Light-modulation of gel stiffness: a glyconucleoside based bolaamphiphile as a photo-cleavable low molecular weight gelator

Abstract

A photo-cleavable glyconucleoside bolaamphiphile (GNBAhv) featuring a nitrophenyl unit is reported. The stiffness of the GNBAhv based gels can be modulated upon light irradiation.

Harnessing Glycolipids for Supramolecular Gelation: A Contemporary Review

“…This light-responsive hydrogel could serve as a promising smart biomaterial, thereby allowing on-demand control of gel stiffness for applications in cellular or tissue engineering [ Figure 24,(59)]. 141 4.6. Miscellaneous Glycolipid Gelators.…”

“…The increase in the storage modulus was observed after the photocleavage of nitrophenyl groups. This light-responsive hydrogel could serve as a promising smart biomaterial, thereby allowing on-demand control of gel stiffness for applications in cellular or tissue engineering [Figure , ( 59 )] …”

Synthetic approaches of carbohydrate based self-assembling systems

“…More recently, an O -nitrobenzyl group was attached to the nucleoside to prepare the glyconucleo-bola-amphiphile amide (GNBA) linked photocleavable gelator 164 . 84 The synthesis of 164 is shown in Scheme 24. A click reaction of N -propargyl thymidine with β-1-azido hepta- O -acetyl-β- d -lactopyranose afforded the intermediate 160 , which was converted to the azide derivative 161 .…”

Hierarchical Self-Aggregation of Multifunctional Steviol Glycosides in Aqueous Solutions

“…Hierarchical molecular self-assembly or self-aggregation in solutions has aroused great attention due to the preprogrammable structuring process as well as the access to advanced structures with some unique and dynamic characteristics. , Generally, different orders of hierarchical assembly are partitioned: in the first step, the original building blocks organize into “first-order” structural motifs, and in the subsequent higher-level step, these motifs become the building blocks for a further “second-order” assembly leading to the formation of larger and more complex structures . Various low-molecular-weight surfactants, such as conventional amphiphiles (containing a polar headgroup and one or two hydrophobic tails), bolaamphiphiles, gemini surfactants, and sugar-based systems, have been reported to readily undergo self-assembly in water to form a wide range of ordered nanostructures, such as micelles, vesicles, fibers, ribbons, and tubes. Among them, micelles are commonly regarded as colloidal structures with a hydrophobic core and hydrophilic shell spontaneously formed by amphiphilic monomers and show unique characteristics, including various morphologies (e.g., spheres, rods, and linear worms), highly controllable shapes and sizes, and multifunctionality .…”