Near-infrared frequency up-conversion fluorescence molecular probe, preparation method and application

A fluorescent molecular probe, near-infrared technology, used in fluorescence/phosphorescence, chemical instruments and methods, material analysis by optical means, etc., can solve the problems of autofluorescence interference, difficult fluorescence, etc., achieve small biological toxicity, reduce interference , good response effect

Active Publication Date: 2020-12-15
CHINA PHARM UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, most of the fluorescent probes for detecting glutathione S-transferase are short-wavelength, and most of them are down-conversion luminescent methods. The fluorescence produced by this probe after responding to glutathione S-transferase is difficult Appears through the living body, and there is a lot of interference from autofluorescence
At present, there are many ways for fluorescent probes to respond to glutathione S-transferase. Using 3,4-dinitrobenzoyl group as the recognition group, the frequency up-conversion fluorescent molecular probe detects glutathione S -Transferase can avoid the interference of autofluorescence in vivo and complex biological samples, which increases the practicability of the probe, but how to obtain molecular probes with better performance still needs further research

Method used

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  • Near-infrared frequency up-conversion fluorescence molecular probe, preparation method and application
  • Near-infrared frequency up-conversion fluorescence molecular probe, preparation method and application
  • Near-infrared frequency up-conversion fluorescence molecular probe, preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Preparation of fluorescent probes for detection of glutathione S-transferase near-infrared frequency upconversion fluorescent probes:

[0035] Add a certain amount of compound 1 into a round bottom flask, slowly add dichloromethane under ice bath and nitrogen protection, stir, and slowly add triethylamine under ice bath and nitrogen protection, after stirring for 5 minutes, place in ice 3,4-dinitrobenzoyl chloride was slowly added under the condition of a bath and nitrogen protection. After stirring for 5 minutes, the ice bath was removed and the mixture was returned to room temperature. After reacting for a period of time, when a certain amount of triethylamine salt is precipitated in the solution, pour the reaction solution in the bottle into a separatory funnel, add distilled water, and mix thoroughly, then add dichloromethane, continue to mix and shake for 2 minutes, and let stand to separate the liquid funnel, after the solution in the separatory funnel was separa...

Embodiment 2

[0040] The difference between this example and this example 1 is that the ratio of compound 1 dichloromethane to triethylamine is 1mmol: 8mL: 0.3mL.

[0041] The molar ratio of compound 1 to 3,4-dinitrobenzoyl chloride is 1:5.

Embodiment 3

[0043] The difference between this example and this example 1 is that the ratio of compound 1 dichloromethane to triethylamine is 1mmol: 6mL: 0.2mL.

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Abstract

The invention discloses a near-infrared frequency up-conversion fluorescence molecular probe as well as a preparation method and application thereof. The molecular formula of the probe is C43H40N5O6 +, and the structural formula is shown in the specification. The glutathione S-transferase detection probe has excellent selectivity and good response effect, and the near-infrared frequency up-conversion fluorescence probe has strong organism penetrability in a near-infrared region in absorption and emission, and has good cell imaging effect.

Description

technical field [0001] The invention relates to a preparation method and use of a molecular probe, in particular to a near-infrared frequency up-conversion fluorescent molecular probe, a preparation method and a use. Background technique [0002] Glutathione S-transferases (EC 2.5.1.18) are a class of phase II detoxification enzymes that play an important role in reducing toxicity and promoting urinary excretion by catalyzing the conjugation of glutathione to reactive metabolites. At the same time, it is highly expressed in a variety of tumor tissues and has a direct relationship with tumor drug resistance. The level of glutathione S-transferase in the blood can usually diagnose liver diseases, such as liver damage, liver cancer, etc. Therefore, accurate detection of glutathione S-transferase activity in complex biological samples and in vivo plays a huge role in the treatment of diseases, the discovery and evaluation of glutathione S-transferase inhibitors and the rapid di...

Claims

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Application Information

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IPC IPC(8): C07D405/06C09K11/06G01N21/64
CPCC07D405/06C09K11/06G01N21/6428G01N21/6458G01N21/6486C09K2211/1029C09K2211/1088
Inventor 刘熠朱文超李婧妍
Owner CHINA PHARM UNIV
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