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A ratiometric fluorescent probe for detecting bisulfite and its application

A ratiometric fluorescent probe and bisulfite technology, applied in fluorescence/phosphorescence, luminescent materials, measuring devices, etc., can solve the problems of single signal detection, inability to image cells, etc., and achieve the effect of broad application prospects

Active Publication Date: 2021-07-09
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Authorized patents [CN102924530B] and [CN102659677B] show probes for specific detection of sulfite, but they have the disadvantages of single-signal detection and inability to image cells, respectively

Method used

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  • A ratiometric fluorescent probe for detecting bisulfite and its application
  • A ratiometric fluorescent probe for detecting bisulfite and its application
  • A ratiometric fluorescent probe for detecting bisulfite and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1 Preparation of the ratio fluorescent probe for detecting bisulfite according to the present invention

[0029] (E)-2-(3-cyano-5,5-dimethyl-4-(4-(piperazin-1-yl)styryl)furan-2(5H)-ylidene)propane Nitrile (0.148g, 0.400mmol) and dansyl chloride (0.108g, 0.400mmol) were stirred at room temperature in dry dichloromethane (15mL) and triethylamine (0.5mL) for 1.5 hours, separated by silica gel column chromatography (dichloromethane Methane / methanol=5 / 1) to obtain the probe of the present invention (65 mg, yield 26.8%).

[0030] Melting point: 275-277°C;

[0031] H NMR spectrum determination: 1 H NMR (300MHz, DMSO-d 6 ):δ=1.74(s,6H),2.83(s,6H),3.22(t,J=5.7Hz,4H),3.51(t,J=5.6Hz,4H),6.94(d,J=15.9Hz ,1H),6.98(d,J=9Hz,2H),7.27(d,J=6.9Hz,1H),7.60-7.71(m,2H),7.74(d,J=9Hz,2H),7.86(d , J=15.9Hz, 1H), 8.17 (dd, J=1.2 and 7.5Hz, 1H), 8.34 (d, J=8.7Hz, 1H), 8.54 (d, J=8.4Hz, 1H).

[0032] Carbon NMR Spectrum Determination: 13 C NMR (75MHz, DMSO-d 6 ):25.91,45.46,45.5...

Embodiment 2

[0037] Prepare a series of 10mL probe solutions of the present invention with EtOH-PBS buffer (5:5, v / v, 10mM PBS, pH6.5), so that the probe concentration is 5 μM, wherein EtOH-PBS is PBS:EtOH=5 :5 buffer solution (pH=6.5).

[0038] Quantitatively add the aqueous solution of 0.2 to 10 equivalents of sodium bisulfite with a micro-injector respectively, and carry out ultraviolet-visible spectrophotometry and fluorescence spectrophotometry test (λ ex = 390nm).

[0039] The result shows: the fluorescent intensity ratio (I 545 / I 637 ) has a linear relationship with the concentration of sodium bisulfite, see figure 1 .

Embodiment 3

[0041] Intracellular fluorescence imaging test:

[0042] Ctr group is under the condition of 37 ℃, HepG2 cells are cultured for 1 hour in the cell culture solution adding the probe of the present invention (5.0 μ M); The probe of the present invention (5.0 μ M) is incubated 1 hour; GSH / Na 2 S 2 o 3 Groups are GSH (250 μM) and Na 2 S 2 o 3 (250μM) was incubated for 1 hour and then incubated with the probe of the present invention (5.0μM) for 1 hour; the fourth column was incubated with TNBS (10mM) for 20 minutes and then GSH (250μM) and Na 2 S 2 o 3 (250 μM) for 1 hour, followed by incubation with the probe of the present invention (5.0 μM) for 1 hour. Cell Imaging see figure 2 a.

[0043] The results show that: the probe of the present invention can detect endogenous bisulfite in cells, see figure 2 b.

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Abstract

The invention discloses a ratiometric fluorescent probe for detecting bisulfite, which uses dansyl fluorophore as a donor, (E)-2-(3-cyano-4-(4-(dimethylamino) Styrene)-5,5-dimethylfuran-2(5H-ylidene)malononitrile fluorophore is used as an acceptor, and the ratio of detecting bisulfite based on fluorescence resonance energy transfer mechanism is constructed by piperazine linkage fluorescent probe. The invention also discloses the application of the ratio fluorescent probe in the detection of bisulfite-containing samples and the application in intracellular lipid droplet localization imaging. It provides a powerful tool for relevant detection or targeting in the field of biomedicine, is expected to play a role in bioscience research, and has broad application prospects.

Description

technical field [0001] The invention relates to a ratio fluorescent probe for detecting bisulfite based on a fluorescence resonance energy transfer mechanism and its application in detecting samples containing bisulfite; it belongs to the field of organic small molecule fluorescent probes. Background technique [0002] Dansyl fluorophore itself has a large molar extinction coefficient and quantum yield, and can be used in chemical sensors and labeling biomolecules. In recent years, the use of ratiometric fluorescence to detect bisulfite and its imaging in living cells has been continuously developed. [0003] Sulfites are widely used food additives, preservatives and bleaching agents and are very effective antimicrobial agents. The human body itself also produces sulfite ions during its metabolism, but high concentrations of sulfite can cause diarrhea, allergies, lower blood pressure, asthma, etc. The WHO stipulates that the permissible intake of sulfite per person per day ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/68C09K11/06G01N21/64
CPCC07D307/68C09K11/06C09K2211/1007C09K2211/1011C09K2211/1044C09K2211/1088G01N21/6402
Inventor 赵宝祥苗俊英张尚立苏乐黄秒飞陈丽娜
Owner SHANDONG UNIV
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