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Evaluation of the transfection efficacies of quaternary ammonium salts prepared from sophorolipids

(2016) ORGANIC & BIOMOLECULAR CHEMISTRY. 14(15). p.3744-3751
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Organization
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.
Keywords
HIGHLY EFFICIENT, CHEMICAL VECTORS, WICKERHAMIELLA-DOMERCQIAE, CATIONIC LIPIDS, GENE DELIVERY, MEDIATED DNA-TRANSFECTION, Transfection, Gene vector, Quaternary ammonium salts, Sophorolipid, POLAR HEADGROUP, CANCER CELLS, BIOSURFACTANTS, DERIVATIVES

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MLA
Delbeke, Elisabeth, Olivier Lozach, Tony Le Gall, et al. “Evaluation of the Transfection Efficacies of Quaternary Ammonium Salts Prepared from Sophorolipids.” ORGANIC & BIOMOLECULAR CHEMISTRY 14.15 (2016): 3744–3751. Print.
APA
Delbeke, E., Lozach, O., Le Gall, T., Berchel, M., Montier, T., Jaffrès, P.-A., Van Geem, K., et al. (2016). Evaluation of the transfection efficacies of quaternary ammonium salts prepared from sophorolipids. ORGANIC & BIOMOLECULAR CHEMISTRY, 14(15), 3744–3751.
Chicago author-date
Delbeke, Elisabeth, Olivier Lozach, Tony Le Gall, Mathieu Berchel, Tristan Montier, Paul-Alain Jaffrès, Kevin Van Geem, and Christian Stevens. 2016. “Evaluation of the Transfection Efficacies of Quaternary Ammonium Salts Prepared from Sophorolipids.” Organic & Biomolecular Chemistry 14 (15): 3744–3751.
Chicago author-date (all authors)
Delbeke, Elisabeth, Olivier Lozach, Tony Le Gall, Mathieu Berchel, Tristan Montier, Paul-Alain Jaffrès, Kevin Van Geem, and Christian Stevens. 2016. “Evaluation of the Transfection Efficacies of Quaternary Ammonium Salts Prepared from Sophorolipids.” Organic & Biomolecular Chemistry 14 (15): 3744–3751.
Vancouver
1.
Delbeke E, Lozach O, Le Gall T, Berchel M, Montier T, Jaffrès P-A, et al. Evaluation of the transfection efficacies of quaternary ammonium salts prepared from sophorolipids. ORGANIC & BIOMOLECULAR CHEMISTRY. 2016;14(15):3744–51.
IEEE
[1]
E. Delbeke et al., “Evaluation of the transfection efficacies of quaternary ammonium salts prepared from sophorolipids,” ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 14, no. 15, pp. 3744–3751, 2016.
@article{7182550,
  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.},
  author       = {Delbeke, Elisabeth and Lozach, Olivier and Le Gall, Tony and Berchel, Mathieu and Montier, Tristan and Jaffrès, Paul-Alain and Van Geem, Kevin and Stevens, Christian},
  issn         = {1477-0520},
  journal      = {ORGANIC & BIOMOLECULAR CHEMISTRY},
  keywords     = {HIGHLY EFFICIENT,CHEMICAL VECTORS,WICKERHAMIELLA-DOMERCQIAE,CATIONIC LIPIDS,GENE DELIVERY,MEDIATED DNA-TRANSFECTION,Transfection,Gene vector,Quaternary ammonium salts,Sophorolipid,POLAR HEADGROUP,CANCER CELLS,BIOSURFACTANTS,DERIVATIVES},
  language     = {eng},
  number       = {15},
  pages        = {3744--3751},
  title        = {Evaluation of the transfection efficacies of quaternary ammonium salts prepared from sophorolipids},
  url          = {http://dx.doi.org/10.1039/C6OB00241B},
  volume       = {14},
  year         = {2016},
}

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