CN116178227B - Chiral iron particles and preparation method and application thereof - Google Patents
Chiral iron particles and preparation method and application thereof Download PDFInfo
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- A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
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- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
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- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
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Abstract
The invention relates to chiral iron particles, a preparation method and application thereof, and belongs to the technical field of inorganic chemistry. According to the preparation method of the chiral iron particles, chiral ligands and ferric salt react in a solvent under the action of a reducing agent to obtain the chiral iron particles; the chiral ligand is amino acid; the amino acid is L-amino acid or D-amino acid. The chiral iron particles have excellent optical activity, have CD activity in a visible light region, and can be used for identifying and detecting polarized light by utilizing the CD in the visible light region. The chiral iron particles have excellent magnetism and can be used in the technical fields of magnetic separation, biological imaging, adjuvants and the like. The chiral iron particle adjuvant can be attached to the surface of a cell membrane and enter dendritic cells, so that antigens can be delivered, and the stability of the antigens is maintained.
Description
Technical Field
The invention belongs to the technical field of inorganic chemistry, and particularly relates to chiral iron particles, and a preparation method and application thereof.
Background
The magnetic nano material has unique physicochemical properties, is widely applied to biomedical fields such as biological magnetic separation, immunoassay, targeted drug delivery, gene transfection, magnetic resonance contrast agents and the like, is an important magnetic nano material, and can be used as a magnetic carrier in the fields such as magnetic separation, quantitative immunodetection, magnetic targeted drug delivery and the like. The particle size, the magnetic substance content, the specific saturation magnetization and the surface functionalization modification of the nano particles have important influences on the separation speed of the nano particles in a medium, the magnetic signal intensity and the combination of the nano particles with biological or drug molecules, so that the controllable preparation of the nano particles is realized, and the nano particles with controllable particle size, high magnetic substance content, specific saturation magnetization and surface functionalization have important significance for biomedical application.
With the continuous and deep application research, higher requirements are put on the performance of the magnetic nano material, and the preparation method of the magnetic nano particles is generally divided into two types, namely a physical method and a chemical method. However, magnetic nanoparticles prepared by the usual physical method are not suitable for application in biology because of uncontrollable size and morphology. The chemical method is to prepare magnetic nano particles through chemical reaction, and the reaction process is usually controllable, so that the biological magnetic nano particles are mostly prepared by the chemical method. The most commonly used chemical preparation methods of magnetic nanoparticles include: coprecipitation, pyrolysis, sol-gel, and microemulsion. The polyol method is an important method for synthesizing nano metal and metal oxide materials, and the method for synthesizing magnetic nano particles by the polyol method developed in recent years has the advantages of simplicity in operation, good controllability and the like and is widely paid attention to researchers.
The adjuvant is an important component in the vaccine, and the inorganic nanometer adjuvant can be used as a temporary warehouse for storing antigens in the process of antiviral immune response, stabilize antigen conformation and prolong antigen exposure time; facilitating recruitment and maturation of immune cells; promoting antigen uptake, presentation and cross presentation; selectively induce different types of immune responses. The key role of metallic elements in the immune response process and their important application in cancer immunotherapy are getting more and more attention. The function of metal ions in immune signaling is not limited to second messengers, for example, the study of the mechanism of manganese and zinc ions as innate immune activators has been reported. With the increasing awareness of metal immunization, other inorganic metal elements and nanoparticles thereof are developed into potential candidate adjuvants due to the unique properties of the inorganic metal elements and nanoparticles besides aluminum adjuvants for long-term application. At present, researchers have developed different types of inorganic nanoadjuvants for use in anti-coronavirus vaccines, mainly including aluminum salt adjuvants, manganese adjuvants, calcium adjuvants, silicon-based adjuvants and gold adjuvants. Along with the deep clinical research of vaccine preparations, the traditional adjuvant also faces the problems of key technology and product performance, has non-uniform physicochemical properties and unclear immune protection mechanism, and greatly limits the stability and immune efficacy of the vaccine preparation.
Disclosure of Invention
Therefore, the invention aims to solve the technical problems that the size and shape of the magnetic nano material are uncontrollable, chiral ligands and magnetic elements are difficult to be effectively combined and the like in the prior art.
