Citation: Dongyang Li, Chen Weijie, Hua Liu Sheng, Chen Xiaoqiang, Yin Jun. The regulation of biothiol-responsive performance and bioimaging application of benzo[c][1, 2, 5]oxadiazole dyes[J]. Chinese Chemical Letters, ;2020, 31(11): 2891-2896. doi: 10.1016/j.cclet.2020.02.047 shu

The regulation of biothiol-responsive performance and bioimaging application of benzo[c][1, 2, 5]oxadiazole dyes

Dongyang Li ^a ,
Chen Weijie ^a ,
Hua Liu Sheng ^a ,
Chen Xiaoqiang ^b ,
Yin Jun ^{a, b, *,}

a.
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, International Joint Research Center for Intelligent Biosensing Technology and Health, College of Chemistry, Central China Normal University, Wuhan 430079, China
b.
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing 211816, China

yinj@mail.ccnu.edu.cn

Received Date: 27 December 2019
Revised Date: 21 February 2020
Accepted Date: 24 February 2020
Available Online: 4 March 2020

Figures(7)

The different oxidation states of sulphur atom play a significant role on functional materials. In this work, a aryl-thioether and its sulphone substituted benzo[c][1, 2, 5]oxadiazole dyes were synthesized and utilized to determine thiol-containing amino acids. The result of selectivity experiments showed they detected the cysteine and homocysteine under physiological condition with negligible interference from other amino acids. In comparison to the thioether dye, the sulphone-based dye exhibited much faster response time for Cys and Hcy. However, the sulphone restricted its thiol-reactivity and bioimaging performance in living cells. By reducing the oxidation state of sulphur atom, we amazedly found that the sulfoxide-based dye still maintained high selectivity ultrafast response time for Cys/Hcy under physiological condition. It was worth mentioning that it also had high reactivity and good bioimaging performance that sulfone compounds did not have.
- Benzo[c][1, 2, 5]oxadiazole dye,
- Sulfoxide,
- Sulphone,
- Thiol response
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