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Boronic Acid for the Traceless Delivery of Proteins into Cells.

ABSTRACT: The use of exogenous proteins as intracellular probes and therapeutic agents is in its infancy. A major hurdle has been the delivery of native proteins to an intracellular site of action. Herein, we report on a compact delivery vehicle that employs the intrinsic affinity of boronic acids for the carbohydrates that coat the surface of mammalian cells. In the vehicle, benzoxaborole is linked to protein amino groups via a "trimethyl lock." Immolation of this linker is triggered by cellular esterases, releasing native protein. Efficacy is demonstrated by enhanced delivery of green fluorescent protein and a cytotoxic ribonuclease into mammalian cells. This versatile strategy provides new opportunities in chemical biology and pharmacology.

SUBMITTER: Andersen KA

PROVIDER: S-EPMC4900815 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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Boronic Acid for the Traceless Delivery of Proteins into Cells.

Andersen Kristen A KA Smith Thomas P TP Lomax Jo E JE Raines Ronald T RT

ACS chemical biology 20151215 2

The use of exogenous proteins as intracellular probes and therapeutic agents is in its infancy. A major hurdle has been the delivery of native proteins to an intracellular site of action. Herein, we report on a compact delivery vehicle that employs the intrinsic affinity of boronic acids for the carbohydrates that coat the surface of mammalian cells. In the vehicle, benzoxaborole is linked to protein amino groups via a "trimethyl lock." Immolation of this linker is triggered by cellular esterase ...[more]

PMID: 26629587

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