Synthesis and Properties of Hydrazine‐Embedded Biphenothiazines and Application of Hydrazine‐Embedded Heterocyclic Compounds to Fluorescence Cell Imaging

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  • Yuri Shindo
    Department of Applied Chemistry Faculty of Science and Technology Keio University 3-14-1 Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan
  • Shogo Nomura
    Biofunctional Synthetic Chemistry Laboratory RIKEN Cluster for Pioneering Research, RIKEN 2-1 Hirosawa, Wako-shi Saitama 351-0198 Japan
  • Yoko Saikawa
    Department of Applied Chemistry Faculty of Science and Technology Keio University 3-14-1 Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan
  • Masaya Nakata
    Department of Applied Chemistry Faculty of Science and Technology Keio University 3-14-1 Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan
  • Katsunori Tanaka
    Biofunctional Synthetic Chemistry Laboratory RIKEN Cluster for Pioneering Research, RIKEN 2-1 Hirosawa, Wako-shi Saitama 351-0198 Japan
  • Kengo Hanaya
    Department of Pharmaceutical Sciences Faculty of Pharmacy Keio University 1-5-30 Shibakoen, Minato-ku Tokyo 105-8512 Japan
  • Takeshi Sugai
    Department of Pharmaceutical Sciences Faculty of Pharmacy Keio University 1-5-30 Shibakoen, Minato-ku Tokyo 105-8512 Japan
  • Shuhei Higashibayashi
    Department of Pharmaceutical Sciences Faculty of Pharmacy Keio University 1-5-30 Shibakoen, Minato-ku Tokyo 105-8512 Japan

書誌事項

公開日
2018-08-10
資源種別
journal article
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/ajoc.201800364
公開者
Wiley

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<jats:title>Abstract</jats:title><jats:p>Hydrazine‐embedded unsubstituted butterfly‐shaped biphenothiazine and its sulfoxides were synthesized by dimerization of 1,9‐dibromophenothiazine, which was prepared by realizing selective debromination at the 3,7‐positions of 1,3,7,9‐tetrabromophenothiazine. <jats:italic>cis/trans</jats:italic>‐Biphenothiazine sulfoxide was selectively prepared by changing the oxidation temperature to control the inversion rate of the butterfly shape of the intermediate. Their butterfly‐shapes, conformations, photophysical properties (UV‐vis absorption, fluorescence), and redox properties were elucidated by X‐ray analysis, DFT calculations, spectral and electrochemical measurements. Fluorescent hydrazine‐embedded biphenothiazine sulfoxides and bicarbazoles were applied to cell imaging of HeLa cells. The bicarbazoles exhibited high fluorescence signals in the cells with low toxicity.</jats:p>

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