Nonionic Dendritic and Carbohydrate Based Amphiphiles: Self‐Assembly and Transport Behavior

Abstract

Herein, a new series of non-ionic dendritic and carbohydrate based amphiphiles is synthesized employing biocompatible starting materials and studied for supramolecular aggregate formation in aqueous solution. The dendritic amphiphiles 12 and 13 possessing poly(glycerol) [G2.0] as hydrophilic unit and C-10 and C-18 hydrophobic alkyl chains, respectively, exhibit low critical aggregation concentration (CAC) in the order of 10 m and hydrodynamic diameters in the 8-10 nm range and supplemented by cryogenic transmission electron microscopy. Ultraviolet-visible (UV-Vis) and fluorescence spectroscopy suggests the effective solubilization of hydrophobic guests by the self-assembled architectures, with the nanotransporters 12 and 13 possessing the highest encapsulation efficiency of 80.74 and 98.03% for curcumin. Efficient uptake of encapsulated curcumin in adenocarcinomic human alveolar basal epithelial (A549) cells is observed by confocal laser scanning microscopy. Amphiphiles 12 and 13 are non-cytotoxic at the concentrations studied, however, curcumin encapsulated samples efficiently reduce the viability of A549 cells in vitro. Experimental studies indicate the ability of amphiphile 13 to encapsulate 1-anilinonaphthalene-8-sulfonic acid (ANS) and curcumin with binding constant of 1.16 × 105 m and 1.43 × 10 m , respectively. Overall, our findings demonstrate the potential of these dendritic amphiphiles for the development of prospective nanocarriers for the solubilization of hydrophobic drugs.

Non-ionic small amphiphile based nanostructures for biomedical applications

“…[60][61][62] In one of their work, they reported small non-ionic dendritic amphiphiles (7a and 7b) possessing polyglycerol G2 dendron as hydrophilic unit and C 10 and C 18 alkyl chains as hydrophobic tails. 63 These amphiphiles exhibited low CMC in the order of 10 À5 M and hydrodynamic diameters in the range of 8-10 nm, with the nano-transporters 7a and 7b possessing the highest (Fig. 16).…”

Self-assembly of carbohydrate-based small amphiphiles and their applications in pathogen inhibition and drug delivery: a review

“…Carbohydrate-based amphiphilic architectures have been successfully synthesized and investigated as advanced nanocarriers for drug delivery applications. 48,49 Carbohydrates, exhibiting a well-defined polyhydroxy architecture whose hydroxyl groups can be selectively modified, have emerged as a potential hydrophilic component for the amphiphiles. Certain advantages associated with carbohydrate-based amphiphilic architectures such as their pH independent self-assembling behaviour, biocompatibility, and mildness to the skin, make them potential candidates for drug delivery applications.…”

“…In an another report, glucose-and galactose-based dimeric amphiphiles were synthesized that self-assembled into supramolecular architectures in an aqueous medium. 49 Of all the three carbohydrate-based amphiphiles 20a-20c (Fig. 20), amphiphile 20b was fairly soluble in water and thus studied for encapsulation of hydrophobic guest molecules such as nimodipine, curcumin and Nile red.…”

Synthesis of d‐glucitolbased Gemini amphiphilic nanotransporters

“…20 Our group has studied the self-assembly and transport behavior of polyglycerol dendron and carbohydrate-based amphiphiles for drug delivery applications. 29,30 Furthermore a series of nonionic D-glucitolbased amphiphiles with phenyl and naphthyl hydrophobic units and triglycerol, glycerol, and mPEG azide hydrophilic moieties were developed to explore their transport behavior. 31 PEG and its derivatives are important in various biological, and pharmaceutical processes due to their explicit physicochemical properties such as water solubility, chemical stability, biocompatibility, nontoxicity, and low interactions with blood components.…”

“…Our group has studied the self‐assembly and transport behavior of polyglycerol dendron and carbohydrate‐based amphiphiles for drug delivery applications 29,30 . Furthermore a series of nonionic d ‐glucitol‐based amphiphiles with phenyl and naphthyl hydrophobic units and triglycerol, glycerol, and mPEG azide hydrophilic moieties were developed to explore their transport behavior 31 .…”