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Isothiazolones; thiol-reactive inhibitors of cysteine protease cathepsin B and histone acetyltransferase PCAF

ORGANIC & BIOMOLECULAR CHEMISTRY (2011)

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ORGANIC & BIOMOLECULAR CHEMISTRY
卷 9, 期 6, 页码 1817-1822

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ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob00464b

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Chemistry, Organic

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Isothiazolones and 5-chloroisothiazolones react chemoselectively with thiols by cleavage of the weak nitrogen-sulfur bond to form disulfides. They show selectivity for inhibition of the thiol-dependent cysteine protease cathepsin B and the histone acetyltransferase p300/CBP associated factor (PCAF) based on their substitution pattern. Furthermore, enzyme kinetics and mass spectroscopy indicate covalent binding of a 5-chloroisothiazolone to cathepsin B, which demonstrates their potential utility as probes for activity-based protein profiling.

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