CN109721693B - Preparation method of alpha-helical-structure epitope/DOX double-template molecularly imprinted fluorescent nanoparticles - Google Patents
Preparation method of alpha-helical-structure epitope/DOX double-template molecularly imprinted fluorescent nanoparticles Download PDFInfo
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Abstract
A preparation method of alpha-helical structure epitope/DOX double-template molecularly imprinted fluorescent nanoparticles takes fluorescent nano-silicon spheres coated with silicon nanoparticles as a carrier, takes P32 protein N-terminal conformation 9 peptide and doxorubicin hydrochloride as double-template molecules, and adopts a precipitation polymerization method to prepare the double-template molecularly imprinted nanoparticles. Si nano particles are coated in silicon dioxide to prepare fluorescent nano silicon spheres and fluorescent double-template molecularly imprinted nano particles, and the fluorescent characteristic can be used for fluorescent imaging of tumor cells; polypeptide with an alpha-helical structure is constructed by trifluoroethanol and is used as a template molecule, so that the target recognition of target tumor cells can be effectively improved; the nano particle adopts the conformational polypeptide and the doxorubicin hydrochloride as double templates, realizes targeted drug delivery while realizing targeted specificity identification of tumor cells, improves the amount of the drug reaching targeted sites, reduces side effects, improves the utilization rate of the drug and enhances the treatment effect.
Description
Technical Field
The invention belongs to the field of preparation of nano materials, and particularly relates to a preparation method of alpha-helical-structure epitope/DOX double-template molecularly imprinted fluorescent nanoparticles.
Background
Molecular imprinting refers to a technique in which a template molecule is embedded in a polymer matrix to create a specific recognition cavity. When the template is dissociated from the polymer matrix, not only the shape of the template is retained, but also the imprinted polymer can specifically recognize the template molecule. This technique has been successfully used to construct a variety of polymeric materials that specifically bind to polypeptides and protein templates, providing a promising vehicle for molecular design, drug discovery, and drug delivery. See: Piotr.Luli ń ski.Mater.Sci.Eng.C Mater.biol.appl.2017,76: 1344-1353; h.c. chen, j.kong, d.y.yuan, g.q.fu.biosens.bioelectron.2014,53: 5-11; maya.z, andrew.j.b., peter.c.s.biomaterials.2014,35: 8659-; s.shinde, a.bunschoton, j.a.kruijtzer, r.m.liskamp, b.sellergren, angelw.chem.int.ed.2012, 51: 8326-. Nowadays, molecularly imprinted polymers are applied as artificial antibodies to tumor markers specifically recognizing the surface of tumor cells, so that research on targeting drug delivery is actively developing. However, most tumor markers are protein structures, and because protein macromolecules are used as template molecules for imprinting, the protein macromolecules have large mass transfer resistance, are difficult to elute and easy to denature, and in addition, the tumor markers are difficult to obtain and expensive, so the development of the tumor markers is limited. To solve this problem, epitope molecular imprinting methods have been developed. See: d.y.li, y.p.qin, h.y.li, x.w.he, w.y.li, Y K zhang.biosens.bioelectrtron.2015, 66: 224-230; r.tchinda., a.tutsch., b.schmid., r.d.sussumuth, z.altintas.biosens.bioelectrron.2019, 123: 260-; demir, m.m.lemberger, M panagiotopouloulouu.acs appl.mater.interfaces,2018,10(4): 3305-; pachelo, P.Rebelo, M Freitas, H.P.A.Nouws, C.Delerure-Matos.Sensors & Actuators: B.chemical,2018: 1008-. The great disadvantage of the epitope molecular imprinting technology is that the template molecules adopted in the imprinting process mostly use linear polypeptide fragments, but the structure of the protein is usually complex and has conformation, for example, many proteins have alpha-helix structures, and the molecularly imprinted polymer prepared by using the linear polypeptide as the template molecule limits the specific recognition of the protein with the complex conformation, thereby reducing the recognition specificity. Therefore, it is important to develop a molecularly imprinted polymer nanoparticle capable of recognizing a protein conformation epitope based on the molecular imprinted polymer nanoparticle. See: s.peng, y.h.wang, n.li and c.li.chem.commun.,2017,53: 11114; Y.Zhang, C.Y.Deng, S.Liu, J.Wu, Z.B.Chen, C.Li, and W.Y.Lu.Angew.Chem.2015,127: 5246-; liu, q.y.bi, y.y.long.nanoscale.2017,9: 5394. Nowadays, the research and development of nano materials as drug carriers are many, but generally, the preparation process is complex. See: l. Marcu, E.Bezak, B.Allen.Critical Reviews in Oncology.2018, 123: 7-20. Therefore, a simple method for synthesizing the double-template molecularly imprinted nano-particle with drug loading function and targeting property needs to be developed.
