CN115626671A - Multifunctional dual-ligand platinum nano-particle and preparation method and application thereof - Google Patents
Multifunctional dual-ligand platinum nano-particle and preparation method and application thereof Download PDFInfo
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 221
- 239000003446 ligand Substances 0.000 title claims abstract description 110
- 239000002105 nanoparticle Substances 0.000 title claims abstract description 104
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 104
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 230000000694 effects Effects 0.000 claims abstract description 21
- 239000007864 aqueous solution Substances 0.000 claims abstract description 19
- 125000003396 thiol group Chemical class [H]S* 0.000 claims abstract description 17
- 238000003756 stirring Methods 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 13
- 239000000758 substrate Substances 0.000 claims abstract description 13
- 102000003992 Peroxidases Human genes 0.000 claims abstract description 10
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims abstract description 10
- 108040007629 peroxidase activity proteins Proteins 0.000 claims abstract description 10
- 238000000108 ultra-filtration Methods 0.000 claims abstract description 10
- 102000016938 Catalase Human genes 0.000 claims abstract description 9
- 108010053835 Catalase Proteins 0.000 claims abstract description 9
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 8
- 108010024636 Glutathione Proteins 0.000 claims abstract description 5
- 229960003180 glutathione Drugs 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 25
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
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- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
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- 238000005119 centrifugation Methods 0.000 claims description 11
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- 238000000034 method Methods 0.000 claims description 9
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002245 particle Substances 0.000 claims description 7
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- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 238000000870 ultraviolet spectroscopy Methods 0.000 claims description 6
- 238000010521 absorption reaction Methods 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 238000001514 detection method Methods 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 2
- LMHAGAHDHRQIMB-UHFFFAOYSA-N 1,2-dichloro-1,2,3,3,4,4-hexafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(Cl)C1(F)Cl LMHAGAHDHRQIMB-UHFFFAOYSA-N 0.000 claims description 2
- CSJDJKUYRKSIDY-UHFFFAOYSA-N 1-sulfanylpropane-1-sulfonic acid Chemical compound CCC(S)S(O)(=O)=O CSJDJKUYRKSIDY-UHFFFAOYSA-N 0.000 claims description 2
- DCYGAPKNVCQNOE-UHFFFAOYSA-N 2,2,2-triphenylacetic acid Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)O)C1=CC=CC=C1 DCYGAPKNVCQNOE-UHFFFAOYSA-N 0.000 claims description 2
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- RJTANRZEWTUVMA-UHFFFAOYSA-N boron;n-methylmethanamine Chemical compound [B].CNC RJTANRZEWTUVMA-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims description 2
- 238000000703 high-speed centrifugation Methods 0.000 claims description 2
- AIRPJJGSWHWBKS-UHFFFAOYSA-N hydroxymethylphosphanium;chloride Chemical compound [Cl-].OC[PH3+] AIRPJJGSWHWBKS-UHFFFAOYSA-N 0.000 claims description 2
- 230000001678 irradiating effect Effects 0.000 claims description 2
- 239000012528 membrane Substances 0.000 claims description 2
- 229960003151 mercaptamine Drugs 0.000 claims description 2
- 238000012544 monitoring process Methods 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
- 238000007789 sealing Methods 0.000 claims description 2
- 229920002545 silicone oil Polymers 0.000 claims description 2
- 239000001119 stannous chloride Substances 0.000 claims description 2
- 235000011150 stannous chloride Nutrition 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 claims description 2
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 claims description 2
- GEPJPYNDFSOARB-UHFFFAOYSA-N tris(4-fluorophenyl)phosphane Chemical compound C1=CC(F)=CC=C1P(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 GEPJPYNDFSOARB-UHFFFAOYSA-N 0.000 claims description 2
- 238000011534 incubation Methods 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 1
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- 206010028980 Neoplasm Diseases 0.000 abstract description 3
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- 230000009977 dual effect Effects 0.000 description 18
- 239000000463 material Substances 0.000 description 10
- 230000002255 enzymatic effect Effects 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 3
- 229960004316 cisplatin Drugs 0.000 description 3
- 239000012621 metal-organic framework Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 238000000026 X-ray photoelectron spectrum Methods 0.000 description 2
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- 230000015572 biosynthetic process Effects 0.000 description 2
