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

Elisabeth I.P. Delbeke; Jonas Everaert; Olivier Lozach; Tony Le Gall; Mathieu Berchel; Tristan Montier; Paul-Alain Jaffres; Petra Rigole; Tom Coenye; Martha Brennich; Niki Baccile; Sophie L.K.W. Roelants; Wim Soetaert; Inge N.A. Van Bogaert; Kevin M. Van Geem; Christian V. Stevens

doi:10.1002/cssc.201900721

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

Domain :

Chemical Sciences / Analytical chemistry

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https://hal.sorbonne-universite.fr/hal-02129348
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Submitted on : Tuesday, May 14, 2019 - 6:51:56 PM
Last modification on : Thursday, December 17, 2020 - 1:40:09 PM

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

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

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