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Design, Synthesis, and in Vitro Gene Delivery Efficacies of Novel Cholesterol-Based Gemini Cationic Lipids and Their Serum Compatibility: A Structure-Activity Investigation

Bajaj, Avinash and Kondiah, Paturu and Bhattacharya, Santanu (2007) Design, Synthesis, and in Vitro Gene Delivery Efficacies of Novel Cholesterol-Based Gemini Cationic Lipids and Their Serum Compatibility: A Structure-Activity Investigation. In: Journal of Medicinal Chemistry, 50 (10). pp. 2432-2442.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jm0611253

Abstract

Five cholesterol-based gemini cationic lipids, which differ in the length of the spacer $[-(CH_2)_n-]$ chain between the head groups, have been synthesized. These lipids are useful as nonviral gene delivery agents, and all cholesterol-based gemini lipids (2a-2e) are better transfecting agents than their monomeric lipid counterpart 1. Transfection efficiency of all the gemini lipids except lipid $2a [-(CH_2)_3-]$ was maintained even when the serum was present during the transfection conditions as compared to the monomeric lipid 1, with which a dramatic decrease in transfection efficiency was observed. With the increase in spacer chain length from propanediyl $[-(CH_2)_3-]$ to pentanediyl $[-(CH_2)_5-]$, transfection efficiency increased both in the absence and presence of serum. However, transfection efficiency decreased with further increase in the length from the pentanediyl $[-(CH_2)_5-]$ to the dodecanediyl $[-(CH_2)_{12}-]$ spacer. Among these gemini lipids 2c showed the highest transfection activity, which was also greater than that of the commercially available formulation.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Amerian Chemical Society.
Department/Centre: Division of Biological Sciences > Molecular Reproduction, Development & Genetics (formed by the merger of DBGL and CRBME)
Division of Chemical Sciences > Organic Chemistry
Date Deposited: 13 Jul 2007
Last Modified: 27 Jan 2012 06:08
URI: http://eprints.iisc.ernet.in/id/eprint/11543

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