Disclosure of Invention
The invention aims to provide a preparation method of alpha-helical-structure epitope/DOX double-template molecularly imprinted fluorescent nanoparticles aiming at the defects and problems of the technology. The method adopts a precipitation polymerization method and a double-template imprinting method, takes silicon nanoparticles as a carrier, takes drug doxorubicin hydrochloride and conformational polypeptide of breast tumor cell surface overexpression protein P32 as double-template molecules, and uses trifluoroethanol to construct the conformational polypeptide with an alpha-helical structure; the monomers and the template molecules have certain interaction, and the prepared composite nanoparticles have good specificity and selectivity for identifying target breast cancer cells; the preparation method is simple, and has good application prospect in selective recognition and drug delivery treatment of target tumor cells in the targeted delivery of actual drugs.
The technical scheme of the invention is as follows:
a preparation method of fluorescent composite nanoparticles based on silicon nanoparticles and alpha-helical structure epitope/adriamycin double-template molecular imprinting technology comprises the following steps of taking the silicon nanoparticles as a carrier, coating silicon dioxide, modifying double bonds on the surface, taking N-terminal 9 peptide of target protein P32 and adriamycin hydrochloride as templates, and synthesizing the molecular imprinting fluorescent composite nanoparticles by adopting a precipitation polymerization method under the room temperature condition:
1) preparing silicon nanoparticles, namely mixing trisodium citrate with glycerol, adding 3-Aminopropyltriethoxysilane (APTES) under the protection of argon, putting the mixture into a microwave reactor for reaction, and obtaining the silicon nanoparticles (Si) after the reaction is carried out for 10-15min at the temperature of 180 ℃;
2) purifying silicon nano particles, namely adding the silicon nano particles into dilute hydrochloric acid, dialyzing overnight to obtain a purified silicon nano particle (SiNPs) solution;
3) adding the purified silicon nano particles into an ethanol solution, adding ammonia water and Tetraethoxysilane (TEOS), and reacting at room temperature for 5-6h to prepare the silicon-coated fluorescent silicon sphere nano particles (Si @ SiO)2)；
4) Dispersing the prepared silicon-coated fluorescent silicon sphere nano particles into a mixed solution of ethanol and water, adding ammonia water and gamma-Methacryloxypropyltrimethoxysilane (MPS), and reacting for 24 hours at room temperature to obtain double-bond modified fluorescent silicon nano particles (Si @ SiO)2@MPS)；
5) Dissolving the prepared double-bond modified fluorescent silicon nano particles, N-isopropylacrylamide (NIPA), trifluoromethyl acrylic acid (TFMA), tert-butylacrylamide (TBAm), N' N-methylene Bisacrylamide (BIS) and doxorubicin hydrochloride (DOX) in a mixed solution of pure water and trifluoroethanol TFE, adding a TFE solution of polypeptide into the reaction mixed solution, vacuumizing, introducing Ar gas for 30-50min, adding an initiator Ammonium Persulfate (APS) and a catalyst (TEMED), reacting at room temperature for 20h under the protection of argon gas, eluting the obtained nano particles by using methanol-acetic acid (the volume ratio is 9:1), and removing a template mixed solution to obtain double-template imprinted polymers (MIPs);
6) adding the prepared MIPs nanoparticles into doxorubicin hydrochloride (DOX) for complete adsorption, and cleaning for three times to obtain DOX-loaded targeted fluorescent nanoparticles MIPs @ DOX.