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- 238000007626 photothermal therapy Methods 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VYFPSYVVFFFYBF-UHFFFAOYSA-N sodium;triphenylphosphane Chemical compound [Na].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VYFPSYVVFFFYBF-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- 206010065553 Bone marrow failure Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- 229910002836 PtFe Inorganic materials 0.000 description 1
- 238000003917 TEM image Methods 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000001659 chemokinetic effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 238000009616 inductively coupled plasma Methods 0.000 description 1
- 238000010983 kinetics study Methods 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 238000002428 photodynamic therapy Methods 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C01G55/00—Compounds of ruthenium, rhodium, palladium, osmium, iridium, or platinum
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- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/243—Platinum; Compounds thereof
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Abstract
The invention discloses a multifunctional dual-ligand platinum nano particle and a preparation method and application thereof. The preparation method comprises the following steps: stirring and reacting chloroplatinic acid aqueous solution and non-mercapto ligand aqueous solution at room temperature for half an hour, adding sodium borohydride aqueous solution, stirring and reacting for half an hour, and obtaining single-ligand platinum nanoparticles; and reacting the glutathione aqueous solution with good biocompatibility with the single-ligand platinum nanoparticles for one hour, then, removing unreacted substrates through ultrafiltration, and carrying out high-speed centrifugal concentration and preservation at 4 ℃ to obtain the multifunctional double-ligand platinum nanoparticles. The dual-ligand platinum nanoparticle set prepared by the invention integrates multiple functions, has catalase and peroxidase activities, shows good photo-thermal property, and has good stability and biocompatibility. The multifunctional dual-ligand platinum nano-particle has the advantages of simple preparation method, low cost, easy industrial production and good application prospect in the fields of tumor treatment and the like.
Description
Technical Field
The invention belongs to the field of functional nano materials, and relates to multifunctional dual-ligand platinum nano particles, and a preparation method and application thereof.
Background
Cisplatin has good anticancer effect, and thus is the first choice for clinical treatment of cancer. However, cisplatin and various derivatives thereof have serious toxic and side effects, such as renal toxicity, neurotoxicity, myelosuppression and the like, and the problems limit the further development and application of cisplatin. With the development of nanotechnology, nanoparticles are widely used in various fields due to their characteristics of small size, large specific surface area, excellent optical properties, and stable physicochemical properties.
In recent years, the emergence of a range of novel therapies, such as photothermal therapy (PTT), photodynamic therapy (PDT) and chemokinetic therapy (CDT), has stimulated the interest of researchers in the study of platinum nanoparticles (PtNPs). Liu synthesized PtFe @ Fe 3 O 4 The catalytic treatment purpose is achieved by utilizing the activity of the peroxidase of the platinum, so that the platinum can catalyze and decompose the hydrogen peroxide into the highly toxic ROS under the slightly acidic condition. However, this material has a lower affinity for the substrate TMB and the enzyme activity is to be improved. Yang utilizes platinum to catalytically decompose hydrogen peroxide into oxygen, plays a role in regulating a tumor hypoxia microenvironment, and constructs a Metal Organic Framework (MOF) material based on platinum modification. However, further practical applications of MOF materials are limited by their powder crystalline state. Song utilizes platinum to have good optical absorption in a near infrared region to prepare a novel photo-thermal agent hollow Pt nano-frame, and the photo-thermal conversion efficiency of the novel photo-thermal agent hollow Pt nano-frame can reach 52.5%. However, the size of the material is large, the biological application is limited, and polyethylene glycol (PEG) needs to be additionally modified to improve the biocompatibility. The material embodies that the platinum-based material has peroxidase activity, catalase activity and good photo-thermal performance, but the material has the disadvantages of complex synthesis process, harsh conditions, poor biocompatibility and limited application. Therefore, the preparation of the platinum nano-particles which have the functions integrated, simple synthesis raw materials, simple steps and good biocompatibility has more practical application value.
