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A kind of small molecule fluorescent probe and its preparation method and application

A fluorescent probe and small molecule technology, applied in the field of fluorescence imaging, can solve the problems of non-target specificity, high cost, and complicated operation.

Active Publication Date: 2022-07-05
JIANGSU NAIQUE BIOLOGICAL ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the current MS clinical diagnosis technology, it mainly relies on magnetic resonance imaging technology, which does not have target specificity, and has the disadvantages of complicated operation and high cost.

Method used

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  • A kind of small molecule fluorescent probe and its preparation method and application
  • A kind of small molecule fluorescent probe and its preparation method and application
  • A kind of small molecule fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Synthesis of Intermediate 5

[0038] Intermediate 5-1 Synthesis: add 3.87g (2.0mmol) 4-(diethylamino)benzoic acid to a 100mL round-bottomed flask, add 60mL freshly distilled thionyl chloride and 0.5mL DMF, heat under reflux at 75°C, react for 4 hours, stop heating , recovering unreacted SOCl 2 , residual S°C l 2 It was evaporated under reduced pressure, and the crude product was recrystallized from ethyl acetate to obtain 0.38 g of intermediate 5-1 as white crystals with a yield of 90%.

[0039] Intermediate 5-2: Synthesis of : refer to the synthesis of intermediate 5-1, using 4-(dimethylamino)benzoic acid to synthesize intermediate 5-2 with a yield of 92%.

Embodiment 2

[0040] Example 2: Synthesis of Intermediate 2

[0041] Intermediate 2-1 Synthesis: 1.59 g (10.0 mmol) of 5-amino-1-naphthol and 2.4 g (11.0 mmol) of di-tert-butyl dicarbonate were placed in a 100 mL round-bottomed flask, 20 mL of tetrahydrofuran was added to dissolve, and then sodium bicarbonate was added. 1.25g (15.0mmol) and 10mL of water were reacted at room temperature, TLC detected the reaction progress (developing solvent: ethyl acetate: n-hexane=1:3, v:v), after the reaction was finished, the tetrahydrofuran solvent was evaporated under reduced pressure and added 100mL Distilled water, a large amount of black solid was precipitated, filtered, washed with a large amount of distilled water and n-hexane successively to obtain Intermediate 2-1 (black solid).

Embodiment 3

[0042] Example 3: Synthesis of Intermediate 3

[0043] Intermediate 3-1 Synthesis of: 25mL round-bottomed flask was fully dried before use, and purged with nitrogen, added magnetron, quickly added 0.12g (5mmol) of sodium hydride and 0.259g (1mmol) of intermediate 2-1, plugged with a rubber stopper, filled with Nitrogen protection, 0 ° C ice bath cooling, add 5 mL of dry DMF, stir for 30 minutes, slowly add 0.568 g (4 mmol) iodomethane dropwise at 0 ° C, react at 0 ° C to room temperature, TLC detects the reaction progress (developing solvent: ethyl acetate Ester: n-hexane=1:3, v:v), after the reaction, 20 mL of distilled water was added to quench the reaction, extracted with ethyl acetate (25 mL×3), the ethyl acetate layers were combined, washed with water (25 mL×3), saturated common salt Washed with water (10 mL×2), the organic layer was dried with anhydrous sodium sulfate, filtered, and the ethyl acetate was evaporated under reduced pressure to obtain the crude product, whi...

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Abstract

The invention discloses a small molecule fluorescent probe and a preparation method and application thereof. The small molecule fluorescent probe of the present invention is shown in formula (I). The small molecule probe of the present invention can be effectively combined with the myelin sheath part, significantly enhance the imaging effect of the myelin sheath part, can be applied to myelin sheath fluorescence imaging, and can provide a new method for the diagnosis and therapeutic effect evaluation of central nervous system diseases such as multiple sclerosis.

Description

technical field [0001] The invention relates to the field of fluorescence imaging, in particular to a small molecule fluorescent probe and a preparation method and application thereof. Background technique [0002] Myelin (Myelin) is a membrane that wraps around the axons of nerve cells and is composed of myelin, which generally appears in the central nervous system of vertebrates. Myelination refers to the process of the development of myelin sheath, which accelerates the speed of nerve excitation when it is transmitted along the nerve fiber, and ensures its directional conduction to avoid mutual interference of information, and can guide axons when some axons are damaged. regeneration. Demyelination refers to the damage to the myelin sheath that occurs after the formation of myelin sheath, which may lead to a variety of central nervous system diseases, the most common of which is Multiple Sclerosis (MS). In the diagnosis and therapeutic evaluation of MS, the pursuit of q...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D335/04C09K11/06G01N21/64
CPCC07D335/04C09K11/06G01N21/64C09K2211/1092Y02P20/55
Inventor 孙宏顺杨永安孙娟钟慧易铭金显友
Owner JIANGSU NAIQUE BIOLOGICAL ENG
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