2007
DOI: 10.1021/jm060128c
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Unsaturated Cationic Ortho Esters for Endosome Permeation in Gene Delivery

Abstract: Two cleavable cationic lipids were designed to trigger the fusogenicity and membrane permeation of their lipoplexes in endosomes via the formation of inverted hexagonal phases (HII). Both lipids contain a cationic head group and an unsaturated hydrophobic dioleylglycerol moiety joined together by a linear or a cyclic ortho ester linker. At pH 7.4, the lipids formed stable complexes with plasmid DNA together with the conelike helper lipid 1,2-dioleoyl-sn-glycero-3-phosphoethanolamine (DOPE). The decrease of pH … Show more

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Cited by 42 publications
(40 citation statements)
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“…The absorbance spectrum of Triton X-100 does not include peaks in the 400-600 nm range recommended for this assay, and therefore, should not interfere with the normalization of experimental data. 20 Furthermore, for negative control samples, one should not observe significant hemolysis after the 1 hr incubation in any of the buffers used (i.e. even the most acidic buffer does not typically generate hemolysis on this timeframe).…”
Section: Discussionmentioning
confidence: 99%
“…The absorbance spectrum of Triton X-100 does not include peaks in the 400-600 nm range recommended for this assay, and therefore, should not interfere with the normalization of experimental data. 20 Furthermore, for negative control samples, one should not observe significant hemolysis after the 1 hr incubation in any of the buffers used (i.e. even the most acidic buffer does not typically generate hemolysis on this timeframe).…”
Section: Discussionmentioning
confidence: 99%
“…The cyclic ortho ester lipid 61 (Fig. 11) also showed a significantly higher transfection efficiency than DOTAP in CV-1 and HTB-129 cells (Chen et al 2007). In this case, two concomitant effects are thought to promptly destabilize the endosome membrane, the acid-catalyzed cleavage of the cationic head groups that caused the aggregation of the lipoplexes and the generated conelike lipid dioleylglycerol (DOG) that favored the formation of the fusogenic hexagonal phase.…”
Section: Release Of Dna In Cytoplasm By Intracellular Disulfide Reducmentioning
confidence: 99%
“…Several ortho ester-containing cationic lipids have been synthesized and characterized for their susceptibility to undergo hydrolysis under mild acid conditions (Zhu et al 2000;By and Nantz 2004;Chen et al 2007). For instance, ortho ester lipid 54 (Fig.…”
Section: Release Of Dna In Cytoplasm By Intracellular Disulfide Reducmentioning
confidence: 99%
“…The gene transfection procedure is similar to a reported method [33,34]. B16F1 cells (a mouse melanoma cell line, CRL-6323) and HeLa cells (a human cervical adenocarcinoma cell line, CCL-2) were cultured in DMEM containing 10% FBS, 4 mM L-glutamine, 1500 mg/L sodium bicarbonate and antibiotics (100 IU/mL penicillin and 100 μg/mL streptomycin) according to ATCC recommendations.…”
Section: Gene Transfection In Cultured Cellsmentioning
confidence: 99%