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Lipid molecule with radiotherapy sensitization, preparation method of lipid molecule and application of lipid molecule in tumor radiotherapy drugs

A functional and lipid-based technology, applied in the field of tumor radiotherapy drugs, can solve the problems of low effective drug concentration, limited application, neurotoxic side effects, etc.

Active Publication Date: 2016-05-04
XUZHOU MEDICAL COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, some nitroimidazole radiosensitizers currently being explored at home and abroad are mainly administered through intravenous infusion, distributed throughout the body through blood circulation, and the effective drug concentration in tumor tissue is low.
Nitroimidazole radiotherapy sensitizers need to be taken in large doses to produce sensitizing effects, which in turn produces severe neurotoxic side effects, which limits their clinical application

Method used

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  • Lipid molecule with radiotherapy sensitization, preparation method of lipid molecule and application of lipid molecule in tumor radiotherapy drugs
  • Lipid molecule with radiotherapy sensitization, preparation method of lipid molecule and application of lipid molecule in tumor radiotherapy drugs
  • Lipid molecule with radiotherapy sensitization, preparation method of lipid molecule and application of lipid molecule in tumor radiotherapy drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Synthesis of compound (C16-R)

[0074] Weigh 560mg (3.15mmol) of 2-methyl-5-nitroimidazole-1-ethanol, 1g (3.5mmol) of hexadecanedioic acid and 668mg (3.5mmol) of EDC into a round bottom flask, add 50mLDMSO, add 854mg (7.0mmol) DMAP, react at 40°C for 24h. At the end of the reaction, the solvent was removed using evacuation. Obtain solid using flash chromatography column MeCN:H 2 O was purified at 60-100%. The solvent was removed using a rotary evaporator to obtain 842 mg of a white solid. The yield was 57.4%. 1 HNMR (400MHz, DMSO-d 6 ) 1.24 (CH 2 ,br,20H), 1.33-1.49 (CH 2 -CH 2 -C=O,m,4H),2.15-2.22(CH 2 -C=O,m,4H),2.45(CH 3 -Im,s,3H), 4.36 (CH 2 -Im,t,J=4.2Hz,2H),4.58(CH 2 -CH 2 -Im,t,J=4.2Hz,2H),8.02(Im-H,s,1H),11.94(HO-C=O,br,1H); MS(m / z):[M-H] - calcdforC 23 h 36 N 3 o 6 438.26, found 438.29. (see figure 1 ).

[0075] Synthesis of compound (X-C16-R)

[0076] Take 109mg (0.9mmol) of N,N-dimethyl-3-amino-1,2-propanediol, 842mg (1.9mmol) of compound...

Embodiment 2

[0078] Synthesis of compound (C14-R)

[0079] Weigh 560mg (3.15mmol) of 2-methyl-5-nitroimidazole-1-ethanol, 905mg (3.5mmol) of tetradecanedioic acid and 668mg (3.5mmol) of EDC into a round bottom flask, add 50mLDMSO, add 854mg (7.0mmol) DMAP, react at 40°C for 24h. At the end of the reaction, the solvent was removed using evacuation. Obtain solid using flash chromatography column MeCN:H 2 O was purified at 60-100%. The solvent was removed using a rotary evaporator to obtain 842 mg of a white solid. The yield was 57.4%. 1HNMR (400MHz, CDCl 3 ) 1.25 (CH 2 ,br,16H), 1.55-1.65 (CH 2 CH 2 C(=O)-O,m,4H),2.26(CH 2 C(=O)-OH,t,J=8.0Hz,2H),2.35(CH 2 C(=O)-O,t,J=8.0Hz,2H),2.51(CH 3 -Im,s,3H), 4.42 (Im-CH 2 ,t,J=4.0Hz,2H),4.58(CH 2 -CH 2 -Im,t,J=4.0Hz,2H),7.97(H-Im,s,1H).(see image 3 ).

[0080] Synthesis of compound (X-C14-R)

[0081] Take 132mg (0.9mmol) of 3-diethylamino-1,2-propanediol, 842mg (1.9mmol) of compound (C14-R) and 366mg (1.92mmol) of EDC into a round bot...

Embodiment 3

[0083] Preparation of radiosensitizing liposomes

[0084]Select the ethanol injection method to prepare liposomes, weigh the compound (X-Cn-R) prepared in Example 1 and the auxiliary lipid molecule, the auxiliary lipid molecule is composed of DSPE-PEG2000, DOPC and cholesterol, the lipid The mass fraction of each raw material in the body is: compound (X-Cn-R), 50%; cholesterol 30%; DOPC, 5%; DSPE-PEG2000, 15%; make it fully dissolved in ethanol; The molecules were fully mixed, and liposomes with radiosensitization effects were prepared by ethanol injection method, and the concentration of liposomes was 3 mg / mL.

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Abstract

The invention discloses a lipid molecule with radiotherapy sensitization, a preparation method of the lipid molecule and application of the lipid molecule in tumor radiotherapy drugs. The general structural formula of the lipid molecule (X-Cn-R) with radiotherapy sensitization is shown as the formula (I). The preparation method of the lipid molecule includes the steps that n-ane-diacid and a compound H-R serve as raw materials and are added into a solvent at the amount-of-substance ratio of 1:1.5 and reacted to obtain Cn-R; the compound (Cn-R) and a compound H-X-H are added into a solvent at the amount-of-substance ratio of 1:(2-3) and reacted to obtain the lipid molecule (X-Cn-R) with radiotherapy sensitization; X-Cn-R and an assistant lipid molecule form nanoliposome with radiotherapy sensitization through an ethanol injection method. The liposome gathers at the tumor part in blood circulation through the enhanced permeation and retention effect (EPR), the effective drug concentration of the radiotherapy sensitization agent at the tumor part is increased, and thus the radiotherapy effect on tumors is enhanced.

Description

technical field [0001] The invention relates to a lipid molecule with radiotherapy sensitization function, its preparation method and its application in tumor radiotherapy drugs. Background technique [0002] Cancer is a serious threat to human life due to its high morbidity and mortality. At present, radiation therapy is one of the main means of treating cancer, but due to the hypoxia of solid tumors, even with the maximum possible radiation dose, the tumor still cannot be cured. Therefore, it is necessary to use radiotherapy sensitizers to increase the sensitivity of tumor cells to radiation, so as to improve the effect of radiotherapy. Nitroimidazole compounds have specific radiosensitizing effects on hypoxic cells, such as imizinidazole and metronidazole, which have entered clinical research. However, some nitroimidazole radiosensitizers currently being explored at home and abroad are mainly administered through intravenous infusion, distributed throughout the body thr...

Claims

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Application Information

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IPC IPC(8): C07D233/94A61K31/4178A61P35/00A61N5/10
CPCA61N5/1001C07D233/94
Inventor 刘洪梅于如同章龙珍张亚飞周秀萍刘颖果
Owner XUZHOU MEDICAL COLLEGE
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