CN103961705A - Preparation method and application of folic acid modified hollow copper sulfide/polydopamine compound - Google Patents
Preparation method and application of folic acid modified hollow copper sulfide/polydopamine compound Download PDFInfo
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Abstract
The invention relates to a preparation method and application of a folic acid modified hollow copper sulfide/polydopamine compound. The preparation method comprises the following steps: preparing copper sulfide nanoparticles of a hollow structure by virtue of a template method; promoting polymerization of dopamine on the surface under an alkaline condition to form a polydopamine layer; fixing folic acid on the surface by virtue of a Schiff base reaction to obtain a multifunctional targeted CuS@DPA-FA nano compound. The compound disclosed by the invention not only has a medicine carrying function but also acts as photothermal therapy; moreover, the compound can be used for detecting the quantity of cancer cells by virtue of a colorimetric method on the basis of a like-peroxidase catalytic activity. Therefore, the compound can be widely applied to such fields as early diagnosis of tumors, medical and photothermal therapy of tumors; meanwhile, the compound has the characteristics of simple preparation process, low cost, high biocompatibility and the like.
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 and the biotechnology that develop based on nanoparticle are received people's extensive concern in the application aspect medicine/gene delivery, bio-sensing, bio-imaging and photo-thermal therapy.In order to improve the hydrophilic, colloidal stability, biocompatibility of nanoparticle and the bonding force with bio-active group, it is most important that the finishing of nanoparticle just seems.Dopamine (DA) is a kind of material in marine mussel with biological stickiness that is present in, and is again a kind of micromolecule simulated albumin matter simultaneously.Under alkaline pH condition, can there is auto polymerization reaction in nanoparticle surface (no matter surface is performance hydrophilic or hydrophobicity) in dopamine (DA), in poly-dopamine (PDA) structure obtaining, contain 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 that has 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 be 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 subject to the impact of environment and size less, less to biology and human toxicity, and 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 and treats cancer [Adv. Mater. 2011,23,3542 – 3547] [Small 2012,8,3143 – 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
2the hydroxyl radical free radical that produces 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 development can be treated photo-thermal with chemotherapy and combine, and brings into play its synergistic technology and can effectively reduce side effect, strengthens therapeutic effect; On the other hand, the Clinics and Practices technology of utilizing the multi-functional characteristic development of inorganic nano material simultaneously to realize cancer also has Research Significance very much.
Summary of the invention
The object of the invention is to provide a kind of preparation and application thereof of hollow copper sulfide/poly-dopamine complex of modified with folic acid, this complex has targeting, photo-thermal therapy, Drug therapy and cancerous cell simultaneously and detects quadruple effect, can effectively realize the synergistic function of diagnosis and treatment.At hollow nano copper sulfate particle finishing one strata dopamine layer, utilize dopamine layer to improve drug loading rate, biocompatibility and the coupling target molecule of complex, the near infrared absorption function of CuS nano-particle and mimetic enzyme catalysis characteristic are combined simultaneously, set up a kind of method that can simultaneously 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) prepare cuprous oxide nano particle;
(2) make the nano copper sulfate particle of hollow structure by the cuprous nano-particle of sulfidation-oxidation;
(3), at the nano copper sulfate particle finishing one strata dopamine layer of hollow structure, form hollow copper sulfide/poly-dopamine nano-complex;
(4), at hollow copper sulfide/poly-dopamine nano-complex finishing folic acid (FA) molecule, make the hollow copper sulfide/poly-dopamine complex of modified with folic acid.
Specifically comprise the following steps:
(1) ascorbic acid reduction Copper hydrate is prepared cuprous oxide nano particle;
(2) make the nano copper sulfate particle of hollow structure by the cuprous nano-particle of sulfidation-oxidation, sulfur used source is Na
2s9H
2o, reaction temperature is 55 DEG C;
(3) in the Tris-HCl of pH=8.5 buffer, 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 the water-soluble solution concussion of 4:1 12h in mass ratio by hollow copper sulfide/poly-dopamine nano-complex and folic acid, utilize simple schiff base reaction to make the hollow copper sulfide/poly-dopamine complex of modified with folic acid.
Hollow copper sulfide/poly-dopamine the complex of the modified with folic acid that method makes as mentioned above, 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 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, cancerous cell quantity is more, be fixed on surperficial complex also more, chromogenic reaction speed is faster, therefore can pass through 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:
Utilize electrostatic attraction effect and π-π effect by Drug absorbability to CuS@PDA-FA carrier.
