CN109721693A - A kind of preparation method of α-helixstructure epitope/DOX double-template molecular engram fluorescent nano particles - Google Patents
A kind of preparation method of α-helixstructure epitope/DOX double-template molecular engram fluorescent nano particles Download PDFInfo
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Abstract
A kind of preparation method of α-helixstructure epitope/DOX double-template molecular engram fluorescent nano particles, to be coated with the fluorescence nano silicon ball of silicon nano as carrier, using 9 peptide of P32 albumen n end conformation and doxorubicin hydrochloride as double-template molecule, bimolecular trace nanoparticle is prepared using precipitation polymerization method.Si nanoparticle cladding is prepared for fluorescence nano silicon ball to the present invention in silica and fluorescent dual module plate molecular imprinting nano particles, the fluorescent characteristic can be used for the fluorescence imaging of tumour cell；It uses trifluoroethanol to construct the polypeptide with α-helixstructure as template molecule, the targets identification to target tumor can be effectively improved；The nanoparticle is double-template using conformational peptides and doxorubicin hydrochloride, target administration is also achieved while realizing targeting specific tumor cell, the amount that drug reaches target site is improved, reduces side effect, utilization ratio of drug is improved, therapeutic effect is enhanced.
Description
Technical field
The invention belongs to the preparation field of nano material, especially a kind of α-helixstructure epitope/DOX double-template
The preparation method of molecular engram fluorescent nano particles.
Background technique
Molecular imprinting technology, which refers to, to be embedded into template molecule in polymer substrate to generate specific recognition cavity
A kind of technology.After template is dissociated from polymer substrate, not only the shape of template is retained, but also the imprinted polymer can also
Specifically to identify the template molecule.The technology has been successfully used to building and has specifically bound with peptide and protein template
Various polymer materials, be MOLECULE DESIGN, drug discovery and drug conveying provides a kind of promising carrier.Referring to:
Piotr.Luliński.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.2014,35:8659-8668；S.Shinde,A.Bunschoten,J.A.Kruijtzer,
R.M.Liskamp,B.Sellergren,Angew.Chem.Int.Ed.2012,51:8326-8329.Nowadays, molecule is printed
Mark polymer as artificial antibody be applied to specific recognition tumor cell surface tumor markers, thus realize targeting to
The research of medicine is just in development like a raging fire.But since most of tumor markers are protein structure, protein macromolecule
As trace template molecule due to its molecular weight it is big, so resistance to mass tranfer is big, it is difficult to elute, and be easy denaturation, along with swollen
Tumor markers are difficult to obtain and expensive, therefore limit its development.In order to solve this problem, antigen has just been developed
Determine base molecular engram method.Referring to: D.Y.Li, Y.P.Qin, H.Y.Li, X.W.He, W.Y.Li, Y K
Zhang.Biosens.Bioelectron.2015,66:224-230；R.Tchinda.,A.Tutsch.,B.Schmid.,
R.D.Sussmuth,Z.Altintas.Biosens.Bioelectron.2019,123:260-268；B.Demir,
M.M.Lemberger,M Panagiotopoulou.ACS Appl.Mater.Interfaces,2018,10(4):3305-
3313；J.G.Pacheco,P.Rebelo,M Freitas,H.P.A.Nouws,C.Delerue-Matos.Sensors&
Actuators:B.Chemical,2018:1008-1014.So far, epitope molecular imprinting technology exists very big
Disadvantage is exactly that the template molecule of printing process use uses linear polypeptide segment mostly, but the structure of protein is usually
Complicated, such as many albumen with conformation have α-helixstructure, using linear polypeptide as molecule prepared by template molecule
Imprinted polymer limits its specific recognition for this kind with complicated conformational protein, and the spy of its identification can be reduced with this
It is anisotropic.So developing a kind of molecularly imprinted polymer nanoparticle that can determine base with identification of protein conformational antigen based on this
Son is most important.Referring to: 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:
5246-5249；S.Liu,Q.Y.Bi,Y.Y.Long.Nanoscale.2017,9:5394.Nowadays, nano material is as drug
The research and development of carrier is a lot of, but its general preparation process is complex.Referring to: L.Marcu, E.Bezak,
B.Allen.Critical Reviews in Oncology Hematology.2018,123:7-20.So needing to develop one
The simple method of kind has the function of have the double-template molecular imprinting nano particles of targeting while carrying medicine for synthesizing.
