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

Yuri Shindo, Shogo Nomura, Yoko Saikawa, Masaya Nakata, Katsunori Tanaka, Kengo Hanaya, Takeshi Sugai, Shuhei Higashibayashi

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

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. cis/trans-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.

Original languageEnglish
Pages (from-to)1797-1801
Number of pages5
JournalAsian Journal of Organic Chemistry
Volume7
Issue number9
DOIs
Publication statusPublished - 2018 Sep 1

Keywords

  • carbazoles
  • fluorescence
  • hydrazines
  • imaging agents
  • phenothiazines

ASJC Scopus subject areas

  • Organic Chemistry

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