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Nanotechnology for Nucleic Acid Delivery pp 1–25Cite as

Sequence-Defined Cationic Lipo-Oligomers Containing Unsaturated Fatty Acids for Transfection

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Part of the book series: Methods in Molecular Biology ((MIMB,volume 1943))

Abstract

Sequence-defined cationic lipo-oligomers containing unsaturated fatty acids are potent nucleic acid carriers that are produced by solid-phase supported synthesis. However, the trifluoroacetic acid (TFA)-mediated removal of acid-labile protecting groups and cleavage from the resin can be accompanied by side products caused by an addition of TFA to the double bonds of unsaturated fatty acids. These TFA adducts are converted into hydroxylated derivatives under aqueous conditions. Here we describe an optimized cleavage protocol (precooling cleavage solution to 4 °C, 20 min cleavage at 22 °C), which minimizes TFA adduct formation, retains the unsaturated hydrocarbon chain character, and ensures high yields of the synthesis.

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Acknowledgments

This work was supported by DFG SFB1032 B4 (to E.W.), SFB1066 B5 (E.W.), DFG FOR1406 (E.W.) and DFG Excellence Cluster Nanosystems Initiative Munich (E.W.).

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Authors and Affiliations

  1. Department of Pharmacy, Pharmaceutical Biotechnology, Center of Nanoscience (CeNS), Ludwig-Maximilians-Universität Butenandtstr, München, Germany

    Sören Reinhard & Ernst Wagner

  2. Nanosystems Initiative Munich (NIM), Schellingstr, München, Germany

    Ernst Wagner

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  1. Sören Reinhard
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  2. Ernst Wagner
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Correspondence to Sören Reinhard .

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Editors and Affiliations

  1. Laboratory of MacroMolecular Cancer Therapeutics (MMCT), Department of Pharmaceutical Chemistry, Center of Pharmaceutical Sciences, Faculty of Life Sciences, University of Vienna, Vienna, Austria

    Manfred Ogris

  2. Laboratory of MacroMolecular Cancer Therapeutics (MMCT), Department of Pharmaceutical Chemistry, Center of Pharmaceutical Sciences, Faculty of Life Sciences, University of Vienna, Vienna, Austria

    Haider Sami

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Reinhard, S., Wagner, E. (2019). Sequence-Defined Cationic Lipo-Oligomers Containing Unsaturated Fatty Acids for Transfection. In: Ogris, M., Sami, H. (eds) Nanotechnology for Nucleic Acid Delivery. Methods in Molecular Biology, vol 1943. Humana Press, New York, NY. https://doi.org/10.1007/978-1-4939-9092-4_1

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  • DOI: https://doi.org/10.1007/978-1-4939-9092-4_1

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