Fluorescent probe containing active molecules of flavonoids and its preparation method and application

A technology of drug active molecules and fluorescent probes, which is applied in the field of fluorescent probes containing flavonoid drug active molecules and its preparation and application, can solve the problems of complex components, restrictions on the clinical application of natural product drugs, and the inability to determine the molecular mechanism of action. Biological function pathways and other issues to achieve good proliferation inhibitory effect

Active Publication Date: 2021-01-01
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a natural product, Scutellaria baicalensis has complex components. At present, scientists are still unable to determine the molecular mechanism of action and the pathway of biological functions that produce drug effects. The resulting problems have always been the bottleneck restricting the clinical application of natural product drugs.

Method used

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  • Fluorescent probe containing active molecules of flavonoids and its preparation method and application
  • Fluorescent probe containing active molecules of flavonoids and its preparation method and application
  • Fluorescent probe containing active molecules of flavonoids and its preparation method and application

Examples

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preparation example Construction

[0041] The present invention also provides a method for preparing the above-mentioned fluorescent probe containing flavonoid drug active molecules, wherein the method comprises the following steps,

[0042] 1) make the compound of structure shown in formula (2) and Carrying out an amide condensation reaction to obtain an intermediate compound represented by the general formula L-Y, wherein n is an integer of 1-6;

[0043] 2) Mannich reaction is carried out between the intermediate compound represented by the general formula L-Y and the compound represented by the formula (1), to obtain a fluorescent probe containing active molecules of flavonoids represented by the general formula X-L-Y.

[0044] According to the present invention, the compound of the structure shown in formula (2) can be commercially available, and can also be synthesized after optimization by conventional methods in the art. When the synthesis is obtained, for example, references (1) Anzalone, A.V.; Wang, ...

preparation example 1

[0079] This preparation example is used to illustrate the preparation of the compound with the structure shown in formula (2).

[0080]

[0081](1) Add 3.23g (20mmol) of 7-hydroxy-2-quinolone (compound 1) into 90mL tetrahydrofuran, slowly add 1.22g (32mmol) lithium aluminum hydride with stirring in an ice bath, heat to reflux, and react overnight. After the reaction was stopped, it was cooled, and 35.0 ml of saturated ammonium chloride solution was added immediately to quench the reaction, extracted with ethyl acetate, and the organic phase was washed with saturated sodium chloride solution, and then concentrated to obtain 2.83 g of a yellow solid with a yield of 95%. ESI-MS(m / z):[M+H] + calcd.for C 9 h 11 NO, 150.09; found, 150.25.

[0082] (2) Add 2.50 g (16.8 mmol) of 7-hydroxy-1,2,3,4-tetrahydroquinoline (compound 2) to 65 mL of acetic acid, and slowly add 2.53 g (67.2 mmol) of sodium borohydride while stirring at room temperature. When about half of the raw materia...

preparation example 2

[0089] This preparation example is used to illustrate the preparation of the compound with the structure shown in formula (6).

[0090]

[0091] (1) Mix 400mg (0.78mmol) of the compound of the structure shown in the formula (2-1) and the mixture of the compound of the structure shown in the formula (2-2) (the mixing molar ratio is 1:1), 179.5mg (0.94mmol) 1-Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI), 126.5 mg (0.94 mmol) 1-hydroxybenzotriazole (HOBT) and 325.5 μL triethylamine were added Into 100mL of dry dichloromethane, stirred at 50°C for 1-2h. Add 285 μL of 1,8-diamino-3,6-dioxahexane and continue the reaction for 24 hours. Add water to terminate the reaction, extract and concentrate to obtain a mixture of the compound represented by formula (6-1) and the compound represented by formula (6-2), which is a dark red solid (0.20 g, yield 40.3%). A part was taken out from the above mixture and separated to obtain the compound with the structure shown in...

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Abstract

The invention relates to the field of fluorescent probes, and discloses a fluorescent probe containing a flavone-based drug active molecule, a preparation method and applications thereof, wherein thefluorescent probe is represented by a general formula X-L-Y, X is a flavone-based drug active structure represented by the following formula (1), Y is a fluorophore represented by the following formula (2), the coupling structure L is defined in the specification, n is an integer of 1-6, and in the formula (1), R<1>, R<4>, R<5> and R<6> are respectively and independently selected from hydrogen, hydroxyl and C1-C6 alkoxy, R<2> is selected from hydrogen or hydroxyl, and R<3> is oxygen. According to the present invention, the fluorescent probe containing the flavone-based drug active molecule hascharacteristics of specific targeting property and high proliferation inhibitory activity on tumor or cancer cells. The formulas (1) and (2) are defined in the specification.

Description

technical field [0001] The invention relates to a fluorescent probe containing flavonoid drug active molecules, a preparation method and application thereof. Background technique [0002] Scutellaria baicalensis is a traditional flavonoid traditional Chinese medicine used for inflammation and detumescence, and has many pharmacological effects such as anti-inflammation, detumescence, anti-virus and anti-cancer. As a natural product, Scutellaria baicalensis has complex components. At present, scientists are still unable to determine the molecular mechanism of action and the pathway of biological functions that produce drug effects. The resulting problems have always been the bottleneck restricting the clinical application of natural product drugs. [0003] Fluorescence microscopy is a newly emerging analysis technique in recent years, and has been widely used in the fields of environmental science, medicine, pharmacy and biology, especially in the fields of medicine and biolog...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/147C09K11/06G01N21/64A61K31/4375A61P35/00
CPCC07D491/147C09K11/06G01N21/6486
Inventor 汪福意梁塑罗群
Owner INST OF CHEM CHINESE ACAD OF SCI
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