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@ARTICLE{Raudszus:864927,
      author       = {Raudszus, Rick and Nowotny, Robert and Gertzen, Christoph
                      G. W. and Schöler, Andrea and Krizsan, Andor and Gockel,
                      Ines and Kalwa, Hermann and Gohlke, Holger and Thieme, René
                      and Hansen, Finn K.},
      title        = {{F}luorescent analogs of peptoid-based {HDAC} inhibitors:
                      {S}ynthesis, biological activity and cellular uptake
                      kinetics},
      journal      = {Bioorganic $\&$ medicinal chemistry},
      volume       = {27},
      number       = {19},
      issn         = {0968-0896},
      address      = {Amsterdam [u.a.]},
      publisher    = {Elsevier},
      reportid     = {FZJ-2019-04530},
      pages        = {115039 -},
      year         = {2019},
      abstract     = {Fluorescent tagging of bioactive molecules is a powerful
                      tool to study cellular uptake kinetics and is considered as
                      an attractive alternative to radioligands. In this study, we
                      developed fluorescent histone deacetylase (HDAC) inhibitors
                      and investigated their biological activity and cellular
                      uptake kinetics. Our approach was to introduce a dansyl
                      group as a fluorophore in the solvent-exposed cap region of
                      the HDAC inhibitor pharmacophore model. Three novel
                      fluorescent HDAC inhibitors were synthesized utilizing
                      efficient submonomer protocols followed by the introduction
                      of a hydroxamic acid or 2-aminoanilide moiety as
                      zinc-binding group. All compounds were tested for their
                      inhibition of selected HDAC isoforms, and docking studies
                      were subsequently performed to rationalize the observed
                      selectivity profiles. All HDAC inhibitors were further
                      screened in proliferation assays in the esophageal
                      adenocarcinoma cell lines OE33 and OE19. Compound 2,
                      6-((N-(2-(benzylamino)-2-oxoethyl)-5-(dimethylamino)naphthalene)-1-sulfonamido)-N-hydroxyhexanamide,
                      displayed the highest HDAC inhibitory capacity as well as
                      the strongest anti-proliferative activity. Fluorescence
                      microscopy studies revealed that compound 2 showed the
                      fastest uptake kinetic and reached the highest absolute
                      fluorescence intensity of all compounds. Hence, the rapid
                      and increased cellular uptake of 2 might contribute to its
                      potent anti-proliferative properties.},
      cin          = {JSC / NIC / ICS-6},
      ddc          = {610},
      cid          = {I:(DE-Juel1)JSC-20090406 / I:(DE-Juel1)NIC-20090406 /
                      I:(DE-Juel1)ICS-6-20110106},
      pnm          = {511 - Computational Science and Mathematical Methods
                      (POF3-511) / Forschergruppe Gohlke $(hkf7_20170501)$},
      pid          = {G:(DE-HGF)POF3-511 / $G:(DE-Juel1)hkf7_20170501$},
      typ          = {PUB:(DE-HGF)16},
      pubmed       = {pmid:31420257},
      UT           = {WOS:000484396400008},
      doi          = {10.1016/j.bmc.2019.07.055},
      url          = {https://juser.fz-juelich.de/record/864927},
}