Novel cationic lipids based on malonic acid amides backbone: transfection efficacy and cell toxicity properties
- PMID: 20329785
- DOI: 10.1021/bc9004624
Novel cationic lipids based on malonic acid amides backbone: transfection efficacy and cell toxicity properties
Abstract
Gene delivery using nonviral approaches has been extensively studied as a basic tool for intracellular gene transfer. Despite intensive research activity, the aim of creating a vector which meets all necessary demands has still not been reached. One possibility to solve the nonviral vector associated problem of low transfection efficacy is the development of new cationic amphiphiles. Therefore, the non-glycerol-based cationic lipids 1-9 have been synthesized and tested for in vitro gene delivery experiments. The backbone structure of the lipids consists of a malonic acid diamide with two long hydrophobic chains. The degree of saturation of the hydrophobic chains and the structure of the polar cationic headgroup were varied. The preparation follows an easy process and facilitates the trouble-free insertion of different alkyl chains. By studying in vitro gene delivery an increase of transfection efficacy was observed when using at least one unsaturated alkyl chain in the hydrophobic part and lysine or bis(2-aminoethyl)aminoethylamid as hydrophilic headgroup. This leads to cationic lipids exhibiting comparable or even higher transfection efficacies compared to the commercially available LipofectAmine and SuperFect.
Similar articles
-
Synthesis and DNA transfection properties of new head group modified malonic acid diamides.Int J Pharm. 2011 May 16;409(1-2):46-56. doi: 10.1016/j.ijpharm.2011.02.022. Epub 2011 Feb 25. Int J Pharm. 2011. PMID: 21354464
-
Design, syntheses and in vitro gene delivery efficacies of novel mono-, di- and trilysinated cationic lipids: a structure-activity investigation.J Med Chem. 2004 Apr 8;47(8):2123-32. doi: 10.1021/jm030541+. J Med Chem. 2004. PMID: 15056009
-
Gene transfection efficacies of novel cationic gemini lipids possessing aromatic backbone and oxyethylene spacers.Biomacromolecules. 2008 Mar;9(3):991-9. doi: 10.1021/bm700930y. Epub 2008 Feb 14. Biomacromolecules. 2008. PMID: 18271549
-
Transfection efficiency of cationic lipids with different hydrophobic domains in gene delivery.Bioconjug Chem. 2010 Apr 21;21(4):563-77. doi: 10.1021/bc900393r. Bioconjug Chem. 2010. PMID: 20121120 Review.
-
Non-viral gene delivery carrier and its three-dimensional transfection system.Int J Pharm. 2010 Feb 15;386(1-2):232-42. doi: 10.1016/j.ijpharm.2009.11.006. Epub 2009 Nov 14. Int J Pharm. 2010. PMID: 19922780 Review.
Cited by
-
The Impact of Alkyl-Chain Purity on Lipid-Based Nucleic Acid Delivery Systems - Is the Utilization of Lipid Components with Technical Grade Justified?Chemphyschem. 2019 Aug 16;20(16):2110-2121. doi: 10.1002/cphc.201900480. Epub 2019 Jul 23. Chemphyschem. 2019. PMID: 31265754 Free PMC article.
-
Relationship between structure and molecular interactions in monolayers of specially designed aminolipids.Nanoscale Adv. 2019 Jul 23;1(9):3529-3536. doi: 10.1039/c9na00355j. eCollection 2019 Sep 11. Nanoscale Adv. 2019. PMID: 36133531 Free PMC article.
-
Deciphering the Functional Composition of Fusogenic Liposomes.Int J Mol Sci. 2018 Jan 24;19(2):346. doi: 10.3390/ijms19020346. Int J Mol Sci. 2018. PMID: 29364187 Free PMC article.
-
Hepatocyte-targeting gene transfer mediated by galactosylated poly(ethylene glycol)-graft-polyethylenimine derivative.Drug Des Devel Ther. 2013;7:211-21. doi: 10.2147/DDDT.S42582. Epub 2013 Mar 26. Drug Des Devel Ther. 2013. PMID: 23576866 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
Miscellaneous