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Hydroxyl acetylated curcumin and application thereof in preparation of ultrasonic sensitive agent for treating atherosclerosis

A technology of hydroxyacetylated curcumin and atherosclerosis, which is applied in the field of medicinal chemistry and can solve problems such as poor photostability

Active Publication Date: 2015-05-13
HARBIN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The technical problem to be solved by the present invention is to overcome the shortcomings of curcumin as an ultrasonic sensitizer in the treatment of atherosclerosis with poor photostability, and to provide a brand-new ultrasonic sensitizer used in the treatment of atherosclerosis by sonodynamic therapy , Hydroxyl acetylation-curcumin (HAC), and its new application as an ultrasound sensitizer in sonodynamic therapy of atherosclerosis

Method used

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  • Hydroxyl acetylated curcumin and application thereof in preparation of ultrasonic sensitive agent for treating atherosclerosis
  • Hydroxyl acetylated curcumin and application thereof in preparation of ultrasonic sensitive agent for treating atherosclerosis
  • Hydroxyl acetylated curcumin and application thereof in preparation of ultrasonic sensitive agent for treating atherosclerosis

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Embodiment 1

[0029] The preparation of embodiment 1 hydroxyacetylated curcumin

[0030] Dissolve 184mg curcumin in 10mL ethyl acetate, add 127.5mg acetic anhydride and 1 drop of H 2 SO 4 , heated to 60°C and stirred, and after 1 h, 5 mL of water was added. Stand to separate the layers, extract the aqueous layer with 5mL ethyl acetate, combine the ethyl acetate layers, and wash with Na 2 SO 4 After drying, the solvent was distilled off. Recrystallization with methanol and acetonitrile, that is. The chemical structural formula of the obtained hydroxyacetylated curcumin is as shown in formula I:

[0031]

[0032] Its three-dimensional structure is as figure 1 shown.

Embodiment 2

[0033] Example 2 Effect of hydroxyacetylated curcumin-mediated sonodynamic therapy on macrophages

[0034] 1. The effect of hydroxyacetylated curcumin (HAC) alone on the viability of macrophages

[0035]Hydroxyacetylated curcumin (prepared in Example 1) was dissolved in RPMI-1640 culture medium, according to different final concentrations (1 μg / ml, 2.5 μg / ml, 5 μg / ml, 7.5 μg / ml, 10 μg / ml, 15 μg / ml , 20μg / ml, 30μg / ml, 40μg / ml) were added to the culture medium of macrophages, incubated for 4 hours, and the cell viability was detected by CCK-8 colorimetry. The inhibitory effect of cell viability was dose-dependent, and high concentration of hydroxyacetylated curcumin could significantly inhibit the cell viability of macrophages. The results were as follows: figure 2 as shown in a.

[0036] Hydroxyacetylated curcumin (prepared in Example 1) was dissolved in RPMI-1640 culture medium, added to the culture medium of macrophages at a final concentration of 5 μg / ml, and incubated fo...

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Abstract

The invention discloses hydroxyl acetylated curcumin and application thereof in preparation of an ultrasonic sensitive agent for treating atherosclerosis. The hydroxyl acetylated curcumin is a novel drug which is synthesized by carrying out acetylation modification on an unstable group, namely hydroxy of curcumin. Compared with curcumin, hydroxyl acetylated curcumin is more stable in chemical property. Hydroxyl acetylated curcumin-mediated sonodynamic therapy mainly comprises the following steps that intracellular hydroxyl acetylated curcumin is ultrasonically activated to generate singlet oxygen, the singlet oxygen acts on mitochondria to open permeability transition pores (PTP) of the mitochondria, mitochondrial outer membrane potential is reduced and the outer membrane is cracked, substances such as cytochrome C, reactive oxygen species (ROS) and the like inside the mitochondria enter cytoplasm to activate a Caspase passage, intranuclear chromatin is destroyed, and finally cell apoptosis is caused. An experiment result shows that the THP-1 macrophage apoptosis can be effectively induced by the hydroxyl acetylated curcumin-mediated sonodynamic therapy, and the cell survival rate is reduced.

Description

technical field [0001] The invention relates to a derivative of curcumin and its application, in particular to a hydroxyacetylated curcumin and its application in preparing an ultrasonic sensitive agent used for treating atherosclerosis by sonodynamic method. It belongs to the field of medicinal chemistry. Background technique [0002] Curcumin is extracted from the rhizome of the traditional Chinese medicine turmeric, which has anti-inflammatory and anti-tumor effects. Ahn JC has confirmed that curcumin as a photosensitizer can induce tumor cell apoptosis, and Wang F et al. have used curcumin as an ultrasound sensitizer for the study of atherosclerosis [Wang F, Gao Q, Guo S, et al. (2013 ) The Sonodynamic Effect of Curcumin on THP-1Cell-Derived Macrophages. Hindawi Publishing Corporation BioMed Research International doi: 10.1155 / 2013 / 737264; Sharma RA, Steward WP, ​​Gescher AJ (2007) Pharmacokinetics and pharmacodynamics of curcumin and inericexpances ined. Advance biolo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/16C07C67/08A61K41/00A61K31/222A61P9/10
CPCA61K41/0033C07C67/08C07C69/21
Inventor 杨力明田野郑龙彬郭淑媛
Owner HARBIN MEDICAL UNIVERSITY
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