Molecular Umbrella-Assisted Transport of an Oligonucleotide across Cholesterol-Rich Phospholipid Bilayers
- 20 October 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (45), 15862-15870
- https://doi.org/10.1021/ja053930x
Abstract
A series of molecular umbrella conjugates, derived from cholic acid, deoxycholic acid, spermidine, lysine, and 5-mercapto-2-nitrobenzoic acid, have been synthesized and found capable of transporting an attached 16-mer oligonucleotide (S-dT16) across liposomal membranes made from 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC), 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphatidyldglycerol (POPG), and cholesterol [POPC/POPG/cholesterol (65/5/30; mol/mol/mol, v/v/v)] at 37 degrees C. Those molecular umbrellas containing four choloyl (or deoxycholoyl) groups resulted in significantly faster rates of transport as compared to those containing only two such moieties. A model that accounts for these membrane transport processes is proposed.This publication has 16 references indexed in Scilit:
- Delivery of Antisense Oligonucleotides Using Cholesterol-Modified Sense Dendrimers and Cationic LipidsBioconjugate Chemistry, 2005
- DNA-based therapeutics and DNA delivery systems: A comprehensive reviewThe AAPS Journal, 2005
- A multipurpose vector system for the screening of libraries in bacteria, insect and mammalian cells and expression in vivoNucleic Acids Research, 2005
- Peptide conjugates for chromosomal gene targeting by triplex-forming oligonucleotidesNucleic Acids Research, 2004
- Comparison of antisense oligonucleotide drug delivery systemsJournal of Controlled Release, 2004
- Cytosolic Delivery of Macromolecules. 3. Synthesis and Characterization of Acid-Sensitive Bis-DetergentsBioconjugate Chemistry, 2004
- Enhanced cellular uptake of a triplex-forming oligonucleotide by nanoparticle formation in the presence of polypropylenimine dendrimersNucleic Acids Research, 2004
- Nanogels for Oligonucleotide Delivery to the BrainBioconjugate Chemistry, 2003
- Kinetic Evidence for the Existence and Mechanism of Formation of a Barrel Stave Structure from Pore-Forming DendrimersJournal of the American Chemical Society, 2003
- Lateral diffusion in binary mixtures of cholesterol and phosphatidylcholines.Proceedings of the National Academy of Sciences of the United States of America, 1979