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@ARTICLE{Wirawan:638310,
author = {Wirawan, Ricky and Frei, Matthias and Heider, Anna and
Papenkordt, Niklas and Friedrich, Florian and Wein, Thomas
and Jung, Manfred and Groll, Michael and Huber, Eva and
Bracher, Franz},
title = {{T}ailored {S}ir{R}eal-type inhibitors enhance {SIRT}2
inhibition through ligand stabilization and disruption of
{NAD}$^+$ co-factor binding},
journal = {RSC medicinal chemistry},
volume = {16},
number = {11},
issn = {2040-2503},
address = {Cambridge},
publisher = {Royal Society of Chemistry},
reportid = {PUBDB-2025-04028},
pages = {5419 - 5440},
year = {2025},
note = {ISSN 2632-8682 not unique: **2 hits**.},
abstract = {Human sirtuin 2 (SIRT2) is an NAD+ dependant enzyme that
has been linked to the pathogenesis of various diseases,
making it a promising target for pharmaceutical
intervention. This study presents a systematic investigation
on the inhibitory effects of SIRT2 inhibitors functionalized
with diverse electrophilic functional groups. Guided by
initial docking studies, we designed and synthesised 14
derivatives of two published potent lead structures 24a and
SirReal2. The most potent and subtype selective SIRT2
inhibitor 29 (RW-78) exhibits an IC50 of 26 nM, which
outperforms its lead structure 24a (IC50 = 79 nM) by a
factor of 3. The increased potency of 29 is explained by
halogen–π interactions with SIRT2 residues as visualized
by X-ray crystallography. Furthermore, 29 interferes with
NAD+ binding, highlighting co-factor displacement as a valid
strategy to inhibit SIRT2. Additionally, we showed cellular
target engagement via NanoBRET assays in HEK293T cells (EC50
= 15 nM). Altogether our findings provide a deeper insight
into the structure–activity relationships of these
SirReal-type inhibitors and offer new avenues for
optimisation of SIRT2 inhibitors.},
cin = {EMBL-User},
ddc = {540},
cid = {I:(DE-H253)EMBL-User-20120814},
pnm = {6G3 - PETRA III (DESY) (POF4-6G3) / DFG project 503267011 -
Sirtuin2 (Sirt2)-Liganden als Hemmstoffe der Desacylierung
langkettiger Acyllysine und chemische Sonden für
induzierten Proteinabbau (503267011) / DFG project
G:(GEPRIS)325871075 - SFB 1309: Chemische Biologie
epigenetischer Modifikationen (325871075)},
pid = {G:(DE-HGF)POF4-6G3 / G:(GEPRIS)503267011 /
G:(GEPRIS)325871075},
experiment = {EXP:(DE-H253)P-P13-20150101},
typ = {PUB:(DE-HGF)16},
doi = {10.1039/D5MD00144G},
url = {https://bib-pubdb1.desy.de/record/638310},
}