CN105906540B - Compound and its preparation method and application - Google Patents
Compound and its preparation method and application Download PDFInfo
- Publication number
- CN105906540B CN105906540B CN201610299299.4A CN201610299299A CN105906540B CN 105906540 B CN105906540 B CN 105906540B CN 201610299299 A CN201610299299 A CN 201610299299A CN 105906540 B CN105906540 B CN 105906540B
- Authority
- CN
- China
- Prior art keywords
- formula
- compound shown
- compound
- gold nanoparticle
- gold
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 0 COCCN=CCOCC[*+] Chemical compound COCCN=CCOCC[*+] 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22F—WORKING METALLIC POWDER; MANUFACTURE OF ARTICLES FROM METALLIC POWDER; MAKING METALLIC POWDER; APPARATUS OR DEVICES SPECIALLY ADAPTED FOR METALLIC POWDER
- B22F9/00—Making metallic powder or suspensions thereof
- B22F9/16—Making metallic powder or suspensions thereof using chemical processes
- B22F9/18—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds
- B22F9/24—Making metallic powder or suspensions thereof using chemical processes with reduction of metal compounds starting from liquid metal compounds, e.g. solutions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
Abstract
The present invention relates to compound and its preparation method and application, specifically, the compound is stereoisomer, dynamic isomer, solvate, metabolite, pharmaceutically acceptable salt or its prodrug of compound shown in compound shown in formula (I) or formula (I), and the compound has active anticancer；Further, gold nanoparticle can be prepared by the use of the compound as reducing agent and stabilizer, prepares gold nanoparticle so as to one-step method, and the gold nanoparticle prepared shows excellent active anticancer.
Description
Technical field
The present invention relates to technical field of pharmaceuticals, specifically, the present invention relates to compound and its preparation method and application, have more
Body, the present invention relates to compound and its preparation method and application shown in formula (I).
Background technology
Gold nanoparticle refers to gold grain of the diameter in 1-100 nanometer ranges, it with metal nanoparticle except being total to
Outside some performances, also with special biological affine effect.In general, the preparation of gold nanoparticle needs two-step method：Chlorine gold
The reduction of acid and the stabilization of gold nanoparticle.Common reducing agent has sodium borohydride, ascorbic acid, and common stabilizer is then
Mercaptan.Gold nanoparticle is widely used in biomedicine, is mainly used for the diagnose and treat of the diseases such as cancer.
However, the preparation method of gold nanoparticle still has much room for improvement at present.
The content of the invention
It is contemplated that solve at least some of the technical problems in related technologies.
The present invention is inventor based on the finding that being obtained：
Selenium element has unique redox property, can regulate and control human body as one of the essential trace elements of the human body
Interior redox equilibrium.Selenium-containing compound can participate in a series of important physiology courses, have anti-oxidant, removing free radical etc.
Beneficial biological effect.Meanwhile some researches show that, some small molecules containing selenium can show good active anticancer, therefore in cancer
Disease therapy field has potential application value.So, gold nanoparticle can be combined with selenium-containing compound, explores it
In further applying for anti-cancer field.On the one hand, the reproducibility based on selenium-containing compound and selenium-metallographic interaction, it is possible to
Realize that one-step method prepares the gold nanoparticle that selenium element is stablized.On the other hand, the gold nanoparticle in the system containing selenizing with closing
Thing may produce cooperative effect, show excellent active anticancer.
According to the first aspect of the invention, the present invention proposes a kind of compound, it is compound shown in formula (I) or formula (I)
The stereoisomer of shown compound, dynamic isomer, solvate, metabolite, pharmaceutically acceptable salt or it before
Medicine,
The compound has active anticancer, and cell apoptosis assay shows that the compound can kill cancer cell, mouse experiment
Show, the compound is inhibited to solid tumor；Further, reducing agent and stabilizer are used as by the use of the compound
Gold nanoparticle can be prepared, specifically, the compound reduction gold chloride (HAuCl4) generate gold nanoparticle and incite somebody to action
It is stablized, and gold nanoparticle is prepared so as to one-step method, and the gold nanoparticle prepared is stable, size uniformity, and
And the gold nanoparticle prepared shows excellent active anticancer, cell apoptosis assay shows, the gold which stablizes
Nano-particle can effectively kill cancer cell；Mouse experiment shows that the gold nanoparticle has solid tumor obvious inhibitory action.
