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Water-soluble fullerene derivative with determined structure as well as preparation method and application thereof

A fullerene derivative, water-soluble technology, applied in the direction of fullerene, nano-carbon, etc., can solve the problems of difficult analysis, uncertain structure, difficult control of the introduction process of hydroxyl group, etc. high rate effect

Active Publication Date: 2019-07-19
BEIJING FUNAKANG BIOTECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Fullerene alcohol has good water solubility, and preserves part of the structure and properties of fullerene spheres. There are many reports in biomedicine, but in the preparation process of fullerene alcohol, the introduction process of hydroxyl group is not easy to control, and the obtained fullerene The alcohol product is a mixture of fullerenols with different positions and numbers of hydroxyl groups
In addition, most of the water-soluble derivatives of fullerenes are unstable, which makes their in vivo analysis difficult

Method used

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  • Water-soluble fullerene derivative with determined structure as well as preparation method and application thereof
  • Water-soluble fullerene derivative with determined structure as well as preparation method and application thereof
  • Water-soluble fullerene derivative with determined structure as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1: C 60 Preparation of Fullerene Monoaddition Carboxylic Acid Derivatives

[0055] (1) Synthesis of di-tert-butyl bromomalonate

[0056] Di-tert-butyl malonate (200mg, 0.92mmol) was dissolved in tetrahydrofuran (100mL). After complete dissolution, 138μL (0.92mmol) of DBU (CAS accession number: 6674-22-2) was added to In the above solution, the reaction was then warmed to room temperature and stirring was continued for 1 h, after which the reaction was cooled to -78 °C and CBr 4 306mg (0.92mmol), continue to stir for 1.5h, after the reaction is over, use saturated NH 4 Cl solution was quenched, then added n-hexane for extraction, the organic layer was washed twice with saturated NaCl, the aqueous layer was extracted twice with dichloromethane, and washed twice with saturated NaCl, then the organic phase was collected and mixed with anhydrous magnesium sulfate After drying, filter the solution after drying and concentrate to obtain a yellow oily liquid; use di...

Embodiment 2

[0067] Embodiment 2: containing hydroxyl C 60 Preparation of Fullerene Carboxylic Acid Derivatives

[0068] (1) Fullerene C 60 monoaddition ester

[0069] Fullerene C 60 (1g, 1.38mmol) was dissolved in o-xylene (500mL), ultrasonically dissolved completely, stirred at room temperature; 234uL (1.38mmol) of diethyl bromomalonate was dissolved in 3mL o-dichlorobenzene, and added dropwise to the above C 60 In o-dichlorobenzene solution; DBU 206uL (1.38mmol) was dissolved in 3mL o-dichlorobenzene, and added dropwise to the above C 60 In o-dichlorobenzene solution; stir at room temperature, and check the progress of the reaction by thin chromatography while stirring. After the reaction is complete, add 167uL glacial acetic acid to quench the reaction, spin the reaction solution to dryness, dissolve the solid in o-xylene, and use toluene as a rinse The reagent was separated by silica gel column chromatography, and the solid was dried overnight at 50°C.

[0070] (2)C 60 Preparat...

Embodiment 3

[0078] Example 3: metal fullerene Gd@C 82 Preparation of Monoaddition Carboxylic Acid Derivatives

[0079] (1) Metallofullerene Gd@C 82 preparation of

[0080] Gd@C 82 Molecules are passed through the arc discharge method in a DC arc discharge furnace ( method) synthesis.

[0081] (2) Metallofullerene Gd@C 82 -C s The Binger addition reaction, the steps include:

[0082] Under room temperature conditions, nitrogen gas was passed into a 50ml three-neck flask for 30min, then 2g of sodium hydride was added, 40ml of chromatographically pure toluene was added, after stirring for a period of time, 2ml of di-tert-butyl bromomalonate was added, and the solution was stirred until the solution was light yellow, then centrifuged to obtain off-white precipitate and light yellow solution, take 150ml Gd@C 82 The toluene solution was added into a 250ml three-necked flask, nitrogen gas was introduced, the above-mentioned light yellow solution was added dropwise, and stirred at room t...

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Abstract

The invention relates to a water-soluble fullerene derivative with a determined structure as well as a preparation method and application thereof. The accurate structure of the fullerene water-solublederivative can be determined, the fullerene water-soluble derivative can be dissolved in water, the preparation method is simple and high in yield, the problem that a fullerene material is difficultto dissolve in water can be well solved, and the fullerene derivative has wide application in biomedicine.

Description

technical field [0001] The invention relates to a preparation method of water-soluble fullerene / metal fullerene derivatives with definite structure. Background technique [0002] As a new type of carbon nanomaterials, fullerenes and metallofullerenes have broad application prospects in many fields such as biology, medicine, superconductivity, optics and catalysis due to their unique structure and physical and chemical properties. In the field of biology and medicine, fullerene and its derivatives have antioxidant activity, cell protection, antibacterial activity, antiviral effect, drug delivery and tumor treatment. However, fullerene itself is difficult to directly dissolve in biologically friendly media, and the residual organic solvents in the preparation process are likely to cause biological toxicity. Fullerene needs to be chemically modified to further improve its biological activity. There are currently three commonly used methods to improve the water solubility of fu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C01B32/156
CPCC01B32/156
Inventor 王春儒吴波刘丽萍
Owner BEIJING FUNAKANG BIOTECH CO LTD
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