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Tris(2-aminoethyl)amine-based α-branched fatty acid amides – synthesis of lipids and comparative study of transfection efficiency of their lipid formulations

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Dittrich,  Matthias
Grenzflächen, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Erdmann, N., Wölk, C., Schulze, I., Janich, C., Folz, M., Drescher, S., et al. (2015). Tris(2-aminoethyl)amine-based α-branched fatty acid amides – synthesis of lipids and comparative study of transfection efficiency of their lipid formulations. European Journal of Pharmaceutics and Biopharmaceutics, 96, 349-362. doi:10.1016/j.ejpb.2015.08.011.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0028-5438-4
Abstract
The synthesis of a new class of cationic lipids, tris(2-aminoethyl)amine-based α-branched fatty acid amides, is described resulting in a series of lipids with specific variations in the lipophilic as well as the hydrophilic part of the lipids. In-vitro structure/transfection relationships were established by application of complexes of these lipids with plasmid DNA (pDNA) to different cell lines. The α-branched fatty acid amide bearing two tetradecyl chains and two lysine molecules (T14diLys) in mixture with the co-lipid 1,2-di-[(9Z)-octadec-9-enoyl]-sn-glycero-3-phosphoethanolamine (DOPE) (1/2, n/n) exhibits effective pDNA transfer in three different cell lines, namely Hep-G2, A549, and COS-7. The presence of 10% serum during lipoplex incubation of the cells did not affect the transfection efficiency. Based on that, detailed investigations of the complexation of pDNA with the lipid formulation T14diLys/DOPE 1/2 (n/n) were carried out with respect to particle size and charge using dynamic light scattering (DLS), ζ-potential measurements and transmission electron microscopy (TEM). Additionally, the lipoplex uptake was investigated by confocal laser scanning microscopy (CLSM). Overall, lipoplexes prepared from T14diLys/DOPE 1/2 (n/n) offer large potential as lipid-based polynucleotide carriers and further justify advanced examinations.