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Near-infrared fluorescent probe for detecting biological mercaptan and preparation method thereof

A fluorescent probe, biological thiol technology, applied in the field of analysis and detection, can solve the problems of short emission wavelength, false positive signal, biological sample interference, etc., and achieve the effect of good selectivity and anti-interference ability

Active Publication Date: 2021-09-17
NORTHWEST UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Generally, fluorescent probe molecules have short emission wavelengths, which are usually interfered by the background of biological samples, resulting in false positive signals

Method used

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  • Near-infrared fluorescent probe for detecting biological mercaptan and preparation method thereof
  • Near-infrared fluorescent probe for detecting biological mercaptan and preparation method thereof
  • Near-infrared fluorescent probe for detecting biological mercaptan and preparation method thereof

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Embodiment

[0071] A kind of preparation method of the near-infrared fluorescent probe of the present invention detects biological thiol, specifically implements according to the following steps:

[0072] The synthetic route is as follows:

[0073]

[0074] Step 1, using isophorone and malononitrile as raw materials, synthesize the following formula (II) intermediate TEM through Knoevenagel condensation reaction;

[0075]

[0076] Specifically: under argon protection, add 0.2g acetic anhydride, 0.4mL glacial acetic acid and 1.8mL piperidine to a 250mL three-necked flask, then add 16.5mL (110mmol) isophorone, 6.6g (110mmol) malononitrile And it was dissolved in 55mL N,N-dimethylformamide, and stirred at 120°C for 6h. Cool to room temperature after the reaction. The reaction mixture solution was poured into ice water, a brown solid was precipitated, dried and purified by column chromatography, the eluent was petroleum ether:dichloromethane=1:1 (v:v), and a yellow solid was obtained;...

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Abstract

The invention discloses a near-infrared fluorescent probe for detecting biological mercaptan and a preparation method thereof. The preparation method comprises the following steps: firstly, taking isophorone and malononitrile as raw materials, and synthesizing TEM through Knoevenagel condensation reaction; taking 2, 4-dihydroxy benzaldehyde and sodium propionate as raw materials, and synthesizing 7-hydroxy-3-methyl-coumarin through cyclization and hydrolysis reaction; then, taking 7-hydroxy-3-methyl-coumarin and N-bromosuccinimide as raw materials, and synthesizing 7-hydroxy-3-formyl-coumarin through halogenation and hydrolysis reaction; then, taking the TEM and the 7-hydroxy-3-formyl-coumarin as raw materials, and synthesizing an intermediate TX-OH through Knoevenagel condensation reaction; and finally, synthesizing the fluorescent probe by taking TX-OH and acryloyl chloride as raw materials. The fluorescent probe has good selectivity on mercaptan and is not interfered by other amino acids. The fluorescent probe can be used for detecting biological mercaptan in a biological sample and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of analysis and detection, and in particular relates to a near-infrared fluorescent probe for detecting biological thiols, and also relates to a preparation method of the near-infrared fluorescent probe. Background technique [0002] Cysteine ​​(Cys), homocysteine ​​(Hcy) and reduced glutathione (GSH) are collectively referred to as biothiols. As a small molecular sulfhydryl species that exists in large quantities in organisms, it plays a very important role in balancing the redox process and mitigating the damage caused by free radicals and toxins. Studies have shown that fluctuations in biothiol levels are highly correlated with many human diseases, such as heart disease, poor growth, skin damage, liver damage, osteoporosis, and Alzheimer's disease. Therefore, the detection of Cys / Hcy / GSH in vivo will have a positive and meaningful impact on understanding the occurrence and development of diseases. [00...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D311/18G01N21/64
CPCC09K11/06C07D311/18G01N21/6428C09K2211/1007C09K2211/1088
Inventor 刘萍凤旭凯李剑利厍梦尧陈娇
Owner NORTHWEST UNIV
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