CO (carbon monoxide) fluorescence probe as well as preparation method and application thereof

A fluorescent probe and probe technology, used in chemical instruments and methods, fluorescence/phosphorescence, luminescent materials, etc., can solve the problems of short excitation wavelength, long reaction time, small Stokes shift, etc., and achieve fluorescence intensity improvement and wide application. Prospects, Effects of Avoiding Photobleaching and Phototoxicity

Inactive Publication Date: 2018-10-23
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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  • CO (carbon monoxide) fluorescence probe as well as preparation method and application thereof
  • CO (carbon monoxide) fluorescence probe as well as preparation method and application thereof
  • CO (carbon monoxide) fluorescence probe as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Synthesis of embodiment 1 CO-7 fluorescent probe

[0031] Compound 7-hydroxycoumarin 1mmol and allyl chloride 2mmol were stirred in 10mL dichloromethane, the reaction temperature was 25°C, the reaction time was 18h, vacuum distillation, vacuum drying, dichloromethane / petroleum ether (V / V=5:1) was used as the eluent to perform silica gel column chromatography to obtain compound CO-7; yield: 87%. That 1 H NMR spectrum as figure 1 Shown:

[0032] 1 H NMR (400 MHz, DMSO-d6) δ 8.10 (d, 1H), 7.81 (d, 1H), 7.45 (d, 1H), 6.61 (dd, J = 4.0 Hz, 1H), 6.51 (d, 1H) , 6.02 (m, 1H), 5.98 (dd, J = 4.0 Hz, 1H), 5.44 (dd, J = 4.0 Hz, 1H), 5.34 (d, 2H).

Embodiment 2

[0033] Example 2 The selectivity of CO-7 fluorescent probes to different molecules or ions

[0034] The CO-7 fluorescent probe in Example 1 was prepared into a stock solution with a concentration of 1 mM.

[0035] 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.

[0036] The following substances: Br - , ClO - , Cu 2+ , F - , Fe 2+ , H 2 o 2 , HClO, Hg 2+ , HPO 4 2- , Mg 2+ , Na + , Na 2 S, NaHS, NO - , NO 3- , OAC - , SCN-, SO 4 2- , Zn 2+ , Hcy , Cys, CO were prepared in phosphate buffer (0.01mM, pH=7.4) to prepare 5 mL stock solution with a concentration of 40 mM.

[0037] 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, ...

Embodiment 3

[0038] Example 3 Fluorescence intensity of CO-7 under different concentrations of CO

[0039]Prepare 10 mL of a mother solution with a concentration of 100 mM CO as in Example 2, and dilute it with water to 17 equidifferent concentrations of 1-9 mM, using water as a control. Dilute the CO-7 mother solution in Example 2 to 5 μM, add different concentrations of CO, and perform fluorescence detection after 60 minutes of reaction (λex = 400 nm, λem = 500 nm), detect the fluorescence intensity in each system, and use the fluorescence intensity - 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-7 has a fluorescence response; as the CO concentration increases, the fluorescence intensity of the reaction system gradually increases, and when the CO concentration reaches 8 mM, the reaction system fluorescence Intensity reaches saturation.

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Abstract

The invention provides a CO (carbon monoxide) detecting two-photon fluorescence probe, which has a structure formula shown in the description. The probe provided by the invention can be used for sensitively detecting the existence of CO in a solution, particularly the cells; at the low concentration, the reaction with CO in the cells can be realized; the resistance to the interference of various active oxygen, amino acid and sulfydryl-containing compounds can be realized. The CO-7 fluorescence probe has the two-photon properties; the photobleaching and phototoxication phenomenon can be avoided; the wide application prospects are realized in the field of biological molecular 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 Applications(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64
CPCC07D311/16C09K11/06C09K2211/1088G01N21/6428G01N21/643G01N2021/6439
Inventor 林伟英高世滢唐永和
Owner UNIV OF JINAN
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