Disclosure of Invention
In order to overcome the defects of the prior art, the invention provides a preparation method of a dual-ligand modified platinum nano particle with good stability and biocompatibility. The preparation method of the multifunctional dual-ligand platinum nanoparticles provided by the invention has the advantages of simple process, less time consumption, low cost and easiness for large-scale production, and meanwhile, the dual-ligand platinum nanoparticles integrate multiple functions, have high-efficiency catalase activity, peroxidase activity and good photo-thermal property, and have a wide application prospect. The invention can be realized by the following technical scheme.
The preparation method of the multifunctional dual-ligand platinum nano-particle comprises the following steps:
and (3) stirring and reacting the chloroplatinic acid aqueous solution and the non-mercapto ligand aqueous solution at room temperature for half an hour, adding a sodium borohydride aqueous solution when the reaction color is changed from light yellow to colorless, stirring and reacting, and stopping the reaction when the solution color is changed into brownish black. Adjusting the pH value of the solution, adding a sulfhydryl ligand solution, stirring at room temperature, reducing the color of the solution to brown, stopping the reaction, removing unreacted substrates by ultrafiltration, then carrying out high-speed centrifugal concentration, and storing at 4 ℃ to obtain the multifunctional double-ligand platinum nanoparticles.
Further: the non-mercapto ligand is triphenylphosphine tri-m-sulfonic acid sodium salt, 4-diphenylphosphine benzoic acid, tri (4-fluorophenyl) phosphine, triphenylphosphine, 2-hydroxyphosphonoacetic acid, triphenylacetic acid and the like.
And further: the reducing agent is sodium borohydride, dimethylamine borane, tetrabutylammonium borohydride, tetrakis hydroxymethyl phosphonium chloride, stannous chloride and the like.
Further: in the reaction solution obtained by mixing chloroplatinic acid and a non-mercapto ligand, the ratio of the amount of the initial chloroplatinic acid to the amount of the non-mercapto ligand is 1; when sodium borohydride is added, the ratio of the initial chloroplatinic acid to the mass of sodium borohydride is 1.
And further: the pH value of the reaction solution after the sodium borohydride is added is 1-6, the reaction temperature is 8-40 ℃, the reaction time is 30min-6h, and the stirring speed is 300-1000rpm/min.
Further: the pH value of the brownish black solution is 6.0-8.0 after adjustment.
Further: the mercapto ligand is glutathione, mercaptobenzoic acid, mercaptoethylamine, mercaptopropanesulfonic acid, mercaptopropionic acid and the like, and the ratio of the initial chloroplatinic acid to the amount of the mercapto ligand is 1 to 1.
Further: the reaction temperature after the sulfhydryl ligand is added is 8-40 ℃, and the reaction time is 30min-6h.
Further: the ultrafiltration tube used for ultrafiltration has a membrane aperture of 3-50kDa, an ultrafiltration centrifugation temperature of 8-40 ℃, a centrifugation revolution of 2000-5000rpm/min, a centrifugation time of 10-30min, a high-speed centrifugation concentration temperature of 8-40 ℃, a centrifugation revolution of 5000-21000rpm/min, and a centrifugation time of 30-60min.
The double-ligand platinum nanoparticles are prepared by the preparation method, the multifunctional double-ligand platinum nanoparticles are monodisperse nanoparticles, and the particle size of a single double-ligand platinum nanoparticle is 1.5-2.8nm.
The catalase activity detection method of the multifunctional double-ligand platinum nanoparticles is obtained by the preparation method.
Adding a hydrogen peroxide solution into a buffer solution, then adding double-ligand platinum nanoparticles with a certain concentration, sealing the opening of a beaker by using a silicone oil solution, stirring the beaker at a certain temperature, and recording the change of the oxygen concentration in the mixed solution in real time by an oxygen dissolving instrument within a period of time.
And further: the concentration of the hydrogen peroxide is 0-20mM.
And further: the pH of the buffer solution is 2.0-7.0.