According to the second aspect of the invention, the present invention proposes a kind of method for preparing compound shown in formula (I), including：
(1) contact of compound shown in compound shown in formula 1 and formula 2, to obtain compound shown in formula 3；
(2) compound shown in formula 3 and the contact of two selenizing disodiums, to obtain compound shown in formula 4；
(3) compound is contacted with compound shown in formula 5 shown in formula 4, to obtain compound shown in formula (I),
Compound shown in the formula (I) can be effectively prepared using the method.
According to some embodiments of the present invention, the step (1) includes：
(1-1) mixes compound shown in the formula 1 with triethylamine, to obtain the first mixed liquor；
(1-2) mixes compound shown in the formula 2 with dichloromethane, to obtain the second mixed liquor；
Second mixed liquor is added dropwise in first mixed liquor by (1-3), in 30 degrees Celsius, when stirring reaction 3 is small,
To obtain compound shown in formula 3.Thus, it is possible to further effectively prepare compound shown in formula (I).
According to some embodiments of the present invention, the step (2) includes：
(2) under 50 degrees Celsius, in acetonitrile, contact compound shown in the formula 3 and two selenizing disodiums, to obtain
Compound shown in formula 4.Thus, it is possible to further effectively prepare compound shown in formula (I).
According to some embodiments of the present invention, the step (3) includes：
(3) at room temperature, in tetrahydrofuran, sodium borohydride and sodium hydroxide are added, make compound shown in the formula 4 with
Compound shown in the formula 5 contacts, to obtain compound shown in formula (I).Thus, it is possible to further effectively prepare formula
(I) compound shown in.
, wherein it is desired to explanation, in the present invention, " compound shown in Formula X " with " compound X " is interchangeable, X
It is the integer of 1-5.
According to the third aspect of the invention we, the present invention proposes a kind of method for preparing gold nanoparticle, makes noted earlierization
The compound that compound or the method noted earlier for preparing compound shown in formula (I) prepare is contacted with gold chloride, to obtain
Obtain the gold nanoparticle.When preparing gold nanoparticle using compound shown in formula (I), first compound shown in formula (I) is dissolved in
In water, after forming stable spheroidal aggravation, gold chloride is added so that gold chloride reduces generation size inside aggregation by selenium
Homogeneous, diameter 2nm or so gold nanoparticle, and then by small molecule containing selenium stablize.The gold nanoparticle of generation can uniformly divide
Cloth is inside aggregation.During gold chloride is reduced, selenium element therein can be aoxidized compound shown in formula (I).Nuclear-magnetism
Resonance hydrogen spectrum shows that the chemical shift for the hydrogen on methylene being connected with selenium can shift to low field；Nuclear magnetic resonance selenium, which is composed, then to be shown, selenium
Chemical shift can also shift to low field.Meanwhile x-ray photoelectron spectroscopy test result indicates that, the electron binding energy of selenium element
Increase, golden electron binding energy then reduce, and illustrate that selenium element is aoxidized, and gold element is reduced.
The method provided by the present invention has the advantage that：(1) using formula (I) compound as reducing agent,
The gold nanoparticle of gold chloride generation size uniformity, a diameter of 2nm or so are reduced, and due to selenium-metallographic interaction, the generation
Gold nanoparticle can shown in formula (I) compound stablize, obtain selenium-containing compound stabilization gold nanoparticle, it is possible to achieve one
Footwork prepares gold nanoparticle, and method is easy, is easy to expand, to introduce different small molecules containing selenium and to realize extensive
Prepare；(2) gold nanoparticle prepared using the method shows excellent active anticancer, and toxic side effect is small, has
Prestige becomes potential cancer therapy drug, and specifically, cell apoptosis assay shows, the gold nanoparticle that selenium element is stablized can be killed effectively
Dead 4T1 mouse mastopathy cells and HepG2 human liver cancer cells, effect are much better than compound shown in exclusive use formula (I) or adopt
The gold nanoparticle prepared with existing method.Mouse experiment shows that the gold nanoparticle that selenium element is stablized has solid tumor
Obvious inhibitory action, effect are also much better than compound shown in exclusive use formula (I) or use what existing method prepared
Gold nanoparticle；Meanwhile the gold nanoparticle for preparing of the method is to the toxic side effect very little of mouse.
