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Reductive cleavage of CC bonds as a new strategy for turn-on dual fluorescence in effective sensing of H2S†
Chemical Science ( IF 7.6 ) Pub Date : 2018-09-11 00:00:00 , DOI: 10.1039/c8sc03430c Chunfei Wang 1 , Xiaoxiang Cheng 1 , Jingyun Tan 1 , Zhaoyang Ding 1 , Wenjing Wang 2 , Daqiang Yuan 2 , Gang Li 1 , Hongjie Zhang 1 , Xuanjun Zhang 1
Chemical Science ( IF 7.6 ) Pub Date : 2018-09-11 00:00:00 , DOI: 10.1039/c8sc03430c Chunfei Wang 1 , Xiaoxiang Cheng 1 , Jingyun Tan 1 , Zhaoyang Ding 1 , Wenjing Wang 2 , Daqiang Yuan 2 , Gang Li 1 , Hongjie Zhang 1 , Xuanjun Zhang 1
Affiliation
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Reductive cleavage of alkenes is rarely reported in synthetic chemistry. Here we report a unique H2S-mediated reductive cleavage of C![[double bond, length as m-dash]](https://www.rsc.org/images/entities/char_e001.gif)
C bonds under mild conditions, which is a successful new strategy for the design of probes for effective sensing of H2S with turn-on dual-color fluorescence. A short series of phenothiazine ethylidene malononitrile derivatives were shown to react with H2S, via reductive cleavage of CC bonds with intramolecular cyclization reactions to form thiophene rings. Enlightened by this new reaction mechanism, four effective probes with turn-off to turn-on fluorescence switches were successfully applied for sensing H2S, an important gaseous signalling molecule in living systems, among which PTZ-P4 exhibited two fluorescent colors after reductive cleavage. The dual-color probe was applied for imaging endogenous H2S and showed distinct differences in brightness in living C. elegans for wild type N2, glp-1 (e2144) mutants (higher levels of endogenous H2S), and cth-1 (ok3319) mutants (lower levels of endogenous H2S). The discovery of H2S-mediated reductive cleavage of CC bonds is expected to be valuable for chemical synthesis, theoretical studies, and the design of new fluorescent H2S probes.
中文翻译：
CC 键的还原裂解作为开启双荧光有效检测 H2S 的新策略†
在合成化学中很少报道烯烃的还原裂解。在这里，我们报告了在温和条件下独特的 H 2 S 介导的 CC 键还原切割，这是一种成功的新策略，可用于设计有效检测具有开启双色荧光的 H 2 S 的探针。一小部分吩噻嗪亚乙基丙二腈衍生物显示出与 H 2 S 反应，通过C C 键的还原裂解和分子内环化反应形成噻吩环。在这种新反应机制的启发下，四种具有关闭到打开荧光开关的有效探针成功应用于感测H 2S是生命系统中重要的气态信号分子，其中PTZ-P4在还原裂解后呈现出两种荧光颜色。双色探针应用于内源性 H 2 S 成像，并显示出活的秀丽隐杆线虫野生型 N2、glp-1 ( e2144 ) 突变体（更高水平的内源性 H 2 S）和cth -1的亮度差异( ok3319 ) 突变体（较低水平的内源 H 2 S）。H 2 S 介导的 C C 键还原断裂的发现有望对化学合成、理论研究和新型荧光 H 2的设计具有重要意义S 探头。
更新日期：2018-09-11
C bonds under mild conditions, which is a successful new strategy for the design of probes for effective sensing of H2S with turn-on dual-color fluorescence. A short series of phenothiazine ethylidene malononitrile derivatives were shown to react with H2S, via reductive cleavage of CC bonds with intramolecular cyclization reactions to form thiophene rings. Enlightened by this new reaction mechanism, four effective probes with turn-off to turn-on fluorescence switches were successfully applied for sensing H2S, an important gaseous signalling molecule in living systems, among which PTZ-P4 exhibited two fluorescent colors after reductive cleavage. The dual-color probe was applied for imaging endogenous H2S and showed distinct differences in brightness in living C. elegans for wild type N2, glp-1 (e2144) mutants (higher levels of endogenous H2S), and cth-1 (ok3319) mutants (lower levels of endogenous H2S). The discovery of H2S-mediated reductive cleavage of CC bonds is expected to be valuable for chemical synthesis, theoretical studies, and the design of new fluorescent H2S probes.
中文翻译：
CC 键的还原裂解作为开启双荧光有效检测 H2S 的新策略†
在合成化学中很少报道烯烃的还原裂解。在这里，我们报告了在温和条件下独特的 H 2 S 介导的 C
C 键还原切割，这是一种成功的新策略，可用于设计有效检测具有开启双色荧光的 H 2 S 的探针。一小部分吩噻嗪亚乙基丙二腈衍生物显示出与 H 2 S 反应，通过C C 键的还原裂解和分子内环化反应形成噻吩环。在这种新反应机制的启发下，四种具有关闭到打开荧光开关的有效探针成功应用于感测H 2S是生命系统中重要的气态信号分子，其中PTZ-P4在还原裂解后呈现出两种荧光颜色。双色探针应用于内源性 H 2 S 成像，并显示出活的秀丽隐杆线虫野生型 N2、glp-1 ( e2144 ) 突变体（更高水平的内源性 H 2 S）和cth -1的亮度差异( ok3319 ) 突变体（较低水平的内源 H 2 S）。H 2 S 介导的 C C 键还原断裂的发现有望对化学合成、理论研究和新型荧光 H 2的设计具有重要意义S 探头。
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