CN103961705B - The preparation of the hollow copper sulfide/poly-dopamine complex of modified with folic acid and application thereof - Google Patents
The preparation of the hollow copper sulfide/poly-dopamine complex of modified with folic acid and application thereof Download PDFInfo
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Abstract
The present invention relates to a kind of preparation and application thereof of hollow copper sulfide/poly-dopamine complex of modified with folic acid.Be there is by template synthesis the nano copper sulfate particle of hollow structure, then dopamine forms a strata dopamine layer at its surface aggregate in the basic conditions, finally by schiff base reaction, folic acid is fixed on its surface, obtains and there is multi-functional targeting CuSDPA-FA nano-complex.It not only has medicine carrying function, also has the effect of photo-thermal therapy simultaneously, and utilizes its class Catalyzed Synthesis By Peroxidase activity also to can be used for colorimetric determination cancer cell number.Therefore can be widely used in the early diagnosis of tumor, the fields such as the medicine of tumor and photo-thermal therapy, there is preparation technology simple simultaneously, with low cost, biocompatibility high.
Description
Technical field:
The present invention relates to field of nanometer technology, biomedicine field, be specifically related to a kind of preparation and application thereof of hollow copper sulfide/poly-dopamine complex of modified with folic acid.
Background technology
In recent years, the nano science developed based on nanoparticle and the application of biotechnology in medicine/gene delivery, bio-sensing, bio-imaging and photo-thermal therapy receive the extensive concern of people.In order to improve the hydrophilic of nanoparticle, colloidal stability, biocompatibility and the bonding force with bio-active group, the finishing of nanoparticle just seems most important.Dopamine (DA) is a kind ofly present in marine mussel the material with biological stickiness, is again a kind of molecule mimetic protein simultaneously.Under ph basic conditions, auto polymerization reaction can be there is in dopamine (DA) in nanoparticle surface (no matter surface is performance hydrophilic or hydrophobicity), in poly-dopamine (PDA) structure obtained containing abundant catechol functional group can with primary amine generation schiff base reaction, for the further modification of nanoparticle surface provides advantage.Therefore can be used as a kind of finishing having very much the function monomer of development potentiality to be applied to nano material.
CuS nanoparticles granule has strong absorption near infrared region, and this is by Cu
2+d-d can with the coefficient result of SPR effect of transition and copper sulfur family nano-particle.Compared with noble metal nano structure, its absorbing wavelength at region of ultra-red is less by the impact of environment and size, and to biological and human toxicity is less, granule preparation cost is low, and therefore CuS nanoparticles particle has potential application foreground in photo-thermal therapy field.Existing bibliographical information nano copper sulfate particle can be used as photo-thermal agent to be come Therapeutic cancer [Adv.Mater.2011,23,3542 – 3547] [Small2012,8,3143 – 3150] [Adv.Mater.2013,25,4452 – 4458].Meanwhile, nano copper sulfate particle is also in the news and has class peroxidase activity, can catalysis H
2o
2produce the hydroxyl radical free radical of strong oxidizing property, efficient oxidation TMB produces chromogenic reaction, and this characteristic is used to detect glucose molecule [Talanta.2013,30,361-367.] [Int.J.Mol.Sci.2013,14,9999-10014].But photo-thermal can be treated and combine with chemotherapy by development, and playing its synergistic technology effectively can reduce side effect, strengthens therapeutic effect; On the other hand, utilize the multi-functional characteristic of inorganic nano material to develop the Clinics and Practices technology simultaneously realizing cancer and also very there is Research Significance.
Summary of the invention
The object of the invention is the preparation and the application thereof that provide a kind of hollow copper sulfide of modified with folic acid/poly-dopamine complex, this complex has targeting, photo-thermal therapy, Drug therapy and cancerous cell simultaneously and detects quadruple effect, effectively can realize the synergistic function of Diagnosis and Treat.At hollow nano copper sulfate particle finishing one strata dopamine layer, DOPA amine layer is utilized to improve drug loading rate, the biocompatibility of complex and the target molecule that is coupled, the near infrared absorption function of CuS nano-particle and mimetic enzyme catalysis characteristic are combined simultaneously, establish a kind of method that simultaneously can realize targeting, photo-thermal therapy, Drug therapy and cancerous cell detection quadruple effect.