The dosage ratio of the trisodium citrate, the glycerol and the 3-aminopropyltriethoxysilane in the step 1) is as follows: 0.31-0.32 g: 8mL of: 1.8-2 mL.
Step 2) the volume ratio of the silicon nanoparticle solution to hydrochloric acid is as follows: 6-8 mL: 12mL, wherein the concentration of the hydrochloric acid is 0.5 mol/L; the molecular interception amount of the dialysis bag is 1000, water is changed once every 8-12 h for 2-3 times, and the total dialysis time is 16-36 h.
The volume ratio of the purified silicon nanoparticle solution, ethanol, ammonia water and tetraethoxysilane in the step 3) is as follows: 5-6 mL: 38-40 mL: 0.667 mL: 0.8 mL.
The volume ratio of the silicon-coated fluorescent silicon sphere nano particles, the ethanol, the water, the ammonia water and the MPS in the step 4) is as follows: 100-500 mg: 160mL of: 24mL of: 2.668 mL: 2-4 mL.
Step 5) the double-bond modified fluorescent silicon nano particle Si @ SiO2@ MPS, NIPA, TFMA, TBAm, BIS, DOX, polypeptide, APS and TEMED are in proportion as follows: 50 mg: 17.8 mg: 10 mg: 8.4 mg: 5.9 mg: 5 mg: 5 mg: 100-: 20-80 mu L, and the concentration of the APS is 60 mg/mL.
Step 6), the ratio of the MIPs to the DOX is as follows: 2 mg: 5-10mL, and the concentration of the DOX is 0.2 mg/mL.
The invention has the advantages and beneficial effects that:
1) the silicon nano particles are used as a novel nano material, have the excellent characteristics of fluorescence and high specific surface area, and can enable the prepared nano particles to have excellent fluorescence property when being applied to the preparation process of the molecularly imprinted polymer;
2) fluorescent silicon sphere nano particles with modified double bonds are used as a carrier, a conformational polypeptide and doxorubicin hydrochloride double templates are adopted to prepare an imprinted polymer, and the surface of the prepared imprinted polymer nano particles contains two imprinted sites which can both specifically identify a target object;
3) the polypeptide is synthesized by adopting a precipitation polymerization method under the condition of room temperature, and trifluoroethanol with a certain proportion is used as a solvent, so that a linear state is converted into a conformational polypeptide with an alpha-helical structure, and the recognition specificity to a target protein is enhanced;
4) in the double-template molecularly imprinted polymer, one template of the two templates plays a role in preparing a targeting site, the other template plays a role in carrying medicine, and targeting identification and medicine release administration are realized simultaneously in application.
Drawings
FIG. 1 is a transmission electron microscope image of a polypeptide imprinted polymer nanoparticle with a dual-template conformation.
FIG. 2 is a laser confocal microscopy image of specific recognition of 4T1 breast cancer cells by dual-template molecularly imprinted nanoparticle MIPs (80 μ g/mL,6 h). (NIPs non-imprinted nanoparticles as a control group, blue MIPs/NIPs and red cell membrane dye DiI).
FIG. 3 is a graph showing the therapeutic effect of DOX-loaded double-template conformation polypeptide imprinted nanoparticles MIPs @ DOX on nude mice with 4T1 mammary gland solid tumor (PBS, NIP)S@ DOX, DOX as negative control group).
