New glycosylated conjugate copolymer N-acetyl-β-d-glucosaminyl-pluronic: Synthesis, self-assembly and biological assays

New glycosylated conjugate copolymer N-acetyl-β-d-glucosaminyl-pluronic: Synthesis, self-assembly and biological assays

•Novel glycosylated copolymer conjugate was successfully synthesized via click chemistry.•8.7nm diameter carbohydrate decorated micelles were produced.•The micelles demonstrated colloidal stability.•The produced nanostructures are neither cytotoxic nor genotoxic.•The assemblies have potential applic...

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Bibliographic Details
Published in:Colloids and surfaces, B, Biointerfaces Vol. 133; pp. 323 - 330
Main Authors: Frizon, Tiago Elias Allievi, Micheletto, Yasmine Miguel Serafini, Westrup, José Luiz, Wakabayashi, Priscila Sayoko Silva, Serafim, Francieli Rocha, Damiani, Adriani Paganini, Longaretti, Luiza Martins, de Andrade, Vanessa Moraes, Giacomelli, Fernando Carlos, Fort, Sébastien, Dal Bó, Alexandre Gonçalves
Format: Journal Article
Language:English
Published: Netherlands Elsevier B.V 01-09-2015
Elsevier
Subjects:
Acetylglucosamine - chemistry
Amphiphilic glycoconjugates
Assaying
Chemical Sciences
Click chemistry
Comet Assay
Conjugates
Copolymers
Fluorescence
Glycosylation
Humans
Micelles
Microscopy, Electron, Transmission
Poloxamer - chemistry
Scattering, Small Angle
Self assembly
Self-assembled micelles
Spectrometry, Fluorescence
Statistics
Synthesis
Thermodynamics
X-Ray Diffraction
Amphiphilic glycoconjugates
Self-assembled micelles
Click chemistry
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Summary:•Novel glycosylated copolymer conjugate was successfully synthesized via click chemistry.•8.7nm diameter carbohydrate decorated micelles were produced.•The micelles demonstrated colloidal stability.•The produced nanostructures are neither cytotoxic nor genotoxic.•The assemblies have potential application as site-directed drug delivery system. This work describes the synthesis of a new glycosylated conjugate copolymer, GlcNAc-PEO75-PPO30-PEO75-GlcNAc (GlcNAc-PluronicF68-GlcNAc), using click chemistry from Pluronic® F68 and propargyl-2-N-acetamido-2-deoxy-β-d-glucopyranoside. Micelles were prepared by the self-assembly of GlcNAc-PluronicF68-GlcNAc in phosphate-buffered solution. The critical micelle concentration was determined by fluorescence spectroscopy, and the value was found to be equal to 5.8mgmL−1. The Gibbs free energy (ΔG) of micellization is negative, indicating that the organization of amphiphiles is governed by the hydrophobic effects in an entropy-driven process. The scattering characterization of GlcNAc-PluronicF68-GlcNAc micelles showed a hydrodynamic radius of 8.7nm and negative zeta potential (−21.0±0.9mV). The TEM image evidences the spherical shape of the objects self-assemble into highly regular micelles having a mean diameter of 10nm. The SAXS profile confirmed the spherical shape of the assemblies comprising a swollen PPO core (Rcore=2.25nm) stabilized by PEO chains following Gaussian statistics. The results of the comet assay showed that the GlcNAc-PluronicF68-GlcNAc micelles were not genotoxic, and the cell viability test was higher than 97% for all concentrations, demonstrating that GlcNAc-PluronicF68-GlcNAc is not toxic.
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ISSN:0927-7765
1873-4367
DOI:10.1016/j.colsurfb.2015.06.035