For achieving the above object, the present invention adopts following technical scheme:
A preparation method for the hollow copper sulfide/poly-dopamine complex of modified with folic acid, comprises the following steps:
(1) cuprous oxide nano particle is prepared;
(2) nano copper sulfate particle of hollow structure is obtained by the cuprous nano-particle of sulfidation-oxidation;
(3) at the nano copper sulfate particle finishing one strata dopamine layer of hollow structure, hollow copper sulfide/poly-dopamine nano-complex is formed;
(4) at hollow copper sulfide/poly-dopamine nano-complex finishing folic acid (FA) molecule, the hollow copper sulfide/poly-dopamine complex of obtained modified with folic acid.
Specifically comprise the following steps:
(1) ascorbic acid reduction Copper hydrate prepares cuprous oxide nano particle;
(2) obtained the nano copper sulfate particle of hollow structure by the cuprous nano-particle of sulfidation-oxidation, sulfur source used is Na
2s9H
2o, reaction temperature is 55 DEG C;
(3) in the Tris-HCl buffer of pH=8.5, utilize the self-polymeric reaction of dopamine at hollow nano copper sulfate particle finishing one strata dopamine layer, form hollow copper sulfide/poly-dopamine nano-complex;
(4) be 4:1 water-soluble solution concussion 12h in mass ratio by hollow copper sulfide/poly-dopamine nano-complex and folic acid, utilize simple schiff base reaction to obtain the hollow copper sulfide of modified with folic acid/gather dopamine complex.
Hollow copper sulfide/poly-dopamine the complex of the modified with folic acid that method described above obtains, its particle diameter is 90-100nm.
The application of the hollow copper sulfide/poly-dopamine complex of modified with folic acid, for photo-thermal therapy.
The application of the hollow copper sulfide/poly-dopamine complex of modified with folic acid, carrying medicament is used for Drug therapy; Described carrying medicament is one or more mixture in amycin, paclitaxel, camptothecine, phthalocyanine, epirubicin, daunorubicin, Methylaminopterin.。
The application of the hollow copper sulfide/poly-dopamine complex of modified with folic acid, for
cancercell detection; Described
cancercell is HepG2 cell, and substrate is 3,3', 5,5'-tetramethyl benzidine.Hollow copper sulfide/poly-dopamine the complex of modified with folic acid has class Catalyzed Synthesis By Peroxidase activity, can catalysis H
2o
2produce the hydroxyl radical free radical of strong oxidizing property, efficient oxidation substrate produces chromogenic reaction, simultaneously, the alternative targeting of this complex is in conjunction with cancerous cell, cancer cell number is more, the complex being fixed on surface is also more, and chromogenic reaction speed is faster, therefore by the quantity of colorimetric determination oxidation substrates oxTMB content indirect detection cancerous cell.
The multifunctional application of the hollow copper sulfide/poly-dopamine complex of modified with folic acid:
Electrostatic attraction effect and π-π is utilized to act on Drug absorbability on CuSPDA-FA carrier.
CuSPDA-FA composite particles after carrying medicament is added in cancerous cell culture fluid by variable concentrations, laser irradiation 5 minutes, utilize MTT experiment to examine or check the photo-thermal therapy of CuSPDA-FA nano-complex and the synergy of Drug therapy and the targeting of complex; Described laser is 808nm, and described cancerous cell is HepG2 cell.