Summary of the invention
Present invention aims at existing insufficient in view of the above technology and problem, provides a kind of α-helixstructure antigen and determine
Determine base/DOX double-template molecular engram fluorescent nano particles preparation method.This method uses precipitation polymerization method and double-template trace
Method is more with the conformation that drug doxorubicin hydrochloride and breast tumor cell surface are overexpressed albumen P32 using silicon nano as carrier
Peptide is double-template molecule, constructs the conformational peptides with α-helixstructure with trifluoroethanol；Monomer used and template molecule it
Between there is certain interaction, prepared composite nanoparticle has the identification of target breast cancer cell special well
Property and selectivity；And preparation method is simple, in the targeted delivery of actual drug to the Selective recognition of target tumor and
Drug treatment has good application prospect.
Technical solution of the present invention:
It is a kind of glimmering based on silicon nano and α-helixstructure epitope/adriamycin double-template molecular imprinting technology
The preparation method of photoreactivation nanoparticle, using silicon nano as carrier, after coated silica, surface modification double bond, with
9 peptide of N-terminal and doxorubicin hydrochloride of target protein P32 is template, glimmering using precipitation polymerization method synthetic molecules trace under room temperature
Photoreactivation nanoparticle, includes the following steps:
1) preparation of silicon nano mixes trisodium citrate with glycerine, and argon gas protection is lower to be added 3- aminopropyl three
Ethoxysilane (APTES), is put into microwave reactor and is reacted, and 160-180 DEG C, obtains silicon nano after 10-15min
(Si)；
2) purifying of silicon nano silicon nano is added in dilute hydrochloric acid, dialysed overnight, the silicon nanometer purified
Particle (SiNPs) solution；
3) silicon nano of purifying is added in ethanol solution, ammonium hydroxide, tetraethoxysilane (TEOS) is added, in room
Temperature is lower to react 5-6h, and fluorescence silicon ball nanoparticle (the Si@SiO of packet silicon is made2)；
4) the packet luminescence from silicon silicon ball nanoparticle being prepared is distributed in the mixed solution of ethyl alcohol and water, ammonia is added
Water, γ-methacryloxypropyl trimethoxy silane (MPS), react for 24 hours under room temperature, obtain the glimmering of double bond modification
Light silicon nano (Si@SiO2@MPS)；
5) by the Fluorescent silicon nanoparticle of the double bond being prepared modification, n-isopropyl acrylamide (NIPA), fluoroform
Base acrylic acid (TFMA), N-tert-butyl acrylamide (TBAm), N ' N- methylene-bisacrylamide (BIS) and doxorubicin hydrochloride
(DOX) it is dissolved in pure water and trifluoroethanol TFE mixed solution, the TFE solution of polypeptide is added in above-mentioned reaction mixture, take out
Vacuum leads to Ar gas 30-50min, adds initiator ammonium persulfate (APS) and catalyst (TEMED), room under argon gas protective condition
Temperature reaction 20h, obtained nanoparticle are eluted with methanol-acetic acid (volume ratio 9:1) mixed liquor, remove template, obtain
Double-template imprinted polymer (MIPs)；
6) doxorubicin hydrochloride (DOX) absorption is added completely in the MIPs nanoparticle of preparation, three times, obtaining load has for cleaning
The targeting fluorescent nano particles MIPs@DOX of DOX.
Step 1) the trisodium citrate, glycerine, 3- aminopropyl triethoxysilane amount ratio are as follows: 0.31-0.32g:
8mL:1.8-2mL.
