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Fluorescent compound and its preparation method, and its application in cross-validation localization of liver tumor lesion tissue

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

Active Publication Date: 2022-05-24
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 its preparation method, and its application in cross-validation localization of liver tumor lesion tissue
  • Fluorescent compound and its preparation method, and its application in cross-validation localization of liver tumor lesion tissue
  • Fluorescent compound and its preparation method, and its application in cross-validation localization of liver tumor lesion tissue

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preparation example Construction

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

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

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

[0059] In actual operation, in step (a), the temperature of the heating reaction is 90-120° C., and the time of heating reaction is 0.5-2 h; in step (a), the molar ratio of 4-formylbenzeneboronic acid and diphenylacetylene 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-processing is also included; the post-processing...

Embodiment 1

[0104] This example provides fluorescent compound A 1 , and its structure is as follows:

[0105]

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

[0107] (1) 2.00 mmol of 4-formylphenylboronic acid, 2.00 mmol of diphenylacetylene, 0.05 mmol of palladium acetate, 2.00 mmol of silver carbonate and 5 mL of a mixed solvent of n-propanol and water (v / v=9:1) were added to 25 mL Into the three-necked flask, nitrogen was introduced, and the three-necked flask was reacted at 95 °C for 120 min under stirring, and the suspension in the three-necked flask was added to a centrifuge tube for 15 min. Wash with methyl chloride, combine the supernatant liquid and washing liquid after removing the catalyst, centrifuge again, and filter under reduced pressure to obtain a clear solution. An appropriate amount of anhydrous sodium sulfate was added to the obtained clear solution, shaken and stood for 10 minutes to remove water, and the sodium sulfa...

Embodiment 2

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

[0118] The method for cross-checking and localizing liver tumor lesions using the fluorescent probe composition includes the following steps:

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

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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 thereof, and an application in cross-validation and localization of liver tumor lesion tissue. The fluorescent compound A of the present invention can produce selective fluorescent lighting response to normal liver cells in the complex liver tumor microenvironment, but does not respond to liver tumor cells in the liver tumor microenvironment. The fluorescent probe composition of the present invention, the fluorescent compound A and the fluorescent compound B can respectively light up normal liver cells and liver tumor cells, realize interactive verification and localization of normal liver cells and liver tumor cells in liver tumor lesion tissue, and improve the detection and identification efficiency. Accuracy.

Description

technical field [0001] The invention relates to the technical field of biosensing and imaging, in particular to a fluorescent compound and a preparation method thereof, as well as its application in the interactive verification and localization of liver tumor lesions. Background technique [0002] Cancer, both primary and secondary, 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 tumor and tumor microenvironment are an inseparable whole, it brings great difficulties to tumor diagnosis and treatment. Therefore, for doctors, the ability to quickly and accurately locate the tumor lesions that are invisible to the naked eye has become a key factor. [0003] At present, fluorescent probes are mostly used to realize imaging recognition, etc. However, due to the special and com...

Claims

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Application Information

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Patent Type & Authority Patents(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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