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Fluorescent mimics of cholesterol that rapidly bind surfaces of living mammalian cells.


ABSTRACT: Mammalian cells acquire cholesterol, a critical membrane constituent, through multiple mechanisms. We synthesized mimics of cholesterol, fluorescent N-alkyl-3?-cholesterylamine-glutamic acids, that are rapidly incorporated into cellular plasma membranes compared with analogous cholesteryl amides, ethers, esters, carbamates, and a sitosterol analogue. This process was inhibited by ezetimibe, indicating a receptor-mediated uptake pathway.

SUBMITTER: Hymel D 

PROVIDER: S-EPMC4620717 | biostudies-literature | 2015 Oct

REPOSITORIES: biostudies-literature

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Fluorescent mimics of cholesterol that rapidly bind surfaces of living mammalian cells.

Hymel David D   Cai Sutang S   Sun Qi Q   Henkhaus Rebecca S RS   Perera Chamani C   Peterson Blake R BR  

Chemical communications (Cambridge, England) 20151001 78


Mammalian cells acquire cholesterol, a critical membrane constituent, through multiple mechanisms. We synthesized mimics of cholesterol, fluorescent N-alkyl-3β-cholesterylamine-glutamic acids, that are rapidly incorporated into cellular plasma membranes compared with analogous cholesteryl amides, ethers, esters, carbamates, and a sitosterol analogue. This process was inhibited by ezetimibe, indicating a receptor-mediated uptake pathway. ...[more]

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