According to some embodiments of the present invention, compound shown in the formula (I) and the molar ratio of the gold chloride are (1-
10)：1.Thus, it is possible to further effectively prepare the gold nano grain, and control compound and institute shown in the formula (I)
Within this range, the gold nanoparticle prepared can keep good pattern and uniformity to the molar ratio for stating gold chloride.
According to the fourth aspect of the invention, the present invention proposes a kind of gold nanoparticle, utilizes preparation gold nano noted earlier
The method of particle prepares.The size of nanometer gold grain it is homogeneous and by selenium element it is stable, show excellent anticancer and live
Property, and toxic side effect is small, is expected to become potential cancer therapy drug.According to the fifth aspect of the invention, the present invention proposes a kind of medicine
Thing, includes compound, method noted earlier shown in compound shown in formula (I), the formula (I) prepared using method noted earlier
The gold nanoparticle or the gold nanoparticle prepared.Can effective treating cancer using the medicine.
According to some embodiments of the present invention, the medicine further includes pharmaceutically acceptable carrier, and excipient is dilute
Release agent, at least one of assistant agent or mediator.
According to the sixth aspect of the invention, compound shown in proposition formula (I) of the present invention, using method noted earlier prepare obtain
The gold nanoparticle or gold nanoparticle that compound, method noted earlier shown in the formula (I) obtained prepare are in medicine preparation
Purposes, wherein, the medicine is used for treating cancer, and optionally, the cancer is breast cancer and/or liver cancer.
Brief description of the drawings
Fig. 1 is the transmission electron microscope picture for the gold nanoparticle that prepared selenium element according to embodiments of the present invention 2 is stablized.
Fig. 2 is the transmission electron microscope picture for the gold nanoparticle that prepared selenium element according to embodiments of the present invention 3 is stablized.
Fig. 3 is the transmission electron microscope picture for the gold nanoparticle that prepared selenium element according to embodiments of the present invention 4 is stablized.
Fig. 4 be according to embodiments of the present invention 5 the EGSe-tMe of small molecule containing selenium by the front and rear nuclear magnetic resonance spectroscopy of oxidation.
Fig. 5 is that the EGSe-tMe of small molecule containing selenium is composed by the front and rear nuclear magnetic resonance selenium of oxidation according to embodiments of the present invention 5.
Fig. 6 is that the gold nanoparticle that selenium element is stablized according to embodiments of the present invention 5 prepares front and rear selenium element and gold dollar
The x-ray photoelectron energy collection of illustrative plates of element.
Fig. 7 is cell apoptosis assay result figure after 4T1 cells and HepG2 cell medications according to embodiments of the present invention 6.
Fig. 8 (A) is relative tumour volume result figure before and after mouse medication according to embodiments of the present invention 6.
Fig. 8 (B) is mouse weight result figure before and after mouse medication according to embodiments of the present invention 6.
Fig. 8 (C) is tumor size comparison chart before and after mouse medication according to embodiments of the present invention 6.
Embodiment
The embodiment of the present invention is described below in detail, the example of the embodiment is shown in the drawings.Below with reference to
The embodiment of attached drawing description is exemplary, it is intended to for explaining the present invention, and is not considered as limiting the invention.Separately
Outside, if do not clearly stated, used all reagents are that in the market is commercially available in the following embodiments, or
It can be synthesized according to this paper or known method, also be that those skilled in the art hold for the reaction condition do not listed
Easily obtain.
Embodiment
Embodiment 1：The synthesis of the small molecule containing selenium
The synthesis of the EGSe-tMe of small molecule containing selenium mainly includes the following steps that：
1) take 2.62g triethylene glycol monomethyl ethers (16mmol) to be mixed with 2.02g triethylamines (20mmol), stirred under ice-water bath.
