Design, synthesis, and biological application of A-D-A-type boranil fluorescent dyes

For the first time, three acceptor-donor-acceptor (A-D-A)-type boranil fluorescent dyes, CSU-BF-R (R = H, CH 3 , and OCH 3 ), featuring phenothiazine as the donor, were designed and synthesized. CSU-BF-R exhibited remarkable photophysical characteristics, including large Stokes shifts (>150 nm),...

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Veröffentlicht in:Organic & biomolecular chemistry 2024-05, Vol.22 (18), p.3725-3731
Hauptverfasser: Luo, Wei, Li, Yiling, Wang, Liang, Qin, Yanhua, Cheng, Qiao, Hu, Guochang, Yao, Chaoyi, Song, Xiangzhi
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Sprache:eng
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Zusammenfassung:For the first time, three acceptor-donor-acceptor (A-D-A)-type boranil fluorescent dyes, CSU-BF-R (R = H, CH 3 , and OCH 3 ), featuring phenothiazine as the donor, were designed and synthesized. CSU-BF-R exhibited remarkable photophysical characteristics, including large Stokes shifts (>150 nm), high fluorescence quantum yields (up to 40%), long-wavelength emissions, and strong red solid-state fluorescence. Moreover, these CSU-BF-R fluorescent dyes were demonstrated to function as highly selective and sensitive ratiometric fluorescent probes for detecting hypochlorous acid (HClO). The preliminary biological applications of CSU-BF-OCH 3 for sensing intracellular HClO in living cells and zebrafish were demonstrated. Therefore, CSU-BF-R possess the potential to further explore the physiological and pathological functions associated with HClO and provide valuable insights into the design of high-performance A-D-A-type fluorescent dyes. Acceptor-donor-acceptor boranil fluorescent dyes, CSU-BF-R (R = H, CH 3 , and OCH 3 ), were developed with strong red fluorescence and large Stokes shifts. CSU-BF-OCH 3 could selectively sense intracellular hypochlorous acid in living cells and zebrafish.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00297k