title: Evaluation of the transfection efficacies of quaternary ammonium salts prepared from sophorolipids.
abstract: Five quaternary ammonium amphiphilic compounds were synthesized from sophorolipid 1. These compounds were formulated in aqueous media and some of them (5 and 6) produced well-defined supramolecular aggregates which were characterized by DLS and zeta measurements. Their capacity to transfect four different eukaryotic cell lines in vitro was assessed. To evaluate the influence of the carbohydrate head group from the sophorolipids on the transfection efficacies, their deglycosylated analogues were also synthesized and tested for gene delivery. For all the compounds, the use of DOPE as a helper lipid in a 1 : 1 molar ratio with the ammonium-based lipids was required to obtain homogeneous formulations. The transfection results indicate that quaternary ammonium-based sophorolipids proved to be more efficient pDNA carriers than their deglycosylated counterparts. Moreover, the presence of the carbohydrate head group clearly contributed to the good biocompatibility of these cationic lipids. These cationic sophorolipid derivatives thus offer good potential for the development of new vectors for gene delivery based on renewable resources.
authors.affiliation: SynBioC, Department of Sustainable Organic Chemistry and Technology, Ghent University, Coupure Linkes 653, 9000 Ghent, Belgium. Chris.Stevens@UGent.be.
authors.forename: E I P
authors.initials: EI
authors.lastname: Delbeke
authors.affiliation: Université de Brest, CEMCA, CNRS UMR 6521, IBSAM, 6 avenue Le Gorgeu, 29238 Brest, France.
authors.forename: O
authors.initials: O
authors.lastname: Lozach
authors.affiliation: IBiSA SynNanoVect platform, IBSAM, Université de Brest, Faculté de médecine Morvan, avenue Camille Desmoulins, 46 rue Félix Le Dantec, CS 51819, 29218 Brest Cedex 2, France and Université de Brest, INSERM UMR 1078, IBSAM, Faculté de médecine Morvan, avenue Camille Desmoulins, 46 rue Félix Le Dantec, CS 51819, 29218 Brest Cedex 2, France.
authors.forename: T
authors.initials: T
authors.lastname: Le Gall
authors.affiliation: Université de Brest, CEMCA, CNRS UMR 6521, IBSAM, 6 avenue Le Gorgeu, 29238 Brest, France and IBiSA SynNanoVect platform, IBSAM, Université de Brest, Faculté de médecine Morvan, avenue Camille Desmoulins, 46 rue Félix Le Dantec, CS 51819, 29218 Brest Cedex 2, France.
authors.forename: M
authors.initials: M
authors.lastname: Berchel
authors.affiliation: IBiSA SynNanoVect platform, IBSAM, Université de Brest, Faculté de médecine Morvan, avenue Camille Desmoulins, 46 rue Félix Le Dantec, CS 51819, 29218 Brest Cedex 2, France and Université de Brest, INSERM UMR 1078, IBSAM, Faculté de médecine Morvan, avenue Camille Desmoulins, 46 rue Félix Le Dantec, CS 51819, 29218 Brest Cedex 2, France and CHRU de Brest, Service de Génétique Moléculaire et d'Histocompatibilité, 5 avenue de Maréchal Foch, 29609 Brest cedex, France and DUMG, Faculté de Médecine et des Sciences de la Santé, 22 avenue Camille Desmoulins, 29328 Brest, France.
authors.forename: T
authors.initials: T
authors.lastname: Montier
authors.affiliation: Université de Brest, CEMCA, CNRS UMR 6521, IBSAM, 6 avenue Le Gorgeu, 29238 Brest, France and IBiSA SynNanoVect platform, IBSAM, Université de Brest, Faculté de médecine Morvan, avenue Camille Desmoulins, 46 rue Félix Le Dantec, CS 51819, 29218 Brest Cedex 2, France.
authors.forename: P-A
authors.initials: PA
authors.lastname: Jaffrès
authors.affiliation: LCT, Department of Chemical Engineering and Technical Chemistry, Ghent University, Technologiepark 914, 9052 Ghentn, Belgium.
authors.forename: K M
authors.initials: KM
authors.lastname: Van Geem
authors.affiliation: SynBioC, Department of Sustainable Organic Chemistry and Technology, Ghent University, Coupure Linkes 653, 9000 Ghent, Belgium. Chris.Stevens@UGent.be.
authors.forename: C V
authors.initials: CV
authors.lastname: Stevens
mesh_terms: D002460:Cell Line; D002470:Cell Survival; D004247:DNA / Q000008:administration & dosage* / Q000235:genetics; D006801:Humans; D008055:Lipids / Q000737:chemistry*; D008081:Liposomes / Q000737:chemistry*; D010714:Phosphatidylethanolamines / Q000737:chemistry; D010957:Plasmids / Q000008:administration & dosage* / Q000235:genetics; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D014162:Transfection / Q000379:methods*
chemical_list: D008055:Lipids; D008081:Liposomes; D010714:Phosphatidylethanolamines; D000644:Quaternary Ammonium Compounds; C094877:dioleoyl phosphatidylethanolamine; D004247:DNA