3.82g paratoluensulfonyl chlorides (20mmol) are dissolved in 10mL dichloromethane, are slowly added dropwise with constant pressure funnel to above-mentioned mixing
Liquid.When then stirring 3 is small under 30 degrees Celsius, solvent evaporated under liquid separation, vacuum, crude product purifies (dichloromethane by column chromatography
Alkane:Ethyl acetate=4:1) compound 3 is obtained.
2) 0.227g sodium borohydrides (6mmol) and 0.474g selenium powders (6mmol) are taken, is placed in 100mL round-bottomed flasks, is added
Water, after opening reacts 5min, 50 degrees Celsius of lower confined reaction 20min, obtain two selenizing disodiums.1.910g compounds 3 (6mmol)
50mL acetonitriles are dissolved in, add above-mentioned system, when 50 degrees Celsius of lower confined reactions 5 are small, acetonitrile, dichloromethane extraction are removed under vacuum
Take, remove solvent and obtain compound 4.
3) the 0.758g 2,4,6- trisbromomethyl trimethylbenzenes for being dissolved in 30mL tetrahydrofurans are added into compound 4
(1.9mmol).0.454g sodium borohydrides (12mmol) and 0.024g sodium hydroxides (0.6mmol) are taken again, are dissolved in 10mL water, are added
Enter above-mentioned mixed system.React at room temperature 5 it is small when, tetrahydrofuran is removed under vacuum, dichloromethane extraction, remove solvent, crude product
(dichloromethane is purified by column chromatography:Methanol=20:1) product EGSe-tMe is obtained.
Embodiment 2：The synthesis for the gold nanoparticle that selenium element is stablized and morphology characterization
Selenium small molecule EGSe-tMe will be contained to be dissolved in pure water, it is 0.5mM to control its concentration.Gold chloride is added thereto, is controlled
It is 0.25mM to make its concentration.A period of time is stood, obtains the gold nanoparticle (AuNP/Se) of selenium element stabilization.It will be prepared
Gold nanoparticle absorption carbon support film copper mesh on, characterized using transmission electron microscope, the results are shown in Figure 1.
Embodiment 3：The synthesis for the gold nanoparticle that selenium element is stablized and morphology characterization
Selenium small molecule EGSe-tMe will be contained to be dissolved in pure water, it is 0.25mM to control its concentration.Gold chloride is added thereto, is controlled
It is 0.25mM to make its concentration.A period of time is stood, obtains the gold nanoparticle (AuNP/Se) of selenium element stabilization.It will be prepared
Gold nanoparticle absorption carbon support film copper mesh on, characterized using transmission electron microscope, the results are shown in Figure 2.
Embodiment 4：The synthesis for the gold nanoparticle that selenium element is stablized and morphology characterization
Selenium small molecule EGSe-tMe will be contained to be dissolved in pure water, it is 2.5mM to control its concentration.Gold chloride is added thereto, is controlled
It is 0.25mM to make its concentration.A period of time is stood, obtains the gold nanoparticle (AuNP/Se) of selenium element stabilization.It will be prepared
Gold nanoparticle absorption carbon support film copper mesh on, characterized using transmission electron microscope, the results are shown in Figure 3.
Embodiment 5：The valence state characterization for the gold nanoparticle that selenium element is stablized
The EGSe-tMe of small molecule containing selenium and the selenium element gold nanoparticle (AuNP/Se) stablized are dissolved in deuterated diformazan respectively
Base sulfoxide, using the chemical shift of nuclear magnetic resonance spectroscopy characterization hydrogen, as shown in figure 4, it is observed that the methylene being connected with selenium
On hydrogen chemical shift to low field move.Using the chemical shift of nuclear magnetic resonance selenium stave sign selenium, as shown in figure 5, can see
The chemical shift for observing selenium is moved to low field.Selenium small molecule EGSe-tMe, gold chloride (HAuCl will be contained4) and selenium element stabilization
Gold nanoparticle (AuNP/Se) is respectively placed on silicon chip, and the electronics of selenium element and gold element is characterized using x-ray photoelectron spectroscopy
With reference to energy, the results are shown in Figure 6, it is observed that the electron binding energy increase of selenium element, the electron binding energy of gold element then subtract
It is small.
