Skip to Main content Skip to Navigation
Journal articles

Novel lipid‐based quaternary ammonium sophorolipid amphiphiles with antimicrobial and transfection activities

Elisabeth I.P. Delbeke 1, 2 Jonas Everaert 1, 3 Olivier Lozach 4 Tony Le Gall 5, 6 Mathieu Berchel 4, 5 Tristan Montier 5, 6, 7, 8 Paul-Alain Jaffres 4, 5 Petra Rigole 9 Tom Coenye 9 Martha Brennich 10, 11 Niki Baccile 12 Sophie L.K.W. Roelants 3, 13 Wim Soetaert 3, 13 Inge N.A. Van Bogaert 14 Kevin M. Van Geem 2 Christian V. Stevens 1, *
* Corresponding author
1 SynBioC Research Group [Ghent]
Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering [Gent]
2 LCT - Department of Materials, Textiles and Chemical Engineering
3 InBio - Department of Biotechnology
4 CEMCA - Chimie, Electrochimie Moléculaires et Chimie Analytique
5 IBISA " SynNanoVect " platform
6 UMR1078S-ECLA, Faculté de Médecine
7 Service de génétique moléculaire et d'histocompatibilité,
8 DUMG - Département Universitaire de Médecine Générale
9 Laboratory of Pharmaceutical Microbiology
10 EMBL - European Molecular Biology Laboratory [Grenoble]
11 ILL - Institut Laue-Langevin
12 LCMCP-SMiLES - Spectroscopie, Modélisation, Interfaces pour L'Environnement et la Santé
LCMCP - Laboratoire de Chimie de la Matière Condensée de Paris
13 Bio Base Europe Pilot Plant
14 Centre for Synthetic Biology
Abstract : Twelve new quaternary ammonium sophorolipids with long alkyl chains on the nitrogen atom were synthesized starting from oleic and petroselinic acid based sophorolipids. These novel derivatives were evaluated for their antimicrobial activity against selected Gram-negative and Gram-positive bacteria and their transfection efficacies on three different eukaryotic cell lines in vitro since good activities were demonstrated for previously synthesized derivatives. Self-assembly properties were also evaluated. All compounds proved to possess antimicrobial and transfection properties, and trends could be observed based on the length of the nitrogen substituent and the total length of the sophorolipid tail. Moreover, all long-chain quaternary ammonium sophorolipids form micelles, which proved to be a prerequisite to induce antimicrobial activity and transfection capacity. These results are promising for future healthcare applications of long-chained quaternary ammonium sophorolipids.
Keywords : renewable resources amphiphiles biological activity drug delivery self-assembly
Document type :
Journal articles
Complete list of metadata
https://hal.sorbonne-universite.fr/hal-02129348
Contributor : Guillaume Laurent <>
Submitted on : Tuesday, February 16, 2021 - 11:49:16 PM
Last modification on : Monday, March 8, 2021 - 11:02:02 AM

Files

Vignette du document
2019_Delbecke_HAL.pdf
Files produced by the author(s)

Identifiers

Collections

INSERM | SU-SCIENCES | IBSAM | SORBONNE-UNIVERSITE | GGFB | CEMCA-BREST | PSL | LCMCP-SMILES | INC-CNRS | LCMCP | CDF | CNRS | UNIV-BREST | SU-TI

Citation

Elisabeth I.P. Delbeke, Jonas Everaert, Olivier Lozach, Tony Le Gall, Mathieu Berchel, et al.. Novel lipid‐based quaternary ammonium sophorolipid amphiphiles with antimicrobial and transfection activities. ChemSusChem, ChemPubSoc Europe/Wiley, 2019, 12 (15), pp.3642-3653. ⟨10.1002/cssc.201900721⟩. ⟨hal-02129348⟩

Export

BibTeX TEI DC DCterms EndNote

Share

Metrics

Record views

414

Files downloads

40