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Synthesis, self-assembly, and immunological activity of α-galactose-functionalized dendron–lipid amphiphiles

dc.rights.licenseopen
dc.contributor.authorTRANT, John
dc.contributor.authorJAIN, Namrata
dc.contributor.authorMAZZUCA, Delfina
dc.contributor.authorMCINTOSH, James
dc.contributor.authorFAN, Bo
dc.contributor.authorHAERYFAR, S. M. Mansour
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 3 LCPO : Polymer Self-Assembly & Life Sciences
dc.contributor.authorLECOMMANDOUX, Sebastien
dc.contributor.authorGILLIES, Elizabeth
dc.date.accessioned2020
dc.date.available2020
dc.date.issued2016
dc.identifier.issn2040-3364
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/19870
dc.description.abstractEnNanoassemblies presenting multivalent displays of biologically active carbohydrates are of significant interest for a wide array of biomedical applications ranging from drug delivery to immunotherapy. In this study, glycodendron–lipid hybrids were developed as a new and tunable class of dendritic amphiphiles. A modular synthesis was used to prepare dendron–lipid hybrids comprising distearylglycerol and 0 through 4th generation polyester dendrons with peripheral protected amines. Following deprotection of the amines, an isothiocyanate derivative of C-linked α-galactose (α-Gal) was conjugated to the dendron peripheries, affording amphiphiles with 1 to 16 α-Gal moieties. Self-assembly in water through a solvent exchange process resulted in vesicles for the 0 through 2nd generation systems and micelles for the 3rd and 4th generation systems. The critical aggregation concentrations decreased with increasing dendron generation, suggesting that the effects of increasing molar mass dominated over the effects of increasing the hydrophilic weight fraction. The binding of the assemblies to Griffonia simplicifolia Lectin I (GSL 1), a protein with specificity for α-Gal was studied by quantifying the binding of fluorescently labeled assemblies to GSL 1-coated beads. It was found that binding was enhanced for amphiphiles containing higher generation dendrons. Despite their substantial structural differences with the natural ligands for the CD1d receptor, the glycodendron–lipid hybrids were capable of stimulating invariant natural killer T (iNKT) cells, a class of innate-like T cells that recognize lipid and glycolipid antigens presented by CD1d and that are implicated in a wide range of diseases and conditions including but not limited to infectious diseases, diabetes and cancer.
dc.language.isoen
dc.publisherRoyal Society of Chemistry
dc.title.enSynthesis, self-assembly, and immunological activity of α-galactose-functionalized dendron–lipid amphiphiles
dc.typeArticle de revue
dc.identifier.doi10.1039/C6NR05030A
dc.subject.halChimie/Polymères
dc.subject.halChimie/Matériaux
dc.subject.halPhysique [physics]/Matière Condensée [cond-mat]/Matière Molle [cond-mat.soft]
bordeaux.journalNanoscale
bordeaux.page17694-17704
bordeaux.volume8
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue40
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-02152994
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-02152994v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Nanoscale&rft.date=2016&rft.volume=8&rft.issue=40&rft.spage=17694-17704&rft.epage=17694-17704&rft.eissn=2040-3364&rft.issn=2040-3364&rft.au=TRANT,%20John&JAIN,%20Namrata&MAZZUCA,%20Delfina&MCINTOSH,%20James&FAN,%20Bo&rft.genre=article


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