Embodiment 6：Cell apoptosis assay and mouse experiment
AuNP/Citrate preparation methods：Gold chloride and sodium citrate are dissolved in 20mL water, make its final concentration be
2.5mM, adds the sodium borohydride that the concentration that 0.6mL is newly prepared is 0.1M, AuNP/Citrate is made while stirring.
Cell used in cell apoptosis assay is 4T1 mouse mastopathy cells and HepG2 human liver cancer cells.
The preparation of the culture medium of 4T1 mouse mastopathy cells：In the culture medium suitable for 4T1 mouse mastopathy cells, point
Do not add what the EGSe-tMe of small molecule containing selenium, gold nanoparticle (AuNP/Citrate) prepared by standard method and selenium element were stablized
Gold nanoparticle (AuNP/Se), so that final concentration of 250 μM of the EGSe-tMe of small molecule containing selenium is obtained, 100 μM, 50 μM, 25 μM,
10 μM, 5 μM, final concentration of 250 μM of gold nanoparticle (AuNP/Citrate) prepared by 1 μM of culture medium, standard method, 100 μ
M, 50 μM, 25 μM, 10 μM, 5 μM, 1 μM of culture medium, final concentration of the 250 of the gold nanoparticle (AuNP/Se) that selenium element is stablized
μM, 100 μM, 50 μM, 25 μM, 10 μM, 5 μM, 1 μM of culture medium.
The preparation of the culture medium of HepG2 human liver cancer cells：In the culture medium suitable for HepG2 human liver cancer cells, it is separately added into
The gold nano that gold nanoparticle (AuNP/Citrate) and selenium element prepared by the EGSe-tMe of small molecule containing selenium, standard method is stablized
Particle (AuNP/Se), so that final concentration of 250 μM of the EGSe-tMe of small molecule containing selenium is obtained, 100 μM, 50 μM, 25 μM, 10 μM, 5 μ
M, final concentration of 250 μM of gold nanoparticle (AuNP/Citrate) prepared by 1 μM of culture medium, standard method, 100 μM, 50 μM,
25 μM, 10 μM, 5 μM, 1 μM of culture medium, final concentration of 250 μM of the gold nanoparticle (AuNP/Se) that selenium element is stablized, 100 μ
M, 50 μM, 25 μM, 10 μM, 5 μM, 1 μM of culture medium.
The medium culture 4T1 mouse mastopathy cells for the 4T1 mouse mastopathy cells that above-mentioned preparation obtains are respectively adopted,
The medium culture HepG2 human liver cancer cells for the HepG2 human liver cancer cells that above-mentioned preparation obtains are respectively adopted, and it is small to record 24
When after cell survival rate, the results are shown in Figure 7, it is observed that selenium element stablize gold nanoparticle can effectively kill cancer
Cell.
Used in mouse experiment, BALB/c mouse, plants 4T1 mouse mastopathy cells, is distinguished using PBS buffer solutions
The 5mM EGSe-tMe of small molecule containing selenium solution, 5mM solution of gold nanoparticles (AuNP/Citrate), 5mM selenium elements is prepared to stablize
Above-mentioned solution, is injected into mice with tumor body, mice with tumor by solution of gold nanoparticles (AuNP/Se) and blank solution respectively
Dosage be 1.5mg/kg, measure tumour relative volume and mouse weight every three days, the results are shown in Figure 8, can be with
It was observed that the gold nanoparticle that selenium element is stablized has solid tumor obvious inhibitory action.
In addition, term " first ", " second " are only used for description purpose, and it is not intended that instruction or hint relative importance
Or the implicit quantity for indicating indicated technical characteristic.Thus, define " first ", the feature of " second " can be expressed or
Implicitly include at least one this feature.In the description of the present invention, " multiple " are meant that at least two, such as two, three
It is a etc., unless otherwise specifically defined.
