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Near-infrared molecular probe based on malondialdehyde response, preparation method and application thereof

A molecular probe and near-infrared technology, applied in the field of biosensors, can solve the problems of insufficient wavelength of MDA probes, probes limited to cell imaging, weakened effectiveness, etc., to improve short wavelength, poor penetration depth, and preparation speed Fast, achieve the effect of sensitivity

Active Publication Date: 2022-01-21
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Most existing methods for the detection of MDA, including 2-thiobarbituric acid (TBA) assays, mass spectrometry, and Raman spectroscopy, require destructive preparation of biological samples; on the other hand, some fluorescent Probes are able to detect MDA, but these fluorescent probes are limited to cellular imaging due to their short wavelength (<600nm), which greatly weakens their usefulness for practical application in vivo
At present, there are no MDA probes that can be used for in vivo imaging. The main reason is that the existing MDA probes have insufficient wavelengths, which limits their application in in vivo imaging.

Method used

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  • Near-infrared molecular probe based on malondialdehyde response, preparation method and application thereof
  • Near-infrared molecular probe based on malondialdehyde response, preparation method and application thereof
  • Near-infrared molecular probe based on malondialdehyde response, preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0062] The preparation of embodiment 1 CS-MDA molecular probe

[0063] like figure 2 Cyclohexanone (1 mL) was added dropwise to concentrated H 2 SO 4 (10 mL), then, 1 g of compound 1 (2-(4-(diethylamino)-2-hydroxybenzoyl)-6-nitrobenzoic acid) was added under stirring, the reaction mixture was stirred vigorously, and Heated at 90°C for 2 hours, then poured into ice water, and then the precipitated precipitate was filtered and washed quickly with water and petroleum ether to finally obtain compound 2(9-(2-carboxy-3-nitrophenyl)-6-( Diethylamino)-1,2,3,4-tetrahydroxanthine), a dark red viscous liquid, can be used in the next step without further purification;

[0064] Compound 2 and compound 3 ((E)-N-(2-(1-ethyl-3,3-dimethylindol-2-yl)vinyl)aniline) were dissolved in AcOH containing AcOH 2 In O, the molar ratio of compound 2 and compound 3 was 1:1, and then the reaction mixture was heated to 55 ° C for 60 minutes, and then the reaction system was extracted with saturated bri...

Embodiment 2

[0066] Example 2 Preparation of CS-A Molecular Probe

[0067] like figure 2 As shown, the synthesis method is the same as in Example 1, except that the compound 3 added is (E)-N-(2-(1-ethyl-3,3-dimethylbenzindol-2-yl)vinyl) aniline.

Embodiment 3

[0068] Example 3 Preparation of CS-B Molecular Probe

[0069] like figure 2 As shown, the synthesis method is the same as in Example 1, except that the added compound 3 is (E)-1-methyl-4-(2-(phenylamino)vinyl)quinoline-1-dimethyl.

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Abstract

The invention discloses a near-infrared molecular probe based on malonaldehyde response, a preparation method and application of the near-infrared molecular probe based on malonaldehyde response, and the near-infrared molecular probe based on malonaldehyde response takes xanthene-derived organic dye as a parent structure and contains an electron withdrawing group nitryl and a malonaldehyde reaction site benzoyl hydrazine group. The molecular conjugation degree is changed through the nucleophilic reaction of the hydrazine group of the o-nitrobenzoyl hydrazine and the MDA, so that the change of absorbance is caused, and the MDA detection is realized. The invention provides application of the molecular probe, a nano-probe NPs for MDA detection and imaging is prepared, the nano-probe takes near-infrared absorption CS-R and amphiphilic polymer DSPE-PEG2000 as main bodies, and a conjugated system of the CS-R in the nano-probe is changed through an addition reaction of MDA, so that fluorescence imaging is realized, detection and imaging with high sensitivity and good specificity on MDA are realized, and the problems of short wavelength and poor penetration depth of a conventional malondialdehyde probe are greatly improved.

Description

technical field [0001] The invention belongs to the technical field of biosensors, and relates to a molecular probe based on malondialdehyde (MDA) response, a preparation method and an application thereof, in particular to a molecular probe for detecting oxidative stress biomarker MDA, preparation thereof method and its application. Background technique [0002] The specific reaction of reactive oxygen species (ROS) with lipids is often referred to as "lipid peroxidation". Non-enzymatic lipid autooxidation or peroxidation of lipids is a free radical-driven chain reaction in which ROS trigger the oxidation of polyunsaturated fatty acids (PUFAs). In addition, the continuous massive oxidation and consumption of PUFAs may change the fluidity and structure of the membrane and increase the permeability of the membrane, eventually leading to the loss of membrane integrity. Malondialdehyde (MDA), 4-hydroxynonenal (4-HNE) and F2-isoprostane are widely accepted biomarkers of oxidati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C07D519/00C09K11/06G01N21/64A61K49/00
CPCC07D491/107C07D519/00C09K11/06G01N21/6428A61K49/0041C09K2211/1029C09K2211/1033C09K2211/1048Y02P20/55
Inventor 张晓兵马原宋国胜
Owner HUNAN UNIV
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