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A molecular umbrella approach to the intracellular delivery of small interfering RNA.


ABSTRACT: A series of diwalled and tetrawalled molecular umbrellas have been synthesized using cholic acid, spermidine, and lysine as starting materials. Coupling of these molecular umbrellas to an octaarginine peptide afforded agents that were capable of promoting the transport of small interfering RNA to HeLa cells, as judged by the knockdown of enhanced green fluorescent protein expression. The efficiency of this knockdown was found to increase with an increasing number of facially amphiphilic walls present, and also when a cleavable disulfide linker was replaced with a noncleavable, maleimido moiety; i.e., a group that is not susceptible to thiolate-disulfide interchange. The knockdown efficiency that was observed for one tetrawalled molecular umbrella-octaargine conjugate was comparable to that observed with a commercially available transfection agent, Lipofectamine 2000, but the conjugate showed less cytotoxicity.

SUBMITTER: Cline LL 

PROVIDER: S-EPMC3218225 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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A molecular umbrella approach to the intracellular delivery of small interfering RNA.

Cline Lauren L LL   Janout Vaclav V   Fisher Michael M   Juliano Rudolph L RL   Regen Steven L SL  

Bioconjugate chemistry 20111013 11


A series of diwalled and tetrawalled molecular umbrellas have been synthesized using cholic acid, spermidine, and lysine as starting materials. Coupling of these molecular umbrellas to an octaarginine peptide afforded agents that were capable of promoting the transport of small interfering RNA to HeLa cells, as judged by the knockdown of enhanced green fluorescent protein expression. The efficiency of this knockdown was found to increase with an increasing number of facially amphiphilic walls pr  ...[more]

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