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 moi...

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Bibliographic Details
Published in:Polymers for Advanced Technologies
Main Authors: Verma, Diksha, Rashmi, Achazi, Katharina, Kumar Singh, Abhishek, Schade, Boris, Haag, Rainer, Sharma, Sunil K.
Format: Article in Journal/Newspaper
Language:English
Published: Wiley 2022
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Online Access:http://dx.doi.org/10.1002/pat.5716
https://onlinelibrary.wiley.com/doi/pdf/10.1002/pat.5716
https://onlinelibrary.wiley.com/doi/full-xml/10.1002/pat.5716
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Summary: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.