> Lipophile Modifikationen
Distearoyl Lipid (5' modification)

Distearoyl lipid-oligonucleotide conjugates consist of a negatively charged DNA and two diamine-linked long hydrocarbon chains (stearic acid). They are thus relatively similar to a natural phospholipid structure and can form micelles. Distearoyl lipids facilitate cell permeability or anchoring of oligonucleotides on the cell surface.
A distearoyl lipid phosphoramidite enables the synthesis of oligonucleotides with the corresponding 5´-modification.

Literature:
1. Liu, H., Zhu, Z., Kang, H., Wu, Y., Sefan, K. & Tan, W., DNA Based Micelles: Synthesis, Micellar Properties and Sizedependent Cell Permeability, Chemistry. 2010 March 22; 16(12): 3791–3797. doi:10.1002/chem.200901546
2. Liu, H., Kwong, B. & Irvine, D.J., Membrane Anchored Immunostimulatory Oligonucleotides for In Vivo Cell Modification and Localized Immunotherapy, Angew. Chem. Int. Ed. 2011, 50, 7052 –7055
3. Altman, M.O., Chang, Y.M., Xiong, X.L. & Tan, W.H., Modifying cellular properties using artificial aptamer-lipid receptors., Sci. Rep. 3, 3343; DOI:10.1038/srep03343 (2013)
4. Chan, Y.M., van Lengerich, B. & Boxer, S.G., Effects of linker sequences on vesicle fusion mediated by lipid-anchored DNA oligonucleotides, PNAS 106 (2009), 983 (www.pnas.org/cgi/doi/10.1073/pnas.0812356106)
Distearoyl Lipid 5' modification: 5´-Distearoyl Lipid
5´-Distearoyl Lipid