Detailed Description
Example 1:
a preparation method of alpha-helical structure epitope/DOX double-template molecularly imprinted fluorescent nanoparticles comprises the following steps:
1) preparing silicon nanoparticles, namely adding 0.318g of trisodium citrate into 8mL of glycerol, adding 2mL of 3-Aminopropyltriethoxysilane (APTES) under the protection of argon, carrying out the reaction in a microwave reactor, and obtaining silicon nanoparticles (Si NPs) after 15 min;
2) purifying silicon nanoparticles, namely adding 8mL of silicon nanoparticles into 12mL (0.5mol/L) of dilute hydrochloric acid, taking the molecular interception of a dialysis bag for dialysis at 1000, changing water once every 8h, changing water for 3 times in total, and obtaining purified silicon nanoparticles (Si NPs) after the total dialysis time is 24h and stays overnight;
3) adding 6mL of purified silicon nanoparticles into 40mL of ethanol solution, adding 0.667mL of ammonia water, adding 0.8mL of Tetraethoxysilane (TEOS), and reacting at room temperature for 6h to obtain silicon-coated fluorescent nanoparticles (Si @ SiO)2)；
4) 500mg of prepared Si @ SiO2Dispersing into a mixed solution of 160mL of ethanol and 24mL of water, adding 2.668mL of ammonia water and 4mL of gamma-Methacryloxypropyltrimethoxysilane (MPS), and reacting for 24h at room temperature to obtain the double-bond modified fluorescent silicon nanoparticles (Si @ SiO)2@MPS)；
5) 50mg of Si @ SiO obtained by the preparation2@ MPS nanoparticle, 17.8mg N-isopropylacrylamide (NIPA), 10mg trisFluoromethyl Methacrylate (TFMA), 8.4mg t-butyl acrylamide (TBAm), 5.9mg N' N-methylene Bisacrylamide (BIS), 5mg doxorubicin hydrochloride (DOX), dissolved in 6.1mL pure water and 3mL trifluoroethanol TFE, weighing 5mg polypeptide, dissolved in 2mL TFE, mixing well, adding the above reaction solution, vacuumizing, introducing Ar gas for 30min, adding 200. mu.L (60mg/mL) of ammonium persulfate as initiator, 20. mu.L of TEMED as catalyst, and reacting at room temperature for 20h under the protection of argon. Eluting the obtained nanoparticles with 9:1 methanol-acetic acid mixed solution, removing the template to obtain bimolecular imprinted polymers (MIPs);
6) adding 5mL (0.2mg/mL) of doxorubicin hydrochloride (DOX) into the prepared 2mg of MIPs nanoparticles, completely adsorbing, and cleaning for three times to obtain DOX-loaded targeted fluorescent composite nanoparticles MIPs @ DOX.
Fig. 1 is a transmission electron microscope image of a polypeptide imprinted polymer nanoparticle with a dual-template conformation, which shows that: the imprinted polymer layer is about 10nm or so.
FIG. 2 is a laser micro-confocal image of specific recognition of 4T1 breast cancer cells by incubating MIPs (80. mu.g/mL) of a polypeptide imprinted polymer nanoparticle with a double-template conformation for 6h with 4T1 cells (non-imprinted nanoparticle NIPs as a control group), showing: the prepared MIPs have specific identification targeting on target 4T1 breast cancer cells, and compared with NIPs, the MIPs have more nanoparticles entering the interior of 4T1 cells.
FIG. 3 is a graph showing the therapeutic effect of DOX-loaded double-template conformation polypeptide imprinted nanoparticles MIPs @ DOX on nude mice with 4T1 mammary gland solid tumor (PBS, NIP)S@ DOX, DOX as negative control group), shown in the figure: the prepared MIPs @ DOX has the best treatment effect on the target 4T1 breast solid tumor.
Example 2:
the synthesis steps of the preparation method of the alpha-helical epitope/DOX double-template molecularly imprinted fluorescent nanoparticle are basically the same as those of the example 1, except that: step 1) 0.315g trisodium citrate is added to 8mL glycerol.
The characterization and MIPs @ DOX application results of the finally prepared double-template conformation epitope imprinted nanoparticles are similar to those of example 1.
Example 3:
the synthesis steps of the preparation method of the alpha-helical epitope/DOX double-template molecularly imprinted fluorescent nanoparticle are basically the same as those of the example 1, except that: step 1) 0.32g trisodium citrate is taken and 8mL glycerol is added.
The characterization and MIPs @ DOX application results of the finally prepared double-template conformation epitope imprinted nanoparticles are similar to those of example 1.
Example 4:
the synthesis steps of the preparation method of the alpha-helical epitope/DOX double-template molecularly imprinted fluorescent nanoparticle are basically the same as those of the example 1, except that: step 2) purification of silicon nanoparticles, 6mL of silicon nanoparticles were added to 12mL (0.5mol/L) of dilute hydrochloric acid.
