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Near-infrared fluorescent probe responding to peroxynitroso anions, and preparation method and application thereof

A technology of peroxynitroso and fluorescent probes, applied in the field of biochemistry, can solve the problems of short half-life and unreported fluorescent probes, and achieve the effects of small light damage, saving reaction costs, and mild reaction conditions

Active Publication Date: 2020-01-10
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, fluorescent probes that can be used to detect ONOO- in Parkinson's disease have not been reported so far
In order to meet the requirements of real-time monitoring and early diagnosis and treatment of PD, we are faced with the following challenges: 1) Due to the short half-life of ONOO-, the ultrafast response to ONOO- is Urgently needed; 2) The probe used in the in vivo detection of PD models should have a large Stokes shift and near-infrared emission wavelength to achieve high resolution and deep tissue penetration depth; 3) The probe should also have High specificity for ONOO-, unaffected by other reactive oxygen species / reactive nitrogen species in vivo

Method used

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  • Near-infrared fluorescent probe responding to peroxynitroso anions, and preparation method and application thereof
  • Near-infrared fluorescent probe responding to peroxynitroso anions, and preparation method and application thereof
  • Near-infrared fluorescent probe responding to peroxynitroso anions, and preparation method and application thereof

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preparation example Construction

[0044] A method for preparing a near-infrared fluorescent probe responsive to peroxynitrite anions, comprising the following steps:

[0045] (1) Put 2-R 1 -6-R 2- Add 4-nitrophenol to the first solvent, add sodium hydride and chloromethyl ether, and react at 20-40°C to obtain 1-(ethoxymethoxy)-2-R 1 -6-R 2 -4-nitrobenzene;

[0046] (2) 1-(ethoxymethoxy)-2-R 1 -6-R 2 -4-nitrobenzene was added to the second solvent, sodium sulfide nonahydrate was added, and the reaction was stirred at room temperature to obtain 4-(ethoxymethoxy)-3-R 1 -5-R 2 -aniline;

[0047] (3) 4-(ethoxymethoxy)-3-R 1 -5-R 2 - Add aniline to the third solvent, add sodium methoxide and paraformaldehyde, stir for 2 to 5 hours, then add sodium borohydride, heat up and react to obtain 4-(ethoxymethoxy)-3-R 1 -5-R 2 -N-Methylaniline;

[0048] (4) Add isophorone and malononitrile to the fourth solvent, add piperidine, acetic acid and acetic anhydride, stir at room temperature for 4-8 hours, then heat up...

Embodiment 1

[0056] Add 2-methoxy-4-nitrophenol (5g, 29.6mmol) into the reactor, dissolve it in anhydrous tetrahydrofuran at 0°C, add sodium hydride (88.8mmol) and stir at 0°C for 0.5h, then add dropwise Chloromethyl ether (59.2 mmol), continued stirring for 1 h, transferred to room temperature and stirred for 3 h. After the reaction is finished, quench sodium hydride with ice water, extract with ethyl acetate, wash with water, dry over anhydrous magnesium sulfate, spin dry the solvent under reduced pressure, and use a developer of dichloromethane / petroleum ether with a volume ratio of 2:3 for column layer Analysis and separation, the target product was obtained with a yield of 95%.

[0057] Compound 3 (2g, 8.8mmol) was added to the reactor, dissolved in ethanol, sodium sulfide nonahydrate (44mmol) was added in batches, and stirred at room temperature for 8h. After the reaction was completed, the solvent was spin-dried under reduced pressure, extracted with ethyl acetate, washed with wate...

Embodiment 2

[0066] Add 2-methyl-4-nitrophenol (4.5g, 29.6mmol) into the reactor, dissolve in anhydrous tetrahydrofuran at 0°C, add sodium hydride (88.8mmol), stir at 0°C for 0.5h, then drop Add chloromethyl ether (59.2 mmol), continue stirring for 1 h, transfer to room temperature and stir for 3 h. After the reaction is finished, quench sodium hydride with ice water, extract with ethyl acetate, wash with water, dry over anhydrous magnesium sulfate, spin dry the solvent under reduced pressure, and use a developer of dichloromethane / petroleum ether with a volume ratio of 2:3 for column layer Analysis and separation, the target product was obtained with a yield of 93%.

[0067] Compound 4 (1.85g, 8.8mmol) was added to the reactor, dissolved in ethanol, sodium sulfide nonahydrate (44mmol) was added in batches, and stirred at room temperature for 8h. After the reaction was completed, the solvent was spin-dried under reduced pressure, extracted with ethyl acetate, washed with water, dried over...

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Abstract

The invention discloses a near-infrared fluorescent probe responding to peroxynitroso anions, and a preparation method and an application thereof. The structure of the near-infrared fluorescent probeis shown in the description. The preparation method has the advantages of easiness in obtaining of raw materials, mild and easily-controlled reaction conditions, and saving of the reaction cost, and the obtained near-infrared fluorescent probe responding to peroxynitroso anions has a high selectivity and can be applied to a Parkinson's disease model.

Description

technical field [0001] The invention relates to a near-infrared fluorescent probe responsive to peroxynitrite anions, a preparation method and application thereof, and belongs to the technical field of biochemistry. Background technique [0002] Parkinson's disease (PD) is a common neurodegenerative disorder that seriously affects people's daily life. Loss of dopaminergic neurons in the substantia nigra of the brain is the main pathological feature of Parkinson's disease. However, the reason for the decrease in dopamine in the substantia nigra neurons has not yet been clarified. Accumulating evidence suggests that damage to dopaminergic neurons is associated with neurotoxicity from overproduced reactive oxygen / nitrogen species in neurons. [0003] Peroxynitrite anion (ONOO - ), composed of nitric oxide (NO) and superoxide anion (O 2 - ) produced, as an important active oxygen species, has high oxidation and nitrification ability. Low concentration of ONOO - Plays an i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C253/30C07C255/42G01N21/64A61K49/00
CPCC09K11/06C07C255/42G01N21/6428A61K49/0021C07C2601/16C09K2211/1007C09K2211/1014
Inventor 刘志鹏孙倩徐佳佳张承武李林
Owner NANJING FORESTRY UNIV
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