Amino Acid–Nucleotide–Lipids: Effect
of Amino Acid on the Self-Assembly Properties
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Abstract
Hybrid amphiphiles
composed of a lipid covalently linked to biomolecules
are attracting considerable attention, owing to their unique physicochemical
and biological properties. Herein, we have synthesized novel amino
acid–nucleotide–lipids (ANLs), presenting phenylalanine
and thymidine residues and saturated or unsaturated diacyl glycerol
lipid moieties to investigate the effect of the specific aminoacid
moieties on both aggregation properties and interactions of ANLs with
single strand polyA RNA. Physicochemical studies (DLS, cryo-TEM, and
small angle X-ray scattering) indicate that phenylanaline amino acids
inserted at the 5′ position of the nucleotide-lipids stabilize
multilamellar systems, whereas unilamellar vesicles are formed preferentially
in the case of nucleotide–lipids (NLs). Both NLs and ANLs exhibit
weak interactions with complementary polyA RNA as revealed by isothermal
titration calorimetry investigations. The multilamellar vesicles obtained
with ANLs could be used as a versatile carrier, suitable for both
hydrophobic and hydrophilic therapeutic molecules