CuS@PDA-FA composite particles after carrying medicament is added in cancerous cell culture fluid by variable concentrations, laser irradiation 5 minutes, utilizes photo-thermal therapy and the synergy of Drug therapy and the targeting of complex of MTT experiment exam CuS@PDA-FA nano-complex; Described laser is 808nm, and described cancerous cell is HepG2 cell.
Utilize the class peroxidase activity of CuS to set up the quantity of colorimetric determination cancerous cell.CuS@PDA-FA nano-complex is added containing in the HepG2 cell culture fluid of different numbers, cultivate after 4h, with PBS(10mM, pH=7.4) buffer washes away unnecessary material, cell is scattered in to PBS(10mM, pH=4.0 again) in solution, then add substrate and H
2o
2carry out Catalytic color reaction, measure the each group of absorption value at 652nm place, by measuring absorption value along with the variation tendency of number of cells is set up the technology of utilizing colorimetric determination cancerous cell quantity; 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 present invention combines the near infrared absorption function of CuS nano-particle and mimetic enzyme catalysis characteristic for the first time, set up a kind of method that can simultaneously realize targeting, photo-thermal therapy, Drug therapy and cancerous cell detection quadruple effect, being expected to the fields such as the early diagnosis and therapy for disease provides technical foundation, possesses economic benefit and social benefit significantly;
2. the introducing of dopamine shell has strengthened the biocompatibility of CuS nano-particle, has improved the load factor of medicine, makes the various target biology molecules of the more convenient modification of composite surface simultaneously, is more conducive to its application in biomedicine;
3. the preparation method of CuS@PDA-FA complex is simple, with low cost, and bio-target molecule coupling is easier, is easy to extensive preparation.
Brief description of the drawings
Fig. 1 is the TEM figure of the hollow CuS@PDA-FA nano-complex that makes of embodiment 1;
Fig. 2 is the heating rate figure of variable concentrations CuS@PDA solution under laser irradiation in embodiment 2;
Fig. 3 is the drug release in vitro curve chart of CuS@PDA-FA complex in embodiment 3;
Fig. 4 is the cytotoxicity test of variable concentrations hollow CuS@PDA-FA nano-complex in embodiment 4;
Fig. 5 is the cell survival rate figure that adds not gained after sample culturing on the same group in embodiment 5;
After the HepG2 cell absorption hollow CuS@PDA-FA nano-complex of different numbers in embodiment 6, there is corresponding absorption value after catalytic reaction in Fig. 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
CuS@PDA-FA nano-complex aqueous solution is carried out to supersound process 0.5h, then drop on copper mesh, after drying, carry out TEM scanning (see figure 1), complex is hollow structure as shown, the about 100nm of size, dopamine shell thickness is 3 ~ 4nm, composite particles size homogeneous, good dispersion.
embodiment 2
25 μ g/mL, 50 μ g/mL and the each 1mL of 100 μ g/mLCuS@PDA solution are added in colorimetric pool, and with the laser irradiation of 808nm wavelength, (power is 2W/cm
2), solution, along with the increase of irradiation time heats up gradually, records variations in temperature every 20s.As can be seen from Figure 2, the CuS@PDA solution of 100 μ g/mL heats up and reaches 45.3 DEG C at 320s, illustrates that its photo-thermal conversion effect is fine.
embodiment 3
By CuS@PDA-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, collects supernatant and calculates the amount of contained DOX wherein according to standard curve, and the load capacity of further calculating DOX is 0.24mg DOX/1mg CuS PDA-FA.Then CuS PDA-FA complex 1mg being adsorbed after medicine is scattered in 2mL PBS(10mM, pH=7.0), in solution, put into and bag filter is added after bag filter to the 50ml PBS solution 24h that dialyses, every 1h, 2h, 3h, 4h, 6h, 12h, 24h gets 3ml solution and surveys fluorescence, and original solution fills into 3ml PBS 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 the DOX fluorescence intensity of surveying the highest, the release that is more conducive to this understanding DOX is described.
embodiment 4
Carry out MTT test with the CuS@PDA-FA complex that concentration is 25 μ g/mL, 50 μ g/mL, 75 μ g/mL and 100 μ g/mL, it is HepG2 cell that cell is selected in MTT test, 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, every group of cell survival rate all, more than 85%, illustrates that the hollow copper sulfide/poly-dopamine complex cell compatibility of modified with folic acid is high.