Further: the reaction temperature of the mixed solution is 10-60 DEG C
And further: the oxygen concentration of the solution is recorded every 10-30s by an oxygen dissolving instrument, and the total recording time is 10-60min.
The method for detecting the peroxidase activity of the multifunctional dual-ligand platinum nanoparticles is obtained by the preparation method.
Adding hydrogen peroxide solution into buffer solution, then adding 3,3', 5' -tetramethyl benzidine solution with certain concentration, finally adding double-ligand platinum nanoparticles, incubating for a period of time at a certain temperature, and testing the absorption of the mixed solution by using an ultraviolet-visible spectrophotometer.
Further: the hydrogen peroxide concentration is as follows: 0-20mM.
Further: the above-mentioned 3', 5' -Tetramethylbenzidine (TMB) concentration was: 0-1.6mM.
Further: the pH of the buffer solution is 2.0-7.0.
And further: the reaction temperature of the mixed solution is 10-60 ℃.
And further: the mixed solution is tested once every 10-60s by an ultraviolet visible light photometer, the total testing time is 0-90min, and the testing wavelength range is 200-800nm.
The photo-thermal performance detection method of the multifunctional dual-ligand platinum nanoparticles is obtained by the preparation method.
Taking a solution of the double-ligand platinum nanoparticles with a certain concentration into a transparent cuvette with the width of 1cm, irradiating the cuvette for a period of time by using laser, closing the laser, cooling the cuvette to room temperature, and monitoring the real-time temperature of the solution by using a thermal imager. The change of the absorption spectrum before and after illumination is tested by an ultraviolet-visible spectrophotometer.
And further: the concentration of the dual-ligand platinum nano particles in the solution is 50-400 ug/mL -1 。
Further: the laser wavelength range is 200-1064nm, and the laser power is 0.5-5W/cm 2 The laser irradiation time is 2-60min.
Further: the real-time temperature of the mixed solution is recorded once every 10 to 90 seconds by a thermal imaging instrument, and the total recording time is 5 to 150min.
Further: the mixed solution is tested by an ultraviolet visible light photometer before and after illumination, and the testing wavelength range is 200-800nm.
The multifunctional dual-ligand platinum nano-particle synthesized by the invention has various enzyme activities of catalase and peroxidase, and also has a good photo-thermal effect.
Compared with the prior art, the invention has the following advantages and technical effects:
(1) The preparation method of the multifunctional dual-ligand platinum nano-particle synthesized by the invention has the advantages of simple process, less time consumption, low cost and easy large-scale production.
(2) The double-ligand platinum nano particle synthesized by the invention has various enzyme activities of catalase and peroxidase and also has a good photo-thermal effect.
Drawings
Fig. 1 is an ultraviolet stability analysis of the dual ligand platinum nanoparticles of example 1.
FIG. 2 is a transmission electron microscope photograph of the dual ligand platinum nanoparticles of example 1.
FIG. 3 is a particle size histogram of the dual ligand platinum nanoparticles of example 1.
Fig. 4 is a graph of the hydrated particle size of the dual ligand platinum nanoparticles of example 1.
FIG. 5 is an X-ray photoelectron spectrum of the dual-ligand platinum nanoparticle of example 1.
FIG. 6 shows dual ligand platinum nanoparticles and different concentrations of H in example 2 2 O 2 Graph of oxygen concentration in the mixed solution as a function of time.
FIG. 7 is a graph of UV-VIS absorption spectra of the solution after mixing of the dual ligand Pt nanoparticles, hydrogen peroxide and TMB in example 3 as a function of time.
FIG. 8 shows the dual ligand platinum nanoparticles in example 4 for different concentrations of substrate H 2 O 2 Enzymatic kinetic diagram of (a).
FIG. 9 is a graph of the enzymatic kinetics of the dual ligand platinum nanoparticles for various concentrations of substrate TMB in example 5.
FIG. 10 is a graph showing the temperature changes of the solution of the dual-ligand platinum nanoparticles in example 6 under different power densities of light.
