Functional molecule with anti-tumor activity, and preparation method and application thereof

A technology of anti-tumor activity and functional molecules, applied in the field of molecular synthesis, can solve problems such as lack of specificity and selectivity, threats to human health, and damage to normal tissues, and achieve good stereoselective, simple and easy-to-operate stereoselective, high The effect of specific and highly selective killing of tumor cells

Pending Publication Date: 2021-08-06
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] As an important cause of human death in the 21st century, cancer is a serious threat to human health. Currently, the main means of treating cancer is chemotherapy. However, due to the lack of specificity and selectivity, it causes harm to normal tissues. Therefore, effective cancer treatment has always been a Focused Issues in Medical Research

Method used

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  • Functional molecule with anti-tumor activity, and preparation method and application thereof
  • Functional molecule with anti-tumor activity, and preparation method and application thereof
  • Functional molecule with anti-tumor activity, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] At 0°C, the excess Fc-COOH (759.132mg, 3.3mmol) was completely dissolved in 5mL of dry anhydrous dichloromethane, EDC (690.084mg, 3.6mmol) was added and stirred for 15min, then BE (702.33mg, 3mmol) was completely dissolved in 3mL of dry anhydrous dichloromethane, then it was added dropwise to the solution of ferrocene in dichloromethane while stirring, after stirring for 15min, DMAP (73.302mg, 0.6mmol) was added, and then at room temperature Under the condition of reaction 24h. After the reaction, with saturated NaHCO 3 The aqueous solution was repeatedly extracted and washed 3 times, and the collected organic phase was dried over anhydrous sodium sulfate and concentrated to dryness. Finally, the crude product was purified by a silica gel column (n-hexane:ethyl acetate=6:1) to obtain Fc-BE as an orange-yellow solid.

[0040] see figure 1 , figure 1 It is the structural formula of the Fc-BE molecule of the present invention. It can be seen from the figure that ferroc...

Embodiment 2

[0047] At 0°C, the excess Fc-COOH (781.2mg, 3.4mmol) was completely dissolved in 5mL of dry anhydrous dichloromethane, EDC (691.11mg, 3.6mmol) was added and stirred for 15min, then BE (703mg, 3mmol ) was completely dissolved in 3mL of dry anhydrous dichloromethane, then it was added dropwise to the solution of ferrocene in dichloromethane while stirring, after stirring for 15min, DMAP (73.5mg, 0.6mmol) was added, and then at room temperature Under reaction 24h. After the reaction was completed, it was extracted and washed three times with saturated NaHCO3 aqueous solution, and the collected organic phase was dried over anhydrous sodium sulfate and concentrated to dryness. Finally, the crude product was purified by a silica gel column (n-hexane:ethyl acetate=6:1) to obtain Fc-BE as an orange-yellow solid.

Embodiment 3

[0049] At 0°C, the excess Fc-COOH (805.11mg, 3.5mmol) was completely dissolved in 5mL of dry anhydrous dichloromethane, EDC (692.084mg, 3.6mmol) was added and stirred for 15min, then BE (701.33mg, 3mmol) was completely dissolved in 3mL of dry anhydrous dichloromethane, then it was added dropwise to the dichloromethane solution of ferrocene while stirring, after stirring for 15min, DMAP (71.302mg, 0.6mmol) was added, and then at room temperature Under the condition of reaction 24h. After the reaction was completed, it was extracted and washed three times with saturated NaHCO3 aqueous solution, and the collected organic phase was dried over anhydrous sodium sulfate and concentrated to dryness. Finally, the crude product was purified by a silica gel column (n-hexane:ethyl acetate=6:1) to obtain Fc-BE as an orange-yellow solid.

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Abstract

The invention discloses a functional molecule with anti-tumor activity, and a preparation method and application thereof, and belongs to the field of molecular synthesis. According to the functional molecule with anti-tumor activity, ferrocenecarboxylic acid in a molecular skeleton is connected with 4-hydroxyphenylboronic acid pinacol ester through an ester group, an ester group bond is hydrolyzed and broken under the stimulation of an acid environment of tumor cells, controllable release of BE and Fc is achieved, then the synergistic effect of reducing GSH and increasing ROS is achieved, and the effect of killing the tumor cells with high specificity and high selectivity is achieved. The preparation method of the functional molecule with anti-tumor activity adopts an esterification reaction of carboxyl and hydroxyl, and has the advantages of high reaction efficiency, mild reaction conditions, good stereoselectivity, simplicity, easiness in operation and the like.

Description

technical field [0001] The invention belongs to the field of molecular synthesis, in particular to a functional molecule with antitumor activity, a preparation method and application thereof. Background technique [0002] As an important cause of human death in the 21st century, cancer is a serious threat to human health. At present, the main means of treating cancer is chemotherapy. However, due to the lack of specificity and selectivity, it causes harm to normal tissues. Therefore, effective cancer treatment has always been a cancer Focus questions in medical research. Compared with human normal cells, tumor cells contain overexpressed reduced glutathione (GSH) and higher hydrogen peroxide (H 2 o 2 ), so it is acidic. Taking advantage of this characteristic, chemodynamic therapy has gradually become a research hotspot in recent years. The principle of chemodynamic therapy is to use the Fenton reaction principle, combined with the acidic microenvironment of the tumor, to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02A61P35/00
CPCC07F17/02A61P35/00
Inventor 白阳尚青青安娜刘彩萍马辑
Owner SHAANXI UNIV OF SCI & TECH
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