Step 2) the silicon nano solution and hydrochloric acid volume ratio are as follows: the concentration of 6-8mL:12mL, the hydrochloric acid is
0.5mol/L；The molecule interception of bag filter is 1000, and it is primary to change water every 8h-12h, is changed altogether water 2-3 times, total dialysis time is
16-36h。
Silicon nano solution, ethyl alcohol, ammonium hydroxide and the tetraethoxysilane volume ratio of the step 3) purifying are as follows: 5-
6mL:38-40mL:0.667mL:0.8mL.
Step 4) the packet luminescence from silicon silicon ball nanoparticle, ethyl alcohol, water, ammonium hydroxide and MPS volume ratio are as follows: 100-
500mg:160mL:24mL:2.668mL:2-4mL.
Fluorescent silicon nanoparticle Si@SiO2@MPS of step 5) double bond modification, NIPA, TFMA, TBAm, BIS, DOX,
The ratio of polypeptide, APS and TEMED are as follows: 50mg:17.8mg:10mg:8.4mg:5.9mg:5mg:5mg:100-400 μ L:20-80 μ
The concentration of L, the APS are 60mg/mL.
The ratio of the step 6) MIPs and DOX are as follows: the concentration of 2mg:5-10mL, the DOX are 0.2mg/mL.
The advantages of the present invention:
1) silicon nano is as a kind of novel nano-material, while having both the good characteristic of fluorescence and high-specific surface area,
Applied to can make prepared nano particle that there is excellent photoluminescent property in the preparation process of molecularly imprinted polymer；
2) to modify the fluorescence silicon ball nanoparticle of double bond as carrier, using conformational peptides and doxorubicin hydrochloride double-template system
Standby imprinted polymer, imprinted polymer nanoparticle surface obtained contains can specific recognition target there are two types of imprinted sites
Object；
3) it is synthesized using precipitation polymerization method under room temperature, a certain proportion of trifluoroethanol is solvent, so that line morphology turns
The conformational peptides for turning to α-helixstructure enhance the identification specificity to target protein；
4) the double-template molecularly imprinted polymer, a kind of template plays the work in preparation targeting site in two kinds of templates
With another kind plays the role of carrying medicine, realizes targeting identification and drug release administration simultaneously in the application.
Detailed description of the invention
Fig. 1 is the transmission electron microscope picture of double-template conformational peptides imprinted polymer nanoparticle.
Fig. 2 is that double-template molecular imprinting nano particles MIPs (80 μ g/mL, 6h) identifies 4T1 mammary tumor cells specific
Laser capture microdissection be total to focused view.(as a control group, blue is MIPs/NIPs to the non-trace nanoparticle of NIPs, and red is cell membrane
Dyestuff DiI).
Fig. 3 is that load has the double-template conformational peptides trace nanoparticle MIPs@DOX of DOX to 4T1 mammary gland solid tumor
Therapeutic effect figure (PBS, NIP of nude miceS@DOX, DOX are as negative control group).
Specific embodiment
Embodiment 1:
A kind of preparation method of α-helixstructure epitope/DOX double-template molecular engram fluorescent nano particles, specifically
Include the following steps:
1) preparation of silicon nano takes 0.318g trisodium citrate that 8mL glycerine is added, and argon gas protection is lower to be added
2mL3- aminopropyl triethoxysilane (APTES), above-mentioned reaction carry out in microwave reactor, and silicon nanoparticle is obtained after 15min
Sub (Si NPs)；
2) 8mL silicon nano is added 12mL (0.5mol/L) dilute hydrochloric acid, takes bag filter by the purifying of silicon nano
Molecule interception is 1000 dialysis, and it is primary to change water every 8h, changes altogether water 3 times, total dialysis time is the silicon purified overnight for 24 hours
Nanoparticle (Si NPs)；
3) the 6mL silicon nano purified is added in 40mL ethanol solution, after 0.667mL ammonium hydroxide is added, is added
0.8mL tetraethoxysilane (TEOS), reacts 6h at room temperature, and fluorescent nano particles (the Si@SiO of packet silicon is made2)；
4) the 500mg Si@SiO that will be prepared2It is distributed in the mixed solution of 160mL ethyl alcohol and 24ml water, is added
2.668mL ammonium hydroxide, 4mL γ-methacryloxypropyl trimethoxy silane (MPS), react for 24 hours under room temperature, obtain