FIG. 11 is a graph showing the temperature change of solutions of dual ligand platinum nanoparticles in example 7 at different concentrations under the same power density illumination.
FIG. 12 is a thermal image of the solution of the dual ligand platinum nanoparticles of example 8 with an extended period of light.
FIG. 13 is a graph of UV absorption spectra of the dual ligand platinum nanoparticle solution of example 8 before and after illumination.
FIG. 14 is a graph of the photoperiod stability of the dual ligand platinum nanoparticle solution of example 8.
Fig. 15 is a calculated graph of photothermal conversion efficiency of the dual ligand platinum nanoparticle solution in example 8.
FIG. 16 is a flow chart of the preparation of multifunctional dual ligand platinum nanoparticles of the present invention.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the present invention is not limited thereto.
In the following specific examples, chloroplatinic acid and triphenylphosphine sodium tri-m-sulfonate referred to were purchased from the Shanghai Michelle chemical technology, inc.; the instrument for analyzing the properties of the double-ligand platinum nanoparticles mainly comprises a JEM-2100F transmission electron microscope, a German Thermoscientific inductively coupled plasma mass spectrometer (iCAPRQ), a Nippon Shimadzu UV-2600 ultraviolet visible spectrophotometer, a Shanghai Reye JPSJ-605F dissolved oxygen tester and the like.
Example 1
The optimal embodiment of the invention for preparing the multifunctional dual-ligand platinum nano-particle is as follows: 178 μ L of chloroplatinic acid aqueous solution (0.225M) is added into a 50mL round bottom flask containing 7.85mL of deionized water at room temperature, 11.67mL of triphenylphosphine sodium trimetaphosphate aqueous solution (5.82 mM) is then added, stirring is carried out at the speed of 650rpm/min at room temperature for 30min, when the reaction color changes from pale yellow to colorless, 300 μ L of sodium borohydride aqueous solution (25 mM) is added, the solution immediately changes to brownish black, after stirring is carried out for 30min at room temperature, the pH is adjusted to 7.4 by dilute hydrochloric acid, 300 μ L of glutathione aqueous solution with the adjusted pH of 7.4 is then added, standing is carried out for 1h at room temperature, the solution color is reduced to brown, the reaction is stopped, a 10kDa ultrafiltration tube is used for centrifugation for 30min at the temperature of 15 ℃ and 3750rpm/min, unreacted substrates are removed, then the 10 μ L of glutathione aqueous solution with the adjusted pH of 7.4 is used for high-speed centrifugal concentration for 10min at the temperature, multifunctional double ligand platinum nanoparticles are obtained, and are placed in a refrigerator for standby at the temperature of 4 ℃.
FIG. 1 shows a TEM image of the synthesized multifunctional dual-ligand platinum nanoparticles, as shown in FIG. 2, with better storage stability.
The synthesized dual ligand platinum nanoparticles were counted by a particle size analysis software (e.g., nanomeasurer 1.2.5), and the particle size was 1.6-2.2nm as shown in fig. 3.
FIG. 4 shows that the hydrated particle size of the synthesized dual-ligand platinum nanoparticles is 4.5-6.3nm.
FIG. 5 is the X-ray photoelectron spectrum of the synthesized dual-ligand Pt nanoparticle with Pt as the main component.
The flow of this embodiment is shown in fig. 16.
Example 2
The best embodiment of the catalase activity test of the multifunctional dual-ligand platinum nanoparticles prepared by the invention is as follows: adding hydrogen peroxide solution with different concentrations into phosphate buffer solution with pH of 6.5, and adding dual-ligand platinum nanoparticles (calculated by platinum atom concentration, final concentration is 10 mug. Multidot.mL) -1 ) The temperature is 25 ℃, the oxygen concentration of the solution is recorded every 30s by an oxygen dissolving instrument, and the total recording time is 10min.
FIG. 6 shows that the dual ligand platinum nanoparticles have good catalase activity.
