CN115850577B - High-biocompatibility polymer, chip and preparation method thereof - Google Patents
High-biocompatibility polymer, chip and preparation method thereof Download PDFInfo
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Abstract
The invention relates to the technical field of chips, and discloses a polymer with high biocompatibility, a chip and a preparation method thereof. A polymer is characterized in that the structural formula of the polymer is shown as a formula A. The invention enables the polymer to have compact active functional groups such as NH2 and azide through the principle of free radical polymerization. The polymer is fixed on the surface of the chip substrate, so that sufficient primers are ensured on the substrate in the PCR amplification process of the chip, and the amplification can be efficiently and uniformly carried out; the amplified DNA cluster has high signal to noise ratio when fluorescent labeling is used.
Description
Technical Field
The invention relates to the technical field of chips, in particular to a polymer with high biological compatibility, a chip and a preparation method thereof.
Background
With the development of biotechnology, the analysis and application of the biotechnology field is developed toward high throughput, rapid and low cost, and more technologies depend on biochips. The chip has the characteristics of good biocompatibility, low adsorption, low steric hindrance, high density, high wetting and the like, provides an in-situ biochemical reaction environment on the solid surface, enables a complex biochemical reaction process to be rapidly and conveniently carried out on the solid surface, and simultaneously combines an optical information or electric information collecting system to realize high-flux and rapid biological detection, biological synthesis preparation and the like. However, the chip in the current market has various defects and limitations such as low density, high adsorption, poor signal to noise ratio and the like, limits the application of various biotechnology and becomes a bottleneck in various biotechnology fields (such as protein detection, gene sequencing, biosynthesis and the like). Therefore, there is a need to develop a highly biocompatible polymer, chip and method of manufacturing the same.
Disclosure of Invention
The present invention aims to solve at least one of the technical problems in the prior art described above. Therefore, the invention provides a polymer and a chip with high biocompatibility and a preparation method thereof.
A first aspect of the invention provides a polymer.
Specifically, the structural formula of the polymer is shown as formula A:
formula A;
r is selected from、/>、/>、/>Any one of them;
R 1 、R 4 respectively and independently represent-C (O) NH 2 、-C(O)OH、、/>、、/>；
R 2 Any one of amino, epoxy, azide, alkynyl, alkenyl, nitrile, isothiocyano, nitrile oxide, tetrazine, triazole and carboxyl;
r3 is selected from any one of-NH-, -O-;
y, m and n are positive integers, and x and z are 0 or positive integers.
Preferably, x is 0 to 12000; y is 5-6000; m is 1-2000; n is 1-2000; z is 0 to 500.
Preferably, the molar ratio of x to y is 1-30:1.
further preferably, the molar ratio of x to y is 1-25:1.
still more preferably, the molar ratio of x, y, z is 1-25:1:0.01-0.1.
Preferably, R is selected from；R 1 Selected from-C (O) NH 2 ；R 2 Selected from azide; r is R 3 Selected from-NH-; r is R 4 Selected from the group consisting of。
Preferably, the polymer comprisesOr->Or->。
In a second aspect, the invention provides a method of preparing a polymer.
Specifically, the preparation method comprises the following steps:
substance B and content R, R 2 、R 3 Placing the radical material into an initiator to react to prepare the polymer;
the substance B contains R 1 Radicals and/or R 4 A group.
Preferably, the temperature of the reaction in the preparation method is 4-65 ℃.
Further preferably, the temperature of the reaction in the preparation method is 10-60 ℃.
Preferably, the initiator comprises at least one of potassium persulfate, ammonium persulfate, azobisisobutyronitrile, azobisisoheptonitrile, cumene hydroperoxide, tert-butyl hydroperoxide, and hydrogen peroxide.
A third aspect of the invention provides a chip.
Specifically, the chip comprises a substrate and the polymer of the first aspect grafted on the surface of the substrate.
Preferably, the substrate surface and polymer contain reactive groups.
