Evaluation of Transport Potential of Alkylated and Fluoroalkylated Amphiphilic Hybrid Nanoarchitectures

Abstract

The unique segregation and self-assembly properties of fluorinated amphiphiles into supramolecular architectures have attracted substantial attention in recent years. In this study, we report the design and synthesis of six newer hybrid nonionic amphiphiles with hydrophobic alkyl/fluoroalkyl chains and hydrophilic polyethylene glycol (PEG) units of different lengths and evaluate and compare their drug delivery applications. On the hydrophobic side, the amphiphiles differ in having either two alkyl chains, two fluoroalkyl chains, or one alkyl and one fluoroalkyl chain. This allowed for a systematic comparison of the physicochemical and transport abilities. The aggregation phenomenon of the amphiphiles was monitored with Cryo-TEM. Cytotoxicity and cellular uptake studies were performed to evaluate the pharmacological potential. Candida antarctica lipase (Novozym-435) immobilized on solid support was used to facilitate the release of the encapsulated cargo. Our study highlights the potential and properties of the fluoroalkyl-based nanocarriers.

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

“…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.…”

“…CONCLUSIONSTwo series of mPEG based double chain amphiphiles(13)(14)(15)(16)(17)(18) have been synthesized with varied substituents on an isophthalate based central core. Physicochemical and spectroscopic data was used to characterize all the amphiphiles.…”