A carbon monoxide fluorescent probe and its preparation method and application

A technology of fluorescent probes and synthesis methods, which is applied in the field of organic small molecule fluorescent probes, can solve the problems of long reaction time, small Stokes shift, short excitation wavelength, etc., achieve increased fluorescence intensity, broad application prospects, avoid photobleaching and The effect of toxic phenomena

Inactive Publication Date: 2020-04-17
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the problems of long reaction time, short excitation wavelength and small Stokes shift of existing probes to carbon monoxide, the present invention provides a fluorescent probe capable of detecting cellular carbon monoxide with sensitive response, low detection limit, good specificity and two-photon properties

Method used

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  • A carbon monoxide fluorescent probe and its preparation method and application
  • A carbon monoxide fluorescent probe and its preparation method and application
  • A carbon monoxide fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The synthesis of embodiment 1 CO-3 fluorescent probe

[0036] (1) In a 100 mL round bottom flask, add 1 mmol of 7-diethylamino-3-aminocoumarin (1), heat to 100°C in 20 mL of 1.5 mol / L hydrochloric acid aqueous solution, and react for 4 hours After suction filtration, the filter cake is 7-diethylamino-3-hydroxycoumarin (2), and the product goes directly to the next step without purification:

[0037] ;

[0038] (2) Stir the compound 7-diethylamino-3-hydroxycoumarin (2) obtained in the previous step with 2mmol of allyl chloride (3) in 10mL of dichloromethane, the reaction temperature is 25°C, and the reaction time is 12h, vacuum distillation, vacuum drying, silica gel column chromatography with dichloromethane / petroleum ether (V / V=5:1) as the eluent to obtain compound CO-3: 7-diethylamino-3-carbonic acid Allyl coumarin; Yield: 77%. That 1 H NMR spectrum as figure 1 Shown:

[0039] 1 H NMR (400 MHz, DMSO-d6) δ 7.89 (s, 1H), 7.45 (d, 1H), 6.77 (dd, J =4.0 Hz, 1H), ...

Embodiment 2

[0041] Example 2 The selectivity of CO-3 fluorescent probes to different molecules or ions

[0042] The CO-3 fluorescent probe in Example 1 was prepared into a stock solution with a concentration of 1 mM.

[0043] Palladium chloride and ruthenium(II) tricarbonyldichloride dimer (CORM-3) were dissolved in DMSO solution to prepare 5 mL of a mother solution with a concentration of 10 mM as the CO mother solution.

[0044] The following substances: Br - , ClO - , Cu 2+ , F - , Fe 2+ , H 2 o 2 , HClO, Hg 2+ , HPO4 2- , Mg 2+ , Na + , Na 2 S, NaHS, NO - , NO 3- , OAC - , SCN - , SO 4 2- , Zn 2+ , Hcy, CO were prepared in phosphate buffer (0.01 mM, pH=7.4) to prepare 5 mL stock solution with a concentration of 40 mM.

[0045] Take 22 test tubes, add 25 μL probe mother solution, 225 μL DMSO and the mother solution of each ion or molecule, and control with an equal amount of water instead of interfering substances; dilute to 5 mL with phosphate buffer (0.01 mM, pH=7....

Embodiment 3

[0046] Example 3 Fluorescence intensity of CO-3 under different concentrations of CO

[0047] Referring to the method of Example 2, 10 mL of CO mother solution with a concentration of 100 mM was prepared, and diluted with water to a total of 17 equidifferent concentrations of 1-9 mM, and water was used as a control. Dilute the CO-3 mother solution in Example 2 to 5 μM, add different concentrations of CO, and perform fluorescence detection (λex = 400 nm, λem = 504 nm) after reacting for 60 min, and detect the fluorescence intensity in each system. -CO concentration curve, such as image 3 shown. It can be seen from the figure that when the CO concentration is the lowest test concentration (1 μM), CO-3 has a fluorescence response; as the CO concentration increases, the fluorescence intensity of the reaction system gradually increases, and when the CO concentration reaches 9 mM, the reaction system fluorescence Intensity reaches saturation.

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Abstract

The invention provides a two-photon fluorescence probe for detecting CO. The structural formula of the probe is shown in the description. The probe can sensitively detect the presence of CO in a solution, especially in a cell; and the probe can react with the CO in the cell at a low concentration, and is resistant to interference of various reactive oxygen, amino acids and thiol-containing compounds. The CO-3 fluorescence probe has two-photon properties, can avoid photobleaching and phototoxicity, and has a broad application prospect in the field of biomolecule detection.

Description

technical field [0001] The invention relates to a sub-fluorescent probe for detecting intracellular CO and an application thereof, belonging to the field of organic small molecule fluorescent probes. Background technique [0002] Carbon monoxide (CO) is one of the important biological signaling molecules that have been confirmed by research in recent decades. In organisms, it can compete with oxygen to bind hemoglobin, thereby hindering the normal transport of oxygen. Excessive intake of exogenous carbon monoxide can lead to carbon monoxide poisoning in the biological body, so carbon monoxide has long been considered to be only a poisonous and harmful substance, but whether there is really endogenous carbon monoxide in the body, and whether endogenous carbon monoxide has Physiological effects have long been ignored by people. Until 1949, Sjostrand discovered that endogenous carbon monoxide could be produced in the human body; then in 1987, Ullrich and Brune found that carbo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06C09K2211/1088G01N21/6428
Inventor 林伟英高世滢唐永和
Owner UNIV OF JINAN
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