In order to solve the technical problems, the invention provides chiral iron particles, and a preparation method and application thereof. By taking ferric salt as an iron source and taking amino acid with two carboxyl groups and two hydroxyl groups as chiral ligands, under the action of a strong alkaline reducing agent, chiral nano materials with different morphologies are obtained by means of layer-by-layer self-assembly, and chiral signals are generated.
The first object of the invention is to provide a preparation method of chiral iron particles, wherein chiral ligand and ferric salt react in a solvent under the action of a reducing agent to obtain the chiral iron particles; the chiral ligand is amino acid; the amino acid is L-amino acid or D-amino acid.
In one embodiment of the invention, the amino acid itself has one sulfhydryl group and two amino groups, and dissociates the negatively charged amino acid in the aqueous phase, which is more beneficial to Fe 3+ Coordination takes place.
In one embodiment of the invention, the iron salt is one or more of ferric nitrate, ferric chloride, and ferric acetate.
In one embodiment of the invention, the reducing agent is one or more of hydrazine hydrate, sodium borohydride, ammonia water, and ascorbic acid. The reducing agent facilitates the formation of Fe 3+ The conversion from trivalent to divalent is beneficial to the combination with amino acids and can improve the stability of the material.
In one embodiment of the invention, the solvent is one or more of water, N-dimethylformamide, ethylene glycol, ethanol, tetrahydrofuran, and dimethyl sulfoxide.
In one embodiment of the invention, the molar ratio of chiral ligand to iron salt is 1-2:1.
in one embodiment of the invention, when the molar ratio of chiral ligand to iron salt is 1:1, obtaining micron iron particles; when the molar ratio of chiral ligand to iron salt is 2:1, obtaining nano iron particles.
In one embodiment of the invention, the temperature of the reaction is 80-200 ℃; the reaction time is 2-10h.
The second object of the invention is to provide the chiral iron particles prepared by the method, wherein the chiral iron particles are L-chiral iron particles or D-chiral iron particles.
In one embodiment of the invention, the chiral iron particles have a particle size of 0.2-5 μm.
In one embodiment of the invention, the chiral iron particles have a circular dichroism spectrum signal characteristic peak of 300-600nm or 1000-1100nm. The CD in the visible light area is utilized to improve the efficiency of temperature improvement in photodynamic therapy and realize the rapid killing of cancer cells.
A third object of the invention is to provide the use of said chiral iron particles in inorganic nanoadjuvants.
Compared with the prior art, the technical scheme of the invention has the following advantages:
(1) The chiral iron particles have excellent optical activity, have CD activity in a visible light region, and can be used for identifying and detecting polarized light by utilizing the CD in the visible light region.
(2) The chiral iron particles have excellent magnetism and can be used in the technical fields of magnetic separation, biological imaging, adjuvants and the like. The chiral iron particle adjuvant can be attached to the surface of a cell membrane and enter dendritic cells, so that antigens can be delivered, and the stability of the antigens is maintained.
Drawings
In order that the invention may be more readily understood, a more particular description of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings, in which:
FIG. 1 is a graph showing CD and UV spectra of chiral iron particles obtained in example 1 of the present invention.
FIG. 2 is a graph showing CD and UV spectra of chiral iron particles obtained in example 2 of the present invention.
FIG. 3 is an SEM image of chiral iron particles of example 2 of the present invention.
Fig. 4 is a TEM image of chiral iron particles obtained in example 2 of the present invention.
FIG. 5 is a Mapping graph of chiral iron particles obtained in example 2 of the present invention.
Fig. 6 is an XRD pattern of chiral iron particles obtained in example 1 of the present invention.
FIG. 7 is an EDX of chiral iron particles obtained in example 1 of the present invention.
FIG. 8 is a graph of the ability of chiral iron particles of example 2 of the present invention to promote DC maturation and antigen presentation; wherein (A) is CD40 + (B) is CD80 + (C) is CD86 + (D) is MHCII.
