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A kind of wash-free glioma image fluorescent molecular probe and its preparation method and application

A fluorescent molecular probe, glioma technology, applied in fluorescence/phosphorescence, chemical instruments and methods, material analysis by optical means, etc., can solve problems such as unfavorable glioma in situ monitoring, and achieve high yield , The effect of wide detection range and low fluorescence background signal

Active Publication Date: 2022-04-05
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in order to obtain a high signal-to-background ratio, cells often need to be washed after co-incubation with the probe to reduce the background fluorescence, which is not conducive to the in situ monitoring of glioma

Method used

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  • A kind of wash-free glioma image fluorescent molecular probe and its preparation method and application
  • A kind of wash-free glioma image fluorescent molecular probe and its preparation method and application
  • A kind of wash-free glioma image fluorescent molecular probe and its preparation method and application

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Embodiment 1

[0036] Synthesis of Fluorescent Probe II

[0037] R in the fluorescent probe structural formula prepared in this embodiment 1 =OCH 3 , R 2 = H, R 3 =CH 3 .

[0038] The synthesis technique route of present embodiment is as figure 1 As shown, it specifically includes the following steps:

[0039] Synthesis of Compound 4-1

[0040]Weigh compound 1-1 anisole (2.70g, 10mmol) and place it in a 250mL round-bottomed flask, add 40mL acetic acid, dissolve and add dropwise compound 2-1 aniline (0.93g, 10mmol) and compound 3 (1.8 g, 10mmol), stirred at 120°C for 5h, during the reaction, the reaction solution gradually changed from gray turbid liquid to light yellow clear liquid; TLC monitored the reaction process, and the dark spots of raw materials gradually decreased, and green fluorescence with relatively less polarity appeared point. After the reaction was completed, the reaction solution was poured into 200mL of water, and a yellow-gray precipitate was precipitated. After t...

Embodiment 2

[0046] Synthesis of Fluorescent Probe III

[0047] R in the fluorescent probe structural formula prepared in this embodiment 1 = H, R 2 = H, R 3 =CH 3 .

[0048] The synthesis technique route of present embodiment is as figure 2 As shown, it specifically includes the following steps:

[0049] Synthesis of Compound 4-2

[0050] Weigh compound 1-2 benzil (2.10g, 10mmol) and place it in a 250mL round bottom flask, add 40mL acetic acid, dissolve and add compound 2 aniline (0.93g, 10mmol) and compound 3 (1.8g, 10mmol), stirred at 120°C for 5h. During the reaction, the reaction solution gradually changed from gray turbid liquid to light yellow clear liquid; TLC monitored the reaction process, and the dark spots of raw materials gradually decreased, and blue fluorescent spots with relatively less polarity appeared. . After the reaction was completed, the reaction solution was poured into 200mL of water, and a yellow-gray precipitate was precipitated. After the system was adj...

Embodiment 3

[0056] Synthesis of Fluorescent Probe III

[0057] R in the fluorescent probe structural formula prepared in this embodiment 1 =OCH 3 , R 2 =CH 3 , R 3 =CH 2 CH 3 .

[0058] The synthesis technique route of present embodiment is as image 3 As shown, it specifically includes the following steps:

[0059] Synthesis of compound 4-3

[0060] Weigh compound 1-1 anisole (2.70g, 10mmol) and place it in a 250mL round-bottomed flask, add 40mL acetic acid, dissolve and add compound 2-2 p-methylaniline (1.07g, 10mmol) dropwise under stirring at room temperature and compound 3 (1.8g, 10mmol), stirred at 120°C for 5h, during the reaction, the reaction solution gradually changed from gray turbid liquid to light yellow clear liquid; TLC monitored the reaction process, the dark spots of raw materials gradually decreased, and the relative polarity appeared smaller green fluorescent dots. After the reaction was completed, the reaction solution was poured into 200mL of water, and a y...

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Abstract

The invention discloses a wash-free glioma image fluorescent molecular probe and its preparation method and application, the structure of which is shown in formula I: wherein: R 1 It is one of fluorine, chlorine, bromine and iodine; R 2 One of hydrogen, halogen, alkyl, alkoxy, amino, dimethylamino; R 3 One of methyl, ethyl, isopropyl, tert-butyl, benzyl and their derivatives. The preparation method of the fluorescent molecular probe for diagnosing brain glioma provided by the invention is simple, the raw materials are cheap and easy to obtain, and are suitable for large-scale production and popularization and application. Since the fluorescent probe has an aggregation-induced luminescent effect, it can effectively avoid the interference of self-absorption and biological background fluorescence, and can avoid errors caused by the concentration of the probe used and the uneven distribution of the probe. In actual detection, the probe has the advantage of being completely wash-free, greatly simplified operation, low fluorescence background signal, high signal-to-noise ratio, fast response, wide detection range, high sensitivity, and high selectivity for glioma in the sample .

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, analysis and detection, and in particular relates to a wash-free glioma image fluorescent molecular probe and its preparation method and application. Background technique [0002] Glioma is a heterogeneous group of primary brain tumors and is the most common malignancy of the central nervous system. According to the classification of the World Health Organization, it can be further divided into four grades, the first and second grades are low-grade gliomas (LGG), and the third and fourth grades are high-grade gliomas (HGG). In general, relatively higher grades were associated with poorer prognosis, with a median survival time of 11.6 years for low-grade gliomas and median survival for glioblastoma, the most common grade IV glioma. Bit survival time is only 14 months. Due to the invasive growth of glioma cells, it is almost impossible to completely resect all tumor areas, resulting in ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/14C09K11/06G01N21/64
CPCC07D409/14C09K11/06G01N21/6402G01N21/6486C09K2211/1029C09K2211/1044C09K2211/1092
Inventor 曾文彬毕桉耀郑凡吴军勇丁季鹏向大雄
Owner CENT SOUTH UNIV
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