Preparation method of fluorescent probe for distinguishing peroxynitrite and hypochlorite on basis of xanthene and coumarin

A nitroso peroxide, fluorescent probe technology, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, fluorescence/phosphorescence, etc., can solve problems such as insufficient discrimination and achieve fast response time , high sensitivity, novel structure effect

Active Publication Date: 2019-07-05
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of this, the purpose of the present invention is to address the deficiencies in the prior art, and through the design of the molecular structure, it provides a kind of water-soluble, quick response, good selectivity, high sensitivity recognition of peroxynitroso and hypochlorine The fluorescent probe molecule of acid radical solves the problem that the current single probe molecule can only detect one of peroxynitrite and hypochlorite, and the discrimination is not enough

Method used

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  • Preparation method of fluorescent probe for distinguishing peroxynitrite and hypochlorite on basis of xanthene and coumarin
  • Preparation method of fluorescent probe for distinguishing peroxynitrite and hypochlorite on basis of xanthene and coumarin
  • Preparation method of fluorescent probe for distinguishing peroxynitrite and hypochlorite on basis of xanthene and coumarin

Examples

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Embodiment 1

[0045] Embodiment 1: the synthesis of fluorescent probe Dual-NC

[0046] Dissolve 10mmol of compound a and 10mmol of compound b in 50mL of trifluoroacetic acid, heat and reflux at 80°C for 18 hours, distill off trifluoroacetic acid under reduced pressure, add 100mL of ice water, adjust the pH to 12 with saturated potassium carbonate, and dichloromethane Extraction, the organic layer was dried with anhydrous sodium sulfate, the solvent was spin-dried under reduced pressure, and separated with a 200-400 mesh silica gel column, the eluent was dichloromethane:methanol=10:1 (volume ratio), and red solid compound 1 was obtained;

[0047] Dissolve 5mmol of compound 1 and 5mmol of fluorenylmethoxycarbonyl chloride in 50mL of anhydrous acetonitrile, stir until dissolved, add 10mmol of sodium bicarbonate, and react for 12h under the protection of argon. After the reaction is complete, filter the filtrate to remove the solvent under reduced pressure, and use Extracted with ethyl acetate,...

Embodiment 2

[0060] Embodiment 2: the synthesis of fluorescent probe Dual-NC

[0061] Dissolve 10mmol of compound a and 10mmol of compound b in 50mL of trifluoroacetic acid, heat and reflux at 80°C for 18 hours, distill off trifluoroacetic acid under reduced pressure, add 100mL of ice water, adjust the pH to 12 with saturated potassium carbonate, and dichloromethane Extraction, the organic layer was dried with anhydrous sodium sulfate, the solvent was spin-dried under reduced pressure, and separated with a 200-400 mesh silica gel column, the eluent was dichloromethane:methanol=10:1 (volume ratio), and red solid compound 1 was obtained;

[0062] Dissolve 5mmol of compound 1 and 15mmol of fluorenylmethoxycarbonyl chloride in 50mL of anhydrous acetonitrile, stir until dissolved, add 10mmol of sodium bicarbonate, and react for 18h under the protection of argon. After the reaction is complete, filter the filtrate to remove the solvent under reduced pressure, and use Extracted with ethyl acetate...

Embodiment 3

[0068] Embodiment 3: the synthesis of fluorescent probe Dual-NC

[0069] Dissolve 10mmol of compound a and 10mmol of compound b in 50mL of trifluoroacetic acid, heat and reflux at 80°C for 18 hours, distill off trifluoroacetic acid under reduced pressure, add 100mL of ice water, adjust the pH to 12 with saturated potassium carbonate, and dichloromethane Extraction, the organic layer was dried with anhydrous sodium sulfate, the solvent was spin-dried under reduced pressure, and separated with a 200-400 mesh silica gel column, the eluent was dichloromethane:methanol=10:1 (volume ratio), and red solid compound 1 was obtained;

[0070] Dissolve 5mmol of compound 1 and 25mmol of fluorenylmethoxycarbonyl chloride in 100mL of anhydrous acetonitrile, stir until dissolved, add 10mmol of sodium bicarbonate, and react for 24h under the protection of argon. After the reaction is complete, filter, and remove the solvent from the filtrate under reduced pressure. Extracted with ethyl acetate...

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Abstract

The invention discloses a preparation method of a fluorescent probe for distinguishing peroxynitrite and hypochlorite on the basis of xanthene and coumarin. According to the method, a xanthene and coumarin dimer is adopted as a fluorescent parent, diphenylphosphinyl chloride which specifically reacts with the peroxynitrite is introduced onto a coumarin parent, and a sulfur-containing five-memberedring which specifically reacts with the hypochlorite is introduced onto the xanthan; different kinds of fluorescence are emitted at different excitation wavelengths when the peroxynitrite and the hypochlorite are present alone or in combination. The fluorescent probe can realize high-selectivity and high-sensitivity detection of the peroxynitrite and hypochlorite and have a broad application prospect in the field of detection of active small molecules.

Description

technical field [0001] The invention relates to the field of organic small molecule fluorescent probes, in particular to a preparation method for distinguishing peroxynitroso and hypochlorite fluorescent probes based on xanthene and coumarin. Background technique [0002] Both peroxynitroso and hypochlorite are active oxygen species, and they are important biologically active substances that exist widely in living organisms. Peroxynitroso (ONOO - ) is a short-lived active species with strong oxidative properties, which is mainly produced by the reaction of nitric oxide (NO) and superoxide anion in the living body. Hypochlorite (ClO - ) In the living body, under the catalysis of myeloperoxidase, hydrogen peroxide reacts with intracellular chloride ions to generate hypochlorite ions. Medical research has shown that abnormal physiological concentrations may cause diseases. When the living body undergoes ischemia-reperfusion, inflammation in the body, drug liver damage, tumor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F9/6561G01N21/64
CPCC09K11/06C07F9/6561G01N21/643C09K2211/1007C09K2211/1014C09K2211/1044C09K2211/1088C09K2211/1092
Inventor 叶勇唐军朱消非竹建名赵方方
Owner ZHENGZHOU UNIV
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