Glycosyl-Nucleolipids as New Bioinspired Amphiphiles

Laurent Latxague,Eric Amigues,Philippe Barthélémy,Amit Patwa

doi:10.3390/molecules181012241

Laurent Latxague, Eric Amigues + Show 2 more

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https://doi.org/10.3390/molecules181012241

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Abstract

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 γlim) compared to the first generation of GNFs.

Highlights

The chemical combination of biological molecules such as nucleic acids [1,2,3], aminoacids [4], peptides [5,6,7,8] or sugar [9,10,11] with lipids, remains an amazing approach to create new hybrid amphiphilic structures
It promotes liposome internalization in adipose stem cells [25] demonstrating again the inherent relevance of GNLs in biomedical applications. Further investigations in this domain led us to synthesize new GNLs featuring either a single F-alkyl chain or a double H-alkyl chain as hydrophobic moieties. In this contribution we report the synthesis of these new compounds, which have been characterized by NMR, MS, tensiometry and differential scanning calorimetry (DSC) experiments
The objectives of the present investigation were to expand the current repertoire of glycosylnucleolipids (GNLs) and study the effect of the structural modifications on their physicochemical properties

Summary

Introduction

The chemical combination of biological molecules such as nucleic acids [1,2,3], aminoacids [4], peptides [5,6,7,8] or sugar [9,10,11] with lipids, remains an amazing approach to create new hybrid amphiphilic structures Owning to their biocompatibility properties and biological functions, hybrid amphiphiles hold considerable potential for biomedical and biotechnological applications. Additional moieties were recently attached to the nucleolipid platforms, including aminoacids [22,23,24] and sugars [25,26]

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