Unsaturated cationic ortho esters for endosome permeation in gene delivery.

Unsaturated cationic ortho esters for endosome permeation in gene delivery. Research Abstract Details 

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Unsaturated cationic ortho esters for endosome permeation in gene delivery. Abstract Text:

Haigang Chen,Huizhen Zhang,Charles M McCallum,Francis C Szoka,Xin Guo,

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 enhanced the hydrolysis of the ortho ester linkers, which removed the cationic head groups and caused the aggregation of the lipoplexes. At pH 5.5, the cationic lipid N-[2-methyl-2-(1',2'-dioleylglyceroxy)dioxolan-4-yl]methyl-N,N,N-trimethylammonium iodide (2) with a cyclic ortho ester linker showed exceptional pH-sensitivity and triggered its lipoplex to permeate model biomembranes within the time span of endosome processing prior to lysosomal degradation. Lipid 2 significantly improved gene transfection in cultured cells compared to the pH-insensitive control lipid 1,2-dioleoyl-3-trimethylammoniopropane (DOTAP).

Unsaturated cationic ortho esters for endosome permeation in gene delivery. Publishing Authors By Initials

H Chen,H Zhang,CM McCallum,FC Szoka,X Guo,

For similar investigative techniques: genetic techniques: gene transfer techniques: transfection research abstracts see: investigative techniques: genetic techniques: gene transfer techniques: transfection research

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MEDLINE DATE:

Unsaturated cationic ortho esters for endosome permeation in gene delivery. Journal Published:

PUBLICATION TYPE: Research Support, Non-U.S. Gov

Journal: Journal of medicinal chemistry

VOLUME: 50

Page Numbers: 4269-78

Journal Abbreviation: J. Med. Chem.

ISSN: 0022-2623

DAY: 10

MONTH: 08

YEAR: 2007

Unsaturated cationic ortho esters for endosome permeation in gene delivery. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 9716531

Unsaturated cationic ortho esters for endosome permeation in gene delivery. Keywords Mesh Terms:

KEYWORDS: Transfection

MESH TERMS: methods

Chemical & Substance for Abstract: Unsaturated cationic ortho esters for endosome permeation in gene delivery. Information

Substance Name: Luciferases, Firefly

Registry Number: EC 1.13.12.7

Grant and Affiliation Information for Unsaturated cationic ortho esters for endosome permeation in gene delivery.

AFFILIATION: Department of Pharmaceutics and Medicinal Chemistry, University of the Pacific, Stockton, California 95211, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: GM074614

ACRONYM: GM

MEDLINETA: J Med Chem

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