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Click-Modified Anandamide siRNA Enables Delivery and Gene Silencing in Neuronal and Immune Cells

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    Click-Modified Anandamide siRNA Enables Delivery and Gene Silencing in Neuronal and Immune Cells
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    § §Center for Integrated Protein Science, Department of Chemistry, and ∥Max von Pettenkofer-Institute and Gene Center, Ludwig-Maximilians-Universität, D-81377, Munich, Germany
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    Cite this: J. Am. Chem. Soc. 2012, 134, 30, 12330–12333
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    https://doi.org/10.1021/ja303251f
    Published July 19, 2012
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    Abstract

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    Click chemistry of alkyne-modified RNA with different receptor ligand azides was used to prepare 3′-folate, 3′-cholesterol, and, as a new entity, 3′-anandamide-modified RNA in high yields and excellent purity. The anandamide-modified RNA shows surprisingly high transfection properties and enables the delivery of siRNA even into difficult-to-transfect RBL-2H3 cells which model neuronal uptake. Furthermore, the system was employed in human immune cells (BJAB), demonstrating silencing effects similar to those of a cationic, benchmark transfection reagent. In addition, the anandamide conjugates were found to be nontoxic. The reported chemistry and the described properties of the anandamide siRNA extend the possibilities of using siRNA-based gene silencing in neuronal and immune cells.

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    Preparation of 1–3, oligonucleotide synthesis, purification and click modification, convocal microscopy studies, dual luciferase assay, and real-time PCR. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Am. Chem. Soc. 2012, 134, 30, 12330–12333
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja303251f
    Published July 19, 2012
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