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Lipid‐based quaternary ammonium sophorolipid amphiphiles with antimicrobial and transfection activities

(2019) CHEMSUSCHEM. 12(5). p.3642-3653
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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 as 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
amphiphiles, biological activity, drug delivery, renewable resources, self-assembly, GENE TRANSFECTION, CETYLTRIMETHYLAMMONIUM BROMIDE, CATIONIC SURFACTANT, MICELLES, FERMENTATION, DEGRADATION, INHIBITORS, BILAYERS, MEDIA, CTAB

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MLA
Delbeke, Elisabeth et al. “Lipid‐based Quaternary Ammonium Sophorolipid Amphiphiles with Antimicrobial and Transfection Activities.” CHEMSUSCHEM 12.5 (2019): 3642–3653. Print.
APA
Delbeke, E., Everaert, J., Lozach, O., Le Gall, T., Berchel, M., Montier, T., Jaffrès, P.-A., et al. (2019). Lipid‐based quaternary ammonium sophorolipid amphiphiles with antimicrobial and transfection activities. CHEMSUSCHEM, 12(5), 3642–3653.
Chicago author-date
Delbeke, Elisabeth, Jonas Everaert, Olivier Lozach, Tony Le Gall, Mathieu Berchel, Tristan Montier, Paul-Alain Jaffrès, et al. 2019. “Lipid‐based Quaternary Ammonium Sophorolipid Amphiphiles with Antimicrobial and Transfection Activities.” Chemsuschem 12 (5): 3642–3653.
Chicago author-date (all authors)
Delbeke, Elisabeth, Jonas Everaert, Olivier Lozach, Tony Le Gall, Mathieu Berchel, Tristan Montier, Paul-Alain Jaffrès, Petra Rigole, Tom Coenye, Martha Brennich, Niki Baccile, Sophie Roelants, Wim Soetaert, Inge Van Bogaert, Kevin Van Geem, and Christian Stevens. 2019. “Lipid‐based Quaternary Ammonium Sophorolipid Amphiphiles with Antimicrobial and Transfection Activities.” Chemsuschem 12 (5): 3642–3653.
Vancouver
1.
Delbeke E, Everaert J, Lozach O, Le Gall T, Berchel M, Montier T, et al. Lipid‐based quaternary ammonium sophorolipid amphiphiles with antimicrobial and transfection activities. CHEMSUSCHEM. 2019;12(5):3642–53.
IEEE
[1]
E. Delbeke et al., “Lipid‐based quaternary ammonium sophorolipid amphiphiles with antimicrobial and transfection activities,” CHEMSUSCHEM, vol. 12, no. 5, pp. 3642–3653, 2019.
@article{8621831,
  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 as 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.},
  author       = {Delbeke, Elisabeth and Everaert, Jonas and Lozach, Olivier and Le Gall, Tony and Berchel, Mathieu and Montier, Tristan and Jaffrès, Paul-Alain and Rigole, Petra and Coenye, Tom and Brennich, Martha and Baccile, Niki and Roelants, Sophie and Soetaert, Wim and Van Bogaert, Inge and Van Geem, Kevin and Stevens, Christian},
  issn         = {1864-5631},
  journal      = {CHEMSUSCHEM},
  keywords     = {amphiphiles,biological activity,drug delivery,renewable resources,self-assembly,GENE TRANSFECTION,CETYLTRIMETHYLAMMONIUM BROMIDE,CATIONIC SURFACTANT,MICELLES,FERMENTATION,DEGRADATION,INHIBITORS,BILAYERS,MEDIA,CTAB},
  language     = {eng},
  number       = {5},
  pages        = {3642--3653},
  title        = {Lipid‐based quaternary ammonium sophorolipid amphiphiles with antimicrobial and transfection activities},
  url          = {http://dx.doi.org/10.1002/cssc.201900721},
  volume       = {12},
  year         = {2019},
}

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