CN108079019A - Water-soluble fullerene nano material and preparation method thereof and anti-oxidant application - Google Patents
Water-soluble fullerene nano material and preparation method thereof and anti-oxidant application Download PDFInfo
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Abstract
The invention discloses a kind of water-soluble fullerene nano materials.The water-soluble fullerene material is fullerene C60The compound of poly-dopamine glutathione, it is the fullerene modification material that fullerene directly and after dopamine alkaline aqueous solution hybrid reaction obtains surface attachment poly-dopamine crosslinking composite bed, the water-soluble products obtained with the water-soluble polypeptide glutathione generation Michael's addition with sulfydryl.Preparation method and anti-oxidant application the invention also discloses above-mentioned water-soluble fullerene nano material.The water-soluble fullerene nano material of the present invention has good biocompatibility, physics and chemical stability are good, preparation condition is mildly controllable, and as the scavenger and antioxidant of a kind of interior free yl, high potential value is shown in biomedical and cosmetic applications field.
Description
Technical field
The invention belongs to field of biomedicine technology, and in particular to a kind of water-soluble fullerene nano material and its preparation side
Method and anti-oxidant application.
Background technology
Fullerene is a kind of new rich carbon nanomaterial, it has enclosed construction by what different number of carbon atom formed
Elementide, due to its unique structure and physicochemical properties, there is boundless application prospect in biomedical sector.
With IhThe C of symmetry60Molecule is the prominent representative of fullerene family, it be made of 12 five-membered rings and 20 hexatomic rings three
Dodecahedron structure has 30 conjugated double bonds, provides the chance for preparing different chemistry or biologic artifact, is known as drug and sets
" chemical pin is inserted " (Chemical pin cushion) in meter.Since fullerene is nonpolar molecule, and the life of biosystem
Life activity is nearly all in water environment, it means that the biological effect research of water-soluble fullerenes derivates will become great
Potential field and direction.Preparation method more at present is that multiple strong poles are modified on Fullerene Carbon cage by chemical reaction
Property group such as-OH ,-COOH and-NH2Etc. enhancing its hydrophily, but chemical synthesis process is complicated, be easily introduced organic reagent, and
Chemical modification can destroy π-pi-conjugated system of Fullerene Carbon cage, reduce its bioactivity.Therefore, explore simple green and to the greatest extent may be used
The water-soluble of carbon basket structure integrality can be kept to be combined to the important step that method is transformation function fullerene nanomaterial.
It can be referred to as " absorbing certainly with radical reaction containing 30 double bonds, substantial amounts of double bond in fullerene molecule structure
By the sponge of base ".The fullerene derivate synthesized using this point can be used in removing the in vivo free radical of biology, play antioxygen
The effect of change.
Dopamine (DA) is a kind of biological neural mediator, and in alkaline conditions, oxygen can occurs in it under the action of dissolved oxygen
Change-cross-linking reaction is formed in various solid material surfaces with the structure similar to mussel adhesion protein and superpower Adhesion property
Poly-dopamine (PDA) thin layer, this method on the bulk properties of material without influence, size to material and and shape it is unlimited
System, use scope are extremely wide.In addition, the polymer P DA of dopamine has good biocompatibility, contain abundant catechol base
, under alkaline environment, these groups are easily oxidized into quinoid structure, so as to containing sulfydryl (- SH), amino (- NH2)
Michael's addition and schiff base reaction occur for hydrophilic or hydrophobic organic molecules, can be further introduced into functional molecular, are material table
The secondary modification and functionalization in face provide preferable platform.Entire modifying process is completed in aqueous solution, and reaction condition is mild,
It avoids using organic solvent pollution on the environment, and the modification of material surface is settled at one go, operating procedure is simple, instead
Answer condition easily controllable with modifying process.
The content of the invention
A technical problem to be solved by this invention is to provide a kind of good water solubility, has good biocompatibility
Water-soluble fullerene nano material.
Second technical problem to be solved by this invention is to provide a kind of mild, the simply controllable water of reaction condition green
The preparation method of dissolubility fullerene nanomaterial.
3rd technical problem to be solved by this invention is to provide above-mentioned water-soluble fullerene applications to nanostructures, clearly
Hydroxyl-removal free radical OH and realize to the effect of the anti-oxidation protection of human epidermal cell HEK- α.
