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
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[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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Application Information
- IPC
- C09K11/06; C07D413/12; G01N21/64
- Inventors
- 樊江莉; 王本花