FIG. 9 shows the ability of chiral iron particles to induce adaptive immunity according to example 2 of the present invention; wherein (A) is TNF-alpha in spleen + CD8 + T and (B) are INF-gamma + CD8 + Flow cytometry analysis of T; (C) Is TNF-alpha in spleen + CD4 + T and (D) are INF-gamma + CD4 + Flow cytometry analysis of T.
Detailed Description
The present invention will be further described with reference to the accompanying drawings and specific examples, which are not intended to be limiting, so that those skilled in the art will better understand the invention and practice it.
The detection method of the invention comprises the following steps:
(1) CD Spectrum testing
The J-1700CD spectrophotometer was equipped with a PMT detector in the 300-1000nm range and an InGaAsNIR detector in the 900-1700nm range for CD studies. Typical scan parameters: temperature: 25 ℃; scanning speed, 200nm/min; data spacing: 0.5nm; bandwidth: 5nm (visible light region bandwidth: 10 nm); digital integration time: 2s.
(2) SEM test
Firstly, taking 0.1mL of stock solution, 6000rpm for 10min, removing the supernatant, dispersing in 1mL of high-purity water, repeating for 2 times, taking the cut silicon wafer, cleaning, drying by nitrogen, then taking 5 mu L of centrifuged sample, dripping the sample on the silicon wafer, naturally airing at room temperature, and taking a Scanning Electron Microscope (SEM) image by using Hitachi SU9000 for shooting, wherein the accelerating voltage is 100kV.
(3) XRD testing
Collect the parallel 30mL,6000rpm,10min, remove the supernatant, disperse in 1mL ethanol, repeat 2 times, then dry overnight in an oven at 60 ℃, grind with a mortar, then perform XRD testing, X-ray diffraction (XRD) on Bruker D8, use Cu K alphaIrradiation, scanning rate of 10min -1 The range is 5-90 degrees, the target voltage is 40kV, and the current is 40mA.
(4) EDX test
The sample preparation method is the same as that of SEM, and the testing instrument is an X-ray photoelectron spectrometer of Kratos Analytical Axis Ultra.
(5) TEM test
Firstly, taking 0.1mL of stock solution, 600 rpm for 10min, removing the supernatant, dispersing in 1mL of high-purity water, repeating for 2 times, then taking 5 mu L of centrifuged sample, dripping the sample on a copper mesh, naturally airing at room temperature, photographing by using a scanning electron microscope (TEM) image, and accelerating the image by using F2100, wherein the accelerating voltage is 200kV.
The invention relates to experimental raw materials:
the raw materials used in the invention are all common commercial products, wherein ferric nitrate hexahydrate, amino acid, ethylene glycol and hydrazine hydrate are all purchased from Tianjin Fuyu fine chemical industry Co.
Example 1
A chiral iron particle and a preparation method thereof specifically comprise the following steps:
0.2mL of Fe (NO) 3 ) 3 (0.1M) was added to 10mL of ethylene glycol, stirred continuously at 500rpm, then 0.5mL of NaOH (1M) was added, stirred uniformly, then 1mL of L-/D-Cys (0.4M) was added, stirred uniformly, 1mL of sodium borohydride, ascorbic acid and hydrazine hydrate were added, stirred uniformly, then autoclave heated at 120℃for 10 hours, and stirring was continued. Washing with water at 8000rpm/10min for three times to obtain L-/D-chiral iron particles.
Example 2
75mL of Fe (NO) 3 ) 3 (0.1M) was added to 500mL of ethylene glycol, stirring was continued at 500rpm, then 75mL of L-/D-Cys (0.1M) was added, stirring was uniform, after the color of the solution turned pale green yellow, 20mL of sodium borohydride, ascorbic acid and hydrazine hydrate were added, stirring was uniform, then oil bath was performed at 80℃for 3 hours. Washing with water at 4000rpm for 6min for three times to obtain L-/D-chiral iron particles.
