Glycosyl-nucleoside fluorinated amphiphiles as components of nanostructured hydrogels

Glycosyl-Nucleolipids as New Bioinspired Amphiphiles

“…In contrast with the 1st generation GNL synthesis, the use of a protected glucose here allowed the exclusive formation of the desired mesylate intermediate which was directly displaced with sodium azide to yield the azido derivative 15 in 92% yield. Following a second 'click' reaction, the N-propargyl-1H,1H,2H,2H-perfluoroundecanoyl amide [29] was reacted with compound 15 in the presence of CuSO 4 in a THF/H 2 O mixture to afford the expected acetyl protected GNF 16. Finally, deacetylation of glucose moiety was carried out with sodium methoxide in methanol at room temperature to give the final compound 17 in 93% yield.…”

“…For example, the fluorinated GNL 1 (aka GNF, Figure 1b) in its hydrogel form has been used as a scaffold for stem cell culture and differentiation [33], and many complementary studies are still underway to take advantage of this particular property. In contrast, the hydrocarbon single chain GNLs were cytotoxic above 100 µM in human hepatocarcinoma cell line for example [29], which was attributed to a detergent effect of the single chain on the cell membrane, leading to fracture initiation and then cellular death. Consequently, in parallel to the fluoroalkyl (F-alkyl) chain, we also synthesized GNLs featuring a double H-alkyl C18 chain linked to a glycerol backbone (Figure 1c), which was expected to avoid any toxicity towards cells.…”

“…Each moiety is separated from the other by a triazole linker resulting from the click-chemistry used for their synthesis (Figure 1a). Most of the GNL amphiphiles exhibit the ability to form gels with either water or organic solvents giving rise to vesicles, nanofibers networks or nanoparticules as evidenced by TEM studies [28,29]. GNLs represent a new class of low molecular weight gelators (LMWGs) [30], which are of particular interest for biomedical applications due to their intrinsic properties, in particular the non-covalent nature of the molecular interactions at work (- stacking between the nucleobases and/or the triazole moieties, intermolecular hydrogen bond, etc).…”

Nucleic Acid Based Fluorinated Derivatives: New Tools for Biomedical Applications

“…GNFs gelators displayed supramolecular networks of varying morphologies, such as nanofibers and helical springs, which are correlated to the presence of fluorocarbon chains. Moreover, fluorocarbon amphiphile GNF 2 proved to be not toxic for human cells (Huh7) whereas hydrocarbon analogue becomes toxic above 100 µM, demonstrating the greater potential of such fluorocarbon nucleoside amphiphiles for biomedical applications [58].…”

Supramolecular metallogels for application in catalysis

“…Structure of GNFs synthesized by double 'click' chemistry. 66 The gels were synthesized through double 'click' chemistry route and spontaneously self-assembled in supramolecular structures in the presence of water or cellular medium. Cell viability studies proved the non-toxicity of these gels for human cells (Huh7).…”