Preparation method of near-infrared fluorescent tracer activating dye ZW800-Bop-NHS

A technology of ZW800-OH and zw800-bop-nhs, which is applied in the field of animal imaging, cell labeling, and near-infrared surgical navigation fluorescent molecules, can solve the problems of limited penetration distance, small particles, high false negative rate, etc., and achieve active target Strong tropism, high product yield and simple process

Active Publication Date: 2022-04-12
NANJING NUOYUAN MEDICAL DEVICES CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Indocyanine green has the following disadvantages: (1) indocyanine green particles are smaller, and have the disadvantages of secondary and tertiary lymph node imaging
(2) The first generation of fluorescence detectors must observe fluorescence in a dark room and cannot display human tissue
Although the second-generation fluorescence detector-fluorescence vascular imaging system overcomes this defect and can obtain real-time images of fluorescently stained lymphatic vessels and lymph nodes on the display screen under natural light conditions

Method used

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  • Preparation method of near-infrared fluorescent tracer activating dye ZW800-Bop-NHS
  • Preparation method of near-infrared fluorescent tracer activating dye ZW800-Bop-NHS

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Embodiment 1

[0025] A preparation method for near-infrared fluorescent tracer activated dye ZW800-Bop-NHS, characterized in that it comprises the following process steps:

[0026] Step A. In a reactor with a stirrer and a thermometer, add 100g of N-methylpyrrolidone, add 4.62g (5mmol) of dye ZW800-OH under stirring, heat to 35-45°C, stir to completely dissolve the dye, and form Solution; step B, in above-mentioned solution, add successively the carboxyl activator N-hydroxysuccinamide 0.63g (5.5mmol) of weighing and condensing agent benzotriazole-1-yloxy tris(dimethylamino) Phosphonium hexafluorophosphate 2.43g (5.5mmol), under stirring, slowly add 50% potassium hydroxide solution dropwise to adjust the Ph value to 7-8; step C, maintain the temperature at 45±5°C, and continue the reaction for 2-3 hours , after the reaction is completed, the ZW800-Bop-NHS mixed reaction solution containing the special activated form is obtained; the solution obtained in step D and step C is decompressed and ...

Embodiment 2

[0028] A preparation method for near-infrared fluorescent tracer activated dye ZW800-Bop-NHS, characterized in that it comprises the following process steps:

[0029] Step A. In a reactor with a stirrer and a thermometer, add 200g of dimethyl sulfoxide, add 4.62g (5mmol) of dye ZW800-OH under stirring, heat at 35-45°C, and stir to completely dissolve the dye to form a solution; Step B, sequentially add weighed carboxyl activator N-hydroxysuccinamide 0.63g (5.5mmol) and condensation agent hexafluorophosphate benzotriazol-1-yl-oxytripyrrolidinylphosphorus 2.86 to the above solution g (5.5mmol), under stirring, slowly add 50% potassium hydroxide solution dropwise, and adjust the Ph value to 7-8; step C, maintain the temperature at 45±5°C, and continue the reaction for 2-3 hours. ZW800-Bop-NHS mixed reaction solution in activated form; step D, the solution obtained in step C is decompressed to recover the solvent, add 400g of isopropanol solvent to the bottom product, stir and bea...

Embodiment 3

[0031] A preparation method for near-infrared fluorescent tracer activated dye ZW800-Bop-NHS, characterized in that it comprises the following process steps:

[0032] Step A. In a reactor with a stirrer and a thermometer, add 200g of dimethyl sulfoxide, add 4.62g (5mmol) of dye ZW800-OH under stirring, heat at 35-45°C, and stir to completely dissolve the dye to form a solution; Step B, add successively weighed carboxyl activator N-hydroxysuccinamide 0.86g (7.5mmol) and condensing agent hexafluorophosphate benzotriazol-1-yl-oxytripyrrolidinylphosphorus 3.9 to the above solution g (7.5mmol), under stirring, slowly add 50% potassium hydroxide solution dropwise, and adjust the Ph value to 7-8; step C, maintain the temperature at 45±5°C, and continue the reaction for 2-3 hours. ZW800-Bop-NHS mixed reaction solution in activated form; step D, the solution obtained in step C is decompressed to recover the solvent, add 400g of isopropanol solvent to the bottom product, stir and beat, ...

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Abstract

The invention discloses a dye activation method for a near-infrared fluorescent tracer, which comprises the following steps: under the action of a near-infrared light dye ZW800-OH acid, an activator and a complexing agent, forming a reactive dye ZW800-Bop-NHS with activation performance, enabling the activated dye to be more easily coupled with polypeptide, and forming an efficient tracer with strong active targeting property and high sensitivity. And the formed near-infrared light dye has the advantages of good water solubility, high fluorescence quantum yield and the like.

Description

technical field [0001] The invention provides a dye activation method for a near-infrared fluorescent tracer, and relates to the fields of near-infrared surgical navigation fluorescent molecules, animal imaging, cell labeling and the like. [0002] technical background [0003] Near-infrared (NIR) light has obvious advantages such as deep penetration, small absorption, and less tissue scattering. It has great potential for application in image-guided interventions and can provide superior signal-to-background ratio (SBR). At present, indocyanine green (ICG), the only NIR fluorophore approved by the US FDA, has been used in various clinical surgical imaging. The advantages and disadvantages of the near-infrared fluorescent dye method have been studied by domestic and foreign scholars. The advantages of indocyanine green: (1) high detection rate, less trauma, no radiation, easy to implement; (2) indocyanine green is injected intradermally or subcutaneously at the outer edge o...

Claims

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Application Information

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IPC IPC(8): C07D403/14C09B23/10C09K11/06A61K49/00G01N21/64
CPCY02E10/542
Inventor蔡惠明王毅庆
OwnerNANJING NUOYUAN MEDICAL DEVICES CO LTD