In the description of this specification, reference term " one embodiment ", " some embodiments ", " example ", " specifically show
The description of example " or " some examples " etc. means specific features, structure, material or the spy for combining the embodiment or example description
Point is contained at least one embodiment of the present invention or example.In the present specification, schematic expression of the above terms is not
It must be directed to identical embodiment or example.Moreover, particular features, structures, materials, or characteristics described can be in office
Combined in an appropriate manner in one or more embodiments or example.In addition, without conflicting with each other, the skill of this area
Art personnel can be tied the different embodiments or example described in this specification and different embodiments or exemplary feature
Close and combine.
Although the embodiment of the present invention has been shown and described above, it is to be understood that above-described embodiment is example
Property, it is impossible to limitation of the present invention is interpreted as, those of ordinary skill in the art within the scope of the invention can be to above-mentioned
Embodiment is changed, changes, replacing and modification.
Claims (11)
- A kind of 1. method for the gold nanoparticle for preparing selenium element stabilization, it is characterised in that compound is contacted with gold chloride, with Just the gold nanoparticle that the selenium element is stablized is obtained,Wherein,The compound is compound shown in formula (I),
- 2. according to the method described in claim 1, it is characterized in that, compound shown in the formula (I) and the gold chloride rub Your ratio is (1-10)：1.
- 3. according to the method described in claim 1, it is characterized in that, preparing the method for compound shown in the formula (I) includes：(1) contact of compound shown in compound shown in formula 1 and formula 2, to obtain compound shown in formula 3；(2) compound shown in formula 3 and the contact of two selenizing disodiums, to obtain compound shown in formula 4；(3) compound is contacted with compound shown in formula 5 shown in formula 4, to obtain compound shown in formula (I),
- 4. method according to claim 3, it is characterised in that step (1) includes：(1-1) mixes compound shown in the formula 1 with triethylamine, to obtain the first mixed liquor；(1-2) mixes compound shown in the formula 2 with dichloromethane, to obtain the second mixed liquor；Second mixed liquor is added dropwise in first mixed liquor by (1-3), in 30 degrees Celsius, when stirring reaction 3 is small, so as to Compound shown in acquisition formula 3.
- 5. method according to claim 3, it is characterised in that step (2) includes：(2) under 50 degrees Celsius, in acetonitrile, contact compound shown in the formula 3 and two selenizing disodiums, to obtain formula 4 Shown compound.
- 6. method according to claim 3, it is characterised in that step (3) includes：(3) at room temperature, in tetrahydrofuran, sodium borohydride and sodium hydroxide are added, make compound shown in the formula 4 with it is described Compound shown in formula 5 contacts, to obtain compound shown in formula (I).
- 7. the gold nanoparticle that a kind of selenium element is stablized, it is characterised in that prepared using any one of claim 1-6 the method Obtain.
- 8. a kind of medicine, it is characterised in that stablize comprising the selenium element that any one of claim 1-6 the method prepares The gold nanoparticle that selenium element described in gold nanoparticle or claim 7 is stablized.
- 9. medicine according to claim 8, it is characterised in that the medicine further includes pharmaceutically acceptable carrier, Excipient, diluent, at least one of assistant agent or mediator.
- 10. gold nanoparticle or claim 7 that the selenium element that any one of claim 1-6 the method prepares is stablized The purposes of the gold nanoparticle that the selenium element is stablized in medicine preparation, wherein, the medicine is used for treating cancer.
