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

The inefficient delivery of drugs having low efficacy to their target sites is significantly hampering the treatment of many diseases and putting enormous pressure on the healthcare system. In this endeavor, the non-ionic amphiphilic nanotransporters are drawing increasing attention over the past decades. Herein, we report the synthesis of a newer A(2)B type non-ionic double chain amphiphilic nanotransporters by using dimethyl 5-hydroxy isophthalate based central core prepared by propargylation followed by ester hydrolysis. The core was subsequently decorated with hydrophobic alkyl (C-8/C-20/perfluoro alkylated C-f8) chains via esterification. Monomethoxy polyethylene glycol (mPEG) moiety (M-n: 750/1000) was then incorporated by click chemistry approach to confer hydrophilicity. The aggregation behavior of synthesized non-ionic amphiphiles in aqueous medium was evaluated by using dynamic light scattering (DLS) and fluorescence spectroscopy. The nanotransport potential of the synthesized amphiphiles was studied by using model hydrophobic guests, that is, the dye Nile red and the drugs nimodipine and curcumin by using ultraviolet-visible (UV/Vis) and fluorescence spectroscopic techniques. Evaluation of the viability of amphiphiles synthesized against HeLa cells showed them to be well tolerated up to the concentration studied. Stimuli responsive release of encapsulated Nile red from the inner core of amphiphile was successfully carried out in the presence of an immobilized enzyme Candida antarctica lipase (Novozym 435). In nutshell, the results obtained from this study may be instrumental in the design and development of promising nanotransporters for biomedical applications.