A Long-Wavelength Fluorescent Probe for Naked Eye Recognition of HSO3-/SO32- in Aqueous Solution and Its Application

doi:10.6023/cjoc202011037

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2417-2423.DOI: 10.6023/cjoc202011037 Previous Articles Next Articles

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一种水溶液中裸眼识别HSO₃^-/SO₃^2-的长波长荧光探针及其应用

王超^a, 王鑫^a, 钟克利^a, 侯淑华^a, 燕小梅^b, 边延江^a^,^*(), 汤立军^a^,^*()

a 渤海大学化学与材料工程学院辽宁锦州 121013
b 大连医科大学检验医学院辽宁大连 116044

收稿日期:2020-11-30 修回日期:2021-01-17 发布日期:2021-02-26
通讯作者: 边延江, 汤立军
基金资助:
国家自然科学基金(21878023); 国家自然科学基金(U1608222); 及辽宁特聘教授支持计划资助项目.

A Long-Wavelength Fluorescent Probe for Naked Eye Recognition of HSO₃^-/SO₃^2- in Aqueous Solution and Its Application

Chao Wang^a, Xin Wang^a, Keli Zhong^a, Shuhua Hou^a, Xiaomei Yan^b, Yanjiang Bian^a(), Lijun Tang^a()

a College of Chemistry and Material Engineering, Bohai University, Jinzhou, Liaoning 121013
b College of Laboratory Medicine, Dalian Medical University, Dalian, Liaoning 116044

Received:2020-11-30 Revised:2021-01-17 Published:2021-02-26
Contact: Yanjiang Bian, Lijun Tang
Supported by:
National Natural Science Foundation of China(21878023); National Natural Science Foundation of China(U1608222); and the Program for Distinguished Professor of Liaoning Province.

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Abstract

3-Cyano-4-(3-formyl-4-hydroxystyryl)-5,5-dimethylfuran-2(5H)-alkylene)malononitrile derivative CDM was synthesized. The correctness of its structure was verified by ¹H NMR, ¹³C NMR and HRMS. CDM can recognize HSO₃^-/SO₃^2- with the naked eye through the fluorescent signal “ON-OFF” in MeCN/Tris ( V∶V=2∶8, pH=7.4) solution, and the color changes from pink to colorless. The probe CDM has good anti-interference ability and fast response speed (200 s), the pH applicable range is 7~14, and the detection limits of the fluorescence and UV absorption spectrum are 6.07 and 1.59 μmol/L. The experimental research shows that CDM can detect HSO₃^-/SO₃^2- in real water samples and sugar samples and, can perform fluorescent image HSO₃^-/SO₃^2- in living cells.

Key words: fluorescent probe, HSO₃^-/SO₃^2-, long wavelength, naked eye recognition, cell imaging

Cite this article

Chao Wang, Xin Wang, Keli Zhong, Shuhua Hou, Xiaomei Yan, Yanjiang Bian, Lijun Tang. A Long-Wavelength Fluorescent Probe for Naked Eye Recognition of HSO₃^-/SO₃^2- in Aqueous Solution and Its Application[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2417-2423.

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Fig. & Tab. 12

Scheme 1. Synthetic route of probe CDM

Figure 1. Fluorescence (a) and UV absorption spectrum (b) of CDM (10 μmol/L) in MeCN/Tris (V∶V=2:8, pH=7.4) solution upon addition of different anions (λ em=610 nm, λ ex=550 nm)

Figure 2. Fluorescence (a) and UV absorption spectrum (b) changes of CDM (10 μmol/L) in MeCN/Tris (V∶V=2∶8, pH=7.4) solution upon addition different concentration of HSO 3– (0~150 μmol/L) (λ ex=550 nm)

Figure 3. Plot of the fluorescence (a) and UV absorption intensity (b) of CDM with different concentration of log [HSO3–]

Figure 4. Changes in fluorescence intensity of CDM (10 μmol/ L) in the presence of different anions (white) and further addition of HSO 3– (150 μmol/L) (red)

Figure 5. Time-dependent fluorescence intensity change of CDM to HSO3–(150 μmol/L)

Figure 6. Fluorescence intensity changes of CDM and CDM+HSO3–at different pH

Sample	Added/ (μmol•L^–1)	Found/ (μmol•L^–1)	Recovery rate/%	CV (n=3)
Tap water	50	49.95	99.9	0.38
	70	69.75	99.6	0.61
	90	90.05	100.0	0.49
Lake water	50	51.35	102.7	0.93
	70	71.05	101.5	0.64
	90	89.56	99.5	1.08
River water	50	49.40	98.8	2.12
	70	71.49	102.1	0.96
	90	90.51	100.6	0.77

Table 1. Detection results of HSO3– in actual water samples

Sample	Added/ (μmol•L^–1)	Found/ (μmol•L^–1)	Recovery rate/%	CV (n=3)
Sugar 1	70	72.12	103.03	2.09
	90	91.50	101.67	1.70
	110	113.66	103.33	2.48
Sugar 2	70	71.36	101.94	0.91
	90	91.79	101.99	1.98
	10	109.86	99.87	1.65

Table 2. Detection results of HSO3– in actual sugar samples

Figure 7. White channel, white channel and merge channel of MCF-7 cells pretreated with CDM (10 µmol/L) incubation with HSO 3– (0, 10, 50, 100, 150 µmol/L) for 30 min

Figure 8. Mechanism of CDM sensing HSO3–

Figure 9. HRMS spectrum of compound CDM+HSO3–

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一种水溶液中裸眼识别HSO₃^-/SO₃^2-的长波长荧光探针及其应用

A Long-Wavelength Fluorescent Probe for Naked Eye Recognition of HSO₃^-/SO₃^2- in Aqueous Solution and Its Application

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一种水溶液中裸眼识别HSO3-/SO32-的长波长荧光探针及其应用