- 11. purposes according to claim 10, it is characterised in that the cancer is breast cancer and/or liver cancer.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610299299.4A CN105906540B (en) | 2016-05-06 | 2016-05-06 | Compound and its preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610299299.4A CN105906540B (en) | 2016-05-06 | 2016-05-06 | Compound and its preparation method and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105906540A CN105906540A (en) | 2016-08-31 |
| CN105906540B true CN105906540B (en) | 2018-04-20 |
Family
ID=56748566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610299299.4A Active CN105906540B (en) | 2016-05-06 | 2016-05-06 | Compound and its preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105906540B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112707853B (en) * | 2020-12-23 | 2021-10-22 | 清华大学 | Tellurium-containing compound, method for preparing tellurium gold nanoparticles by using tellurium-containing compound and application of tellurium gold nanoparticles in preparing antitumor drugs |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102327620A (en) * | 2011-07-29 | 2012-01-25 | 暨南大学 | Application of nano-selenium in antineoplastic drug carrier |
| CN103113277A (en) * | 2013-03-05 | 2013-05-22 | 清华大学 | Selenium-containing compound as well as preparation method and pharmaceutical composition thereof |
| CN103263673A (en) * | 2013-06-07 | 2013-08-28 | 南开大学 | Polysaccharide-gold-nanoparticle supermolecule assembled body as well as preparation method and application thereof |
-
2016
- 2016-05-06 CN CN201610299299.4A patent/CN105906540B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102327620A (en) * | 2011-07-29 | 2012-01-25 | 暨南大学 | Application of nano-selenium in antineoplastic drug carrier |
| CN103113277A (en) * | 2013-03-05 | 2013-05-22 | 清华大学 | Selenium-containing compound as well as preparation method and pharmaceutical composition thereof |
| CN103263673A (en) * | 2013-06-07 | 2013-08-28 | 南开大学 | Polysaccharide-gold-nanoparticle supermolecule assembled body as well as preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| 具有选择性抗癌活性的含硒配位组装体: 活性氧物种的调控;李天予等;《化学学报》;20141231;第72卷;第1079-1084页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105906540A (en) | 2016-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Xu et al. | Adsorption properties study of boron nitride fullerene for the application as smart drug delivery agent of anti-cancer drug hydroxyurea by density functional theory | |
| Cioran et al. | Mercaptocarborane-capped gold nanoparticles: electron pools and ion traps with switchable hydrophilicity | |
| US9242003B2 (en) | Surface-modified heavy metal nanoparticles, compositions and uses thereof | |
| Xu et al. | Inclusion complex of nateglinide with sulfobutyl ether β-cyclodextrin: Preparation, characterization and water solubility | |
| Oramas-Royo et al. | Synthesis and cytotoxic activity of metallic complexes of lawsone | |
| JP5043015B2 (en) | Use of metal furol for producing metal furol and tumor (cancer) growth inhibitory drug | |
| Kraka et al. | Enediynes, enyne‐allenes, their reactions, and beyond | |
| Kaushik et al. | Exploration of docetaxel palmitate and its solid lipid nanoparticles as a novel option for alleviating the rising concern of multi-drug resistance | |
| CN105906540B (en) | Compound and its preparation method and application | |
| Afzali et al. | Designing an Au/reduced graphene oxide modified carbon paste electrode for the electrochemical quantification of agnuside | |
| CN104815340A (en) | Magnetic resonance imaging guided targeting metal organic framework drug carrier preparation method | |
| Nakayama et al. | Controlled release of drug from cyclodextrin-intercalated layered double hydroxide | |
| CN108586551A (en) | The preparation and application of IR780-LA/CPT-ss-CPT nanoparticles | |
| Murugan et al. | Supramolecular interaction of primaquine with native β-cyclodextrin | |
| CN107501372A (en) | Chiral N-heterocyclic carbine gold compound and its production and use | |
| CN107375324B (en) | A kind of synthetic method of stannic oxide/graphene nano silver | |
| CN111558043B (en) | Preparation method of terpene micromolecule assembled redox response photosensitive drug | |
| do Amaral et al. | New trans-[Ru (NO)(NO2)(dppb)(o-bdqi)]+ complex as NO donor encapsulated Pluronic F-127 micelles | |
| CN103864011A (en) | Gold nanoparticle array with continuously changing surface pi bond density | |
| Han et al. | A procedurally activatable nanoplatform for chemo/chemodynamic synergistic therapy | |
| CN103664836B (en) | Crystal form A of 7 β, 10 β-dimethoxy docetaxel deuterated acetone compound and preparation method thereof | |
| Liu et al. | Atomic Precise Gold Nanoclusters: Toward the Customize Synthesis, Precision Medicine | |
| CN112707853B (en) | Tellurium-containing compound, method for preparing tellurium gold nanoparticles by using tellurium-containing compound and application of tellurium gold nanoparticles in preparing antitumor drugs | |
| CN113501848B (en) | Ruthenium complex nano-scale particle, preparation method and application thereof and antitumor drug | |
| CN103819428B (en) | Crystal formation of the solvate of 7 β, 10 β-dimethoxy docetaxel and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |