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Issue 22, 2017
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Photochromic histone deacetylase inhibitors based on dithienylethenes and fulgimides

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Abstract

Histone deacetylases (HDACs) play a crucial role in numerous biological processes and therefore are targeted in anticancer research and in the field of epigenetics. Dithienylethenes (DTEs) and fulgimides were functionalized with hydroxamic acids, which is a known moiety binding to zinc dependent HDACs, to gain photoswitchable HDAC inhibitors. The new DTE based inhibitors showed moderate photochromic properties in polar solvents and the inhibitory activity changes up to a factor of four. The photochromic performance of the prepared fulgimide inhibitors was very good, even in aqueous buffer. They achieved a maximum three-fold difference in inhibitory activity. Docking experiments using the crystal structures of the tested enzymes gave a rationale for the observed moderate differences in the activities of the inhibitors.

Graphical abstract: Photochromic histone deacetylase inhibitors based on dithienylethenes and fulgimides

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Supplementary files

Article information


Submitted
21 Apr 2017
Accepted
16 May 2017
First published
16 May 2017

Org. Biomol. Chem., 2017,15, 4882-4896
Article type
Paper

Photochromic histone deacetylase inhibitors based on dithienylethenes and fulgimides

D. Wutz, D. Gluhacevic, A. Chakrabarti, K. Schmidtkunz, D. Robaa, F. Erdmann, C. Romier, W. Sippl, M. Jung and B. König, Org. Biomol. Chem., 2017, 15, 4882
DOI: 10.1039/C7OB00976C

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