Example 3
The optimal embodiment of the peroxidase activity test of the multifunctional dual-ligand platinum nanoparticles prepared by the invention is as follows: at room temperature, hydrogen peroxide solution (final concentration of 10 mM) was added to phosphate buffer salt having pH of 6.5, followed by 3,3', 5' -tetramethylbenzidine solution (final concentration of 0.2 mM), and finally, bis-ligand platinum nanoparticles (final concentration of 10. Mu.g.mL, calculated as platinum atom concentration) were added -1 ) The absorption spectrum of the solution was measured every 40s with an ultraviolet-visible spectrophotometer.
FIG. 7 shows that the dual ligand platinum nanoparticles have good peroxidase activity.
Example 4
Substrate H of multifunctional dual-ligand platinum nano-particle prepared by the invention 2 O 2 The most preferred embodiment of the enzymatic kinetics study of (a) is as follows:hydrogen peroxide solutions of different concentrations (final concentrations of 0,1,5, 10, 15, 20mM, respectively) were added to phosphate buffer salt of pH 6.5, followed by 3,3', 5' -tetramethylbenzidine solution (final concentration of 0.2 mM), and finally, the bis-ligand platinum nanoparticles (final concentration of 10. Mu.g.mL, calculated as platinum atom concentration) were added at room temperature -1 ) And (5) absorbing the solution every 10 seconds by using an ultraviolet visible light photometer, and detecting for 30min.
FIG. 8 shows multifunctional dual-ligand platinum nanoparticles vs substrate H 2 O 2 Has an enzymatic kinetics Km of 4.46mM for the substrate H 2 O 2 Has high affinity.
Example 5
The optimal embodiment of the enzymatic kinetic study of the substrate TMB of the multifunctional dual ligand platinum nanoparticles prepared in the present invention is as follows: hydrogen peroxide solutions (final concentration of 10 mM) were added to phosphate buffered saline pH 6.5, followed by 3,3', 5' -tetramethylbenzidine solutions (final concentrations of 0.1,0.2,0.4,0.8,1.2mM, respectively) at different concentrations and finally bis-ligand platinum nanoparticles (final concentration of 10. Mu.g.mL, calculated as platinum atom concentration) at room temperature -1 ) And testing the solution absorption every 10s by using an ultraviolet visible light photometer for 30min.
FIG. 9 shows that the multifunctional dual-ligand platinum nanoparticles have an enzymatic kinetics Km of 0.214mM for the substrate TMB and a higher affinity for the substrate TMB.
Example 6
The embodiment of the relation between the photo-thermal performance and the power density of the multifunctional dual-ligand platinum nanoparticle solution prepared by the invention is as follows: taking multifunctional platinum nanoparticles (calculated by platinum atom concentration, concentration is 150 ug. ML) -1 ) In a transparent cuvette with a width of 1cm, 808nm lasers (0.2, 0.4,0.6,0.8,1.0, 1.2W.cm) with different powers were used -2 ) The irradiation was carried out for 10 minutes and the temperature of the biligand platinum nanoparticle solution was monitored every 60 seconds using a thermal imager.
FIG. 10 shows that the temperature of the multifunctional bis-ligand platinum nanoparticles gradually increases with the time of illumination, while the higher the power density, the faster the temperature increase.
Example 7
The embodiment of the relation between the photo-thermal property and the material concentration of the multifunctional dual-ligand platinum nanoparticle solution prepared by the invention is as follows: taking multifunctional platinum nanoparticle solution with different concentrations (calculated by platinum atom concentration, concentration is 0, 50, 100, 150, 200 ug. ML) -1 ) In a transparent cuvette with a width of 1cm, using a laser at 808nm (1W. Cm) -2 ) The irradiation was carried out for 10 minutes and the temperature of the solution of the biligand platinum nanoparticles was monitored every 60 seconds with a thermal imager.
FIG. 11 shows that the temperature of the multifunctional dual-ligand platinum nanoparticles gradually increases with the increase of the illumination time, and the temperature increases faster with higher material concentration.
