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

Rosalina Wisastra; Massimo Ghizzoni; Harm Maarsingh; Adriaan J. Minnaard; Hidde J. Haisma; Frank J. Dekker

doi:10.1039/c0ob00464b

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

Rosalina Wisastra, Massimo Ghizzoni, Harm Maarsingh, Adriaan J. Minnaard, Hidde J. Haisma, Frank J. Dekker^*

^*Bijbehorende auteur voor dit werk

Onderzoeksoutput › Academic › peer review

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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.

Originele taal-2	English
Pagina's (van-tot)	1817-1822
Aantal pagina's	6
Tijdschrift	Organic and Biomolecular Chemistry
Volume	9
Nummer van het tijdschrift	6
DOI's	https://doi.org/10.1039/c0ob00464b
Status	Published - 2011

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CCDC 763229: Experimental Crystal Structure Determination
Wisastra, R. (Contributor), Ghizzoni, M. (Contributor), Maarsingh, H. (Contributor), Minnaard, A. (Contributor), Haisma, H. (Contributor) & Dekker, F. (Contributor), University of Groningen, 25-jan.-2010
DOI: 10.5517/cctm69x
Dataset
CCDC 763228: Experimental Crystal Structure Determination
Wisastra, R. (Contributor), Ghizzoni, M. (Contributor), Maarsingh, H. (Contributor), Minnaard, A. (Contributor), Haisma, H. (Contributor) & Dekker, F. (Contributor), University of Groningen, 25-jan.-2010
DOI: 10.5517/cctm68w
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title = "Isothiazolones; thiol-reactive inhibitors of cysteine protease cathepsin B and histone acetyltransferase PCAF",

abstract = "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.",

keywords = "BIOTINYLATED AFFINITY LABEL, NF-KAPPA-B, INFLAMMATION",

author = "Rosalina Wisastra and Massimo Ghizzoni and Harm Maarsingh and Minnaard, {Adriaan J.} and Haisma, {Hidde J.} and Dekker, {Frank J.}",

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language = "English",

volume = "9",

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T1 - Isothiazolones; thiol-reactive inhibitors of cysteine protease cathepsin B and histone acetyltransferase PCAF

AU - Wisastra, Rosalina

AU - Ghizzoni, Massimo

AU - Maarsingh, Harm

AU - Minnaard, Adriaan J.

AU - Haisma, Hidde J.

AU - Dekker, Frank J.

N1 - Cited By (since 1996): 1

PY - 2011

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N2 - 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.

AB - 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.

KW - BIOTINYLATED AFFINITY LABEL

KW - NF-KAPPA-B

KW - INFLAMMATION

U2 - 10.1039/c0ob00464b

DO - 10.1039/c0ob00464b

M3 - Article

VL - 9

SP - 1817

EP - 1822

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

SN - 1477-0520

IS - 6

ER -

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

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CCDC 763229: Experimental Crystal Structure Determination

CCDC 763228: Experimental Crystal Structure Determination

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