Water-soluble sulphurous acid hydrogen root ratiometric fluorescent probe and application thereof

A ratiometric fluorescent probe, bisulfite technology, applied in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve the problems of single-signal detection, inability to cell imaging, etc., and achieve the effect of broad application prospects

Inactive Publication Date: 2015-09-30
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Authorized patents [CN102924530B] and [CN102659677B] show probes for specific detection of sulfite,

Method used

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  • Water-soluble sulphurous acid hydrogen root ratiometric fluorescent probe and application thereof
  • Water-soluble sulphurous acid hydrogen root ratiometric fluorescent probe and application thereof
  • Water-soluble sulphurous acid hydrogen root ratiometric fluorescent probe and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Synthesize 3-formyl-7-diethylaminocoumarin and 5-acetylbenzimidazole by known methods, and then react the two to obtain 3-((3'-benzimidazole)-carbonyl with red fluorescence propene)-7-diethylaminocoumarin. specifically is:

[0027] Add 3-formyl-7-diethylaminocoumarin (1, 5.0mmol), 5-acetylbenzimidazole (2, 7.5mmol) and 1mL piperidine into 100mL absolute ethanol, heat to reflux , reacted for 9 hours and cooled to room temperature, a red solid precipitated out, suction filtered, washed three times with ethanol, and the crude product was recrystallized with ethanol to obtain a bright red solid that was 3-((3'-benzimidazole)-carbonylpropene)-7 -Diethylaminocoumarin (BICO), melting point: 287-292°C, yield 61%. single crystal figure 1 .

[0028] Infrared measurement (KBr, cm -1 ):3250(NH),3063(ArH),2969(CH 2 CH 3 ), 1721 (C=O), 1563 (C=C).

[0029] H NMR spectrum determination: 1 H NMR (400MHz, DMSO-d 6 ): δ=1.09(t, J=7.0Hz, 6H, CH3 ), 3.47 (q, J=7.0Hz, 4H, CH 2 ),...

Embodiment 2

[0035] Add 10 mL of 3-((3'-benzimidazole)-carbonylpropene)-7-diethylaminocoumarin to a solution of PBS buffer (CTAB 1mM, pH=7.4) with a micro-syringe , respectively quantitatively add 10 equivalents of Cys, GSH, mercaptoethanol, 2-aminopyridine, HSO 3 - ,CH 3 CO 2 - ,ClO 3 - ,CN - ,CO 3 2- ,H 2 PO 4 - , HCO 3 2- ,HPO 4 2- , F - , Cl - ,Br - , I - ,IO 3- ,NO 2- ,NO 3 - ,S 2- ,S 2 o 3 2- , SO 3 2- , SO 4 2- After 1 hour of action, UV-visible spectrophotometry and fluorescence spectrophotometry were tested, showing that the probe 3-((3'-benzimidazole)-carbonylpropene)-7-diethylaminocoumarin Bisulfite has good selectivity, and the comparison before and after adding bisulfite shows that the fluorescence emission wavelength has a blue shift of 147nm, which has a very good ratio response. See image 3 , 4.

Embodiment 3

[0037] Intracellular fluorescence imaging test:

[0038] The two groups A and B are the control group. Control group A: A549 cells were treated with 1.0 μM 3-((3'-benzimidazole)-carbonylpropene)-7-diethylaminocoumarin at 37°C. Cultivate in the cell culture medium of 1.0μM 2-(3-acetyl)coumarin-based acrylate for 1 hour; control group B: A549 cells were cultured in the cell culture medium of 1.0μM 2-(3-acetyl)coumarin-based acrylate for 1 hour, and washed three times with PBS buffer solution , and then again in 5 mM NaHSO containing 3 Soak in the cell culture medium for 0.5 hours.

[0039] Fluorescence imaging showed that 3-((3'-benzimidazole)-carbonylpropene)-7-diethylaminocoumarin penetrated into the cells. In the control group, the blue channel of A cells has no fluorescence, and the red channel has bright fluorescence. In the control group B, the blue channel showed fluorescence, and the red channel fluorescence was quenched. See Figure 5 .

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Abstract

The invention discloses a water-soluble sulphurous acid hydrogen root ratiometric fluorescent probe. The probe is 3-((3'-benzimidazole)-carbonyl propylene)-7-diethylin coumarin containing alpha, beta-unsaturated ketone, and the chemical structural formula is displayed as a first formula. The probe and a sulphurous acid hydrogen root can be selectively acted, red color is changed into blue color, and naked eye distinguishment can be achieved, a fluorescent ratio response effect is obtained, and analysis can be conducted through ultraviolet absorption and the fluorospectrophotometry. Sulphurous acid hydrogen root ions can be detected in a ratio mode, ratio imaging inside cells is achieved, and the content of the sulphurous acid hydrogen root in a liquid sample can rapidly detected by made test strips. The probe is expected to play a role in industrial manufacture and food detection and biological science, a wide application prospect is obtained.

Description

technical field [0001] The invention relates to a bisulfite fluorescent probe, in particular to a water-soluble bisulfite ratio fluorescent probe and an application thereof, belonging to the field of organic small molecule fluorescent probes. Background technique [0002] The coumarin fluorophore itself has a large molar extinction coefficient and quantum yield, and can achieve near-infrared luminescence after modification, which can be used in luminescent materials, chemical sensors and labeling biomolecules. In recent years, the use of ratiometric fluorescence effect to detect bisulfite and its imaging in living cells has been continuously developed. [0003] Sulfites are widely used food additives around the world. They can be used as food preservatives and bleaching agents, and are very effective antibacterial agents. The human body itself also produces sulfite ions during its metabolism, but high concentrations of sulfite can cause diarrhea, allergies, lower blood pres...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D405/06G01N21/64
Inventor 赵宝祥苗俊英戴溪张涛
Owner SHANDONG UNIV
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