Fluorescent silicon nanoparticle (the Si@SiO of double bond modification2@MPS)；
5) the 50mg Si@SiO that will be prepared2@MPS nanoparticle, 17.8mg n-isopropyl acrylamide (NIPA),
10mg trifluoromethyl acrylate (TFMA), 8.4mg N-tert-butyl acrylamide (TBAm), 5.9mg N ' N- methylene-bisacrylamide
(BIS), 5mg doxorubicin hydrochloride (DOX) is dissolved in 6.1mL pure water and 3mL trifluoroethanol TFE, weighs 5mg polypeptide and is dissolved in 2mL TFE
It mixes and above-mentioned reaction solution is added, vacuumize, lead to Ar gas 30min, 200 μ L (60mg/mL) of initiator ammonium persulfate, catalyst is added
20 μ L of TEMED reacts at room temperature 20h under argon gas protective condition.Obtained nanoparticle is carried out with the methanol-acetic acid mixed liquor of 9:1
Elution removes template, obtains bimolecular imprinted polymer (MIPs)；
6) 5mL (0.2mg/mL) doxorubicin hydrochloride (DOX) absorption is added completely in the 2mg MIPs nanoparticle of preparation, clearly
It washes and obtains the targeting fluorescent composite nanoparticle MIPs@DOX that load has DOX three times.
Fig. 1 is the transmission electron microscope picture of double-template conformational peptides imprinted polymer nanoparticle, is shown in figure: imprinted polymer
Layer is about 10nm or so.
Fig. 2 is double-template conformational peptides imprinted polymer nanoparticle MIPs (80 μ g/mL) and 4T1 cell incubation 6h, right
The laser capture microdissection of 4T1 mammary tumor cells specific identification is total to focused view (non-trace nanoparticle NIPs is as a control group), in figure
Display: prepared MIPs has specific recognition targeting to target 4T1 breast cancer cell, enters 4T1 compared to NIPs, MIPs
The nanoparticle of cell interior is more.
Fig. 3 is that load has the double-template conformational peptides trace nanoparticle MIPs@DOX of DOX to 4T1 mammary gland solid tumor
Therapeutic effect figure (PBS, NIP of nude miceS@DOX, DOX are as negative control group), show in figure: prepared MIPs@DOX is to mesh
Mark 4T1 mammary gland solid tumor has best therapeutic effect.
Embodiment 2:
A kind of preparation method of α-helixstructure epitope/DOX double-template molecular engram fluorescent nano particles, synthesis
Step is substantially the same manner as Example 1, the difference is that: step 1) takes 0.315g trisodium citrate that 8mL glycerine is added.
Final preparation double-template conformational antigen determines base trace nanoparticle characterization and MIPs@DOX application result and implements
Example 1 is similar.
Embodiment 3:
A kind of preparation method of α-helixstructure epitope/DOX double-template molecular engram fluorescent nano particles, synthesis
Step is substantially the same manner as Example 1, the difference is that: step 1) takes 0.32g trisodium citrate that 8mL glycerine is added.
Final preparation double-template conformational antigen determines base trace nanoparticle characterization and MIPs@DOX application result and implements
Example 1 is similar.
Embodiment 4:
A kind of preparation method of α-helixstructure epitope/DOX double-template molecular engram fluorescent nano particles, synthesis
Step is substantially the same manner as Example 1, the difference is that: 6mL silicon nano is added for the purifying of step 2) silicon nano
12mL (0.5mol/L) dilute hydrochloric acid.
Final preparation double-template conformational antigen determines base trace nanoparticle characterization and MIPs@DOX application result and implements
Example 1 is similar.
Embodiment 5:
A kind of preparation method of α-helixstructure epitope/DOX double-template molecular engram fluorescent nano particles, synthesis
Step is substantially the same manner as Example 1, the difference is that: the 100mg Si@SiO that step 4) is prepared2It is distributed to 160mL second
In alcohol, 24mL water mixed solution, 2.668mL ammonium hydroxide, 2mL γ-methacryloxypropyl trimethoxy silane is added
(MPS), Fluorescent silicon nanoparticle (the Si@SiO for obtaining double bond modification for 24 hours is reacted under room temperature2@MPS)。
Final preparation double-template conformational antigen determines base trace nanoparticle characterization and MIPs@DOX application result and implements
Example 1 is similar.