The class peroxidase activity of CuS is utilized to set up the quantity of colorimetric determination cancerous cell.CuSPDA-FA nano-complex is added in the HepG2 cell culture fluid containing different number, cultivates after 4h, with PBS(10mM, pH=7.4) buffer washes away unnecessary material, and cell is scattered in PBS(10mM, pH=4.0 again) in solution, then add substrate and H
2o
2carry out Catalytic color reaction, measure each group of absorption value at 652nm place, by measurement absorption value along with the variation tendency of number of cells sets up the technology utilizing colorimetric determination cancer cell number; Described substrate is 3,3', 5,5'-tetramethyl benzidine (TMB), and ultimate density is 0.4mM.
Advantage of the present invention is as follows:
1. the near infrared absorption function of CuS nano-particle and mimetic enzyme catalysis characteristic combine first time by the present invention, establish a kind of method that simultaneously can realize targeting, photo-thermal therapy, Drug therapy and cancerous cell detection quadruple effect, the field such as early diagnosis and therapy be expected to for disease provides technical foundation, possesses economic benefit and social benefit significantly;
2. the introducing of dopamine shell enhances the biocompatibility of CuS nano-particle, improves the load factor of medicine, makes the various targeting biological molecules of the more convenient modification of composite surface simultaneously, is more conducive to its application in biomedicine;
The preparation method of 3.CuSPDA-FA complex is simple, with low cost, and bio-target molecule coupling is easier, is easy to extensive preparation.
Accompanying drawing explanation
Fig. 1 is the TEM figure of the hollow CuSPDA-FA nano-complex that embodiment 1 obtains;
Fig. 2 is the heating rate figure of variable concentrations CuSPDA solution under laser irradiates in embodiment 2;
Fig. 3 is the drug release in vitro curve chart of CuSPDA-FA complex in embodiment 3;
Fig. 4 is the cytotoxicity test of variable concentrations hollow CuSPDA-FA nano-complex in embodiment 4;
Fig. 5 is the cell survival rate figure adding gained after different group sample culturing in embodiment 5;
Fig. 6 is absorption value corresponding after there is catalytic reaction after the HepG2 cell adsorption hollow CuSPDA-FA nano-complex of different number in embodiment 6;
Fig. 7 is the optical photograph of colorimetric determination number of cells experiment in embodiment 6.
Detailed description of the invention
Below by concrete exemplifying embodiment, technical scheme of the present invention is described further, but can not limits the scope of the invention with this.
Embodiment 1
CuSPDA-FA nano-complex aqueous solution is carried out supersound process 0.5h, then drops on copper mesh, carry out TEM after drying and scan (see figure 1), complex is hollow structure as shown, size is about 100nm, and dopamine shell thickness is 3 ~ 4nm, composite particles size uniformity, good dispersion.
Embodiment 2
25 μ g/mL, 50 μ g/mL and each 1mL of 100 μ g/mLCuSPDA solution are added in colorimetric pool, irradiates with the laser of 808nm wavelength that (power is 2W/cm
2), solution heats up gradually along with the increase of irradiation time, records variations in temperature every 20s.As can be seen from Figure 2, the CuSPDA solution of 100 μ g/mL heats up at 320s and reaches 45.3 DEG C, illustrates that its photothermal deformation effect is fine.
Embodiment 3
By CuSPDA-FA complex and amycin (DOX) in mass ratio 4:1 ratio add PBS(10mM, pH=7.4) in solution, room temperature concussion 24h, centrifugalize, and with PBS(10mM, pH=7.4) solution washing, collect supernatant calculates wherein contained DOX amount according to standard curve, and the load capacity calculating DOX is further 0.24mgDOX/1mgCuSPDA-FA.Then 1mg is adsorbed the CuSPDA-FA complex after medicine and be scattered in 2mLPBS(10mM, pH=7.0), in solution, after putting into bag filter, bag filter is added 50mlPBS solution and to dialyse 24h, every 1h, 2h, 3h, 4h, 6h, 12h, 24h gets 3ml solution and surveys fluorescence, and original solution fills into 3mlPBS solution again, and testing result is shown in Fig. 3.In Fig. 3, curve 1 is room temperature, pH=7.4; Curve 2 is room temperature, pH=5.0; Curve 3 is laser irradiation, pH=5.0; Under laser irradiation condition in pH=5.0 buffer solution to survey DOX fluorescence intensity the highest, the release being more conducive to DOX is with this understanding described.
Embodiment 4
With concentration be 25 μ g/mL, the CuSPDA-FA complex of 50 μ g/mL, 75 μ g/mL and 100 μ g/mL carries out MTT test, MTT test selects cell to be HepG2 cell, survey 490nm place absorption value, calculate the cell survival rate of each group according to the absorption value of blank group.As can be seen from Figure 4, often organize cell survival rate all more than 85%, illustrate that the hollow copper sulfide/poly-dopamine complex cell compatibility of modified with folic acid is high.
Embodiment 5
Added in cell culture fluid by the sample of difference group equivalent concentration and cultivate 6h, (power is 2W/cm in the laser irradiation of 3-6 group taking-up 808nm wavelength
2) continue after 5min to cultivate 6h, survey 490nm place absorption value, calculate the cell survival rate of each group according to the absorption value of blank group.Wherein tested sample is specially: sample 1 is blank, sample 2 is the CuS-PDA complex after absorption DOX, sample 3 is CuS-PDA complex (laser irradiation), sample 4 is CuS-PDA-FA complex (laser irradiation), sample 5 is the CuS-PDA complex (laser irradiation) after absorption DOX, sample 6 is the CuS-PDA-FA complex (laser irradiation) after absorption DOX, and often organize concentration and be 50 μ g/mL, cell used is HepG2 cell; As can be seen from Figure 5, wherein 3 and 4 groups of contrasts are known, and after laser irradiates, hollow CuSPDA nano-complex heats up and can make cell death, and hollow CuSPDA-FA complex plays the effect of targeting, cause CuSPDA nano-complex local concentration in cell higher, photo-thermal effect is more obvious; 2,5 and 6 groups of contrasts are known, the CuSPDA nano-complex of load DOX can by cell endocytic, then in cell, DOX is discharged, cause cell death, after laser irradiates, the photo-thermal therapy of DOX Drug therapy and CuSPDA nano-complex creates synergism makes cell survival rate reduce, and CuSPDA-FA nano-complex local concentration in cell is higher, synergism is more obvious, and therefore the cell survival rate of the 6th group is minimum.
Embodiment 6
By the HepG2 cell dispersal of different number in cell culture fluid, then CuSPDA-FA solution is added (ultimate density is 20 μ g/mL) in cell culture fluid, PBS(10mM is used after cultivating 4h, pH=7.4) buffer washes away unnecessary material, by cell dispersal in PBS(10mM, pH=4.0), in solution, TMB(ultimate density 0.4mM is then added) after mix homogeneously, add H
2o
2(ultimate density is 25mM), at 45 DEG C of temperature, reaction 5min, then measures the absorption value of each sample at 652nm place.Survey HepG2 cell quantity and be specially: 1.2 × 10
2, 6 × 10
2, 1.2 × 10
3, 6 × 10
3, 1.2 × 10
4, 6 × 10
4, 1.2 × 10
5individual; As can be seen from Figure 6 along with the increase of cell number, the CuSPDA-FA nano-complex that cell surface combines is more, catalysis H
2o
2oxidation TMB speed is just faster, and the more solution colours of oxTMB of generation are darker (as shown in Figure 7, from left to right, color burn), higher in the absorption value at 652nm place.The experimental result of Fig. 6 and Fig. 7 shows, can utilize the class peroxidase activity of CuSPDA-FA nano-complex and the targeting of folic acid, set up the technology of colorimetric determination particular cancer cell quantity.
Claims (9)
1. a preparation method for the hollow copper sulfide/poly-dopamine complex of modified with folic acid, is characterized in that: comprise the following steps:
(1) cuprous oxide nano particle is prepared;
(2) nano copper sulfate particle of hollow structure is obtained by the cuprous nano-particle of sulfidation-oxidation;
(3) at the nano copper sulfate particle finishing one strata dopamine layer of hollow structure, hollow copper sulfide/poly-dopamine nano-complex is formed;
(4) at hollow copper sulfide/poly-dopamine nano-complex finishing folate molecule, the hollow copper sulfide/poly-dopamine complex of obtained modified with folic acid.
