies of Nucleoside Phosphocholine Amphiphiles
- 27 May 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (24) , 7533-7539
- https://doi.org/10.1021/ja039597j
Abstract
A family of new uridine phosphocholine amphiphiles that were prepared using a convenient four-step synthetic route is described. Physicochemical studies (differential scanning calorimetry, small-angle X-ray scattering, UV−vis and circular dichroism spectroscopies, light microscopy, transmission electronic microscopy, and scanning electron microscopy) show that these amphiphiles spontaneously assemble into supramolecular structures including vesicles, fibers, hydrogels, and organogels. In aqueous solution, the amphiphiles possessing saturated alkyl chains self-assemble into DNA-like helical fibers in the crystalline state below Tm and compact bilayers above the melting temperature (Tm). The transition from bilayers to fibers is thermally reversible. Above a threshold concentration (>6% w/w), a hydrogel is formed due to an entangled network of the fibers. A therapeutic agent such as DNA can be entrapped within the hydrogel structure. In addition to forming bilayer vesicles and hydrogels in aqueous solution, these nucleoside amphiphiles also form organogels in cyclohexane above Tm. Scanning electron microscopy shows a continuous multilamellar phase in the organogels.Keywords
This publication has 36 references indexed in Scilit:
- Polynucleotide Can Stabilize Nucleobase-appended Cholesterol GelsChemistry Letters, 2003
- Combinatorial Library of Low Molecular‐Weight Organo‐ and Hydrogelators Based on Glycosylated Amino Acid Derivatives by Solid‐Phase SynthesisChemistry – A European Journal, 2003
- Molecular Recognition Capabilities of a Nucleolipid Amphiphile (3‘,5‘-Distearoyl)-2‘-Deoxythymidine to Adenosine at the Air/Water Interface and Langmuir−Blodgett Films Studied by Molecular SpectroscopyLangmuir, 2000
- Supramolecular Structures of Novel Carbohydrate-Based PhospholipidsJournal of the American Chemical Society, 2000
- Multinuclear NMR Investigation of Phosphatidylcholine OrganogelsThe Journal of Physical Chemistry, 1996
- Molecular Recognition between Uncharged Molecules in Aqueous MicellesJournal of the American Chemical Society, 1994
- Cooperative Binding of Adenine via Complementary Hydrogen Bonding to an Imide Functionalized Monolayer at the Air-Water InterfaceChemistry Letters, 1992
- Molecular Self-Assembly and Nanochemistry: a Chemical Strategy for the Synthesis of NanostructuresScience, 1991
- Perspectives in Supramolecular Chemistry—From Molecular Recognition towards Molecular Information Processing and Self‐OrganizationAngewandte Chemie International Edition in English, 1990
- NMR studies of nucleic acids. Deuterium isotope effects on carbon-13 chemical shifts in hydrogen-bonded complexes of pyrimidines and purinesJournal of the American Chemical Society, 1988