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A Ratiometric Fluorescent Probe for Detecting Hydrogen Peroxide and Its Application

A fluorescent probe and hydrogen peroxide technology, applied in the field of analytical chemistry, to achieve the effects of easy preparation, convenient use, and simple synthesis process

Inactive Publication Date: 2017-04-12
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the search found that there are few reports on ratiometric fluorescent probes for the detection of hydrogen peroxide and their applications.

Method used

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  • A Ratiometric Fluorescent Probe for Detecting Hydrogen Peroxide and Its Application
  • A Ratiometric Fluorescent Probe for Detecting Hydrogen Peroxide and Its Application
  • A Ratiometric Fluorescent Probe for Detecting Hydrogen Peroxide and Its Application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Preparation of 2-(3-(7-diethylamino)coumarin)-4-(2-benzoic acid)-7-diethylamino-benzopyran perchlorate:

[0028] Dissolve m-diethylaminophenol (1.65g, 10mmol) and phthalic anhydride (1.48g, 10mmol) in 20ml of toluene, reflux for 6 hours under nitrogen protection, add 30ml of 36% NaOH aqueous solution after cooling at 60°C, Continue the reaction for 2 hours, then cool at room temperature, adjust the pH to 5 with 1N HCl, filter, dry, and recrystallize to obtain light gray intermediate 1, which is: 2-(4-diethylamino-o-hydroxyphenyl) benzoic acid.

[0029] Add intermediate 1 (1.56g, 5mmol) and 3-acetyl-7-ethylenediamino-coumarin (1.29g, 5mmol) to 6ml of concentrated sulfuric acid, react at 90°C for 12 hours, and cool to room temperature Finally, pour it into ice water, add 70% perchloric acid, filter, and purify the solid by column chromatography to obtain a dark blue product, which is: 2-(3-(7-diethylamino) Coumarin)-4-(2-benzoic acid)-7-diethylamino-benzopyra...

Embodiment 2

[0032] Example 2: 2-(3-(7-diethylamino) coumarin)-4-(2-benzoic acid)-7-diethylamino-benzopyran perchlorate to different substances selective identification

[0033] Prepare ten 5 mL portions of 5 mM 2-(3-(7-diethylamino)coumarin)-4-(2-benzoic acid)-7-diethylamino-benzopyran perchlorate in PBS solution (containing 5% methanol), and then sequentially added 50 μL of hydrogen peroxide, sodium hypochlorite, nitric oxide, cysteine, hydroxyl radicals, di-tert-butyl peroxide, Di-tert-butanol peroxide, glutathione, vitamin C and sodium nitrate in PBS. Fluorescence detection (λ Ex =380nm); Calculate the fluorescence intensity ratio I at 471nm and 693nm in each system 471 / I 693 , see the result image 3 . Wherein it is shown that the 2-(3-(7-diethylamino)coumarin)-4-(2-benzoic acid)-7-diethylamino-benzopyran perchlorate is effective against peroxidation Hydrogen selectivity is significantly enhanced.

Embodiment 3

[0034] Example 3: 2-(3-(7-diethylamino)coumarin)-4-(2-benzoic acid)-7-diethylamino-benzopyran perchlorate and hydrogen peroxide linear relationship

[0035] Prepare 1 mL of PBS solution system of hydrogen peroxide with a gradient of 0-5 mM concentration, and then add 9 mL of probe PBS solution (containing 5% methanol) with a concentration of 50 μM for fluorescence detection (λ Ex =380nm,λ Em =471nm and 693nm), calculate the fluorescence intensity in each system, and the fluorescence intensity ratio I471 / I693 at 471nm and 693nm, establish the standard curve of fluorescence intensity and hydrogen peroxide concentration, the standard curve is shown in Figure 4 .

[0036] Fluorescence probe 2-(3-(7-diethylamino)coumarin)-4-(2-benzoic acid)-7-diethylamino-benzopyran perchlorate of the present invention The lower limit of detection was 0.079 μM (S / N=3).

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Abstract

The invention discloses a ratio-dependent fluorescent probe for detecting hydrogen peroxide. The ratio-dependent fluorescent probe is an anthocyanin-like derivative, has the chemical structure as shown in the formula (1) and is particularly 2-(3-(7-diethylamino) coumarin)-4-(2-phenmethyl)-7-diethylamino-benzopyran perchlorate. The probe disclosed by the invention is cheap and available, convenient to use, capable of specifically reacting together with hydrogen peroxide to generate a coumarin derivative with stronger fluorescence emission capacity, free of interference from other related oxides in the process of detecting hydrogen peroxide, favorable in hydrogen peroxide selectivity and capable of accurately detecting hydrogen peroxide in living cells.

Description

technical field [0001] The invention relates to a ratio-type fluorescent probe for detecting hydrogen peroxide and an application thereof, belonging to the technical field of analytical chemistry. Background technique [0002] Reactive oxygen species (ROS) is a general term for oxygen-containing free radicals and oxygen-containing non-free radicals in organisms, and plays a very important role in many physiological and pathological processes. Physiological and pathological processes such as oxidative stress and inflammation in organisms usually produce various reactive oxygen species through enzymatic and non-enzymatic reactions. Modern biomedical research shows that active oxygen produced in the body is closely related to the occurrence and development of many diseases and the aging process of the body. As an important reactive oxygen species, hydrogen peroxide (H 2 o 2 ) as an important signaling molecule, participates in various signal transduction processes, and is al...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/16G01N21/64C09K11/06
Inventor 林伟英董宝利宋学真唐永和
Owner UNIV OF JINAN
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