To solve above-mentioned first technical problem, water-soluble fullerene nano material provided by the invention is a kind of fowler
Alkene-poly-dopamine-glutathione compound, it be by original fullerene directly and dopamine alkaline aqueous solution hybrid reaction, obtain
The fullerene modification material of composite bed is crosslinked to surface attachment poly-dopamine, then the water-soluble polypeptide paddy Guang again and with sulfydryl
Michael's addition, the water-soluble products finally obtained occur for sweet peptide (GSH).
The fullerene is C for general formula2mThe cage structure being made of carbon atom fullerene, can wherein 30≤m≤60
Choosing, including fullerene C60, fullerene C70, fullerene C76, fullerene C78, fullerene C82, fullerene C84In any one.
To solve above-mentioned second technical problem, the preparation method of the water-soluble fullerene nano material designed by the present invention
Comprise the following steps：
1) fullerene is added in the Tris-HCl buffer solutions that concentration is 10~50mmol/L (pH=8.5), ultrasound
Make within 10~30 minutes it homodisperse.Then dopamine hydrochloride is added in above-mentioned system, 10~30 DEG C are protected from light and are stirred to react 8
~for 24 hours, rotating speed is 500~1000r/min.
2) by above-mentioned product centrifugal treating, washed with solvent until upper strata centrifugate is transparent, abandon solution, lower sediment is put
Enter vacuum drying chamber, up to fullerene-poly-dopamine product after drying.
3) above-mentioned fullerene-poly-dopamine product and glutathione are added to the hydrogen-oxygen that concentration is 0.01~0.1mol/L
Change in sodium solution, 10~30 DEG C be stirred to react 8~for 24 hours, rotating speed is 500~1000r/min.
4) centrifugal treating abandons precipitation, takes upper strata centrifugate, with 0.22~0.45 μm of aperture membrane filtration, filtrate retention
The bag filter that molecular weight is 3000 is dialysed is less than 0.8 μ S/cm to electrical conductivity.Acquired solution is freeze-dried to obtain water solubility after dialysis
Fullerene nanomaterial fullerene-poly-dopamine-glutathione compound.
Preferably, the step 1 |) in, by weight, fullerene and dopamine hydrochloride are 1：(1~4).More preferably
Ground, by weight, fullerene and dopamine hydrochloride are 1：(1~2).
Preferably, in the step 2) and step 3), reaction temperature is 20~25 DEG C, and the reaction time is 10~15h, is stirred
Rotating speed is 750~850r/min.
Preferably, in the step 3), by weight, fullerene-poly-dopamine product and glutathione are 1：(1~4).
It is highly preferred that by weight, fullerene-poly-dopamine product and glutathione are 1：(1~2).
Preferably, in the step 4), the aperture of the filter membrane is 0.22~0.30 μm.
To solve above-mentioned 3rd technical problem, the present invention also provides above-mentioned water-soluble fullerene nano material fowlers
Alkene-poly-dopamine-glutathione compound is removed hydroxyl radical free radical OH and is realized to the anti-oxidant of human epidermal cell HEK- α
Protective effect.
The present invention has the advantages that：
1) fullerene-poly-dopamine-glutathione compound provided by the invention, since poly-dopamine contains catechol
And amido functional group, this structure not only can establish covalent and non-covalent (hydrogen bond, Van der Waals force or accumulation with fullerene surface
Active force) interaction, and provide secondary response for modified surface and (Michael occurs with water-soluble polypeptide glutathione
Addition) needed for active group, finally maintaining the base of Fullerene Carbon caged molecule stability in itself and physicochemical properties
On plinth, the dissolubility of fullerene in water is improved.
2) water-soluble fullerene nano material water dispersible of the present invention is good, and physics and chemical stability are good, preparation method temperature
With it is controllable, and in whole process without use any organic reagent, it can be ensured that its biologic applications field security, while
Eliminate the follow-up removal required complex process of residual organic solvent.
3) water-soluble fullerene nano material of the present invention has stronger water solubility, good biocompatibility, without cell toxicant
Property, removing free radical is efficient, it can be achieved that acting on the anti-oxidation protection of human epidermal cell HEK- α, and being that one kind is good resists
Oxidant can play more application values in biomedical and cosmetic applications field.
