Glycosyl-Nucleolipids as new bioinspired amphiphiles

Four new Glycosyl-NucleoLipid (GNL) analogs featuring either a single fluorocarbon or double hydrocarbon chains were synthesized in good yields from azido thymidine as starting material. Physicochemical studies (surface tension measurements, differential scanning calorimetry) indicate that hydroxybu...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2013-09, Vol.18 (10), p.12241-12263
Main Authors: Latxague, Laurent, Patwa, Amit, Amigues, Eric, Barthélémy, Philippe
Format: Article
Language:English
Subjects:
amphiphiles
Calorimetry, Differential Scanning
Click Chemistry
Cytotoxicity
fluorocarbon
Glucose - chemistry
Glycerol
glycosyl
Hydrocarbons
Lipids
nucleolipid
nucleoside
Nucleosides - chemical synthesis
Perfluorocarbons
Phase transitions
Sugar
Surface Tension
Surface-Active Agents - chemical synthesis
Zidovudine - chemistry
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Summary:Four new Glycosyl-NucleoLipid (GNL) analogs featuring either a single fluorocarbon or double hydrocarbon chains were synthesized in good yields from azido thymidine as starting material. Physicochemical studies (surface tension measurements, differential scanning calorimetry) indicate that hydroxybutanamide-based GNLs feature endothermic phase transition temperatures like the previously reported double chain glycerol-based GNLs. The second generation of GNFs featuring a free nucleobase reported here presents a better surface activity (lower glim) compared to the first generation of GNFs.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules181012241