Example 8
The optimal embodiment of the test of the photo-thermal conversion efficiency of the multifunctional dual-ligand platinum nano-particle prepared by the invention is as follows: take 150ug mL -1 The double ligand platinum nano-particles are placed in a transparent cuvette with the width of 1cm and are treated by a laser (1W cm) with the wavelength of 808nm -2 ) After 10 minutes of irradiation, the laser was turned off and allowed to cool for 20 minutes. The cycle experiment is repeated for four times to research the photo-thermal stability of the material, the temperature of the dual-ligand platinum nanoparticles is monitored by a thermal imager, the absorption spectrum change before and after illumination is tested by an ultraviolet-visible spectrophotometer, and finally the photo-thermal conversion efficiency of the dual-ligand platinum nanoparticles is calculated.
FIG. 12 shows that the temperature of multifunctional dual-ligand platinum nanoparticles gradually increases with the increase of illumination time.
FIG. 13 shows that the absorption spectrum of the multifunctional dual-ligand platinum nanoparticles is unchanged before and after illumination.
FIG. 14 shows that multifunctional dual-ligand platinum nanoparticles have good photoperiod stability.
Fig. 15 is a calculated graph of the photothermal conversion efficiency of the bifunctional biligand platinum nanoparticle, which indicates that the photothermal conversion efficiency of the bifunctional biligand platinum nanoparticle is 43.3%, and the photothermal performance is good.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such modifications are intended to be included in the scope of the present invention.
Claims (10)
1. The preparation method of the multifunctional dual-ligand platinum nanoparticles is characterized in that chloroplatinic acid aqueous solution and non-mercapto ligand aqueous solution are stirred and reacted for half an hour at room temperature, when the reaction color is changed from light yellow to colorless, aqueous solution of a reducing agent is added, the stirring reaction is carried out, the solution color is changed into brownish black, the reaction is stopped, the pH value of the solution is adjusted, mercapto ligand solution is added, the stirring is carried out at room temperature, the solution color is reduced to brown, the reaction is stopped, unreacted substrates are removed through ultrafiltration, then the high-speed centrifugal concentration is carried out, and the storage is carried out at 4 ℃ to obtain the multifunctional dual-ligand platinum nanoparticles;
the non-mercapto ligand is triphenylphosphine tri-m-sulfonic acid sodium salt, 4-diphenylphosphine benzoic acid, tri (4-fluorophenyl) phosphine, triphenylphosphine, 2-hydroxyphosphonoacetic acid or triphenylacetic acid;
the reducing agent is sodium borohydride, dimethylamine borane, tetrabutylammonium borohydride, tetrakis hydroxymethyl phosphonium chloride or stannous chloride.
2. The method for preparing multifunctional dual-ligand platinum nanoparticles according to claim 1, wherein in the reaction solution obtained by mixing the chloroplatinic acid aqueous solution and the non-mercapto ligand aqueous solution, the ratio of the initial chloroplatinic acid to the non-mercapto ligand substances is 1; and when the aqueous solution of the reducing agent is added, the ratio of the initial chloroplatinic acid to the amount of the reducing agent is 1.
3. The preparation method of the multifunctional dual-ligand platinum nanoparticle as claimed in claim 1, wherein the pH of the reaction solution after adding the aqueous solution of the reducing agent is 1-6, the reaction temperature is 8-40 ℃, the reaction time is 30min-6h, and the stirring speed is 300-1000rpm/min;
the pH value of the brownish black solution is 6.0-8.0 after adjustment.
4. The method for preparing multifunctional dual-ligand platinum nanoparticles according to claim 1, wherein the sulfhydryl ligand is glutathione, mercaptobenzoic acid, mercaptoethylamine, mercaptopropanesulfonic acid or mercaptopropionic acid; the ratio of the amounts of the starting chloroplatinic acid to the mercapto ligand species is 1.
5. The method for preparing multifunctional dual-ligand platinum nanoparticles as claimed in claim 1, wherein the reaction temperature after adding the sulfhydryl ligand is 8-40 ℃ and the reaction time is 30min-6h.