Description of the drawings
Fig. 1 fullerenes C60The hydration grain size curve of-poly-dopamine-glutathione compound in pure water.
Fig. 2 is fullerene C60, fullerene C60- poly-dopamine and fullerene C60- poly-dopamine-glutathione compound
Infrared spectrum.
Fig. 3 is the fullerene C of various concentration60- poly-dopamine-glutathione compound removes the ESR spectrograms of free radical.
Fig. 4 is the fullerene C of various concentration60- poly-dopamine-glutathione compound and cell survival rate relational graph.
Fig. 5 is the fullerene C of various concentration60- poly-dopamine-glutathione compound is deposited under hydrogen peroxide effect with cell
Motility rate relational graph.
Specific embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail.
1 fullerene C of embodiment60The preparation of-poly-dopamine-glutathione compound
1) 100mgC is taken60It is added in the Tris-HCl buffer solutions that 30mL concentration is 10mmol/L (pH=8.5), ultrasound
Make within 20 minutes it homodisperse.Then 200mg dopamine hydrochlorides are added in above-mentioned system, 25 DEG C are protected from light and are stirred to react 10h,
Rotating speed is 1000r/min.
2) above-mentioned product under the conditions of 8000r/min is centrifuged 5 minutes, is washed respectively with distilled water and absolute ethyl alcohol, directly
Supreme layer centrifugate is transparent, lower sediment is put into vacuum drying chamber for 24 hours, temperature conditionss are set as 40 DEG C.
3) above-mentioned dried fullerene C is taken60- poly-dopamine product 100mg and 200mg glutathione (molecular weight 600)
The sodium hydroxide solution that 20mL concentration is 0.1mol/L is added to, 25 DEG C are stirred to react 10h, rotating speed 1000r/min.
4) centrifugal treating is carried out after 15mL distilled water being added in step 3) product, precipitation is abandoned, takes upper strata centrifugate, is used
0.22 μm of membrane filtration, filtrate is dialysed with the bag filter that molecular cut off is 3000 is less than 0.8 μ S/cm to electrical conductivity.After dialysis
Acquired solution is freeze-dried to obtain fullerene C60- poly-dopamine-glutathione compound.
As shown in Figure 1, the pure water in pH=7.0 is determined using dynamic light scattering (DLS, Zetasizer Nano ZSP)
The hydration grain size of middle nano particle, fullerene C60The average grain diameter of-poly-dopamine-glutathione compound is 145nm.
As shown in Figure 2, body C60Infrared signature absorption of vibrations be located at 527,576,1187 and 1430cm-1, work as C60Surface
In cladding after poly-dopamine, there is 1530cm-1Feature phenyl ring skeletal vibration peak, and final product fullerene C60- poly- DOPA
Then there is 1404cm in amine-glutathione compound-1C-N stretching vibrations, 1628cm-1C=O stretching vibrations and 2935,
2832cm-1CH2Stretching vibration peak.
2 fullerene C of embodiment60The removing free radical performance test of-poly-dopamine-glutathione compound.
For using the obtained water-soluble fullerene material of this method, free radical is measured using spin trapping method (ESR)
Removal effect.Concrete operations are：For the free radical that hydrogen peroxide and ferrous ion reaction generate, DMPO (5,5- diformazans are utilized
Base -1- pyrrolin-N- oxides) as spin trapping agent, detection DMPO and the product DMPO-OH of hydroxyl radical reaction generation
Signal.
1) blank test：The concentration of green vitriol is 0.4mmol/L, and the pH value of PBS is the concentration of 7.4, DMPO
For 0.4mol/L, the mass concentration of hydrogen peroxide is 5%, take respectively more than each 50 μ L of four kinds of solution be uniformly mixed, finally to above-mentioned
50 μ l deionized waters are added in mixed solution, ESR tests is carried out, obtains being not added with the blank test of any active material
The ESR signals of DMPO-OH, the DMPO-OH ESR signal graphs of blank test as shown in Figure 3.
2) in actual test：Green vitriol PBS, DMPO, the concentration and dosage of hydrogen peroxide are and above-mentioned " blank is tried
Test " it is identical, it is separately added into the fullerene C of 50 μ L various concentrations60- poly-dopamine-glutathione aqueous solution (25,50,100,150
With 200 μ g/mL), its ESR signal is tested after mixing.The results are shown in Figure 3：Water-soluble fullerene nano material can be shown
It writes ground and removes hydroxyl radical free radical, with the raising of the fullerene concentration of addition, the performance of removal hydroxyl radical free radical also increases therewith
By force.
