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A Hydrogen Peroxide Enhanced Fluorescent Probe Based on Rhodamine Derivatives

A fluorescent probe and hydrogen peroxide technology, applied in the field of analytical chemistry, can solve the problems of short excitation wavelength and unsuitability for small animals, and achieve the effects of rapid detection, simple and easy synthesis process, and easy preparation

Inactive Publication Date: 2019-03-15
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, most of the developed fluorescent probes for hydrogen peroxide focus on blue or green fluorophores, but this method uses a short excitation wavelength, which is not suitable for small animal live imaging, so it has certain limitations

Method used

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  • A Hydrogen Peroxide Enhanced Fluorescent Probe Based on Rhodamine Derivatives
  • A Hydrogen Peroxide Enhanced Fluorescent Probe Based on Rhodamine Derivatives
  • A Hydrogen Peroxide Enhanced Fluorescent Probe Based on Rhodamine Derivatives

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Preparation of fluorescent probes:

[0029] Dissolve intermediate 1 (1 mmol), N,N-bis(trifluoromethanesulfonyl)aniline (1 mmol) and N,N-diisopropylethylamine (2 mmol) in 5 ml DMF and react 6 at room temperature After 1 hour, 5 ml of water was added, extracted with 5 ml of ethyl acetate, and the oil phase was vacuum-dried to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate:petroleum ether = 1:5) to obtain the pure intermediate 2 (yield 73%). Intermediate 2 (1 mmol), bis-linked pinacol borate (1 mmol), 1,1-bis(diphenylphosphino)ferrocenedichloropalladium dichloromethane complex (0.2 mmol) and potassium acetate (1.5 mmol) were dissolved in 10 ml of toluene, and refluxed for 6 h under nitrogen protection. After the reaction, the solvent was removed in vacuo to obtain a crude product. The crude product was purified by column chromatography (eluent: ethyl acetate:petroleum ether = 1:4) to obtain a pure probe (yield 69%)...

Embodiment 2

[0031] Selective Identification of Different Substances by Fluorescent Probes

[0032] Prepare 10 parts of 5 mL of 5 μM fluorescent probe PBS solution (containing 5% methanol) in advance, and then add 50 μL of 100 μM hydrogen peroxide, sodium hypochlorite, nitric oxide, semi Cystine, hydroxyl radical, di-tert-butyl peroxide, di-tert-butanol peroxide, glutathione, vitamin C and sodium nitrate in PBS. Perform fluorescence detection (λ Ex = 580 nm); calculate the fluorescence intensity I at 638 nm in each system 638 , see the result image 3 . It shows that the fluorescent probe has better selectivity to hydrogen peroxide.

Embodiment 3

[0034] Linear relationship between fluorescent probe and hydrogen peroxide

[0035] Prepare 1 mL of PBS solution system of hydrogen peroxide with a gradient concentration, and then add 9 mL of probe PBS solution (containing 5% methanol) with a concentration of 50 μM to perform fluorescence detection (λ Ex = 580 nm, λ Em = 638 nm), calculate the fluorescence intensity in each system, and the fluorescence intensity I at 638 nm 638 , to establish a standard curve of fluorescence intensity and hydrogen peroxide concentration, the standard curve is shown in Figure 4 . The detection limit of the fluorescent probe of the present invention is 0.071 μM (S / N = 3).

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Abstract

The invention discloses a hydrogen-peroxide-enhanced fluorescent probe based on Rhodamine derivatives, having a chemical structural formula shown as in formula (1) which is shown the description. The hydrogen-peroxide-enhanced fluorescent probe based on Rhodamine derivatives is low in price, easy to obtain and convenient to use, is capable of specifically reacting with hydrogen peroxide to generate a Rhodamine derivative having greater fluorescence emitting capacity, is never disturbed by other related oxides during the detection of hydrogen peroxide, has good selectivity for hydrogen peroxide, and can detect hydrogen peroxide in live cells and live animals accurately.

Description

technical field [0001] The invention relates to a hydrogen peroxide fluorescent probe based on rhodamine derivatives, which belongs to the technical field of analytical chemistry. Background technique [0002] Reactive oxygen species (ROS) are ubiquitous in living organisms and are a general term for oxygen-containing free radicals and oxygen-containing non-free radicals, which play an important role in many physiological and pathological processes. ROS are usually produced by enzymatic and non-enzymatic reactions in physiological and pathological processes such as oxidative stress and inflammation in organisms. hydrogen peroxide (H 2 o 2 ), as an important reactive oxygen species, is an important signaling molecule, which is widely involved in various signal transduction processes in biological systems, and is also a marker of oxidative stress and other related diseases. The production of hydrogen peroxide in organisms is related to the activation of leukocyte oxidase by...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06C09K2211/1088C09K2211/1096G01N21/6486
Inventor 林伟英董宝利宋学真孔秀琪王超张楠
Owner UNIV OF JINAN
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