Carboxy-DiI compound as well as preparation method and application thereof

A compound and product technology, applied in the field of detection, can solve the problems of inapplicable detection and evaluation, and achieve the effects of high fluorescent labeling efficiency, high specificity, and good selectivity

Active Publication Date: 2020-10-09
武汉市第四医院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for patients with chronic heart disease, especially those with chronic myocardial infarction, the blood supply and oxygen supply of the heart cannot be separated from the coronary microcirculation system, and the conventional carbocyanine dye is not suitable for its detection and evaluation

Method used

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  • Carboxy-DiI compound as well as preparation method and application thereof
  • Carboxy-DiI compound as well as preparation method and application thereof
  • Carboxy-DiI compound as well as preparation method and application thereof

Examples

Experimental program
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Embodiment 1

[0029] This embodiment provides a synthetic method of Carboxy-DiI type compound A, comprising the following steps:

[0030] S1, referring to the following reaction formula, at 25°C, dissolve compound 1 (10.0g, 1.00eq, HCl) in 80mL acetic acid solution (containing compound 1a, 7.71g, 9.57mL, 2.00eq), and heat to 130°C , Reacted for 16h to obtain a reaction mixture containing compound 2. After washing the reaction mixture with 200 mL of water, the reaction mixture was extracted three times with ethyl acetate, each time 100 mL, to obtain an organic layer mixture, which was then washed with saturated NaHCO 3 Adjust the pH of the aqueous solution to 8, absorb water with anhydrous sodium sulfate, and dry in vacuo to obtain compound 2 as a brown oil with a yield of 88.6% and a purity of 94.4%. The reaction process of compound 2 is monitored by LCMS, and the results are as attached figure 1 shown.

[0031]

[0032] S2, referring to the following reaction formula, compound 2 (4.0...

Embodiment 2

[0039] This embodiment provides a method for detecting arterial blood vessel distribution using Carboxy-DiI compound labeling, comprising the following steps:

[0040] (1) Heart perfusion, preparation of tissue samples:

[0041]The experimental rats were subjected to cardiac perfusion 45 minutes after ligation of the left anterior descending artery. Before the start of cardiac perfusion, connect 2 three-way stopcocks and 3 10mL syringes, which are respectively filled with PBS buffer solution and working solution containing Carboxy-DiI compounds (take 5 mg of Carboxy-DiI compound A prepared in Example 1) Dissolve the powder in 1mL of absolute ethanol, then transfer to dissolve in 50mL of buffer solution mixed with PBS buffer solution and 5% glucose solution at a volume ratio of 1:4) and 4% paraformaldehyde, and empty the air bubbles in the syringe . Use a 25-gauge butterfly needle to puncture and fix it from the left ventricle, open the right atrium and cut an opening to drai...

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Abstract

The invention relates to a Carboxy-DiI compound as well as a preparation method and application thereof; the Carboxy-DiI compound is used as a fluorescent dye with higher water solubility, is high influorescence efficiency, can be used for arterial perfusion of a living heart and uniform labeling of micro-artery vascular endothelial cells, and is good in specificity and high in sensitivity.

Description

technical field [0001] The invention relates to the detection field, in particular to a Carboxy-DiI type compound and its preparation method and application. Background technique [0002] Fluorescent dyes have been widely used as labeled probes in the fields of chemistry and biology, especially in life sciences, clinical molecular diagnosis, and immune function analysis. Among them, Cy series fluorescent dyes are the most widely used dyes, which have the advantages of large molar extinction coefficient, good stability, and high fluorescence quantum yield. For example, in the range of absorption and emission in the infrared (NIR) visible region, carbonylated cyanine dye, as a probe reagent that is helpful for biological imaging, has the advantages of small refractive index, deep tissue penetration, and small background autofluorescence interference. attention for years. However, for patients with chronic heart disease, especially those with chronic myocardial infarction, th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08C09K11/06G01N21/64G01N21/84
CPCC07D209/08C09K11/06G01N21/6428G01N21/84C09K2211/1029G01N2021/6439
Inventor 顾晔王玉婷刘晓刚
Owner 武汉市第四医院
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