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 journalArticle

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

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hydrazine
Sulfoxides
Heterocyclic Compounds
sulfoxide
Fluorescence
Imaging techniques
Dimerization
X ray analysis
Discrete Fourier transforms
Toxicity
Conformations
Oxidation
Temperature

Keywords

  • carbazoles
  • fluorescence
  • hydrazines
  • imaging agents
  • phenothiazines

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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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.",
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author = "Yuri Shindo and Shogo Nomura and Yoko Saikawa and Masaya Nakata and Katsunori Tanaka and Kengo Hanaya and Takeshi Sugai and Shuhei Higashibayashi",
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AU - Shindo, Yuri

AU - Nomura, Shogo

AU - Saikawa, Yoko

AU - Nakata, Masaya

AU - Tanaka, Katsunori

AU - Hanaya, Kengo

AU - Sugai, Takeshi

AU - Higashibayashi, Shuhei

PY - 2018/9/1

Y1 - 2018/9/1

N2 - 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.

AB - 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.

KW - carbazoles

KW - fluorescence

KW - hydrazines

KW - imaging agents

KW - phenothiazines

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