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Hydrogen sulfide molecule fluorescent probe with mitochondrial targeting and two-photon property as well as preparation method and application of hydrogen sulfide molecule fluorescent probe

A fluorescent probe and two-photon technology, applied in the field of analytical chemistry, can solve the problems of lack of targeted probes, lack of hydrogen sulfide detection tools, lack of hydrogen sulfide probes, etc., to achieve strong anti-interference ability of other molecules, Improved selection specificity and simple post-processing

Inactive Publication Date: 2017-01-04
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, currently for H 2 The detection of S lacks targeted probes, and cannot detect hydrogen sulfide in a specific organelle in the cell, especially the lack of hydrogen sulfide probes targeting mitochondria in cells, thus lacking the ability to detect hydrogen sulfide in the process of cell disease. A detection tool for the change of hydrogen sulfide concentration in mitochondria

Method used

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  • Hydrogen sulfide molecule fluorescent probe with mitochondrial targeting and two-photon property as well as preparation method and application of hydrogen sulfide molecule fluorescent probe
  • Hydrogen sulfide molecule fluorescent probe with mitochondrial targeting and two-photon property as well as preparation method and application of hydrogen sulfide molecule fluorescent probe
  • Hydrogen sulfide molecule fluorescent probe with mitochondrial targeting and two-photon property as well as preparation method and application of hydrogen sulfide molecule fluorescent probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Synthesis of compound 1-1:

[0036]

[0037] 4-Bromo-1,8 naphthalene dioic anhydride (2.77g, 10mmol, 1eq), β-alanine (1.34g, 15mmol, 1.5eq) were dissolved in 30mL of methanol, under nitrogen protection, heated at reflux at 75°C for 6h. The reaction was detected with a TCL plate. After the reaction was complete, it was cooled to room temperature, and solids were precipitated. The solid was filtered and dried to obtain a crude product with a yield of 68%. Directly cast the next reaction.

[0038] Synthesis of compound 1-2:

[0039]

[0040]Triphenylphosphine (2.0g, 7.54mmol, 1eq), 3-bromopropylamine hydrobromide (1.65g, 7.54mmol, 1eq) were dissolved in 20mL of acetonitrile, under nitrogen protection, and heated at reflux at 85°C for 16h. The reaction was detected with a TCL plate, and after the reaction was complete, it was cooled to room temperature. Add 20mL of petroleum ether, a solid precipitates out, the solid is filtered and washed with petroleum ether to ...

Embodiment 2

[0048] Compound Mito-H 2 S hydrogen sulfide fluorescent probe with Na 2 The change of fluorescence spectrum with the increase of S addition equivalent

[0049] Get the Mi prepared by Example 1 t o-H 2 The S fluorescent probe was dissolved in dimethyl sulfoxide (DMSO) to make a 1 mmol / L stock solution. Take 30μL from the stock solution and add it to a 5mL centrifuge tube, dilute to 3mL with a solution of PBS buffer solution (0.1mol / L, pH=7.4) and DMSO with a volume ratio of 2:1, and add different equivalents (0-30eq) The standard solution of sodium sulfide was used to measure its fluorescence properties with 440nm excitation light. Fluorescence spectra such as figure 2 shown. Depend on figure 2 It can be seen that with Na 2 The fluorescence increases gradually with the increase of S addition equivalent.

Embodiment 3

[0051] Compound Mito-H 2 Selectivity of S fluorescent probes to different molecules or ions

[0052] Take 30 μL from the fluorescent probe stock solution in Example 2 and add it to a 5 mL centrifuge tube, dilute it to 3 mL with a solution of PBS buffer solution (0.1 mol / L, pH=7.4) and DMSO at a volume ratio of 2:1, and prepare A series of solutions, add the competing molecule standard solution of equimolar quantity respectively, one of them adds the sodium sulfide standard solution of equimolar quantity, take 440nm as the fluorescence emission spectrum change of excitation light detection solution after 30min, by image 3 and Figure 4 As a result, it can be found that other ion pair compounds Mito-H 2 The fluorescence of S has almost no effect, and the addition of sodium sulfide solution makes the compound Mito-H 2 The fluorescence of S was significantly enhanced.

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Abstract

The invention discloses a hydrogen sulfide molecule fluorescent probe with mitochondrial targeting and a two-photon property as well as a preparation method and application of the hydrogen sulfide molecule fluorescent probe, and belongs to the technical field of analytical chemistry. A molecular formula of the probe is C35H29N5O3PBr, and a structural formula of the probe is shown in a formula I (shown in the description). The hydrogen sulfide molecule fluorescent probe prepared by the preparation method disclosed by the invention is simple in preparation and matured in synthetic route, can be used for quickly and accurately detecting hydrogen sulfide of mitochondria in cells, can perform fluorescence imaging, and is applied to sensing detection of hydrogen sulfide in a water environment and a biological cell system. Besides, the probe has the characteristics of good selectivity, high response speed, high capability of resisting jamming of other molecules, and the like.

Description

technical field [0001] The invention relates to a hydrogen sulfide molecular fluorescent probe with mitochondrial targeting and two-photon properties, a preparation method and application thereof, and belongs to the technical field of analytical chemistry. Background technique [0002] Hydrogen sulfide (H 2 S) is catalyzed by enzymes in organisms, and as a gas signal molecule in the human body, it plays an extremely important role in regulating human physiological functions. For example, regulating vascular tension, myocardial contraction, nerve conduction and insulin secretion, etc.; hydrogen sulfide can also effectively remove reactive oxygen species and reactive nitrogen species, such as hydrogen peroxide, superoxide anion, hypochlorous acid, peroxynitroso, etc.; Hydrogen sulfide can participate in the change of hemoglobin; participate in the reduction of nitroso compounds in the body; regulate the functions of various enzymes in the body. Experiments have shown that hy...

Claims

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Application Information

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IPC IPC(8): C07F9/576C09K11/06G01N21/64
CPCC07F9/5765C09K11/06C09K2211/1029G01N21/6428G01N21/6486
Inventor 林伟英任明光邓贝贝周凯
Owner UNIV OF JINAN
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