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Identification of the Binding Site of Chroman-4-one Based Sirtuin 2 Selective Inhibitors using Photoaffinity Labeling in Combination with Tandem Mass Spectrometry

Journal article
Authors Tina Seifert
Marcus Malo
Johan Lengqvist
Carina Sihlbom
Elina Jarho
Kristina Luthman
Published in Journal of Medicinal Chemistry
Volume 59
Issue 23
Pages 10794-10799
ISSN 0022-2623
Publication year 2016
Published at Core Facilities, Proteomics
Department of Chemistry and Molecular Biology
Pages 10794-10799
Language en
Links doi.org/10.1021/acs.jmedchem.6b0111...
Subject categories Other Chemistry Topics, Organic Chemistry

Abstract

Photoaffinity labeling (PAL) was used to identify the binding site of chroman-4-one-based SIRT2-selective inhibitors. The photoactive diazirine 4, a potent SIRT2 inhibitor, was subjected to detailed photochemical characterization. In PAL experiments with SIRT2, a tryptic peptide originating from the covalent attachment of photoactivated 4 was identified. The peptide covers both the active site of SIRT2 and the proposed binding site of chroman-4-one-based inhibitors. A high-power LED was used as source for the monochromatic UV light enabling rapid photoactivation.

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