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Hypoxic microenvironment responsive fluorescent probe as well as preparation method and application thereof

A fluorescent probe and microenvironment technology, applied in the field of biochemical analysis, can solve the problem of low measurement efficiency and achieve the effects of low fluorescent background signal, low cytotoxicity, and easy preparation and purification

Inactive Publication Date: 2020-08-11
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

o 2 Needle electrode method, as a clinical detection of local O 2 The gold standard for concentration, local O can be accurately measured by inserting a fine needle electrode into the tumor site 2 Concentration changes in different pathological states, but this method is not efficient to measure and is invasive

Method used

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  • Hypoxic microenvironment responsive fluorescent probe as well as preparation method and application thereof
  • Hypoxic microenvironment responsive fluorescent probe as well as preparation method and application thereof
  • Hypoxic microenvironment responsive fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The preparation of fluorescent probe shown in formula I:

[0039] This embodiment provides the preparation method of the fluorescent probe shown in formula I, and its synthetic route is as follows:

[0040]

[0041] Specific steps are as follows:

[0042] Step 1: Take 1g of 3-hydroxy-N,N-diethylaniline and 0.9g of phthalic anhydride in 30mL of toluene solution, stir and reflux at 110°C for 8h, filter with suction to obtain a purple-red solid, dissolve it in ethanol Crystallized to obtain a purplish red solid, namely intermediate 1, its 1 H NMR and 13 C NMR spectrum see attached figure 1 and 2 .

[0043] Step 2: Take 40mL of concentrated sulfuric acid in a 125mL reaction bottle, and place it in an ice-salt bath for 5 minutes, weigh 0.6411g of 6-amino-1,2,3,4-tetrahydro-1-naphthone, and slowly add it to In sulfuric acid, stir for 5 minutes, then weigh 1.3924 g of intermediate 1 and add it to the above system, stir for 3 minutes, transfer to reflux reaction at 90 ...

Embodiment 2

[0046] The spectral properties of the fluorescent probe shown in formula I:

[0047] Dissolve the fluorescent probe of the present invention in methanol to make a 20 μM solution, and measure its absorption spectrum with a UV-visible spectrophotometer. The results are shown in the attached Figure 9 , its maximum absorption wavelength is located at 509nm; In addition, the fluorescent probe (10 μ M) of the present invention is reacted with reducing agent sodium dithionite (SDT) in PBS, and the fluorescence emission spectrum before and after the reaction is measured on a fluorescence spectrophotometer, the result See attached Figure 10 , the background fluorescence signal of the probe itself is low, but after reacting with sodium dithionite, there is a significant fluorescence enhancement at 615nm.

Embodiment 3

[0049]The fluorescent probe shown in formula I responds to the fluorescence of SDT:

[0050] Take 50 μL of the methanol solution (1 mmol / L) of the fluorescent probe shown in formula I in a 5 mL stoppered colorimetric tube, add an appropriate amount of PBS solution, and add different volumes of SDT solution (50 mmol / L, dissolved in double-distilled water), to The PBS solution was adjusted to 5 mL, and mixed evenly so that the concentration of the probe was 10 μM, and the concentration of SDT was respectively 0, 0.5, 1, 1.5, and 2 μM, and the fluorescence emission spectrum was measured after mixing. see attached results Figure 11 , the fluorescence at 615nm increases gradually with the concentration of SDT.

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Abstract

The invention relates to a hypoxic microenvironment responsive fluorescent probe and a preparation method and application thereof. The structure of the fluorescent probe is shown as a formula I, and the probe structure contains reducible azo groups. Cell experiments prove that the fluorescent probe provided by the invention can react with azo reductase overexpressed by cells under a hypoxic condition to generate remarkable fluorescence enhancement, so that fluorescence response on the hypoxic microenvironment is realized. Meanwhile, the fluorescent probe provided by the invention also has theadvantages of low background fluorescence signal, good biocompatibility, simple structure, definite composition, easiness in preparation and purification and the like, so that the fluorescent probe has a good application prospect in the aspects of early diagnosis of tumors, preoperative evaluation, intraoperative navigation and the like.

Description

technical field [0001] The invention relates to a fluorescent probe responding to hypoxic microenvironment and its preparation method and application, belonging to the technical field of biochemical analysis. Background technique [0002] When the tumor grows rapidly, the oxygen demand of the tumor cells will increase, and the internal blood supply of the tumor is insufficient, which makes it difficult to meet the oxygen demand for tumor cell proliferation and metabolism, which eventually leads to the obvious hypoxic state of some intratumoral microenvironments (3- 0.1% O 2 ). Hypoxia is a common feature of all solid tumors, and most tumors have a certain internal hypoxic microenvironment during their growth. At present, hypoxic status has become an important indicator for evaluating the degree of tumor progression clinically. Therefore, the development of a convenient, sensitive, and specific hypoxic microenvironment detection and even imaging technology will help clinic...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D311/78A61K49/00
CPCC09K11/06C07D311/78A61K49/0021C09K2211/1088
Inventor 李洪玉袁泽利丁尚丽
Owner ZUNYI MEDICAL UNIVERSITY
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