am7b06037_si_004.cif (680.36 kB)
Surface-Tuned and Metal-Ion-Responsive Supramolecular Gels Based on Nucleolipids
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posted on 2017-06-14, 00:00 authored by Ashok Nuthanakanti, Seergazhi G. SrivatsanSupramolecular
synthons based on nucleic acid components, nucleobases and nucleosides,
and their derivatives have been highly useful in constructing wide
varieties of nanoarchitectures. While most of the design strategies
have focused on developing biocompatible delivery vehicles, the potential
of nucleoside hybrids in assembling smart materials with tunable and
sensing properties, though challenging, is gaining significant attention.
Here, we describe the development of novel functional materials with
surface tunability and metal-ion responsiveness by using simple nucleolipid
supramolecular synthons derived by attaching various fatty acids to
the 3′-O or 3′,5′-O positions of the sugar residue of thymidine nucleoside. 3′,5′-O-Difatty acid-substituted thymidines formed typical organogels
in pure organic solvents, whereas, 3′-O-monofatty
acid-substituted thymidine nucleolipids formed water-induced gels.
A detailed morphological and structural analysis using microscopy,
single-crystal and powder X-ray diffraction, and NMR techniques clearly
revealed the molecular interactions invoked by nucleobase, sugar,
fatty acid chain, and water in setting up the path for hierarchical
self-assembly and gelation of thymidine nucleolipids. Interestingly,
the surface property of the xerogel film fabricated using 3′-O-monosubstituted nucleolipid gels could be switched from
highly hydrophobic to hydrophilic and vice versa depending
on the nature of the organic solvent–water mixture used in
the gelation process. On the contrary, the gelation process of disubstituted
thymidine nucleolipids was highly sensitive to the presence of Hg2+ ions as the metal ion formed a T–Hg–T base
pair, thereby disrupting the H-bonding interactions that favored the
gelation. Taken together, straightforward synthesis and modification-dependent
gelation behavior, surface tunability, and metal-ion responsiveness
underscore the potential of these supramolecular nucleolipid synthons
in constructing novel functional materials.
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powder X-ray diffractionmodification-dependent gelation behaviorgelation processmaterialNucleolipids Supramolecular synthonssurface tunabilitymonofatty acid-substituted thymidine nucleolipidsMetal-Ion-Responsive Supramolecular Gelsnucleosidemetal-ion responsivenesssupramolecular nucleolipid synthonsnucleolipid supramolecular synthonsNMRbiocompatible delivery vehiclesdisubstituted thymidine nucleolipidsDifatty acid-substituted thymidines
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