embodiment 5
By not on the same group the sample of equivalent concentration add and in cell culture fluid, cultivate 6h, 3-6 group is taken out laser irradiation with 808nm wavelength, and (power is 2W/cm
2) continue to cultivate 6h after 5min, survey 490nm place absorption value, calculate the cell survival rate of each group according to the absorption value of blank group.Wherein the sample of testing is specially: sample 1 is blank, sample 2 is for adsorbing the CuS-PDA complex after DOX, sample 3 is CuS-PDA complex (laser irradiation), sample 4 is CuS-PDA-FA complex (laser irradiation), sample 5 is for adsorbing the CuS-PDA complex (laser irradiation) after DOX, sample 6 is for adsorbing the CuS-PDA-FA complex (laser irradiation) after DOX, and every group of concentration is 50 μ g/mL, and cell used is HepG2 cell; As can be seen from Figure 5, wherein 3 and 4 groups of contrasts are known, after laser irradiation, hollow CuS@PDA nano-complex heats up and can make cell death, and hollow CuS@PDA-FA complex plays the effect of targeting, cause the interior CuS@PDA nano-complex local concentration of cell higher, photo-thermal effect is more obvious; 2,5 and 6 groups of contrasts are known, the CuS@PDA nano-complex of load DOX can be by cell endocytic, then in cell, discharge DOX, cause cell death, after laser irradiation, the photo-thermal therapy of DOX Drug therapy and CuS@PDA nano-complex has produced synergism reduces cell survival rate, and CuS@PDA-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
The HepG2 cell of different numbers is scattered in cell culture fluid, then CuS@PDA-FA solution is added to (ultimate density is 20 μ g/mL) in cell culture fluid, after cultivating 4h, use PBS(10mM, pH=7.4) buffer washes away unnecessary material, cell is scattered in to PBS(10mM, pH=4.0), in solution, then add TMB(ultimate density 0.4mM) 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.The HepG2 cell quantity of surveying is 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; Along with the increase of cell number, the CuS@PDA-FA nano-complex of cell surface combination is just more, catalysis H as can be seen from Figure 6
2o
2oxidation TMB speed is just faster, and the more solution colours of oxTMB of generation darker (as shown in Figure 7, from left to right, color burn) are just 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 CuS@PDA-FA nano-complex and the targeting of folic acid, sets up the technology of colorimetric determination particular cancer cell quantity.
Claims (9)
1. a preparation method for the hollow copper sulfide of modified with folic acid/poly-dopamine complex, is characterized in that: comprise the following steps:
(1) prepare cuprous oxide nano particle;
(2) make the nano copper sulfate particle of hollow structure by the cuprous nano-particle of sulfidation-oxidation;
(3), at the nano copper sulfate particle finishing one strata dopamine layer of hollow structure, form hollow copper sulfide/poly-dopamine nano-complex;
(4), at hollow copper sulfide/poly-dopamine nano-complex finishing folate molecule, make the hollow copper sulfide/poly-dopamine complex of modified with folic acid.
2. the preparation method of the hollow copper sulfide of modified with folic acid according to claim 1/poly-dopamine complex, is characterized in that: the described cuprous oxide nano particle of step (1) reduces Copper hydrate by ascorbic acid and makes.
3. the preparation method of the hollow copper sulfide of modified with folic acid according to claim 1/poly-dopamine complex, is characterized in that: step (2) is specially and adopts Na
2s. 9H
2the cuprous nano-particle of O sulfidation-oxidation, makes the nano copper sulfate particle of hollow structure.
4. the preparation method of the hollow copper sulfide of modified with folic acid according to claim 1/poly-dopamine complex, 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, adjusting pH is 8.5, and dopamine must gather dopamine layer in nano grain surface auto polymerization.
5. the preparation method of the hollow copper sulfide of modified with folic acid according to claim 1/poly-dopamine complex, it is characterized in that, step (4) is specially: be the water-soluble solution concussion of 4:1 12h in mass ratio by hollow copper sulfide/poly-dopamine nano-complex and folic acid, make the hollow copper sulfide/poly-dopamine complex of modified with folic acid.
6. hollow copper sulfide/poly-dopamine complex of the modified with folic acid that preparation method as claimed in claim 1 makes, is characterized in that: the particle diameter of complex is 90-100nm.
7. an application for the hollow copper sulfide/poly-dopamine complex of the modified with folic acid that preparation method as claimed in claim 1 makes, is characterized in that: for photo-thermal therapy.
8. an application for the hollow copper sulfide/poly-dopamine complex of the modified with folic acid that preparation method as claimed in claim 1 makes, is characterized in that: carrying medicament is for Drug therapy; Described carrying medicament is one or more mixture in amycin, paclitaxel, camptothecine, phthalocyanine, epirubicin, daunorubicin, Methylaminopterin.
9. in the modified with folic acid that a preparation method as claimed in claim 1 makes
emptysulfuration
copper/poly-dopamine is multiple
closethe application of thing, is characterized in that: detect for cancerous cell quantity; Described cancerous cell is HepG2 cell.
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