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Fluorescent compound and preparation method thereof, and application of fluorescent compound in interactive verification and positioning of liver tumor focus tissue

A fluorescent compound, liver tumor technology, applied in the field of biosensing and imaging, can solve problems such as difficult tumor diagnosis and treatment, and achieve the effects of short time-consuming, fast and accurate identification, and convenient operation

Active Publication Date: 2021-04-02
HUBEI UNIV OF EDUCATION +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Since the tumor and the tumor microenvironment are an inseparable whole, it brings great difficulties to the diagnosis and treatment of tumors.

Method used

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  • Fluorescent compound and preparation method thereof, and application of fluorescent compound in interactive verification and positioning of liver tumor focus tissue
  • Fluorescent compound and preparation method thereof, and application of fluorescent compound in interactive verification and positioning of liver tumor focus tissue
  • Fluorescent compound and preparation method thereof, and application of fluorescent compound in interactive verification and positioning of liver tumor focus tissue

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preparation example Construction

[0056] The present invention also provides a preparation method for the above-mentioned fluorescent compound, comprising the following steps:

[0057] (a) 4-formylphenylboronic acid and tolan are heated and reacted under a protective atmosphere under the action of palladium acetate and silver carbonate to obtain an intermediate;

[0058] (b) The intermediate reacts with the alkyl 2-cyanoacetate under the action of an organic base.

[0059] In actual operation, in step (a), the temperature of heating reaction is 90~120 ℃, and the time of heating reaction is 0.5~2h; In step (a), the molar ratio of 4-formylphenylboronic acid and tolan is 1:(0.8~1.2), preferably 1:1.

[0060] In a specific embodiment of the present invention, step (a) further includes a solvent, and the solvent includes n-propanol and water.

[0061] In a specific embodiment of the present invention, in step (a), after the heating reaction, post-treatment is also included; the post-treatment includes: filtering ...

Embodiment 1

[0104] This embodiment provides fluorescent compound A 1 , its structural formula is as follows:

[0105]

[0106] The fluorescent compound A 1 The preparation method comprises the steps:

[0107] (1) Add 2.00mmol of 4-formylphenylboronic acid, 2.00mmol of toluene, 0.05mmol of palladium acetate, 2.00mmol of silver carbonate and 5mL of a mixed solvent of n-propanol and water (v / v=9:1) to 25mL Nitrogen was introduced into the three-necked flask, and under stirring, after reacting at 95°C for 120 minutes, the suspension in the three-necked flask was added to a centrifuge tube and centrifuged for 15 minutes. The supernatant was filtered under reduced pressure to remove the catalyst. Wash with methyl chloride, combine the supernatant and washing liquid after removing the catalyst, centrifuge again and filter under reduced pressure to obtain a clear solution. Add an appropriate amount of anhydrous sodium sulfate to the obtained clear solution, shake and stand to remove water f...

Embodiment 2

[0117] The fluorescent probe composition provided in this embodiment includes fluorescent compound A 1 and fluorescent compound B 1 .

[0118] The method for cross-confirming localization of liver tumor lesions by using the fluorescent probe composition comprises the following steps:

[0119] (1) Fluorescent compound A 1 Dissolved in DMSO to prepare fluorescent compound A 1 The concentration is 1×10 -2 mol / L solution I 1 ; Dilute solution I with high-glucose DMEM medium 1 Formulated as Fluorescent Compound A 1 The concentration is 1×10 -5 mol / L solution I 2 . fluorescent compound B 1 Dissolved in DMSO to prepare fluorescent compound B 1 The concentration is 1×10 -2 mol / L solution II 1 ; Dilute solution II with high glucose DMEM medium 1 Formulated as Fluorescent Compound B 1 The concentration is 1×10 -5 mol / L solution II 2 .

[0120] (2) Inactivate human liver tumor cell lines (HepG2 cell, Hep3B cell, SMMC7721 cell) and human normal liver cell lines (LO2 cell...

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Abstract

The invention relates to the technical field of biosensing and imaging, in particular to a fluorescent compound, a preparation method of the fluorescent compound and application of the fluorescent compound to interactive verification and positioning of liver tumor focus tissue. The fluorescent compound A disclosed by the invention can generate selective fluorescent lighting response to normal hepatocytes in a complex hepatoma microenvironment, and does not respond to hepatoma cells in the hepatoma microenvironment. According to the fluorescent probe composition disclosed by the invention, thefluorescent compound A and the fluorescent compound B can respectively lighten normal hepatocytes and hepatoma cells, so that the normal hepatocytes and hepatoma cells in hepatoma lesion tissues are interactively verified and positioned, and the detection and recognition accuracy is improved.

Description

technical field [0001] The invention relates to the technical field of biosensing and imaging, in particular to a fluorescent compound, a preparation method thereof, and an application in cross-validation and localization of liver tumor lesion tissue. Background technique [0002] Regardless of whether it is primary or secondary cancer, it has become the second most important disease that seriously threatens global human health. Among them, primary liver cancer is one of the most common malignant tumors with high morbidity and mortality, and the five-year survival rate is only 14%. Since the tumor and the tumor microenvironment are an inseparable whole, it brings great difficulties to the diagnosis and treatment of tumors. Therefore, for doctors, the key factor is whether they can easily and quickly locate tumor lesions that are invisible to the naked eye. [0003] At present, fluorescent probes are mostly used to achieve imaging recognition by lighting up fluorescent mark...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/41C07C45/68C07C47/548C07C253/30C09K11/06G01N21/64
CPCC07C255/41C07C45/68C07C253/30C09K11/06G01N21/6402C09K2211/1007C07C47/548
Inventor 陈笛笛李民毛慧灵董宇平
Owner HUBEI UNIV OF EDUCATION
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