Test example 1
The chiral Fe particles prepared in examples 1-2 were tested using a circular dichroism instrument by first taking 1mL of stock solution, 600 rpm,10min, removing the supernatant, dispersing in 1mL of high purity water, repeating 2 times, and then testing at a temperature ranging from 300-1700 nm: 25 ℃; scanning speed, 200nm/min; data spacing: 0.5nm; bandwidth: 5nm (visible light region bandwidth: 10 nm); digital integration time: 2s, the results correspond to fig. 1 and 2, respectively. As can be seen from the data in the figure, the characteristic peaks of CD signals mainly appear at 300-600nm and 1000-1100nm, which is beneficial to the utilization rate of circularly polarized light.
Test example 2
Characterizing and analyzing chiral Fe particles prepared in example 2, firstly taking 0.1mL of stock solution, 6000rpm for 10min, removing supernatant, dispersing in 1mL of high-purity water, repeating for 2 times, taking a cut silicon wafer, cleaning, drying with nitrogen, then taking 5 mu L of centrifuged sample, dripping the sample on the silicon wafer, naturally airing at room temperature, photographing by using Hitachi SU9000 in a Scanning Electron Microscope (SEM) image, accelerating the voltage to be 100kV, and then carrying out Mapping to collect element signals, wherein the result is shown in figures 3-4;
firstly, taking 0.1mL of stock solution, 6000rpm for 10min, removing the supernatant, dispersing in 1mL of high-purity water, repeating for 2 times, then taking 5 mu L of centrifuged sample, dripping the sample on a copper mesh, naturally airing at room temperature, photographing a scanning electron microscope (TEM) image by using F2100, and setting the accelerating voltage to be 200kV, wherein the result is shown in figure 5;
as is evident from fig. 3-5, fe, C, O, S elements are uniformly dispersed, indicating that the material is uniformly synthesized.
Test example 3
Chiral Fe particles prepared in example 1 were tested by XRD, a parallel sample was collected at 30mL,600 rpm,10min, the supernatant was removed, dispersed in 1mL ethanol, repeated 2 times, then dried overnight in an oven at 60 ℃ and then ground with a mortar, then XRD tested, X-ray diffraction (XRD) was performed on Bruker D8 using Cu ka radiation at a scan rate of 10min -1 The range is 5-90 degrees, the target voltage is 40kV, the current is 40mA, the result is shown in figure 6, and the material has a better crystal structure.
Test example 4
The chiral Fe particles prepared in example 1 were tested by EDX, sample preparation method and SEM as well as test conditions: as a result of the X-ray photoelectron spectrometer of Kratos Analytical Axis Ultra, as shown in fig. 7, it can be seen from the figure that Fe ions exist mainly in the form of ferric iron, and S and O are mainly derived from amino acids.
Test example 5
DC cells were inoculated in normal or STS medium for 24h and then in medium containing 10X 6/CT 26 cell lysates, 23. Mu.g/mL chiral iron particles of example 2 for 24h. The DCs were then collected for flow-through detection. anti-CD40-PerCP/Cy5.5, anti-perforin PE-CD80, anti-PE-MHC II are used respectively + anti-CD86-APC antibody staining. Flow cytometer analysis was performed using BD LSR Fortessa. The data were analyzed using FlowJo software and the results are shown in fig. 8. As can be seen from the figure, the levels of co-stimulatory factors CD40, CD80 and CD86 and MHC-II involved in the antigen presentation process were significantly increased in DC treated with Chiral iron particles compared to DC treated without Chiral iron particles, and the levels of MHC-II of DC co-stimulatory factors CD40, CD80, CD86 and proteins after Chiral D-Fe treatment were highest. It is demonstrated that chiral iron particles can be effective in promoting DC maturation and antigen presentation.
