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Near-infrared fluorescent molecular probe as well as preparation method and application thereof

A fluorescent molecular probe and near-infrared technology, applied in fluorescence/phosphorescence, chemical instruments and methods, and material analysis through optical means, can solve problems such as small changes in fluorescent signals, weak biological penetration, and unfavorable image analysis , to achieve high yield, wide detection range and low fluorescence background signal

Pending Publication Date: 2022-03-08
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, fluorescent probes have been widely used in the field of biomedicine, but they also have some shortcomings, that is, the change of the fluorescent signal before and after the reaction is usually small (enhancement 1-2 times)
The emission wavelength is short and the biological penetration is weak, which is unfavorable for image analysis

Method used

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  • Near-infrared fluorescent molecular probe as well as preparation method and application thereof
  • Near-infrared fluorescent molecular probe as well as preparation method and application thereof
  • Near-infrared fluorescent molecular probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of Fluorescent Probe II

[0047] R in the fluorescent probe structural formula prepared in this embodiment 1 = H, R 2 =H.

[0048] The synthesis technique route of present embodiment is as figure 1 As shown, it specifically includes the following steps:

[0049] Synthesis of compound 3

[0050] Weigh compound 1 (1.96g, 10mmol) and place it in a 250mL round-bottomed flask, add 40mL of methanol, and after dissolving, drop in compound 2 (1.25g, 10mmol) under stirring at room temperature, and stir at room temperature for 5h. During the reaction, the reaction solution gradually From gray turbid liquid to light yellow clear liquid; TLC monitors the reaction process, the dark spots of raw materials gradually decrease, and blue fluorescent spots with relatively less polarity appear. After the reaction was completed, the reaction solution was poured into 200 mL of water, and a large amount of light yellow solid precipitated out. The light yellow solid was obtained...

Embodiment 2

[0061] Synthesis of Fluorescent Probe III

[0062] R in the fluorescent probe structural formula prepared in this embodiment 1 =CH 3 , R 2 =H.

[0063] The synthesis technique route of present embodiment is as figure 2 As shown, the specific steps include:

[0064] Synthesis of compound 3

[0065] Weigh compound 1 (1.96g, 10mmol) and place it in a 250mL round-bottomed flask, add 40mL of methanol, and after dissolving, drop in compound 2 (1.40g, 10mmol) under stirring at room temperature, and stir at room temperature for 5h. During the reaction, the reaction solution gradually From gray turbid liquid to light yellow clear liquid; TLC monitors the reaction process, the dark spots of raw materials gradually decrease, and blue fluorescent spots with relatively less polarity appear. After the reaction was completed, the reaction solution was poured into 200 mL of water, and a large amount of light yellow solid precipitated out. The light yellow solid was obtained by suction ...

Embodiment 3

[0075] Synthesis of Fluorescent Probe IV

[0076] R in the fluorescent probe structural formula prepared in this embodiment 1 =CH 3 , R 2 =CH 3 .

[0077] The synthesis technique route of present embodiment is as Figure 4 As shown, the specific steps include:

[0078] Synthesis of compound 3

[0079]Weigh compound 1 (1.96g, 10mmol) and place it in a 250mL round-bottomed flask, add 40mL of methanol, and after dissolving, drop in compound 2 (1.40g, 10mmol) under stirring at room temperature, and stir at room temperature for 5h. During the reaction, the reaction solution gradually From gray turbid liquid to light yellow clear liquid; TLC monitors the reaction process, the dark spots of raw materials gradually decrease, and blue fluorescent spots with relatively less polarity appear. After the reaction was completed, the reaction solution was poured into 200 mL of water, and a large amount of light yellow solid precipitated out. The light yellow solid was obtained by sucti...

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Abstract

The invention discloses a near-infrared fluorescent molecular probe as well as a preparation method and application thereof. The structure of the near-infrared fluorescent molecular probe is shown as a formula I, wherein R1 is one of hydrogen, methyl, fluorine, chlorine, bromine and iodine; r2 is one of hydrogen, halogen, alkyl, alkoxy, amido and dimethylamino. The preparation method of the fluorescent molecular probe for diagnosing AD is simple, raw materials are cheap and easy to obtain, the synthesis process is simple, the yield is high, and the fluorescent molecular probe is suitable for large-scale production, popularization and application. The fluorescent probe has near-infrared fluorescence emission, so that the interference of self-absorption and biological background fluorescence can be effectively avoided, and errors caused by the use concentration of the probe, uneven distribution of the probe and the like can be avoided. In addition, the probe is greatly simplified in operation, low in fluorescence background signal and high in signal-to-noise ratio in actual detection. The fluorescent probe is rapid in response, wide in detection range and high in sensitivity, and has high selectivity on AD samples. The probe provided by the invention has a wide application prospect in the aspect of AD diagnosis.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and analysis and detection, in particular to the technical field of Alzheimer's disease (AD) judgment and analysis, namely a near-infrared fluorescent molecular probe and its preparation method and application. Background technique [0002] Alzheimer's disease (AD) is a progressive neurodegenerative brain disease that is considered an incurable disease, and the formation and accumulation of amyloid β (Aβ) plaques in the brain is considered a key to the early diagnosis of AD. important pathological markers. Commercial thioflavin derivatives (ThT or ThS) are well known gold standard probes for in vitro histological staining of amyloid fibrils. Inherent drawbacks, including distorted signals from fluorescence enrichment quenching effects, unavoidable noise from constant-brightness modes, and limited blood-brain barrier (BBB) ​​permeability, severely hinder their translation to in vivo imag...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/10C09K11/06G01N21/64A61K49/00
CPCC07D417/10C09K11/06G01N21/6428G01N21/6458A61K49/0032C09K2211/1029C09K2211/1007C09K2211/1037
Inventor 曾文彬毕桉耀郑凡吴军勇丁季鹏高峰容鹏飞张声旺向大雄
Owner CENT SOUTH UNIV
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