title: New glycosylated conjugate copolymer N-acetyl-β-D-glucosaminyl-pluronic: Synthesis, self-assembly and biological assays.
abstract: 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.
authors.affiliation: Laboratório de Processamento de Polímeros Avançados - LAPPA, Universidade do Extremo Sul Catarinense, 88806-000 Criciúma, SC, Brazil.
authors.forename: Tiago Elias Allievi
authors.initials: TE
authors.lastname: Frizon
authors.affiliation: Laboratório de Processamento de Polímeros Avançados - LAPPA, Universidade do Extremo Sul Catarinense, 88806-000 Criciúma, SC, Brazil.
authors.forename: Yasmine Miguel Serafini
authors.initials: YM
authors.lastname: Micheletto
authors.affiliation: Laboratório de Processamento de Polímeros Avançados - LAPPA, Universidade do Extremo Sul Catarinense, 88806-000 Criciúma, SC, Brazil.
authors.forename: José Luiz
authors.initials: JL
authors.lastname: Westrup
authors.affiliation: Laboratório de Processamento de Polímeros Avançados - LAPPA, Universidade do Extremo Sul Catarinense, 88806-000 Criciúma, SC, Brazil.
authors.forename: Priscila Sayoko Silva
authors.initials: PS
authors.lastname: Wakabayashi
authors.affiliation: Laboratório de Processamento de Polímeros Avançados - LAPPA, Universidade do Extremo Sul Catarinense, 88806-000 Criciúma, SC, Brazil.
authors.forename: Francieli Rocha
authors.initials: FR
authors.lastname: Serafim
authors.affiliation: Laboratório de Biologia Celular e Molecular, PPGCS, Universidade do Extremo Sul Catarinense, Av. Universitária, 1105, 88806-000 Criciúma, SC, Brazil.
authors.forename: Adriani Paganini
authors.initials: AP
authors.lastname: Damiani
authors.affiliation: Laboratório de Biologia Celular e Molecular, PPGCS, Universidade do Extremo Sul Catarinense, Av. Universitária, 1105, 88806-000 Criciúma, SC, Brazil.
authors.forename: Luiza Martins
authors.initials: LM
authors.lastname: Longaretti
authors.affiliation: Laboratório de Biologia Celular e Molecular, PPGCS, Universidade do Extremo Sul Catarinense, Av. Universitária, 1105, 88806-000 Criciúma, SC, Brazil.
authors.forename: Vanessa Moraes
authors.initials: VM
authors.lastname: de Andrade
authors.affiliation: Centro de Ciências Naturais e Humanas, Universidade Federal do ABC, 09210-170 Santo André, SP, Brazil.
authors.forename: Fernando Carlos
authors.initials: FC
authors.lastname: Giacomelli
authors.affiliation: Univ Grenoble Alpes, CERMAV, F-38000 Grenoble, France.
authors.forename: Sébastien
authors.initials: S
authors.lastname: Fort
authors.affiliation: Laboratório de Processamento de Polímeros Avançados - LAPPA, Universidade do Extremo Sul Catarinense, 88806-000 Criciúma, SC, Brazil; Univ Grenoble Alpes, CERMAV, F-38000 Grenoble, France. Electronic address: adalbo@unesc.net.
authors.forename: Alexandre Gonçalves
authors.initials: AG
authors.lastname: Dal Bó
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry*; D020552:Comet Assay; D006031:Glycosylation; D006801:Humans; D008823:Micelles; D046529:Microscopy, Electron, Transmission; D020442:Poloxamer / Q000737:chemistry*; D053838:Scattering, Small Angle; D013050:Spectrometry, Fluorescence; D013816:Thermodynamics; D014961:X-Ray Diffraction
chemical_list: D008823:Micelles; D020442:Poloxamer; D000117:Acetylglucosamine
keywords: Amphiphilic glycoconjugates; Click chemistry; Self-assembled micelles