Embodiment 6:
A kind of preparation method of α-helixstructure epitope/DOX double-template molecular engram fluorescent nano particles, synthesis
Step is substantially the same manner as Example 1, the difference is that: the 300mg Si@SiO that step 4) is prepared2It is distributed to 160mL second
In alcohol, 24mL water mixed solution, 2.668mL ammonium hydroxide, 3mL γ-methacryloxypropyl trimethoxy silane is added
(MPS), Fluorescent silicon nanoparticle (the Si@SiO for obtaining double bond modification for 24 hours is reacted under room temperature2@MPS)。
Final preparation double-template conformational antigen determines base trace nanoparticle characterization and MIPs@DOX application result and implements
Example 1 is similar.
Embodiment 7:
A kind of preparation method of α-helixstructure epitope/DOX double-template molecular engram fluorescent nano particles, synthesis
Step is substantially the same manner as Example 1, the difference is that: 6mL is added in the 2mg MIPs nanoparticle of preparation in step 6)
Completely, cleaning is three times for (0.2mg/mL) doxorubicin hydrochloride (DOX) absorption.
Final preparation double-template conformational antigen determines base trace nanoparticle characterization and MIPs@DOX application result and implements
Example 1 is similar.
Embodiment 8:
A kind of preparation method of α-helixstructure epitope/DOX double-template molecular engram fluorescent nano particles, synthesis
Step is substantially the same manner as Example 1, the difference is that: 7mL is added in the 2mg MIPs nanoparticle of preparation in step 6)
Completely, cleaning is three times for (0.2mg/mL) doxorubicin hydrochloride (DOX) absorption.
Final preparation double-template conformational antigen determines base trace nanoparticle characterization and MIPs@DOX application result and implements
Example 1 is similar.
Embodiment 9:
A kind of preparation method of α-helixstructure epitope/DOX double-template molecular engram fluorescent nano particles, synthesis
Step is substantially the same manner as Example 1, the difference is that: 8mL is added in the 2mg MIPs nanoparticle of preparation in step 6)
Completely, cleaning is three times for (0.2mg/mL) doxorubicin hydrochloride (DOX) absorption.
Final preparation double-template conformational antigen determines base trace nanoparticle characterization and MIPs@DOX application result and implements
Example 1 is similar.
Embodiment 10:
A kind of preparation method of α-helixstructure epitope/DOX double-template molecular engram fluorescent nano particles, synthesis
Step is substantially the same manner as Example 1, the difference is that: 9mL is added in the 2mg MIPs nanoparticle of preparation by step 6)
Completely, cleaning is three times for (0.2mg/mL) doxorubicin hydrochloride (DOX) absorption.
Final preparation double-template conformational antigen determine base trace composite nanoparticle characterization and MIPs@DOX application result and
Embodiment 1 is similar.
