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A kind of near-infrared fluorescent dye and its preparation method and application

A fluorescent dye and near-infrared technology, applied in the field of medicine, can solve the problems of lack of lymphatic targeting, strong liver and kidney toxicity, and high price, and achieve the effect of simple, effective, high stability, and simple and easy method

Active Publication Date: 2022-03-08
SHANDONG UNIV QILU HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the price of indocyanine green is relatively high, and it has the disadvantages of strong liver and kidney toxicity and lack of lymphatic targeting after intravenous injection, which limits its clinical application.

Method used

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  • A kind of near-infrared fluorescent dye and its preparation method and application
  • A kind of near-infrared fluorescent dye and its preparation method and application
  • A kind of near-infrared fluorescent dye and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1 Preparation of ICG-SH

[0050] The synthetic route is as follows:

[0051]

[0052] Dissolve 200mg of ICG-NHS in 25mL of dichloromethane, add 50μL of triethylamine, stir for 5 minutes, dissolve 100mg of trityl-protected aminothiol in 5mL of dichloromethane and slowly add to the reaction solution, and react at room temperature in the dark Stir for 6 hours. The reaction solution was concentrated to 5 mL and then poured into 50 mL of diethyl ether to obtain a green precipitate, which was dissolved in dichloromethane and placed on a silica gel column for separation to obtain 75 mg of trityl-protected ICG-SH.

[0053] Dissolve 75 mg of trityl-protected ICG-SH in 5 mL of trifluoroacetic acid, add 5 mL of triethylsilane, and react in the dark at room temperature for 4 hours. After the reaction solution is concentrated, it is poured into 25 mL of ether to obtain a green precipitate, and the precipitate is dissolved in In methanol, HPLC separation and purificati...

Embodiment 2

[0056] The preparation method of embodiment 2 ICG-SH-GNPs

[0057] Slowly drop 1ml of DMSO solution of ICG-SH (protected from light) into 1ml of acrylamide solution of nano-gold with a particle size of 20 nm, the molar ratio of ICG-SH to nano-gold is 1:4, stir for 3 hours, and dialyze at 3500Ka bag, and dialyzed for 48 hours to obtain pure ICG-SH-GNPs solution, which was stored in a 4°C refrigerator for later use. The electron microscope image of ICG-SH-GNPs is shown in image 3 shown.

Embodiment 3

[0059] Experimental method: patients with endometrial cancer were slowly injected with 0.5ml of ICG-SH (prepared in Example 1) at 0, 3, and 9 o'clock in the cervical stroma. Like the case, the result is like figure 2 shown.

[0060] figure 2 It is the imaging results of lymph nodes at different time points after local injection of ICG-SH in the cervix, where A is the imaging results of lymph nodes 10 minutes after injection, B is the imaging results of lymph nodes 30 minutes after injection, and C is the imaging results of lymph nodes 60 minutes after injection. like result.

[0061] according to figure 2 It can be seen that ICG-SH can stain lymph nodes well after infrared irradiation, and the staining time can last for more than 60 minutes. figure 2 As can be seen in Figure C, the lymph nodes can still be clearly traced after 60 minutes of injection, and have not spread to the entire cervical tissue, indicating that ICG-SH has higher stability, less diffusion and long...

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Abstract

The invention provides a near-infrared fluorescent dye and its preparation method and application. The near-infrared fluorescent dye is called ICG-SH, and its structure is as shown in formula (I). The compound ICG-SH retains the indocyanine green The luminescent group has stable properties and stronger stability.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a near-infrared fluorescent dye and its preparation method and application. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] The symptoms of endometrial cancer are typical, 68% of patients are diagnosed at the early stage of the disease (FIGO stage I), and the five-year survival rate is as high as 80%. At present, it is believed that early stage patients should receive comprehensive staging surgery, including hysterectomy plus double adnexectomy and systematic pelvic and para-aortic lymph node dissection. Postoperative pathological findings of lymph node metastasis should receive adjuv...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/90C09B23/08C09K11/06A61K49/00
CPCC09B23/086C09K11/06A61K49/0034A61K49/005C09K2211/1029Y02P20/55
Inventor 宋坤孔北华姚舒李莉鲁在君王凯
Owner SHANDONG UNIV QILU HOSPITAL
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