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Nature of linkage between the cationic headgroup and cholesteryl skeleton controls gene transfection efficiency.

Ghosh, Yamuna Krishnan and Visweswariah, Sandhya S and Bhattacharya, Santanu (2000) Nature of linkage between the cationic headgroup and cholesteryl skeleton controls gene transfection efficiency. In: FEBS Letters, 473 (3). pp. 341-344.

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Three novel cationic cholesterol derivatives with different modes of linkage between the cationic headgroup and the cholesteryl backbone have been synthesized and used as mixtures with 1,2-dioleoyl-$L$-$\alpha$-glycero-3-phosphatidyl ethanolamine (DOPE) for liposome-mediated gene transfection. A pronounced improvement in gene transfer efficiency was observed when the cationic center was appended to the cholesteryl backbone using an ether linkage as opposed to when the linkages were based on either ester or urethane groups. Amphiphiles with ether links such as cholest-5-en-$3\beta$-oxyethane-N,N,N-trimethyl ammonium bromide (2) and cholest-5-en-$3\beta$-oxyethane-N,N-dimethyl-N-2-hydroxyethyl ammonium bromide (3) showed transfection efficiencies considerably greater than commercially available gene transfer reagents. Notably, the transfection ability of 2 with DOPE in the presence of serum was significantly greater than Lipofectamine® and Lipofectin®. Interestingly, 3 did not require the helper lipid DOPE for transfection. This suggests that these newly described cholesterol-based amphiphiles should be very promising in liposome-mediated gene transfection. The advantage that the ether linkage possesses would be important in the design of newer, more efficient cholesterol-based delivery reagents.

Item Type: Journal Article
Publication: FEBS Letters
Publisher: Federation of European Biochemical Societies
Additional Information: Copyright of this article belongs to Federation of European Biochemical Societies
Keywords: Cationic liposome;Cationic cholesterol amphiphile;Ether linkage;DNA transfection
Department/Centre: Division of Biological Sciences > Molecular Reproduction, Development & Genetics
Division of Chemical Sciences > Organic Chemistry
Date Deposited: 03 Oct 2007
Last Modified: 19 Sep 2010 04:40
URI: http://eprints.iisc.ac.in/id/eprint/12051

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