Claims (8)
1. a kind of α-helixstructure epitope/DOX double-template molecular engram fluorescent nano particles preparation method, is received with silicon
Rice corpuscles is carrier, and after packet silicon, surface modification double bond is adopted using 9 peptide of N-terminal and doxorubicin hydrochloride of target protein P32 as template
With precipitation polymerization method synthetic molecules trace fluorescent composite nanoparticle under room temperature, include the following steps:
1) preparation of silicon nano mixes trisodium citrate with glycerine, and argon gas protection is lower to be added three ethoxy of 3- aminopropyl
Base silane (APTES), is put into microwave reactor and is reacted, and 160-180 DEG C, obtains silicon nano after 10-15min
(Si)；
2) purifying of silicon nano silicon nano is added in dilute hydrochloric acid, dialysed overnight, the silicon nano purified
(SiNPs) solution；
3) silicon nano of purifying is added in ethanol solution, ammonium hydroxide, tetraethoxysilane (TEOS) is added, at room temperature
5-6h is reacted, fluorescence silicon ball nanoparticle (the Si@SiO of packet silicon is made2)；
4) the packet luminescence from silicon silicon ball nanoparticle being prepared is distributed in the mixed solution of ethyl alcohol and water, ammonium hydroxide, γ-is added
Methacryloxypropyl trimethoxy silane (MPS), react under room temperature obtain for 24 hours double bond modification fluorescence silicon receive
Rice corpuscles (Si@SiO2@MPS)；
5) by the Fluorescent silicon nanoparticle of the double bond being prepared modification, n-isopropyl acrylamide (NIPA), trifluoromethyl third
Olefin(e) acid (TFMA), N-tert-butyl acrylamide (TBAm), N ' N- methylene-bisacrylamide (BIS) and doxorubicin hydrochloride (DOX) are molten
In pure water and trifluoroethanol TFE mixed solution, the TFE solution of polypeptide is added in above-mentioned reaction mixture, is vacuumized, led to
Ar gas 30-50min adds initiator ammonium persulfate (APS) and catalyst (TEMED), reacts at room temperature under argon gas protective condition
20h, obtained nanoparticle are eluted with methanol-acetic acid mixed liquor, are removed template, are obtained double-template imprinted polymer
(MIPs)；
6) doxorubicin hydrochloride (DOX) absorption is added completely in the MIPs nanoparticle of preparation, three times, obtaining load has DOX for cleaning
Targeting fluorescent nano particles MIPs@DOX.
2. the preparation method of fluorescent nano particles according to claim 1, it is characterised in that: the step 1) citric acid three
Sodium, glycerine, 3- aminopropyl triethoxysilane amount ratio are as follows: 0.31-0.32g:8mL:1.8-2mL.
3. the preparation method of fluorescent nano particles according to claim 1, it is characterised in that: the step 2) silicon nano
Solution and hydrochloric acid volume ratio are as follows: 6-8mL:12mL, the concentration of the hydrochloric acid are 0.5mol/L.
4. the preparation method of fluorescent nano particles according to claim 1, it is characterised in that: the silicon of the step 3) purifying is received
Rice corpuscles solution, ethyl alcohol, ammonium hydroxide and tetraethoxysilane volume ratio are as follows: 5-6mL:38-40mL:0.667mL:0.8mL.
5. the preparation method of fluorescent nano particles according to claim 1, it is characterised in that: step 4) the packet luminescence from silicon silicon
Ball nanoparticle, ethyl alcohol, water, ammonium hydroxide and MPS volume ratio are as follows: 100-500mg:160mL:24mL:2.668mL:2-4mL.
6. the preparation method of fluorescent nano particles according to claim 1, it is characterised in that: step 5) the double bond modification
The ratio of Fluorescent silicon nanoparticle Si@SiO2@MPS, NIPA, TFMA, TBAm, BIS, DOX, polypeptide, APS and TEMED are as follows:
50mg:17.8mg:10mg:8.4mg:5.9mg:5mg:5mg:100-400 the concentration of μ L:20-80 μ L, the APS are 60mg/
mL。
7. the preparation method of fluorescent nano particles according to claim 1, it is characterised in that: first in the step 5) eluent
The volume ratio of alcohol and acetic acid is 9:1.
8. the preparation method of fluorescent nano particles according to claim 1, it is characterised in that: the step 6) MIPs and DOX
Ratio are as follows: the concentration of 2mg:5-10mL, the DOX be 0.2mg/mL.
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| CN112694577B (en) * | 2020-12-02 | 2022-08-19 | 江苏科技大学 | Imprinted mesoporous material and preparation method and application thereof |
| CN115093848A (en) * | 2022-08-11 | 2022-09-23 | 郑州中科生物医学工程技术研究院 | Yellow fluorescent silicon quantum dot and preparation method and application thereof |
| CN115093848B (en) * | 2022-08-11 | 2023-10-20 | 郑州中科生物医学工程技术研究院 | Yellow fluorescent silicon quantum dot and preparation method and application thereof |
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