The characterization and MIPs @ DOX application results of the finally prepared double-template conformation epitope imprinted nanoparticles are similar to those of example 1.
Example 5:
the synthesis steps of the preparation method of the alpha-helical epitope/DOX double-template molecularly imprinted fluorescent nanoparticle are basically the same as those of the example 1, except that: step 4) preparing 100mg of Si @ SiO2Dispersing into 160mL of ethanol and 24mL of water mixed solution, adding 2.668mL of ammonia water and 2mL of gamma-Methacryloxypropyltrimethoxysilane (MPS), and reacting for 24h at room temperature to obtain double-bond modified fluorescent silicon nanoparticles (Si @ SiO)2@MPS)。
The characterization and MIPs @ DOX application results of the finally prepared double-template conformation epitope imprinted nanoparticles are similar to those of example 1.
Example 6:
the synthesis steps of the preparation method of the alpha-helical epitope/DOX double-template molecularly imprinted fluorescent nanoparticle are basically the same as those of the example 1, except that: step 4) preparing 300mg of Si @ SiO2Dispersing into 160mL of ethanol and 24mL of water mixed solution, adding 2.668mL of ammonia water and 3mL of gamma-Methacryloxypropyltrimethoxysilane (MPS), and reacting for 24h at room temperature to obtain double-bond modified fluorescent silicon nanoparticles (Si @ SiO)2@MPS)。
The characterization and MIPs @ DOX application results of the finally prepared double-template conformation epitope imprinted nanoparticles are similar to those of example 1.
Example 7:
the synthesis steps of the preparation method of the alpha-helical epitope/DOX double-template molecularly imprinted fluorescent nanoparticle are basically the same as those of the example 1, except that: and 6) adding 6mL (0.2mg/mL) of doxorubicin hydrochloride (DOX) into the prepared 2mg of MIPs nanoparticles, completely adsorbing, and washing for three times.
The characterization and MIPs @ DOX application results of the finally prepared double-template conformation epitope imprinted nanoparticles are similar to those of example 1.
Example 8:
the synthesis steps of the preparation method of the alpha-helical epitope/DOX double-template molecularly imprinted fluorescent nanoparticle are basically the same as those of the example 1, except that: and 6), adding 7mL (0.2mg/mL) of doxorubicin hydrochloride (DOX) into the prepared 2mg of MIPs nanoparticles, completely adsorbing, and washing for three times.
The characterization and MIPs @ DOX application results of the finally prepared double-template conformation epitope imprinted nanoparticles are similar to those of example 1.
Example 9:
the synthesis steps of the preparation method of the alpha-helical epitope/DOX double-template molecularly imprinted fluorescent nanoparticle are basically the same as those of the example 1, except that: and 6), adding 8mL (0.2mg/mL) of doxorubicin hydrochloride (DOX) into the prepared 2mg of MIPs nanoparticles, completely adsorbing, and washing for three times.
The characterization and MIPs @ DOX application results of the finally prepared double-template conformation epitope imprinted nanoparticles are similar to those of example 1.
Example 10:
the synthesis steps of the preparation method of the alpha-helical epitope/DOX double-template molecularly imprinted fluorescent nanoparticle are basically the same as those of the example 1, except that: and step 6), adding 9mL (0.2mg/mL) of doxorubicin hydrochloride (DOX) into the prepared 2mg of MIPs nanoparticles, completely adsorbing, and washing for three times.
The characterization and MIPs @ DOX application results of the finally prepared double-template conformation epitope imprinted composite nanoparticles are similar to those of example 1.