3 fullerene C of embodiment60Cytotoxicity and the antioxygenic property test of-poly-dopamine-glutathione compound.
1 fullerene C60Test of-poly-dopamine-glutathione the compound to human epidermal cell HEK- α toxicity
Cell toxicity test is tested by CCK-8 (Cell Counting Kit-8) kit, specific steps
Including：
1) human epidermal cell HEK- α are diluted to 5 with DMEM culture mediums (improvement Du Shi Eagle's mediums) first ×
104A/ml is added in 96 orifice plates, per 200 μ l of hole, is incubated overnight；
2) liquid is changed, adds in various concentration (25,50,100,150 and 200 μ g/mL) fullerene C60- poly-dopamine-gluathione
The DMEM solution of peptide complexes；
3) it is incubated overnight, adds CCK-8 indicator, its absorbance value is measured at 450nm with microplate reader；
4) control group (control groups) of non-dosing is normalized, the cell of various concentration dosing group is calculated by following formula
Survival rate：
In formula, blank group is the group only containing DMEM culture mediums
Control group is the group (not adding in drug) containing cell, DMEM culture mediums
Experimental group refers to containing cell, DMEM culture mediums and fullerene C60The group of-poly-dopamine-glutathione compound；
5) cell survival rate that calculates is as shown in figure 4, under various concentration, fullerene C60- poly-dopamine-glutathione is multiple
The experimental group cell of object effect is closed without occurring under apparent apoptosis or even some concentration, drug goes out to nourish for cells show
Effect so that cell survival rate is more than control group.
2 fullerene C60The antioxygenic property test of-poly-dopamine-glutathione compound
Antioxygenic property experiment is tested by CCK-8 (Cell Counting Kit-8) kit, specific to walk
Suddenly include：
1) human epidermal cell HEK- α are diluted to 5 with DMEM culture mediums (improvement Du Shi Eagle's mediums) first ×
104A/ml is added in 96 orifice plates, per 200 μ l of hole, is incubated overnight；
2) liquid is changed, adds in various concentration (25,50,100,150 and 200 μ g/mL) fullerene C60- poly-dopamine-gluathione
The DMEM solution of peptide complexes is incubated 3h jointly；
3) liquid is changed, the hydrogen peroxide solution for adding in 20mM/L is incubated 1h jointly；
4) liquid is changed, after adding in DMEM culture mediums overnight incubation, adds CCK-8 indicator, it is measured at 450nm with microplate reader
Absorbance value；
5) control group (control groups) of non-dosing is normalized, the cell of various concentration dosing group is calculated by following formula
Survival rate：
In formula, blank group is the group only containing DMEM culture mediums
Control group is the group (not adding in drug) containing cell, DMEM culture mediums
Experimental group refers to containing cell, DMEM culture mediums, hydrogen peroxide and fullerene C60- poly-dopamine-glutathione is compound
The group of object；
6) cell survival rate calculated is as shown in figure 5, hydrogen peroxide has cell apparent injury effect, cell survival rate
It is down to 50%.The fullerene C of various concentration60- poly-dopamine-glutathione compound effect experimental group cell survival rate then compared with
Apparent increase, illustrate that its acts on the anti-oxidation protection of cell.Wherein using 100mg/mL as optimum value, the survival rate of cell reaches
To 77%.
Claims (10)
1. a kind of water-soluble fullerene nano material, it is characterised in that：The water-soluble fullerene nano material is fullerene-poly-
Dopamine-glutathione compound, the fullerene-poly-dopamine-glutathione compound be by fullerene directly and DOPA
Surface is generated after amine alkaline aqueous solution hybrid reaction and is coated with the fullerene modification material of poly-dopamine crosslinking composite bed, then is passed through
Compound obtained from the upper glutathione of Michael addition reaction bonding.
2. water-soluble fullerene nano material according to claim 1, it is characterised in that：The fullerene is C for general formula2m
The cage structure being made of carbon atom fullerene, wherein 30≤m≤60.
3. water-soluble fullerene nano material according to claim 2, it is characterised in that：The fullerene is fullerene
C60, fullerene C70, fullerene C76, fullerene C78, fullerene C82, fullerene C84In any one.
