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      Intracellular modulation of excited-state dynamics in a chromophore dyad: differential enhancement of photocytotoxicity targeting cancer cells

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      Author
      Kolemen, S.
      Işık, M.
      Kim, G. M.
      Kim D.
      Geng, H.
      Buyuktemiz, M.
      Karatas, T.
      Zhang, X. F.
      Dede, Y.
      Yoon, J.
      Akkaya, E. U.
      Date
      2015
      Source Title
      Angewandte Chemie (International Edition)
      Print ISSN
      1433-7851
      Electronic ISSN
      1521-3773
      Publisher
      Wiley-VCH Verlag
      Volume
      54
      Issue
      18
      Pages
      5340 - 5344
      Language
      English
      Type
      Article
      Item Usage Stats
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      Abstract
      The photosensitized generation of reactive oxygen species, and particularly of singlet oxygen [O2(a1Dg)], is the essence of photodynamic action exploited in photodynamic therapy. The ability to switch singlet oxygen generation on/off would be highly valuable, especially when it is linked to a cancer-related cellular parameter. Building on recent findings related to intersystem crossing efficiency, we designed a dimeric BODIPY dye with reduced symmetry, which is ineffective as a photosensitizer unless it is activated by a reaction with intracellular glutathione (GSH). The reaction alters the properties of both the ground and excited states, consequently enabling the efficient generation of singlet oxygen. Remarkably, the designed photosensitizer can discriminate between different concentrations of GSH in normal and cancer cells and thus remains inefficient as a photosensitizer inside a normal cell while being transformed into a lethal singlet oxygen source in cancer cells. This is the first demonstration of such a difference in the intracellular activity of a photosensitizer.
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      http://hdl.handle.net/11693/22059
      Published Version (Please cite this version)
      http://dx.doi.org/10.1002/anie.201411962
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