A Response Rate Matching Dual-Reactable Probe for Fluorescent Recognition of Hydrogen Sulfide

doi:10.6023/cjoc201905038

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (11): 3277-3282.DOI: 10.6023/cjoc201905038 Previous Articles Next Articles

Special Issue: 荧光探针-生物传感合辑；有机超分子化学合辑

一种响应速率匹配的双反应探针用于荧光识别硫化氢

解畅, 马趁, 贾旭, 张学琪, 魏超*(), 张平竹, 李小六*()

河北大学化学与环境科学学院河北省化学生物学重点实验室药物化学与分子诊断教育部重点实验室河北保定 071002

收稿日期:2019-05-16 发布日期:2019-07-17
通讯作者: 魏超,李小六 E-mail:weichao@hbu.edu.cn;lixl@hbu.cn
基金资助:
国家自然科学基金(21778013);河北省自然科学基金(B2018201234);河北省高等学校科学技术研究(QN2017015);保定市科学研究与发展计划(16zg031);河北大学实验室开放(sy201833);河北大学实验室开放(KYZJX18144)

A Response Rate Matching Dual-Reactable Probe for Fluorescent Recognition of Hydrogen Sulfide

Xie Chang, Ma Chen, Jia Xu, Zhang Xueqi, Wei Chao*(), Zhang Pingzhu, Li Xiaoliu*()

Key Laboratory of Chemical Biology of Hebei Province, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, College of Chemistry and Environmental Science, Hebei University, Baoding, Hebei 071002

Received:2019-05-16 Published:2019-07-17
Contact: Wei Chao,Li Xiaoliu E-mail:weichao@hbu.edu.cn;lixl@hbu.cn
Supported by:
the National Natural Science Foundation of China(21778013);the Natural Science Foundation of Hebei Province(B2018201234);the Colleges and Universities Science Technology Research Project of Hebei Province(QN2017015);the Science Technology Research and Development Guidance Programme Project of Baoding City(16zg031);the Open Fund of Laboratory in Hebei University(sy201833);the Open Fund of Laboratory in Hebei University(KYZJX18144)

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Abstract

A dual-reactable H₂S fluorescent probe was designed and synthesized by employing ortho-fluoro-substituted coumarin azide and 7-nitrobenzofurazan-piperazine as the H₂S reactive groups and the fluorescence quenching groups. The recognition behaviors of the probe to H₂S were investigated and the results showed that the probe exhibited high selectivity and sensitivity. The fluorescence off-on enhancement was ca. 3600-fold, and the detection limit was 4.0×10^-8 mol/L. The results of enzyme activity test indicated that the probe could be used for cystathionine β-synthase (CBS) activity detection and inhibitor screening. Furthermore, the probe was successfully applied for the imaging of H₂S in living cells.

Key words: hydrogen sulfide, response rate, dual-reactable, fluorescent probe

Cite this article

Xie Chang, Ma Chen, Jia Xu, Zhang Xueqi, Wei Chao, Zhang Pingzhu, Li Xiaoliu. A Response Rate Matching Dual-Reactable Probe for Fluorescent Recognition of Hydrogen Sulfide[J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3277-3282.

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Fig. & Tab. 8

Figure 1. Reported H2S fluorescent probe 1~4 and probe 5 in this work

Figure 2. Fluorescence kinetics of probe 1~5 (1.0×10－6 mol/L) in reaction with H2S (2.5×10－4 mol/L) (a) Time-dependent emission intensity at 440 nm of probe 5 after adding H2S. (b) The relationship between fluorescence intensity at 440 nm and reaction time of probe 1~5 on treatment with H2S

Probe	k_obs/s^－1	K₂/(L·mol^－1·s^－1)	T_1/2/min
1	3.88×10^－3	15.5	2.97
2	1.74×10^－3	6.95	6.65
3	3.31×10^－3	13.2	3.49
4	1.30×10^－3	5.20	8.88
5	1.94×10^－3	7.79	5.93

Table 1. Kinetic parameters of probe 1~5 in reaction with H2S

Figure 3. Selectivity and linear relationship of probe 5 (a) Fluorescence responses of probe 5 incubated with various analytes. 1, probe 5; 2, SO32－; 3, SO42－; 4, S2O32－; 5, H2O2; 6, HClO; 7, NO2－; 8, Zn2+; 9, Fe3+; 10, Vc; 11, Cys; 12, Hcy; 13, GSH; 14, H2S. (b) Fluorescence response of probe 5 with different concentrations of H2S (Insert: The emission intensity at 440 nm of probe 5 with different concentrations of H2S). Probe 1.0×10－6 mol/L, Cys and Hcy 1.0×10－3 mol/L, GSH 5×10－3 mol/L, other interferents 1.0×10－4 mol/L; H2S 0~1.50×10－4 mol/L

Figure 4. Optical stability (a) and thermal stability (b) of the probes UV lamp power 18 W for the optical stability test, 37 and 50 ℃ for the thermal stability test

Figure 5. UV-Vis spectrum of probe 5 (1.0×10－6 mol/L) in reaction with H2S (1.0×10－4 mol/L)

Figure 6. Detection of CBS activity using probe 5 (a) The time-dependent emission intensity at 440 nm of probe 5, 10 mmol/L L-Cys and 0~10 μg CBS enzyme. (b) The fluorescence intensity at 440 nm of probe 5 before and after treatment with inhibitors. Probe 1.0×10－5 mol/L, CBS 0.01 μg/μL, inhibitors 1.0×10－3 mol/L

Figure 7. Confocal imaging of H2S in HeLa cells using probe 5 (a, b) Cells incubated with probe 5 only; (c, d) Cells co-incubated with probe 5 and D-cysteine; (e, f) Cells incubated with probe 5 firstly, and then incubated with H2S

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一种响应速率匹配的双反应探针用于荧光识别硫化氢

A Response Rate Matching Dual-Reactable Probe for Fluorescent Recognition of Hydrogen Sulfide

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