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

A technology of anti-tumor activity and functional molecules, applied in the field of molecular synthesis, can solve the problems of normal tissue harm, threat to human health, lack of specificity and selectivity, etc., achieve high specificity and high selectivity to kill tumor cells, improve The level of reactive oxygen species in tumor cells and the effect of stereoselective type

Inactive Publication Date: 2022-02-18
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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. Howev

Method used

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

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Experimental program
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Effect test

Embodiment 1

[0043] At 0°C, the excess Fc-COOH (460.088mg, 2mmol) was completely dissolved in 3.5mL of dry anhydrous dichloromethane, EDC (460.056mg, 2.4mmol) was added and stirred for 15min, then CA-OH (515.449 mg, 2.2mmol) was completely dissolved in 1mL of dry anhydrous dichloromethane, then it was added dropwise to the solution of ferrocene in dichloromethane while stirring, after stirring for 15min, DMAP (48.868mg, 0.4mmol) was added, Then react at room temperature for 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-CA as an orange-yellow solid.

[0044] see figure 1 , figure 1 It is the structural formula of the Fc-CA molecule of the present invention. It can be seen from the figure that the ferrocenecarboxylic a...

Embodiment 2

[0051] At 0°C, the excess Fc-COOH (462.088 mg, 2 mmol) was completely dissolved in 3.5 mL of dry anhydrous dichloromethane, EDC (460.056 mg, 2.4 mmol) was added and stirred for 15 min, then CA-OH (515.852 mg, 2.2mmol) was completely dissolved in 1mL of dry anhydrous dichloromethane, then it was added dropwise to the solution of ferrocene in dichloromethane while stirring, after stirring for 15min, DMAP (48.459mg, 0.4mmol) was added, Then react at room temperature for 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-CA as an orange-yellow solid.

Embodiment 3

[0053] At 0°C, the excess Fc-COOH (462.786mg, 2mmol) was completely dissolved in 3.5mL of dry anhydrous dichloromethane, EDC (462.176mg, 2.2mmol) was added and stirred for 15min, then CA-OH (515.449 mg, 2.2mmol) was completely dissolved in 1mL of dry anhydrous dichloromethane, then it was added dropwise to the solution of ferrocene in dichloromethane while stirring, after stirring for 15min, DMAP (49.846mg, 0.4mmol) was added, Then react at room temperature for 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-CA as an orange-yellow solid.

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Abstract

The invention discloses a functional molecule with anti-tumor activity, 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 CA-OH through an ester group, acetal bonds in the compound are hydrolyzed and broken under the stimulation of an acid environment of tumor cells, so that the controllable release of CA and Fc is realized, the ROS level is further amplified, 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 normal human cells, tumor cells contain 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 generate reactive oxygen species (mainly OH...

Claims

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Application Information

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IPC IPC(8): C07F17/02A61P35/00
CPCC07F17/02A61P35/00
Inventor 白阳马辑尚青青阎晓晨刘明英
Owner SHAANXI UNIV OF SCI & TECH
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