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Preparation of mitochondrion-targeting radioprotectant and application of mitochondrion-targeted radioprotectant in radiation damage protection

An anti-radiation and tablet technology, applied in the field of medicine, can solve the problems of severe side effects, high cytotoxicity, and short half-life, and achieve the effect of preventing cell apoptosis, obvious protective effect, and realizing protective effect

Inactive Publication Date: 2018-12-14
FOURTH MILITARY MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned drugs still have many limitations, such as high cytotoxicity, low solubility, short half-life, and serious side effects, etc., which cannot meet the clinical needs.

Method used

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  • Preparation of mitochondrion-targeting radioprotectant and application of mitochondrion-targeted radioprotectant in radiation damage protection
  • Preparation of mitochondrion-targeting radioprotectant and application of mitochondrion-targeted radioprotectant in radiation damage protection
  • Preparation of mitochondrion-targeting radioprotectant and application of mitochondrion-targeted radioprotectant in radiation damage protection

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Synthesis method of compound 1

[0021] (1) Synthesis of p-hydroxybenzaldehyde nitroxide radical

[0022] Weigh 0.275g (2.25mol) of p-hydroxybenzaldehyde and 0.50g of 2,3-dimethyl-2,3-dihydroxyaminobutane, dissolve in 30mL methanol, stir, reflux at 78°C for 24h, spin dry, and obtain the solid Add to 30mL CH 2 Cl 2 Medium, stirring, 0℃, add saturated NaIO 4 Until the solution is dark blue. Let stand, separate into layers, take the organic phase, spin-dry to obtain the crude product. TLC detection, column chromatography to obtain pure product.

[0023] (2) Synthesis of 5-carboxypentyl phosphine bromide

[0024] Weigh 2.62g (TPP, 10mmol) of triphenylphosphine and 2.07g (10.5mmol) of 6-bromohexanoic acid, dissolve in anhydrous acetonitrile, protect under nitrogen, and react under reflux for 16h. The pure product is obtained after recrystallization.

[0025] (3) Synthesis of compound 1

[0026] Weigh 0.199g (0.8mmol) of p-hydroxybenzaldehyde nitroxide radical, 0.469g (1....

Embodiment 2

[0027] Example 2: Synthesis method of compound 2

[0028] (1) Synthesis of vanillin nitroxide radical

[0029] Weigh 0.342g (2.25mol) of vanillin and 0.50g of 2,3-dimethyl-2,3-dihydroxylaminobutane, dissolve in 30mL methanol, stir, reflux at 78°C for 24h, spin dry, and add the resulting solid to 30mL CH 2 Cl 2 Medium, stirring, 0℃, add saturated NaIO 4 Until the solution is dark blue. Let stand, separate into layers, take the organic phase, spin-dry to obtain the crude product. TLC detection, column chromatography to obtain pure product.

[0030] (2) Synthesis of 5-carboxypentyl phosphine bromide

[0031] Weigh 2.62g (TPP, 10mmol) of triphenylphosphine and 2.07g (10.5mmol) of 6-bromohexanoic acid, dissolve in anhydrous acetonitrile, protect under nitrogen, and react under reflux for 16h. The pure product is obtained after recrystallization.

[0032] (3) Synthesis of compound 2

[0033] Weigh 0.237g (0.8mmol) of vanillin nitroxide radical, 0.469g (1.2mmol) of 5-carboxypentylphosphoniu...

Embodiment 3

[0034] Example 3: Synthesis method of compound 3

[0035] (1) Synthesis of p-hydroxybenzaldehyde nitroxide radical

[0036] Weigh 0.275g (2.25mol) of p-hydroxybenzaldehyde and 0.50g of 2,3-dimethyl-2,3-dihydroxyaminobutane, dissolve in 30mL methanol, stir, reflux at 78°C for 24h, spin dry, and obtain the solid Add to 30mL CH 2 Cl 2 Medium, stirring, 0℃, add saturated NaIO 4 Until the solution is dark blue. Let stand, separate into layers, take the organic phase, spin-dry to obtain the crude product. TLC detection, column chromatography to obtain pure product.

[0037] (2) Synthesis of 6-bromohexylphosphonium bromide

[0038] Weigh 2.62g (TPP, 10mmol) of triphenylphosphine and 7.3g (30mmol) of 1,6-dibromohexane, dissolve in anhydrous acetonitrile, and reflux for 12h. TLC detection, column chromatography to obtain pure product.

[0039] (3) Synthesis of compound 3

[0040] Weigh 0.199g (0.8mmol) of p-hydroxybenzaldehyde nitroxide radical, 0.51g (1mmol) of 6-bromohexyl phosphine bromide...

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PUM

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Abstract

The invention relates to preparation of a mitochondrion-targeting radioprotectant and an application of the mitochondrion-targeting radioprotectant in radiation damage protection and belongs to the technical field of medicine. The medicine combines free radicals of nitroxide and triphenylphosphine cations through covalent bonds, and the whole molecule is driven to be quickly enriched on mitochondrion in a potential dependence manner under the joint drive of cell membrane potential and mitochondrion membrane potential, so that the mitochondrion targeting of the compound is realized, and the synthesis method is simple; meanwhile, the radioprotectant has higher free radical scavenging capacity, has the protection degree for anti-oxidative damage of mitochondrion multiple times higher than that of traditional nonselective antioxidants, has better inhibition functions on radiation damage and has the effects equivalent to those of a positive control drug WR2721.

Description

Technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to a new type of drug structure that protects against radiation damage with a mitochondrial targeting function. Background technique [0002] In recent years, with the widespread application of nuclear technology in the fields of national defense, industry, agriculture, and medical care, the relationship between ionizing radiation and humans has become closer. In particular, China has entered a period of rapid development of nuclear technology. For example, in the national defense industry, workers related to the manufacture and use of nuclear submarines and nuclear weapons have problems with ionizing radiation damage and protection; the development of national aerospace industry, astronauts in space The environment also has high-energy ionizing radiation and γ-ray damage and protection to the body; under the current international situation, the possibility of using nuclear w...

Claims

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Application Information

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IPC IPC(8): C07F9/6506A61P39/00
CPCA61P39/00
Inventor 王海波李博刘玉枝王晋丁桂荣
Owner FOURTH MILITARY MEDICAL UNIVERSITY
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