Supplementary material from "Isoform-selective HDAC1/6/8 inhibitors with an imidazo-ketopiperazine cap containing stereochemical diversity"
Version 3 2018-03-24, 06:58
Version 2 2018-03-24, 06:57
Version 1 2018-03-15, 13:13
Posted on 2018-03-24 - 06:58
A series of hydroxamic acids linked by different lengths to a chiral imidazo-ketopiperazine scaffold were synthesized. The compounds with linker lengths of 6 and 7 carbon atoms were the most potent in histone deacetylase (HDAC) inhibition, and were specific submicromolar inhibitors of the HDAC1, HDAC6 and HDAC8 isoforms. A docking model for the binding mode predicts binding of the hydroxamic acid to the active site zinc cation and additional interactions between the imidazo-ketopiperazine and the enzyme rim. The compounds were micromolar inhibitors of the MV4-11, THP-1 and U937 cancer cell lines. Increased levels of histone H3 and tubulin acetylation support a cellular mechanism of action through HDAC inhibition.This article is part of a discussion meeting issue ‘Frontiers in epigenetic chemical biology’.
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Lecointre, Bertrand; Narozny, Remy; Borrello, Maria Teresa; Senger, Johanna; Chakrabarti, Alokta; Jung, Manfred; et al. (2018). Supplementary material from "Isoform-selective HDAC1/6/8 inhibitors with an imidazo-ketopiperazine cap containing stereochemical diversity". The Royal Society. Collection. https://doi.org/10.6084/m9.figshare.c.4032565.v3
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AUTHORS (12)
BL
Bertrand Lecointre
RN
Remy Narozny
MB
Maria Teresa Borrello
JS
Johanna Senger
AC
Alokta Chakrabarti
MJ
Manfred Jung
MM
Martin Marek
CR
Christophe Romier
JM
Jelena Melesina
WS
Wolfgang Sippl
LB
Laurent Bischoff
AG
A. Ganesan