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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.

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          Author and article information

          Journal
          Org. Biomol. Chem.
          Organic & biomolecular chemistry
          Royal Society of Chemistry (RSC)
          1477-0539
          1477-0520
          May 24 2017
          Affiliations
          [1 ] Institute of Organic Chemistry, University of Regensburg, 93053 Regensburg, Germany. burkhard.koenig@ur.de.
          [2 ] Institute of Pharmaceutical Sciences, University of Freiburg, 79104 Freiburg, Germany.
          [3 ] Department of Pharmaceutical Chemistry, Martin Luther University of Halle Wittenberg, 06120 Halle/Saale, Germany.
          [4 ] Département de Biologie Structurale Intégrative, Institut de Génétique et Biologie Moléculaire et Cellulaire (IGBMC), Université de Strasbourg (UDS), CNRS, INSERM, 67404 Illkirch Cedex, France.
          Article
          10.1039/c7ob00976c
          28537315
          96fdc780-0f9c-494a-a4ce-d9754b45f883

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