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Fluorescent probe and preparation method thereof, and application in detecting superoxide anions

A technology of fluorescent probes and synthesis methods, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effects of good chemical stability and photophysical stability, short response time, and simple synthesis steps

Inactive Publication Date: 2015-02-25
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current detection of O in cells and in vivo 2 ˙- The TP fluorescent probe has not been reported

Method used

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  • Fluorescent probe and preparation method thereof, and application in detecting superoxide anions
  • Fluorescent probe and preparation method thereof, and application in detecting superoxide anions
  • Fluorescent probe and preparation method thereof, and application in detecting superoxide anions

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Embodiment 1: the synthesis of probe I

[0030] Proceed as follows:

[0031] in N 2 Under protection, melamine (1.5 mmol) and caffeic acid (3.0 mmol) were dissolved in DMF and CH 2 Cl 2 The mixture (DMF 1.2mL, CH 2 Cl 2 6.0 mL), HOBT (0.636 g, 3.0 mmol) and EDC.HCL (0.576 g, 3.0 mmol) were added, and stirred at room temperature overnight (12 h). After concentrated by rotary evaporation to obtain the crude product, the product is separated and purified by a silica gel thin-layer chromatography plate. The preparation method of the silica gel thin-layer chromatography plate is: put 30g silica gel GF254 in a beaker, add 80ml of 0.5% sodium carboxymethyl cellulose aqueous solution, Make a paste. Pour the prepared slurry onto a clean and dry 20×20 glass slide, and dry it at room temperature for use; the eluent is a mixture of ethyl acetate-cyclohexane, wherein the volume ratio of ethyl acetate:cyclohexane It is 5:1. Finally, a light yellow product was obtained, namel...

Embodiment 2

[0034] Embodiment 2: the synthesis of fluorescent probe

[0035] in N 2 Under protection, melamine (1.0 mmol) and caffeic acid (3.5 mmol) were dissolved in DMF and CH 2 Cl 2 The mixture (DMF 2.0mL, CH 2 Cl 2 6.0 mL), HOBT (0.636 g, 3.0 mmol) and EDC.HCL (0.576 g, 3.0 mmol) were added, and stirred at room temperature overnight (12 h). After concentrated by rotary evaporation to obtain the crude product, the product is separated and purified by silica gel thin-layer chromatography. The preparation method of the silica gel thin-layer chromatography is the same as in Example 1; the eluent is ethyl acetate-cyclohexane mixed solution, wherein ethyl acetate : The volume ratio of cyclohexane is 4:1. Finally, a light yellow product is obtained, which is a fluorescent probe.

Embodiment 3

[0036] Embodiment 3: the synthesis of fluorescent probe

[0037] in N 2 Under protection, melamine (1.0 mmol) and caffeic acid (2.0 mmol) were dissolved in DMF and CH 2 Cl 2 The mixture (DMF 1.2mL, CH 2 Cl 2 5.0 mL), HOBT (3.5 mmol) and EDC.HCL (3.5 mmol) were added, and stirred at room temperature overnight (12 h). After concentrated by rotary evaporation to obtain the crude product, the product is separated and purified by silica gel thin-layer chromatography. The preparation method of the silica gel thin-layer chromatography is the same as in Example 1; the eluent is ethyl acetate-cyclohexane mixed solution, wherein ethyl acetate : The volume ratio of cyclohexane is 2:1. Finally, a light yellow product is obtained, which is a fluorescent probe.

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Abstract

The invention discloses a fluorescent probe and a preparation method thereof, and application in detecting superoxide anions. The structural formula of the fluorescent probe is disclosed in the specification. The preparation method comprises the following steps: in an inert gas protective atmosphere, dissolving melamine and caffeic acid in a DMF (N,N-dimethylformamide) and CH2Cl2 mixed solution, adding HOBT (N-hydroxybenzotriazole) and EDC.HCL (1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride), and stirring to react at room temperature for 8-16 hours; after the reaction, concentrating to remove the solvent, thereby obtaining the fluorescent probe crude product; and separating and purifying the fluorescent probe crude product with a silica gel thin-layer chromatographic sheet to obtain the fluorescent probe pure product. The fluorescent probe has the advantages of novel structure, high sensitivity, high selectivity and high light stability.

Description

technical field [0001] The invention relates to a fluorescent probe, a preparation method thereof, and an application in detecting superoxide anions, belonging to the technical field of biological detection. Background technique [0002] A large amount of evidence shows that reactive oxygen species (ROS) are closely related to the occurrence and development of many diseases, such as degenerative diseases, ischemia and perfusion injury during surgery, and so on. Due to the superoxide anion radical (O 2 ˙- ) are precursors of other ROS (including hydrogen peroxide, peroxynitrosyl anion, etc.), thus revealing that O 2 ˙- The relationship between the level and disease is particularly important. [0003] High sensitivity is a clear advantage of single-photon (OP) fluorescence imaging, so OP fluorescence microscopy was used to visualize intracellular O 2 ˙- level is an effective detection O 2 ˙- Methods. However, the detection of intracellular O 2 ˙- There are still man...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D251/70G01N21/64
Inventor 唐波李平张雯肖海滨
Owner SHANDONG NORMAL UNIV
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