6. The method for preparing multifunctional double-ligand platinum nanoparticles as claimed in claim 1, wherein the ultrafiltration tube used in ultrafiltration has a membrane pore size of 3-50kDa, an ultrafiltration centrifugation temperature of 8-40 ℃, a centrifugation speed of 2000-5000rpm/min, a centrifugation time of 10-30min, a high-speed centrifugation concentration temperature of 8-40 ℃, a centrifugation speed of 5000-21000rpm/min, and a centrifugation time of 30-60min.
7. The dual-ligand platinum nanoparticles prepared by the preparation method of any one of claims 1 to 6, wherein the multifunctional dual-ligand platinum nanoparticles are monodisperse nanoparticles, and the particle size of a single dual-ligand platinum nanoparticle is 1.5-2.8nm; the hydrated particle size of the dual-ligand platinum nano-particle is 4.0-7.0nm.
8. The use of the dual-ligand platinum nanoparticles as claimed in claim 7, wherein the dual-ligand platinum nanoparticles are used for detecting catalase activity, comprising the following steps:
adding hydrogen peroxide solution into the buffer solution, and adding 5-25 μ g/mL in terms of platinum atom number -1 Sealing the opening of the beaker by using silicone oil liquid, stirring, and recording the change of the oxygen concentration in the mixed solution in real time by using an oxygen dissolving instrument within a period of time; the concentration of the hydrogen peroxide is 0-20mM; the pH value of the buffer solution is 2.0-7.0; the stirring temperature is 10-60 ℃; the solution is dissolvedThe oxygen meter records the oxygen concentration in the solution once every 10-30s, and the total recording time is 10-60min.
9. The use of the dual-ligand platinum nanoparticles as claimed in claim 7, wherein the dual-ligand platinum nanoparticles are used for peroxidase activity detection, and the method comprises the following steps:
adding hydrogen peroxide solution into buffer solution, adding 3,3', 5' -tetramethyl benzidine solution, and adding 5-25 μ g/mL of platinum atom number -1 Incubating the double-ligand platinum nano particles, and testing the absorption of the mixed solution by using an ultraviolet visible spectrophotometer; the hydrogen peroxide concentration is as follows: 0-20mM; the concentration of the 3', 5' -tetramethyl benzidine TMB is as follows: 0-1.6mM; the pH value of the buffer solution is 2.0-7.0; the incubation temperature is 10-60 ℃, and the incubation time is 0-90min; the incubated mixed solution is tested once every 10-60s by an ultraviolet visible light photometer, the total testing time is 0-90min, and the testing wavelength range is 200-800nm.
10. The use of the dual-ligand platinum nanoparticles as claimed in claim 7, wherein the dual-ligand platinum nanoparticles are used for photothermal property detection, comprising the following steps:
putting the dual-ligand platinum nanoparticle solution into a transparent cuvette with the width of 1cm, irradiating by using laser, closing the laser, cooling to room temperature, and monitoring the real-time temperature of the solution by using a thermal imager; testing the change of the absorption spectrum before and after illumination by using an ultraviolet visible light photometer; the concentration of the dual-ligand platinum nano particles in the solution is 50-400 ug-mL -1 (ii) a The wavelength range of the used laser is 200-1064nm, and the laser power is 0.5-5W/cm 2 The laser irradiation time is 2-60min; recording the real-time temperature of the mixed solution once every 10-90s by using a thermal imager, wherein the total recording time is 5-150min; the mixed solution is tested by an ultraviolet visible light photometer before and after illumination, and the testing wavelength range is 200-800nm.
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| US20140221199A1 (en) * | 2011-04-11 | 2014-08-07 | Council Of Scientific & Industrial Research | Stable oxide encapsulated metal clusters and nanoparticles |
| CN111229321A (en) * | 2020-01-16 | 2020-06-05 | 吉林大学 | Glutathione-protected platinum alloy nano-cluster with strong catalytic function, preparation method and application thereof |
| CN111408369A (en) * | 2020-04-16 | 2020-07-14 | 桂林理工大学 | Nano gold-platinum bimetallic @ carbon material oxygen reaction catalyst and preparation method thereof |
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