4. the preparation method of claims 1 to 3 any one of them water-soluble fullerene nano material, it is characterised in that：The party
Method includes the following steps：
1) fullerene is added in the Tris-HCl buffer solutions for the pH=8.5 that concentration is 10~50mmol/L, ultrasound 10~
Make within 30 minutes it homodisperse；Then add in dopamine hydrochloride in above-mentioned system, 10~30 DEG C be protected from light be stirred to react 8~
For 24 hours, rotating speed is 500~1000r/min；
2) by above-mentioned product centrifugal treating, it is transparent washs supreme layer centrifugate with solvent, lower sediment is put into vacuum drying chamber,
Up to fullerene-poly-dopamine product after drying；
3) above-mentioned fullerene-poly-dopamine product and glutathione are added to the sodium hydroxide that concentration is 0.01~0.1mol/L
In solution, 10~30 DEG C be stirred to react 8~for 24 hours, rotating speed is 500~1000r/min；
4) centrifugal treating abandons precipitation, takes upper strata centrifugate, and with 0.22~0.45 μm of aperture membrane filtration, filtrate uses retention molecule
The bag filter measured as 3000 is dialysed is less than 0.8 μ S/cm to electrical conductivity；Acquired solution freeze-drying obtains water-soluble richness after dialysis
Strangle alkene nano material fowler alkene-poly-dopamine-glutathione compound.
5. the preparation method of water-soluble fullerene nano material according to claim 4, it is characterised in that：The step 1
|) in, by weight, fullerene and dopamine hydrochloride are 1：(1~4).
6. the preparation method of water-soluble fullerene nano material according to claim 5, it is characterised in that：The step 1
|) in, by weight, fullerene and dopamine hydrochloride are 1：(1~2).
7. the preparation method of water-soluble fullerene nano material according to claim 5 or 6, it is characterised in that：The step
Rapid reaction temperature is 20~25 DEG C 2) and in step 3), and the reaction time is 10~15h, and speed of agitator is 750~850r/min.
8. the preparation method of water-soluble fullerene nano material according to claim 5 or 6, it is characterised in that：The step
It is rapid 3) in, by weight, fullerene-poly-dopamine product and glutathione are 1：(1~4).
9. the preparation method of water-soluble fullerene nano material according to claim 8, it is characterised in that：The step 3)
In, by weight, fullerene-poly-dopamine product and glutathione are 1：(1~2).
10. claims 1 to 3 any one of them water-soluble fullerene nano material is to the antioxygen of human epidermal cell HEK- α
Change protective effect.
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| CN108904303A (en) * | 2018-08-16 | 2018-11-30 | 苏州火睿新材料科技有限公司 | Fullerene-compound cosmetic material of essential oil-polypeptide and preparation method thereof |
| CN109777100A (en) * | 2019-02-19 | 2019-05-21 | 西北师范大学 | A kind of preparation method of redox graphene-poly-dopamine-glutathione composite material |
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| CN113384480A (en) * | 2021-06-17 | 2021-09-14 | 张家界金驰天问农业科技有限公司 | Giant salamander peptide-fullerene compound and preparation method and application thereof |
| CN113893182A (en) * | 2021-09-18 | 2022-01-07 | 北京福纳康生物技术有限公司 | Water-soluble fullerene compound and preparation method and application thereof |
| CN113893182B (en) * | 2021-09-18 | 2024-03-15 | 苏州仁生泽发生物科技有限公司 | Water-soluble fullerene compound and preparation method and application thereof |
| WO2023107144A1 (en) * | 2021-12-10 | 2023-06-15 | Peter Butzloff | Nitric oxide c60-gsh-atp and use |
| CN114149582A (en) * | 2021-12-23 | 2022-03-08 | 中国兵器工业第五九研究所 | Novel efficient chelate antioxidant as well as preparation method and application thereof |
| CN114149582B (en) * | 2021-12-23 | 2023-04-21 | 中国兵器工业第五九研究所 | Novel efficient chelate antioxidant and preparation method and application thereof |
| CN118252801A (en) * | 2024-03-25 | 2024-06-28 | 徐州医科大学 | Reduced glutathione modified fullerol composite nano-particle and preparation method and application thereof |
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