2. the preparation method of the hollow copper sulfide/poly-dopamine complex of modified with folic acid according to claim 1, is characterized in that: the cuprous oxide nano particle described in step (1) is obtained by ascorbic acid reduction Copper hydrate.
3. the preparation method of the hollow copper sulfide/poly-dopamine complex of modified with folic acid according to claim 1, is characterized in that: step (2) is specially and adopts Na
2s9H
2the cuprous nano-particle of O sulfidation-oxidation, the nano copper sulfate particle of obtained hollow structure.
4. the preparation method of the hollow copper sulfide/poly-dopamine complex of modified with folic acid according to claim 1, it is characterized in that: step (3) is specially: the nano copper sulfate particle of hollow structure is added in Tris-HCl buffer, add dopamine, adjust pH to be 8.5, dopamine must gather DOPA amine layer in nano grain surface auto polymerization.
5. the preparation method of the hollow copper sulfide/poly-dopamine complex of modified with folic acid according to claim 1, it is characterized in that, step (4) is specially: the hollow copper sulfide/poly-dopamine complex by hollow copper sulfide/poly-dopamine nano-complex and folic acid being 4:1 water-soluble solution concussion 12h, obtained modified with folic acid in mass ratio.
6. hollow copper sulfide/poly-dopamine complex of the modified with folic acid that obtains of preparation method as claimed in claim 1, is characterized in that: the particle diameter of complex is 90-100nm.
7. the complex that preparation method obtains as claimed in claim 1 is preparing the application in photo-thermal therapy medicine.
8. the complex that preparation method obtains as claimed in claim 1 is preparing the application in pharmaceutical carrier, and described medicine is one or more the mixture in amycin, paclitaxel, camptothecine, phthalocyanine, epirubicin, daunorubicin, Methylaminopterin.
9. the complex that preparation method obtains as claimed in claim 1 is preparing the application in cancer cell number detection of drugs, and described cancerous cell is HepG2 cell.
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| CN104831534B (en) * | 2015-03-06 | 2016-08-31 | 哈尔滨工业大学宜兴环保研究院 | A kind of super-hydrophobic super-oleophylic cloth preparation method for material |
| CN105056234B (en) * | 2015-09-01 | 2017-12-22 | 郑州大学 | A kind of active targeting nanosphere of photo-thermal therapy tumour and preparation method and application |
| CN105267979B (en) * | 2015-11-13 | 2018-03-16 | 西安交通大学 | The method that polymerization prepares gossypol and its derivative poly-dopamine nano-carrier |
| CN105823766B (en) * | 2016-03-22 | 2019-01-25 | 北京大学 | A kind of methods and applications of real-time quantitative fluorescence monitoring molecular engram process |
| CN109580607B (en) * | 2018-12-13 | 2021-06-29 | 泉州师范学院 | Preparation and application of MXene-CuS nano composite material |
| CN112310333B (en) * | 2019-07-23 | 2022-05-17 | 珠海冠宇电池股份有限公司 | Sulfide pole piece material, preparation method thereof and lithium battery |
| CN111658250B (en) * | 2020-06-05 | 2022-10-28 | 北京爱霖医疗科技有限公司 | Nickel-titanium alloy self-expansion stent and preparation method thereof |
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| CN113018500B (en) * | 2021-03-10 | 2022-04-12 | 西华师范大学 | Synergistic chemical and photodynamic antibacterial and antiviral coating and preparation method thereof |
| CN115888628A (en) * | 2022-11-30 | 2023-04-04 | 南京信息工程大学 | Cu 2-x Preparation method and application of S adsorption material |
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| CN102146288A (en) * | 2011-01-05 | 2011-08-10 | 中国科学院宁波材料技术与工程研究所 | Preparation method of water-soluble material in core-shell or core-corona-shell structure |
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