Near infrared fluorescence probe adopting nile blue as parent, preparation method thereof and applications thereof

A fluorescent probe, Nile blue technology, applied in the field of near-infrared fluorescent probes, can solve the problems of lack of imaging specificity, increase accurate diagnosis, large radioactivity, etc., achieve good cell membrane permeability, low biological toxicity, synthetic easy effect

Active Publication Date: 2014-05-28
SICHUAN ANKERUI NEW MATERIAL TECH CO LTD
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

However, the above methods have the following defects in practical imaging applications: lack of imaging specificity, large radiation damage, inability to independently label and diagnose tumors, inability to perform in-depth imaging of tumors, etc.
However, the problem still exists in the application of this type of diagnostic agent is: when there is no target cell with high COX-2 expression in the tissue, organ or individual as the detection object, the fluorescence still exists, which will affect the increase of COX-2 expression Accurate diagnosis at the early stage, in practical application, it is very likely to cause inaccurate diagnosis at the early stage of tumor or inflammation

Method used

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  • Near infrared fluorescence probe adopting nile blue as parent, preparation method thereof and applications thereof
  • Near infrared fluorescence probe adopting nile blue as parent, preparation method thereof and applications thereof
  • Near infrared fluorescence probe adopting nile blue as parent, preparation method thereof and applications thereof

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preparation example Construction

[0046] On the other hand, the present invention provides the preparation method of the near-infrared fluorescent probe of the present invention using Nile Blue as a parent, comprising the steps of:

[0047] 1) 1-bromonaphthalene and H 2 N-R 3 -NH 2 According to the molar ratio of 1:1-1:5 reaction, the preparation of compound Ⅲ:

[0048]

[0049] The reaction temperature is 80-150°C, the reaction time is 1-24 hours, and the reaction solvent is selected from dichloromethane, ethylene glycol monomethyl ether, methanol, DMF or a mixture thereof;

[0050] In a preferred embodiment, the reaction temperature is 90-140°C, the reaction time is 10-20 hours, the reaction solvent is selected from ethylene glycol monomethyl ether, methanol, DMF or a mixture thereof, 1-bromonaphthalene and H 2 N-R 3 -NH 2 Mole is 1:1-1:4;

[0051] In a further preferred embodiment, the reaction temperature is 100-130°C, the reaction time is 12-18 hours, the reaction solvent is selected from ethylen...

Embodiment 1

[0077] 1.1 Synthesis of fluorescent probe compound II:

[0078]

[0079] (1) Synthesis of intermediate 1

[0080] N,N-Dimethyl-m-aminophenol (62.72mmol) was added to a round bottom flask containing a mixed solution of 30ml of concentrated hydrochloric acid and 10mL of water, and the temperature was kept at -5°C in an ice bath. Formulated with NaNO 2 (4.36g, 63.20mmol) in 30mL aqueous solution, and slowly added dropwise to the flask, mechanically stirred for 2h, filtered to obtain a brownish yellow solid, washed with 100mL saturated aqueous sodium acetate solution to obtain dark red solid intermediate 1, yield 86%.

[0081] (2) Synthesis of intermediate 2

[0082] 1-Bromonaphthalene (4.12 g) and hexamethylenediamine (4.65 g) were added to a round bottom flask containing 40 ml of ethylene glycol monomethyl ether solution, followed by CuI (190 mg) and CsCO 3 (3.0g), the solution changed from brown-yellow to blue-green. Heating to 125°C and reflux continued for 24 hours to ...

Embodiment 2

[0107] 2.1 Synthesis of fluorescent probe compound II':

[0108]

[0109] (1) Synthesis of Intermediate 1

[0110] N,N-Dimethyl-m-aminophenol (62.72mmol) was added to a round bottom flask containing a mixed solution of 30ml of concentrated hydrochloric acid and 10mL of water, and the temperature was kept at -5°C in an ice bath. With NaNO 2 (4.36g, 63.20mmol) in 30mL aqueous solution, and slowly added dropwise to the flask, mechanically stirred for 2h, filtered to obtain a brownish yellow solid, washed with 100mL saturated aqueous sodium acetate solution to obtain dark red solid intermediate 1, yield 86%.

[0111] (2) Synthesis of intermediate 2

[0112] 1-Bromonaphthalene (3.11 g) and hexamethylenediamine (2.64 g) were added to a round bottom flask containing 40 ml of ethylene glycol monomethyl ether solution, followed by CuI (190 mg) and CsCO 3 (3.0g), the solution changed from brown-yellow to blue-green. Heating to 125°C and reflux continued for 24 hours to stop the r...

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Abstract

The invention relates to a near infrared fluorescence probe adopting nile blue as a parent, a preparation method thereof and applications thereof. The fluorescence probe has a structure shown as the general formula I as the attached drawing 1. The fluorescence probe can effectively improve deficiencies of tumor labeling fluorescence probes at present, can sensitively and accurately response to target cells COX-2 expression amount of which is abnormal, and is suitable for effective specific near infrared fluorescence probes labeling living tumor cells. The fluorescence probe provided by the invention is simple in synthesis and products are easy to obtain. The fluorescence probe provided by the invention has a very low fluorescence background in non-tumor cells and high fluorescence signals in tumor cells, and has strong specific labeling function for tumor cells. In addition, compounds of the type have good cell membrane permeability, low biotoxicity, low phototoxicity and low photobleaching capability and can locate a special organelle of a certain kind tumor cell.

Description

technical field [0001] The invention relates to a kind of near-infrared fluorescent probe with Nile blue as the matrix, its preparation method, and the application of the fluorescent probe in the preparation of biomarker kits, especially tumor cell marker kits. Background technique [0002] According to the statistics of the World Health Organization (WHO), in the 1980s, there were about 7 million new cancer patients in the world every year, and about 5 million people died of cancer every year. Cancer is attacking human beings with an irresistible trend. It is an important work to find a simple, fast, effective and sensitive cancer marker technology. The existing marker imaging methods mainly include: X-ray detection technology, ultrasonic detection technology, CT detection technology, nuclear magnetic resonance (MRI) detection technology, infrared thermal imaging detection technology, near-infrared scanning detection technology, PET-CT detection technology, etc. . However...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D413/12G01N21/64
Inventor 樊江莉王本花彭孝军仉华
Owner SICHUAN ANKERUI NEW MATERIAL TECH CO LTD
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