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Fluorescence angiography material and preparation method and application thereof

A fluorescent dye and fluorescence technology, applied in the field of fluorescent materials, can solve the problems of slow metabolism of fluorescein, short imaging time of fluorescein, and large toxic and side effects of fluorescein, and achieve high biocompatibility, high water solubility, and low biological toxic effects

Inactive Publication Date: 2017-08-08
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of the above-mentioned deficiencies in the prior art, the purpose of the present invention is to provide a fluorescent imaging material and its preparation method and application, aiming to solve the problems of the existing fluorescein staining method, such as the large toxic and side effects of fluorescein on the human body and the metabolism of fluorescein in the body. The problem of relatively slow speed and short imaging time of fluorescein method

Method used

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  • Fluorescence angiography material and preparation method and application thereof
  • Fluorescence angiography material and preparation method and application thereof
  • Fluorescence angiography material and preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0053] The preparation steps of flavonoid dye FL341 (structural formula is as follows):

[0054] Add 50 mmoles of 1-acetyl-2-hydroxyl-4,5-dimethylolbenzene and 50 mmoles of p-dimethylaminobenzaldehyde into a reaction flask containing 200 ml of ethanol, and place the reaction flask on ice Cool in a water bath, add 50 ml of 20%wt sodium hydroxide solution dropwise, stir for 10 hours, pour into 500 ml of ice water, and neutralize with dilute hydrochloric acid with a concentration of 3 mol / L. After the neutralization is completed, the reaction solution is placed in a refrigerator to stand overnight, and then the obtained precipitate is filtered and dried to obtain a crude chalcone product. Get 10 millimoles of chalcone crude product and dissolve it in 10 milliliters of tetrahydrofuran, then add 50 milliliters of ethanol solution, and dropwise add 10 milliliters of potassium hydroxide solution with a mass fraction of 20%, after the addition is completed, the reaction solution is pl...

Embodiment 2

[0057] The preparation steps of flavonoid dye FL339 are as follows:

[0058] Add 50 millimoles of 1-acetyl-2-hydroxyl-6-hydroxymethylbenzene and 50 millimoles of p-diethylaminobenzaldehyde into a reaction flask containing 250 milliliters of ethanol, and place the reaction flask in an ice-water bath Cool, add 40 ml of 20%wt sodium hydroxide solution dropwise, stir for 12 hours, pour into 400 ml of ice water, and neutralize with a concentration of 3 mol / liter of dilute hydrochloric acid. After the neutralization, the reaction solution was placed in the refrigerator to stand overnight, and the precipitate was filtered and dried to obtain the crude chalcone. Get 10 millimoles of chalcone crude product and dissolve it in 10 milliliters of tetrahydrofuran, then add 40 milliliters of ethanol solution, and dropwise add 15 milliliters of potassium hydroxide solution with a mass fraction of 20%, after the addition is completed, the reaction solution is washed with ice Cool in a water b...

Embodiment 3

[0061] The preparation steps of the FL341-HSA complex fluorescence contrast material are as follows:

[0062] Dissolve 3.41 mg of flavonoid dye FL341 in 10 ml of ethanol, stir evenly until completely dissolved, and prepare 10 -3 mol / liter FL341 flavonoid fluorescent dye mother solution; 100 mg of human serum albumin (HSA) was dissolved in 10 ml of phosphate buffer solution (pH=7.4), heated at 37 degrees Celsius, stirred evenly until completely dissolved, and prepared into 10 mg / ml of HSA protein solution mother solution; slowly drop 100 microliters of FL341 flavonoid fluorescent dye mother solution into 10 ml of HSA protein solution mother solution, and stir evenly for 20 minutes until the solution is more transparent, and the prepared FL341-HSA complex Fluorescence contrast material.

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Abstract

The invention provides a fluorescence angiography material and a preparation method and application thereof. The fluorescence angiography material is prepared by combining flavonoid fluorescent dye having a high fluorescence quantum yield and a hydrophobic cavity in a high-biocompatibility protein, wherein a structural formula of the flavonoid fluorescent dye is shown in the description; R1, R2, R3, R4, R5 and R6 are different substituents; R1, R2, R3 and R4 are H, hydroxy(-OH), hydroxymethyl(-OCH3) or dimethylamino(-N(CH3)2); R5 and R6 are methyl(-CH3), ethyl(-CH2CH3), butyl(-CH2CH2CH2CH3) or hydroxybutyl(-CH2CH2CH2CH2OH). The fluorescence angiography material has the characteristics of low biological toxicity, high fluorescence quantum yield, high fluorescent stability, high water solubility and high biocompatibility.

Description

technical field [0001] The invention relates to the field of fluorescent materials, in particular to a fluorescent contrast material and its preparation method and application. Background technique [0002] Diseases related to blood vessels have been very common for a long time. Taking fundus blood vessels as an example, such as diabetic retinopathy, retinal vasculitis, vascular occlusive disease, choroidal hemangioma, acute retinal necrosis, and maculopathy of various etiologies are common clinically. Since the fundus blood vessels are inside the eyeball, it is difficult to directly observe the lesion with ordinary optical techniques. Fundus fluorescein angiography can be used to accurately image the entire vascular and choroidal tissues of the fundus of the eye to help doctors make correct diagnoses for patients. [0003] Now the international common fundus fluorescein angiography is mainly fluorescein staining (FluoresceinFundus Angiography, FFA method). The doctor qui...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C09B57/00C07D311/30A61K49/00G01N1/30G01N21/64
CPCC09K11/06A61K49/0021A61K49/0056C07D311/30C09B57/00C09K2211/1007C09K2211/1088G01N1/30G01N21/6486G01N2001/302
Inventor 刘斌
Owner SHENZHEN UNIV
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