Synthesis of d‐glucitolbased Gemini amphiphilic nanotransporters

Abstract

A newer class of Gemini amphiphiles was prepared using D-glucitol as a template. C 18 alkyl chains are incorporated on the template to confer hydrophobicity while monomethoxy polyethylene glycol (mPEG) moiety of varied size imparts hydrophilicity. An acetonide group mounted on glucitol moiety is used to maintain rigidity in the amphiphilic architecture and to study its impact on aggregation and transport ability.The aggregation behavior of the synthesized amphiphiles was studied through fluorescence spectroscopy, dynamic light scattering (DLS), and cryo-transmission electron microscopy (cryo-TEM). Their nanotransport potential was demonstrated using hydrophobic model guests like the fluorescent dye Nile red and the pharmacologically active agent curcumin. Cytotoxicity and cellular uptake studies were carried out over HeLa cancer cells to evaluate their biological applicability. The ester functionalities in the amphiphiles enable them to exhibit sensitivity towards hydrolases. Candida antarctica lipase (Novozym-435) has been successfully utilized to facilitate the enzyme-assisted release of the encapsulated dye.

Trends in the Diversification of the Detergentome

“…Ester groups are a prominent example for cleavable linkers, which can be induced via low pH values or esterases (Figure 16). [171] Disulfide bonds are linkers that can be cleaved by reducing agents, like glutathione which is also found in cells, thus enabling a redoxtriggered micelle degradation and release of encapsulated drugs (Figure 16). [147b] Other disulfide detergents reported by Xue et al revealed good extraction yields and efficient stabilization of membrane proteins comparable to commercially available detergents.…”

Synthesis and transport potential study of A2B type double chain amphiphilic architectures

“…29 As per the earlier optimized procedure of our group, 0.12 mg of the dye in 5 mg/mL of the nanocarrier solution was prepared for encapsulation as a stock solution. T A B L E 2 Transport efficiency, transport capacity, and encapsulation efficiency of nanocarriers (13,16,17,18) for Nile red, nimodipine, and curcumin. cerebral blood flow by flowing intra-arterial, intravenous, or oral administration in humans as well as in animals.…”

“…Two series of nonionic double chain amphiphiles (mPEG-750 and mPEG-1000) were synthesized (13)(14)(15)(16)(17)(18) by varying the alkyl (C 8 /C 20 ) and perfluoroalkyl (C f8 ) moiety. Except 14 and 15 all other amphiphilic systems of both series were found to be soluble in water and form nanosized aggregates as established by DLS study.…”

“…Polyethylene glycols (PEGs) of varying size have invariably been used in such amphiphilic systems to confer hydrophilicity due to its favorable characteristics, for example, nontoxicity, biocompatibility, non‐recognition by endothelial system, ease of functionalization 15,16 …”

“…Polyethylene glycols (PEGs) of varying size have invariably been used in such amphiphilic systems to confer hydrophilicity due to its favorable characteristics, for example, nontoxicity, biocompatibility, non-recognition by endothelial system, ease of functionalization. 15,16 In recent year's perfluoroalkyl and polyperfluoroalkyl substances (PFAS) are being considered as rather newer and interesting entrant for providing hydrophobic surface they offers high thermal and chemical stability and unique surface tension lowering properties to the molecule. [17][18][19] This is mainly due to the hydrophobic nature of fluorocarbon chains that allow them to concentrate at the liquid-liquid interface.…”