Test example 6
10X 6/CT 26 cell lysates were mixed with 200. Mu.g of chiral iron particles of the different configurations of example 2, respectively, and then inoculated subcutaneously with 100. Mu.L in the right inguinal region of C57BL/6 mice. Spleens were collected on day 7 and mechanically disrupted in DMEM medium containing 5% fetal bovine serum. After centrifugation at 400g for 5min, the collected cells were washed with 3mL of pH 7.2ACK buffer (NH 4 Cl:0.15M, potassium bicarbonate: 10mM, EDTA:0.1 mM) was resuspended at 4℃for 5min to lyse the erythrocytes. The lysis procedure was quenched by the addition of 10mL of cold PBS and single cells were collected by a 40 μm cell filter. Flow cytometric detection is then performed. Staining was performed with anti-TNF- α -PE/Cy7 and anti-IFN- γ -PerCP/Cy5.5 antibodies, respectively, and the data was analyzed using FlowJo software, and the results are shown in FIG. 9. As can be seen from the figure, mouse spleen cells inoculated with chiral iron particles had a high frequency of CD8 after stimulation with CT26 lysate + IFN-γ + T cells and CD4 + IFN-γ + T cells, in which the level of D-chiral iron particle priming is highest. Confirmation ofChiral iron particles can effectively induce antigen-specific T cell responses. Cytokines associated with immune responses were also subsequently measured, and the results showed that chiral iron particle groups significantly increased TNF- α secretion compared to PBS groups. In summary, the chiral iron particles of the present invention can induce strong adaptive immunity.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations and modifications of the present invention will be apparent to those of ordinary skill in the art in light of the foregoing description. It is not necessary here nor is it exhaustive of all embodiments. And obvious variations or modifications thereof are contemplated as falling within the scope of the present invention.
Claims (6)
1. The application of chiral iron particles in inorganic nanometer adjuvant is characterized in that the preparation method of the chiral iron particles comprises the following steps that chiral ligands and ferric salt react in a solvent under the action of a reducing agent to obtain the chiral iron particles; the chiral ligand is amino acid; the amino acid is L-amino acid or D-amino acid; the reducing agent is one or more of hydrazine hydrate, sodium borohydride, ammonia water and ascorbic acid.
2. The use of chiral iron particles in an inorganic nanoadjuvant according to claim 1, wherein the iron salt is one or more of ferric nitrate, ferric chloride and ferric acetate.
3. The use of chiral iron particles in an inorganic nanoadjuvant according to claim 1, wherein the temperature of the reaction is 80-200 ℃; the reaction time is 2-10h.
4. Use of chiral iron particles according to claim 1 in inorganic nanoadjuvants, wherein the chiral iron particles are L-chiral iron particles or D-chiral iron particles.
5. Use of chiral iron particles according to claim 1 in inorganic nanoadjuvants, characterized in that the chiral iron particles have a particle size of 0.2-5 μm.
6. Use of chiral iron particles according to claim 1 in inorganic nanoadjuvants, characterized in that the circular dichroism spectrum signal characteristic peak of the chiral iron particles is 300-600nm or 1000-1100nm.
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| WO2017201701A1 (en) * | 2016-05-26 | 2017-11-30 | 普惠德生技股份有限公司 | Use of composition comprising ferrous amino acid chelate for manufacture of medicine for reducing lactic acid |
| CN116370657A (en) * | 2022-12-09 | 2023-07-04 | 江南大学 | Chiral iron-based super-particle nano material and preparation method and application thereof |
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| US6716814B2 (en) * | 2001-08-16 | 2004-04-06 | Albion International, Inc. | Enhancing solubility of iron amino acid chelates and iron proteinates |
| US20070270591A1 (en) * | 2006-05-16 | 2007-11-22 | Ashmead H Dewayne | Iron (II) amino acid chelates with reducing agents attached thereto |
| US8741375B2 (en) * | 2011-06-07 | 2014-06-03 | Zinpro Corporation | Mixed amino acid metal salt complexes |
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| WO2017201701A1 (en) * | 2016-05-26 | 2017-11-30 | 普惠德生技股份有限公司 | Use of composition comprising ferrous amino acid chelate for manufacture of medicine for reducing lactic acid |
| CN116370657A (en) * | 2022-12-09 | 2023-07-04 | 江南大学 | Chiral iron-based super-particle nano material and preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| "The preparation and characterization of some complexes of iron(II) with amino acids";Fitzsimmons, Brian W.等;《Inorganica Chimica Acta》;第106卷(第2期);第109-114页 * |
| Fitzsimmons, Brian W.等."The preparation and characterization of some complexes of iron(II) with amino acids".《Inorganica Chimica Acta》.1985,第106卷(第2期),第109-114页. * |
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