Biflavone derivative fluorescent probe, preparation method thereof and application of biflavone derivative fluorescent probe in brain glioma imaging

A technology of fluorescent probes and derivatives, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of lack of fluorescent probes

Active Publication Date: 2020-10-09
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Technical problem to be solved: In order to solve the problem of lack of fluorescent probes currently available for glioma, the present invention provides a biflavone derivative fluorescent probe and its preparation method and its application in the detection of glioma

Method used

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  • Biflavone derivative fluorescent probe, preparation method thereof and application of biflavone derivative fluorescent probe in brain glioma imaging
  • Biflavone derivative fluorescent probe, preparation method thereof and application of biflavone derivative fluorescent probe in brain glioma imaging
  • Biflavone derivative fluorescent probe, preparation method thereof and application of biflavone derivative fluorescent probe in brain glioma imaging

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Step 1. Compound (II): Preparation of 2,2'-(1,4-phenylene)bis(3-hydroxy-4a,8a-dihydro-4H-chromium-4-one)

[0037] 2-Hydroxyacetophenone (0.68g, 5 mmol) and terephthalaldehyde (0.67g, 5 mmol) were dissolved in 40 ml of methanol and NaOH (1.5g, 0.0375mmol) was added, heated to reflux for 6 h, cooled to The mixture was stirred at room temperature for 12h. Then NaOH solution (0.5 mol / L, 5 mL) and 30% H 2 o 2 Solution (9.9mol / L, 5 mL), the reaction solution was stirred at room temperature for 6 h, poured into ice water (200 mL) after the reaction was completed, put it in the refrigerator for 6 h, and filtered to obtain intermediate compound (Ⅱ) 2 ,2'-(1,4-phenylene)bis(3-hydroxy-4a,8a-dihydro-4H-chromium-4-one). 1 H NMR (400 MHz, DMSO-d6) δ 8.71(s, 4H), 8.05 (d, J = 8.0 Hz, 2H), 7.58 (dd, J = 20.2, 7.9 Hz, 4H), 7.24 (t, J = 7.6 Hz, 2H).

[0038]

[0039] Step 2. Preparation of probe molecule 1,4-phenylbis(4-oxo-4H-benzopyran-2,3-diyl)diacrylate (PPDC)

[0040] Weigh t...

Embodiment 2

[0043] The first step, the preparation of compound (II): 2,2'-(1,4-phenylene)bis(3-hydroxy-4a,8a-dihydro-4H-chromium-4-one) is the same as in Example 1 same.

[0044] Step 2. Preparation of probe molecule 1,4-phenylbis(4-oxo-4H-benzopyran-2,3-diyl)diacrylate (PPDC)

[0045] Weigh the intermediate compound (Ⅱ) 2,2'-(1,4-phenylene)bis(3-hydroxy-4a,8a-dihydro-4H-chromium-4-one) (0.3986 g, 1 mmol), Add 40 ml of n-hexane, add hexahydropyridine (300 µL, 2 mmol) under ice-water bath, react for 40 min, then add acryloyl chloride (180 µL, 2 mmol) dropwise, and continue to react for about 30 min under ice-water bath , and then raised to room temperature to react, and the end point of the reaction was monitored by thin-layer chromatography (TLC) spotting. After about 10 h, the reaction was completed (the reaction solution changed from red to orange). After the reaction was completed, the filtrate was spin-dried by a rotary evaporator, and eluted with ethyl acetate:petroleum ether=1:3 t...

Embodiment 3

[0047] The first step, the preparation of compound (II): 2,2'-(1,4-phenylene)bis(3-hydroxy-4a,8a-dihydro-4H-chromium-4-one) is the same as in Example 1 same.

[0048] Step 2. Preparation of probe molecule 1,4-phenylbis(4-oxo-4H-benzopyran-2,3-diyl)diacrylate (PPDC)

[0049] Weigh the intermediate compound (Ⅱ) 2,2'-(1,4-phenylene)bis(3-hydroxy-4a,8a-dihydro-4H-chromium-4-one) (0.3986 g, 1 mmol), Add 40 ml of ethanol, add sodium ethoxide (450 µL, 3 mmol) under ice-water bath, and react for 40 min, then add acryloyl chloride (240 µL, 3 mmol) dropwise, continue to react for about 30 min under ice-water bath, and then rise to React at room temperature, and monitor the end point of the reaction by spotting a thin-layer chromatography (TLC) plate. After about 10 h, the reaction ends (the reaction solution changes from red to orange). After the reaction was completed, the filtrate was spin-dried by a rotary evaporator, and eluted with ethyl acetate:petroleum ether=1:3 to obtain the ...

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Abstract

The invention discloses a biflavone derivative fluorescent probe, a preparation method thereof and application of the biflavone derivative fluorescent probe in brain glioma imaging. The chemical nameof the biflavone derivative fluorescent probe is 1, 4-phenyl bis (4-oxo-4H-benzopyran-2, 3-diyl) diacrylate (PPDC), and the molecular formula of the biflavone derivative fluorescent probe is C30H22O8.The probe PPDC is obtained through two-step synthesis, shows great Stokes shift (261 nm), and can effectively overcome the defect of biological application blockage caused by fluorescence self-absorption. Fluorescence analysis research shows that the compound can be used for high-sensitivity detection of cysteine with the detection limit being 0.01 mu M; in addition, the probe can be used for effectively distinguishing interferent glutathione and homocysteine of cysteine in an organism. Accurate detection of trace cysteine in brain glial cells is helpful for early diagnosis of brain glioma. In view of the defects of current brain glioma in early detection and accurate excision, the method is expected to realize accurate surgical navigation in clinical surgical excision of the brain glioma, and has a good application prospect.

Description

technical field [0001] The invention specifically relates to a biflavone derivative fluorescent probe, a preparation method thereof and application in brain glioma imaging, and belongs to the field of organic small molecule biological fluorescent probes. Background technique [0002] Glioma originates from the carcinogenesis of glial cells in the brain and spinal cord, and is the most common primary brain tumor. Malignant gliomas account for 80% of all gliomas, and the 5-year mortality rate ranks third among systemic tumors. bit. Studies have shown that gliomas grow infiltratingly and have no clear boundary with normal brain tissue. It is difficult to completely remove the tumor without damaging the normal brain tissue. To solve this problem, advanced detection methods and intraoperative navigation methods, such as intraoperative neuronavigation, intraoperative magnetic resonance imaging, intraoperative B-ultrasound imaging, and intraoperative neurophysiological monitoring ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30C09K11/06A61K49/00G01N21/64
CPCC07D311/30C09K11/06G01N21/6428A61K49/0021C09K2211/1088C09K2211/1007G01N2021/6417
Inventor 江玉亮钟秀丽
Owner NANJING NORMAL UNIVERSITY
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