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J Am Chem Soc. 2017 Oct 18;139(41):14396-14398. doi: 10.1021/jacs.7b06597. Epub 2017 Oct 10.

Cytosolic Delivery of Proteins by Bioreversible Esterification.

Author information

1
Department of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.

Abstract

Cloaking its carboxyl groups with a hydrophobic moiety is shown to enable a protein to enter the cytosol of a mammalian cell. Diazo compounds derived from (p-methylphenyl)glycine were screened for the ability to esterify the green fluorescent protein (GFP) in an aqueous environment. Esterification of GFP with 2-diazo-2-(p-methylphenyl)-N,N-dimethylacetamide was efficient. The esterified protein entered the cytosol by traversing the plasma membrane directly, like a small-molecule prodrug. As with prodrugs, the nascent esters are substrates for endogenous esterases, which regenerate native protein. Thus, esterification could provide a general means to deliver native proteins to the cytosol.

PMID:
28976737
PMCID:
PMC5856659
DOI:
10.1021/jacs.7b06597
[Indexed for MEDLINE]
Free PMC Article

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