Claims (8)
1. A preparation method of alpha-helical structure epitope/DOX double-template molecularly imprinted fluorescent nanoparticles comprises the following steps of taking silicon nanoparticles as a carrier, modifying double bonds on the surface after silicon coating, taking N-terminal 9 peptide of target protein P32 and doxorubicin hydrochloride as templates, and synthesizing the molecularly imprinted fluorescent composite nanoparticles by a precipitation polymerization method at room temperature:
1) preparing silicon nanoparticles, namely mixing trisodium citrate with glycerol, adding 3-Aminopropyltriethoxysilane (APTES) under the protection of argon, putting the mixture into a microwave reactor for reaction, and obtaining the silicon nanoparticles (Si) after the reaction is carried out for 10-15min at the temperature of 180 ℃;
2) purifying silicon nano particles, namely adding the silicon nano particles into dilute hydrochloric acid, dialyzing overnight to obtain a purified silicon nano particle (SiNPs) solution;
3) adding the purified silicon nano particles into an ethanol solution, adding ammonia water and Tetraethoxysilane (TEOS), and reacting at room temperature for 5-6h to prepare the silicon-coated fluorescent silicon sphere nano particles (Si @ SiO)2)；
4) Dispersing the prepared silicon-coated fluorescent silicon sphere nano particles into a mixed solution of ethanol and water, adding ammonia water and gamma-Methacryloxypropyltrimethoxysilane (MPS), and reacting for 24 hours at room temperature to obtain double-bond modified fluorescent silicon nano particles (Si @ SiO)2@MPS)；
5) Dissolving the prepared double-bond modified fluorescent silicon nanoparticles, N-isopropylacrylamide (NIPA), trifluoromethyl acrylic acid (TFMA), tert-butylacrylamide (TBAm), N ' N-methylene Bisacrylamide (BIS) and doxorubicin hydrochloride (DOX) in a mixed solution of pure water and trifluoroethanol TFE, adding a TFE solution of polypeptide into the reaction mixed solution, vacuumizing, introducing Ar gas for 30-50min, adding an initiator Ammonium Persulfate (APS) and a catalyst N, N, N ', N ' -Tetramethylethylenediamine (TEMED), reacting at room temperature for 20h under the protection of argon, eluting the obtained nanoparticles with a mixed solution of methanol-acetic acid, and removing a template to obtain double-template imprinted polymers (MIPs);
6) adding the prepared MIPs nanoparticles into doxorubicin hydrochloride (DOX) for complete adsorption, and cleaning for three times to obtain DOX-loaded targeted fluorescent nanoparticles MIPs @ DOX.
2. The method of preparing fluorescent nanoparticles of claim 1, wherein: the dosage ratio of the trisodium citrate, the glycerol and the 3-aminopropyltriethoxysilane in the step 1) is as follows: 0.31-0.32 g: 8mL of: 1.8-2 mL.
3. The method of preparing fluorescent nanoparticles of claim 1, wherein: step 2) the volume ratio of the silicon nanoparticle solution to hydrochloric acid is as follows: 6-8 mL: 12mL, and the concentration of the hydrochloric acid is 0.5 mol/L.
4. The method of preparing fluorescent nanoparticles of claim 1, wherein: the volume ratio of the purified silicon nanoparticle solution, ethanol, ammonia water and tetraethoxysilane in the step 3) is as follows: 5-6 mL: 38-40 mL: 0.667 mL: 0.8 mL.
5. The method of preparing fluorescent nanoparticles of claim 1, wherein: the volume ratio of the silicon-coated fluorescent silicon sphere nano particles, the ethanol, the water, the ammonia water and the MPS in the step 4) is as follows: 100-500 mg: 160mL of: 24mL of: 2.668 mL: 2-4 mL.
6. The method of preparing fluorescent nanoparticles of claim 1, wherein: step 5) the double-bond modified fluorescent silicon nano particle Si @ SiO2@ MPS, NIPA, TFMA, TBAm, BIS, DOX, polypeptide, APS and TEMED are in proportion as follows: 50 mg: 17.8 mg: 10 mg: 8.4 mg: 5.9 mg: 5 mg: 5 mg: 100-: 20-80 mu L, and the concentration of the APS is 60 mg/mL.
7. The method of preparing fluorescent nanoparticles of claim 1, wherein: the volume ratio of methanol to acetic acid in the eluent in the step 5) is 9: 1.
8. The method of preparing fluorescent nanoparticles of claim 1, wherein: step 6), the ratio of the MIPs to the DOX is as follows: 2 mg: 5-10mL, and the concentration of the DOX is 0.2 mg/mL.
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