CN106220651B - A kind of class of anthrone containing amino oxygen functionalization graphene material and preparation method thereof and as the application prepared on antitumor drug - Google Patents
A kind of class of anthrone containing amino oxygen functionalization graphene material and preparation method thereof and as the application prepared on antitumor drug Download PDFInfo
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- CN106220651B CN106220651B CN201610564223.XA CN201610564223A CN106220651B CN 106220651 B CN106220651 B CN 106220651B CN 201610564223 A CN201610564223 A CN 201610564223A CN 106220651 B CN106220651 B CN 106220651B
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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Abstract
A kind of class of anthrone containing amino oxygen functionalization graphene material and preparation method thereof and the stable class drug of anthrone containing amino oxygen is obtained by carboxylated graphene and the class covalent bond of anthrone containing amino oxygen as the application prepared on antitumor drug.Cell experiment shows that the drug has good antitumous effect.The object of the present invention is to provide a kind of building-up process is simple and convenient, the preparation method of the efficient class of anthrone containing the amino oxygen functionalization graphene drug of low toxicity.The method can simply and easily prepare antitumor drug, also provide the developing way of compound functional material antitumor drug.
Description
Technical field
The present invention relates to biomedicine technical fields, and in particular to a kind of class functionalization graphene material of anthrone containing amino oxygen
And preparation method thereof and as the application prepared on antitumor drug.
Background technology
Tumour is the common common disease for endangering human health, frequently-occurring disease, mostly can be in the tumour that whole body occurs
Eye occurs, and wherein mela-noma of choroid (choroidalmelanoma) is the most common intraocular malignant of adult.It is disliking
In three big therapies of property tumour, drug therapy occupies an important position.In antitumor drug design field, with DNA, RNA
It is designed the main think of that often people consider based on various secondary structures and oncogene transcription, expression equally correlated process
Road because many compounds often through with cancer cell DNA in conjunction with and influence its replicate or block related gene, albumen expression
And show active anticancer.Modern pharmacology research proves, the ketone compounds of anthracene containing amino oxygen can by with topoisomerase II,
The rakes points such as DNA alkylations, the intercalation of DNA, crosslinking DNA, alpha-glucosidase and aromatase enzyme act on and generate antitumor action.Carboxyl fossil
Black alkene is a kind of new carbon haveing excellent performance, and has high specific surface area, the abundant functional group in surface, good biofacies
The characteristics such as capacitive.
Invention content
In order to solve the problems, such as existing technology, the present invention provides a kind of class functionalization graphene materials of anthrone containing amino oxygen
Material and preparation method thereof and as the application prepared on antitumor drug.
The technical solution that the present invention uses is：A kind of class functionalization graphene material of anthrone containing amino oxygen, it is described
The class functionalization graphene material of anthrone containing amino oxygen is carboxylated graphene-amino oxygen anthrone class compound, chemical structural formula
It is as follows：
A kind of preparation method of the class of anthrone containing amino oxygen functionalization graphene material, includes the following steps：It is added in bottle
Mass concentration is the carboxylated graphene dispersing solution of 0.05-0.5g/L, adds catalyst, the object of anthrone containing amino oxygen is added dropwise
The ethanol solution of matter, stirring in water bath heat 2-24h, obtained product utilization membrane filtration, and freeze-drying contains to get described
Amino oxygen anthrone class functionalization graphene compound.
The class quality of anthrone containing amino oxygen is 0.005g-0.05g.
The catalyst is N- hydroxysuccinimides and dicyclohexylcarbodiimide.
N- hydroxysuccinimides and dicyclohexylcarbodiimide usage ratio are 1: 1 in the catalyst.
The water bath heating temperature is 30-70 DEG C.
A kind of class functionalization graphene material of anthrone containing amino oxygen is as the application prepared on antitumor drug.The present invention
Advantageous effect be：A kind of class functionalization graphene material of anthrone containing amino oxygen and preparation method thereof and antitumor as preparing
Application on drug obtains stable anthrone containing amino oxygen by carboxylated graphene and the class covalent bond of anthrone containing amino oxygen
Class drug.Cell experiment shows that the drug has good antitumous effect.The object of the present invention is to provide a kind of building-up processes
It is simple and convenient, the preparation method of the less toxic efficiently class of anthrone containing amino oxygen functionalization graphene drug.The method can be simply square
Just prepare antitumor drug, also provide the developing way of compound functional material antitumor drug.
Description of the drawings
Fig. 1 be the functionalization graphene of anthrone containing amino oxygen before modified after ultraviolet spectrogram.
Toxicity test point of Fig. 2 anthrones containing amino oxygen functionalization graphene to human choroidal melanoma cells OCM-1
Analysis figure.
Specific implementation mode
It in order to illustrate more clearly of the content of present invention, is described as follows with specific embodiment, specific embodiment does not limit this hair
Bright context.
