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Preparation method of tirapazamine-gold nanoparticle compound and application of tirapazamine-gold nanoparticle compound

A technology of gold nanoparticles and tirapazamine, which is applied in the field of preparation of tirapazamine-gold nanoparticle composites, can solve problems such as not having functional groups, and achieve the effect of improving the radiation dose effect

Active Publication Date: 2015-05-06
INST OF MODERN PHYSICS CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The gold nanoparticles currently used as radiation sensitizers are only surfactant-coated gold nanoparticles without other functional groups.

Method used

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  • Preparation method of tirapazamine-gold nanoparticle compound and application of tirapazamine-gold nanoparticle compound
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  • Preparation method of tirapazamine-gold nanoparticle compound and application of tirapazamine-gold nanoparticle compound

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Embodiment 1

[0059] Embodiment 1: a kind of tirapazamine-gold nanoparticle composite, its main feature is that the tirapazamine of outer layer is connected with inner core gold nanoparticle by connecting part, and its structure can be simplified to formula (I) ,See figure 1 .

[0060] The gold nanoparticle is 1.5-400nm, and has a magnetic-gold nanoparticle core-shell structure; the surface of the gold nanoparticle is covered with a protective group (PG), and the protective group includes mercapto polyethylene glycol Alcohol (PEG), sodium citrate, N-(2-mercaptopropionyl)-glycine (tiopronin), thiol-containing amino acids and their salts, lipoic acid, sulfhydryl-containing C 3 -C 18 One or more mixed combinations of acids and their salts;

[0061] Described TPZ is tirapazamine;

[0062] Linking part is selected from SH-(CH 2 ) n -(CHR 1 ) m -CO-,SH-(CH 2 ) n -(CH 2 O) m -CH 2 -CO-,R 1 3 N + -(CH 2 ) n-CO-,R 1 3 N + -(CH 2 ) n -(CH 2 O) m -CH 2 -CO-,R 1 S-S-CH(R 2 )...

Embodiment 2

[0063] Embodiment 2: described tirapazamine-gold nanoparticle complex, described gold nanoparticle size is preferably 10-100nm gold nanoparticle or ferric oxide magnetic-gold nanoparticle with core-shell structure; The linking part described is preferably (see figure 2 ):

[0064] where n=1-18, m=1-18, R 1 and R 2 for C 1 -C 5 of alkyl.

[0065] All stereoisomers, geometric isomers and tautomers of the general formula (I) of the present invention, wherein each atom includes all isotopes. When one or more chiral centers are present in the molecule, the complex according to formula (I) may be in the form of a pharmaceutically acceptable racemic mixture or in the form of a single stereoisomer. The complexes of the invention also include tautomeric forms. Tautomeric forms result from the exchange of a single bond with an adjacent double bond accompanied by the migration of a proton; the complexes of the invention also include atoms of all isotopes, whether in intermediate ...

Embodiment 3

[0067] Embodiment 3: the preparation method of tirapazamine-gold nanoparticle composite, its steps are:

[0068] The first step, synthesis of tirapazamine-linking part: dissolve 1.0 g of acid containing mercapto or disulfide bond in 50 mL of dichloromethane, add 5.0 mL of triethylamine, stir overnight, then add 1-ethyl-( 3-Dimethylaminopropyl) carbodiimide hydrochloride 1.0g, and N-hydroxybenzotriazole 0.8g, stirred at room temperature for 5.0 hours, then added tirapazamine 2.0g, stirred overnight; added water 20mL , liquid separation, column chromatography after the organic phase is concentrated, and the product tirapazamine-connecting part is obtained;

[0069] The second step, the preparation of gold nanoparticles: add 1000mL solvent respectively in the there-necked flask, add 100mL concentration 10% chloroauric acid solution simultaneously, heat to boil; Add 100mL 1% surfactant solution rapidly, boil 200min, stop Heating and cooling to room temperature; centrifugation at ...

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Abstract

The invention discloses a preparation method of a tirapazamine-gold nanoparticle compound and an application of the tirapazamine-gold nanoparticle compound. The tirapazamine-gold nanoparticle compound is mainly characterized by being formed by connecting tirapazamine on an outer layer and kernel gold nanoparticles through a connecting part; the preparation method of the tirapazamine-gold nanoparticle compound comprises the following three steps: (1) condensing the tirapazamine and carboxylic acid containing sulfydryl or a disulfide bond into a tirapazamine-connecting part under the action of a condensing agent; and (2) preparing the gold nanoparticles; and (3) dissolving the tirapazamine-connecting part into a solvent, adding the mixture to water-soluble gold nanoparticles, and preparing the tirapazamine-gold nanoparticle compound through ligands interchange reaction. The preparation method has the advantages that the tirapazamine-gold nanoparticle compound is capable of enhancing the yield of free radicals under the irradiation of an X ray; the biggest enhancement coefficient can reach 4 times; radiation injuries to hepatoma carcinoma cells caused by the X ray are enhanced by the tirapazamine-gold nanoparticle compound; and the enhancement of the X ray in hepatoma carcinoma cell lethal effect can reach 20%.

Description

technical field [0001] The invention relates to a preparation method and application of tirapazamine-gold nanoparticle composite. Background technique [0002] Cancer is a common and frequently-occurring disease that seriously endangers human life and health. It has become the number one killer of human beings in the new century and one of the largest public health problems in the world (Globocan, IARC, 2010, 2008). According to the "2012 China Cancer Registration Annual Report" released: "One person is diagnosed with cancer every 6 minutes nationwide, 8,550 people become cancer patients every day, and one person dies of cancer in every seven to eight people." "National Cancer Incidence The situation is grim, and the morbidity and mortality are on the rise, with about 3.5 million new cancer cases and 2.5 million cancer deaths every year. Radiation therapy, surgery and chemotherapy are the three conventional means of cancer treatment at present. In the current treatment of p...

Claims

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Application Information

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IPC IPC(8): A61K47/48A61K31/53A61K41/00A61P35/00
Inventor 陈卫强李强刘岩刘玺
Owner INST OF MODERN PHYSICS CHINESE ACADEMY OF SCI
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