TY - JOUR
T1 - Synthesis and Properties of Hydrazine-Embedded Biphenothiazines and Application of Hydrazine-Embedded Heterocyclic Compounds to Fluorescence Cell Imaging
AU - Shindo, Yuri
AU - Nomura, Shogo
AU - Saikawa, Yoko
AU - Nakata, Masaya
AU - Tanaka, Katsunori
AU - Hanaya, Kengo
AU - Sugai, Takeshi
AU - Higashibayashi, Shuhei
N1 - Funding Information:
ThisworkwassupportedbytheJapanSocietyforthe PromotionofScience(JSPS)KAKENHIGrantNumbers17K19131 (S. H.), 26102002 (S. H.), and JST ACT −C Grant Number JPMJCR12YZ(S.H.).Thisworkwasalsoperformedwiththe supportoftheRussianGovernmentProgramfortheCompet-itiveGrowth,grantedtoKazanFederalUniversity(K.T.).
Funding Information:
We thank Prof. Shin-ichiro Kato in The University of Shiga Prefecture for providing the spectral data of N-ethylcarbazole. This work was supported by the Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Numbers 17K19131 (S. H.), 26102002 (S. H.), and JST ACT?C Grant Number JPMJCR12YZ (S. H.). This work was also performed with the support of the Russian Government Program for the Competitive Growth, granted to Kazan Federal University (K. T.).
Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2018/9
Y1 - 2018/9
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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U2 - 10.1002/ajoc.201800364
DO - 10.1002/ajoc.201800364
M3 - Article
AN - SCOPUS:85053062541
SN - 2193-5807
VL - 7
SP - 1797
EP - 1801
JO - Asian Journal of Organic Chemistry
JF - Asian Journal of Organic Chemistry
IS - 9
ER -