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Cholesterol derivative-modified multi-molybdenum oxygen cluster hybrid and preparation and application thereof

A technology of cholesterol derivatives and polymolybdenum oxygen clusters, which can be used in drug combinations, inorganic active ingredients, organic active ingredients and other directions, can solve the problems of poor anti-breast cancer cell effect and the like, and achieves cheap raw materials, simple preparation method and high yield. Effect

Active Publication Date: 2019-03-01
ZHONGBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The research results showed that the anti-breast cancer cell effect of the hybrid was very poor, and the survival rate of breast cancer cells was still as high as 70% when the dose was 400µg / mL (Bioorganic & MedicinalChemistry Letters. 2013, 23: 1462.)

Method used

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  • Cholesterol derivative-modified multi-molybdenum oxygen cluster hybrid and preparation and application thereof
  • Cholesterol derivative-modified multi-molybdenum oxygen cluster hybrid and preparation and application thereof
  • Cholesterol derivative-modified multi-molybdenum oxygen cluster hybrid and preparation and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Weigh 0.8g chemical formula as [(C 4 h 9 ) 4 N] 3 (MnMo 6 o 18 )[(OCH 2 ) 3 CNH 2 ] 2 Polymolybdenum oxide clusters, 1.49g 3,3'-dicholesterol succinimidazole monoester dipropylamino succinic acid monoamide, 0.24g 1-ethyl-(3-dimethylaminopropyl) carbodiimide Hydrochloride, 0.15g N -Hydroxysuccinimide and 20mg triethylamine were dissolved in a mixed solvent of 120mL chloroform and 60mL acetonitrile, and reacted at 22°C for 24h.

[0047] The reaction solution was washed three times with deionized water, the organic phase was collected, and the solvent was spin-dried to obtain a crude product. The crude product was redissolved in chloroform, and added to cyclohexane for precipitation. The precipitate was collected and dried in vacuum to obtain the cholesterol derivative-modified polymolybdenum-oxygen cluster hybrid.

[0048] figure 1 and figure 2 The IR spectra and H NMR spectra of the above products are given respectively. Combined with the above spectrum, ...

Embodiment 2

[0050] Weigh 1.2g of chemical formula as [(C 4 h 9 ) 4 N] 3 (MnMo 6 o 18 )[(OCH 2 ) 3 CNH 2 ] 2 Polymolybdenum oxide clusters, 2.23g 3,3'-dicholesterol succinimidazole monoester dipropylamino succinic acid monoamide, 0.37g 1-ethyl-(3-dimethylaminopropyl) carbodiimide Hydrochloride, 0.22g N -Hydroxysuccinimide and 30mg triethylamine were dissolved in a mixed solvent of 180mL chloroform and 90mL acetonitrile, and reacted at 30°C for 48h.

[0051] The reaction solution was washed three times with deionized water, the organic phase was collected, and the solvent was spin-dried to obtain a crude product. The crude product was redissolved in chloroform, and added to cyclohexane for precipitation. The precipitate was collected and dried in vacuum to obtain the cholesterol derivative-modified polymolybdenum-oxygen cluster hybrid.

Embodiment 3

[0053] Weigh 1.5g of chemical formula as [(C 4 h 9 ) 4 N] 3 (MnMo 6 o 18 )[(OCH 2 ) 3 CNH 2 ] 2 Polymolybdenum oxide clusters, 2.79g 3,3'-dicholesterol succinimidazole monoester dipropylamino succinic acid monoamide, 0.46g 1-ethyl-(3-dimethylaminopropyl) carbodiimide Hydrochloride, 0.28g N -Hydroxysuccinimide and 55 mg of triethylamine were dissolved in a mixed solvent of 226 mL of chloroform and 113 mL of acetonitrile, and reacted at 38° C. for 72 h.

[0054] The reaction solution was washed three times with deionized water, the organic phase was collected, and the solvent was spin-dried to obtain a crude product. The crude product was redissolved in chloroform, and added to cyclohexane for precipitation. The precipitate was collected and dried in vacuum to obtain the cholesterol derivative-modified polymolybdenum-oxygen cluster hybrid.

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Abstract

The invention discloses a cholesterol derivative-modified multi-molybdenum oxygen cluster hybrid. The chemical formula of the cholesterol derivative-modified multi-molybdenum oxygen cluster hybrid is[(C4H9)4N]3{(MnMo6O18)[CNH(CH2O)3O72H116N3O8]2} and is shown as the structural formula (I), wherein POM=MnMo6O18, and TBA=[(C4H9)4N]+. The cholesterol derivative-modified multi-molybdenum oxygen cluster hybrid is prepared by taking a multi-molybdenum oxygen cluster with a chemical formula of [(C4H9)4N]3(MnMo6O18)[(OCH2)3CNH2]2, 3, 3'-dicholesterol succinyl imidazole monoester dipropyl amine succinate monoamide, 1-ethyl-(3-dimethyl aminopropyl) carbondiimide hydrochloride, N-hydroxysuccinimide and trimethylamine as raw materials for reaction in a chloroform-acetonitrile mixed solvent system. The cholesterol derivative-modified multi-molybdenum oxygen cluster hybrid is applied to preparation of anti-breast cancer drugs and achieves high killing effects on human breast adenocarcinoma cell lines (MCF-7).

Description

technical field [0001] The invention relates to biomolecule-modified heteropolyacid hybrids, in particular to a polymolybdenum-oxygen cluster hybrid modified by cholesterol derivatives, a preparation method and anticancer application of the hybrid. Background technique [0002] In recent years, due to industrial pollution and people's bad living habits, cancer has become one of the important factors of death among urban and rural residents in our country. According to the survey, an average of 7 people are diagnosed with cancer every minute in our country, and 4 people die of cancer. How to treat cancer has become a major problem that humans need to solve. [0003] Before the 1940s, cancer treatments mainly included surgery and radiotherapy. However, surgical treatment and radiotherapy are local treatments. Due to the characteristics of rapid metastasis of cancer cells, the effect of surgical treatment and radiotherapy is limited, especially for patients with advanced canc...

Claims

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Application Information

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IPC IPC(8): A61K33/32A61K47/55A61K31/575A61P35/00
CPCA61K31/575A61K33/32A61K47/55A61P35/00A61K2300/00
Inventor 杨海宽宋平邱绍升王钰婷李文旋张哲菁
Owner ZHONGBEI UNIV
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