Fluorescent probe for detecting carbon monoxide and application thereof

A fluorescent probe, carbon monoxide technology, applied in the field of analytical chemistry

Inactive Publication Date: 2019-09-13
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are no reports of any targeted fluorescent probes that can selectively detect ER CO in living cells.

Method used

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  • Fluorescent probe for detecting carbon monoxide and application thereof
  • Fluorescent probe for detecting carbon monoxide and application thereof
  • Fluorescent probe for detecting carbon monoxide and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 Synthesis of Fluorescent Probes

[0034] (1) Synthesis of N-(2-aminoethyl)-4-methylphenyl-1-sulfonamide:

[0035]

[0036] Dissolve ethylenediamine (10 mmol) in 10 mL of dichloromethane, and add 30 mmol of triethylamine and 10 mL of dichloromethane dissolved in 4-toluenesulfonyl chloride (7.5 mmol) at 0°C, at room temperature Stir for 12 hours, then add 50 mL of dichloromethane, wash with 15% potassium bicarbonate solution and ultrapure water for 2-3 times, separate the organic phase, evaporate the organic solvent under reduced pressure, separate by column chromatography, rinse The solvent is petroleum ether / dichloromethane (V / V=50:1-10:1), and the compound N-(2-aminoethyl)-4-methylphenyl-1-sulfonamide (1) is obtained, and the product Rate: 83%. That 1 H NMR (400 MHz, CDCl 3 ) δ 7.75 (d, J = 8.0 Hz, 2H), 7.30 (d, J = 8.0 Hz, 2H), 2.96 (t, J = 5.6 Hz, 2H), 2.79 (t, J = 5.6 Hz, 2H), 2.42 (s, 3H); 13 C NMR (100 MHz, CDCl 3 ) δ 143.4, 136.9, 129.8, 1...

Embodiment 2

[0040] Example 2 Responses of fluorescent probes to different concentrations of CO

[0041] Prepare 5 mL of an aqueous solution with a concentration of 1 mM CO and the fluorescent probe mother solution prepared in Example 1 with a concentration of 1 mM as spares. Prepare the probe at a concentration of 10 µM, interact with different concentrations of CO (0-50 µM), and perform fluorescence detection (λ ex = 430 nm, λ em = 525 nm), calculate the fluorescence intensity in each system, and establish the standard curve of fluorescence intensity and CO concentration. like image 3 As shown, within the test concentration range, with the increase of CO concentration, the fluorescence intensity of the reaction system gradually increases linearly.

Embodiment 3

[0042] Example 3 Response kinetics of fluorescent probes to different concentrations of CO

[0043] Prepare 5 mL of an aqueous solution with a concentration of 1 mM CO and a mother solution of a fluorescent probe for detecting CO of the present invention with a concentration of 1 mM as backup. The solutions of probe and CO were prepared, the concentrations were: probe 10 μM; CO concentration: 0, 25, 50 μM. Perform fluorescence detection (λ ex = 430 nm, λ em = 525 nm), tested every 1 min for 60 min, calculated the fluorescence intensity in each system over time, and established a standard curve of fluorescence intensity and action time. like Figure 4 As shown, the fluorescence intensity of the reaction system reached saturation after about 50 min of reaction.

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PUM

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Abstract

The invention provides a fluorescent probe for detecting carbon monoxide. The fluorescent probe has a chemical structural formula as described in the specification. The above fluorescent probe can detect carbon monoxide in a solution, a cell or an organism. The CO fluorescent probe provided by the invention belongs to a small-molecule fluorescent probe. At present, small-molecule fluorescent probes directed at CO recognition are seldom reported; and in particular, fluorescent probes for recognizing CO in endoplasmic reticulums of cell have not been reported yet. According to the fluorescent probe for detecting CO provided by the invention, fluorescence is significantly enhanced when CO is added into the fluorescent probe, and such a result and phenomenon lay a theoretical foundation for biological imaging application of the probe and indicate that the probe has potential application value in the field of laser fluorescence biomarkers. Correspondingly, the detection of CO by the probe of the invention via the fluorescence imaging technology can be used for evaluating and studying the content and physiological functions of CO in cells; and in particular, the probe can also detect COin the endoplasmic reticulums of cells, so the probe has potential application value in the study of the physiological functions of CO in the endoplasmic reticulums of cells.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to a fluorescent probe for detecting carbon monoxide and an application thereof. Background technique [0002] Carbon monoxide (CO) has long been considered a toxic pollutant because of its strong affinity with hemoglobin, which can lead to fatal consequences when inhaled. CO is often referred to as the "silent killer" because it is odorless, colorless, and exceptionally difficult to perceive. Despite its lethal properties, it is evident from various studies that CO is also a gas transport molecule with important therapeutic potential in the prevention of inflammation, vascular diseases and even cancer. It plays an important control role in various physiological and pathological processes occurring in the nervous, cardiovascular and immune systems. CO can also prevent acute and chronic hypertension and vasoconstriction by stimulating soluble guanylate cycl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1007C09K2211/1029G01N21/6428G01N21/643G01N2021/6432
Inventor 林伟英张云艳唐永和
Owner UNIV OF JINAN
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