Abstract

Newer non-ionic amphiphiles have been synthesized using biocompatible materials and by following a greener approach i.e., D-glucitol has been used as a template, and hydrophobic and hydrophilic segments were incorporated on it by using click chemistry. The hydrophilic segments in turn were prepared from glycerol using an immobilized Candida antarctica lipase (Novozym-435)-mediated chemoenzymatic approach. Surface tension measurements and dynamic light scattering studies reflect the self-assembling behavior of the synthesized amphiphilic architectures in the aqueous medium. The results from UV-Vis and fluorescence spectroscopy establish the encapsulation of guests in the hydrophobic core of self-assembled amphiphilic architectures. The results of 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium (MTS) assay indicate that the amphiphiles are well tolerated by the used A549 cell lines at all tested concentrations.

Highlights

  • The natural biological constructs such as proteins, lipids, nucleic acids, etc. display self-assembling behavior governed by various non-covalent interactions [1]

  • The residue was extracted with chloroform, the organic layer was washed with saturated solution of Ethylenediamine tetraacetic acid (EDTA) (3 × 100 mL), and the organic layer was dried over anhydrous sodium sulfate

  • In an endeavor to create novel cytocompatible amphiphilic constructs as nanocarriers for biomedical applications, we have synthesized a series of D-glucitol-based amphiphiles employing biocompatible and green hydrophilic moieties and aromatic hydrophobic moieties

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Summary

Introduction

The natural biological constructs such as proteins, lipids, nucleic acids, etc. display self-assembling behavior governed by various non-covalent interactions [1]. Among the plethora of architectures capable of exhibiting self-assembling properties, low molecular weight amphiphiles, in particular the Gemini amphiphiles, have attracted much attention of researchers, both in academia and industry, due to their superior physicochemical properties as compared to their ionic, in particular the cationic counterparts [4,5,6,7,8,9]. We report the synthesis and biophysical characterization of novel non-ionic novel non-ionic amphiphilic constructs constituted from glucitol-3,4-monoacetonide-1,6-diazide as a amphiphilic constituted from glucitol-3,4-monoacetonide-1,6-diazide as a template and template andconstructs conjugating it with biocompatible synthons.

Materials
Instrumentation and Methods
Guest Encapsulation and Quantification
Cytotoxicity Study
Synthetic Procedures for Hydrophobic Backbone and Amphiphilic Architectures
Compound 6
Compound 10
General Procedure for Synthesis of Compounds 7 and 11
Synthesis of Amphiphile 20
Synthesis of Amphiphile 21
Synthesis of Amphiphile 22
Synthesis of Amphiphile 23
Synthesis of Amphiphile 24
Synthesis of Amphiphile 25
Results and Discussion
Synthesis and Characterization
Critical
Hydrophilic–Lipophilic Balance Determination
Dynamic
Encapsulation Study
Nile Red Encapsulation Study
Dexamethasone Encapsulation
Conclusions
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