Embodiment 1
It takes the carboxylated graphene solution of a concentration of 0.05mg/L to be placed in the three-necked bottle of 250mL, catalyst n-hydroxyl is added
50 μ L of base succimide and dicyclohexylcarbodiimide, wherein N- hydroxysuccinimides and dicyclohexylcarbodiimide dosage
Ratio is 1: 1, and the ethanol solution 20mL of 0.02g anthrones containing amino oxygen is added dropwise, and heats 5h in 30 DEG C of stirred in water bath, obtains
Product filtering, freeze-drying, preserve to get the class functionalization graphene drug of anthrone containing amino oxygen.
Embodiment 2
It takes the carboxylated graphene solution of a concentration of 0.10mg/L to be placed in the three-necked bottle of 250mL, catalyst n-hydroxyl is added
80 μ L of base succimide and dicyclohexylcarbodiimide, wherein N- hydroxysuccinimides and dicyclohexylcarbodiimide dosage
Ratio is 1: 1, and the ethanol solution 20mL of 0.02g anthrones containing amino oxygen is added dropwise, and heats 9h in 45 DEG C of stirred in water bath, obtains
Product filtering, freeze-drying, preserve to get the class functionalization graphene drug of anthrone containing amino oxygen.
The class functionalization graphene of anthrone containing amino oxygen with high-efficiency low-toxicity antitumor action prepared according to the above experiment
Composite material, it can be seen that building-up process is easy to operate, and yield is high.The product compound of anthrone containing amino oxygen of gained, to tumour
Cell has stronger bio-toxicity.Fig. 1 is the functionalization graphene of anthrone containing amino oxygen rear ultraviolet spectrogram before modified, wherein
(a) carboxylated graphene；(b) amino oxygen anthrone；(c) carboxylated graphene-amino oxygen anthrone.As can be seen from FIG. 1, with raw material carboxylic
Base graphite alkene is compared with amino oxygen anthrone, and product has carboxylated graphene and amino oxygen anthrone simultaneously on ultraviolet spectrogram
Characteristic peak, but there is faint blue shift in ultraviolet peak, illustrates that the electron transition for occurring n → π * in product, product are prepared into
Work(.Fig. 2 is cell toxicant of the product amino oxygen anthrone class functionalization graphene to human choroidal melanoma OCM-1 cells for 24 hours
Property experimental result, as can be seen from the figure amino oxygen anthrone class functionalization graphene to OCM-1 cells have obvious inhibiting effect,
The amino oxygen anthrone class functionalization graphene polymer composite of targets neoplastic cells prepared by the above experiment, building-up process operation
Simply, yield is high.The product anti-tumor target of gained is more, has good inhibiting effect to tumour cell, to find new resist
Tumour medicine provides new approaches.
Claims (7)
1. a kind of class functionalization graphene material of anthrone containing amino oxygen, which is characterized in that the class function of anthrone containing amino oxygen
Graphite alkene material is carboxylated graphene-amino oxygen anthrone class compound, and chemical structural formula is as follows：
。
2. a kind of preparation method of the class of anthrone containing amino oxygen functionalization graphene material described in claim 1, which is characterized in that
Include the following steps：The carboxylated graphene dispersing solution that mass concentration is 0.05-0.5g/L is added in bottle, adds catalysis
Agent, is added dropwise the ethanol solution of the substance of anthrone containing amino oxygen, and stirring in water bath heats 2-24h, obtained product utilization filter membrane
Filtering is freeze-dried to get the class functionalization graphene compound of anthrone containing amino oxygen.
3. the preparation method of the class of anthrone containing amino oxygen functionalization graphene material according to claim 2, which is characterized in that
The material mass of anthrone containing amino oxygen is 0.005g-0.05g.
4. the preparation method of the class of anthrone containing amino oxygen functionalization graphene material according to claim 2, which is characterized in that
The catalyst is N- hydroxysuccinimides and dicyclohexylcarbodiimide.
5. the preparation method of the class of anthrone containing amino oxygen functionalization graphene material according to claim 4, which is characterized in that
N- hydroxysuccinimides and dicyclohexylcarbodiimide usage ratio are 1 in the catalyst：1.
6. the preparation method of the class of anthrone containing amino oxygen functionalization graphene material according to claim 2, which is characterized in that
The water bath heating temperature is 30-70 DEG C.
7. a kind of class of anthrone containing amino oxygen functionalization graphene material answering on preparing antitumor drug described in claim 1
With.
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| CN108047236B (en) * | 2017-11-29 | 2020-04-24 | 温州医科大学 | Aminoxanthenone modified graphene AG, preparation method thereof and application of Aminoxanthenone modified graphene AG in preparation of hydrazine yellow fluorescence detection reagent |
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