Preferably, the active group contained on the surface of the substrate is at least one of amino, epoxy, azide, alkynyl, alkenyl, nitrile, isothiocyano, nitrile oxide, tetrazine, triazole and carboxyl.
Further preferably, the preparation method of the substrate surface comprises the following steps: cleaning and activating the substrate material, placing the substrate material into a closed cavity with adjustable pressure and temperature, simultaneously placing a vaporizable silane coupling agent in the cavity, and placing the substrate material under the pressure of 10 -9~ 10 bar, maintaining the temperature at 25-150 ℃ for a certain time to finish the preparation of the substrate surface.
The substrate material is at least one selected from glass, silicon chip and organic glass.
The cleaning and activating steps are selected from one of the following ways:
pathway 1: ultrasonic treatment is carried out on absolute ethyl alcohol (30-60 ℃) for 10-30 min, 1-3M sodium hydroxide (30-60 ℃) for 10-30 min, and pure water (30-60 ℃) for 10-30 min;
pathway 2: the piranha solution (concentrated sulfuric acid: hydrogen peroxide=7:3) is heated to boiling for 10-30 min, and pure water (30-60 ℃) is subjected to ultrasonic treatment for 10-30 min.
In order to further activate the surface of the chip substrate, 150W plasma can be optionally used for 1-10 min.
The silane coupling agent is at least one selected from 3-aminopropyl triethoxysilane, 3-aminopropyl trimethoxysilane, 4- (triethoxy) silicon-based butyronitrile, [3- (triethoxysilyl) propyl ] carbamic acid 2-propynyl ester, allyl trimethoxysilane, [ bicyclo [2.2.1] hept-5-en-2-yl ] triethoxysilane, and gamma- (2, 3-epoxypropoxy) propyl trimethoxysilane.
Preferably, the chip further comprises a biological component, the biological component comprising a reactive group.
Further preferably, the active group contained in the biological component is at least one of amino, epoxy, azide, alkynyl, alkenyl, nitrile, isothiocyano, nitrile oxide, tetrazine, triazole and carboxyl.
Preferably, the biological component is selected from at least one of nucleotide sequence, amino acid sequence, antigen, antibody, biological enzyme, protein, polypeptide.
A fourth aspect of the invention provides a method of manufacturing a chip.
Specifically, the preparation method comprises the following steps:
(1) Firstly, carrying out chemical reaction on active groups on the biological components and active groups on the surface of a polymer to form covalent connection, and preparing a semi-finished product;
(2) And grafting the semi-finished product on the surface of a substrate, wherein the grafting mode is covalent connection and/or non-covalent connection, so as to prepare the chip.
Preferably, the non-covalent attachment means includes hydrogen bonding, hydrophobic forces.
In a fifth aspect, the invention provides the use of a chip for amplifying a DNA cluster.
Specifically, the generation of DNA clusters is performed on a chip using isothermal amplification techniques.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides the polymer with compact active functional groups such as NH by the principle of free radical polymerization 2 And (3) azides. The polymer is fixed on the surface of the chip substrate, so that sufficient primers are ensured on the substrate in the PCR amplification process of the chip, and the amplification can be efficiently and uniformly carried out; the amplified DNA cluster has high signal to noise ratio when fluorescent labeling is used.
Drawings
FIG. 1 is a Gel Permeation Chromatography (GPC) diagram of polymers SP1, SP2, SP 3;
FIG. 2 is a Salus Pro laser scan of the surface of the chip substrate;
FIG. 3 is a Salus Pro laser scan of the surface of the chip substrate;
FIG. 4 is a Salus Pro laser scan of a chip DNA cluster.
Detailed Description
In order to make the technical solutions of the present invention more apparent to those skilled in the art, the following examples will be presented. It should be noted that the following examples do not limit the scope of the invention.
The starting materials, reagents or apparatus used in the following examples are all available from conventional commercial sources or may be obtained by methods known in the art unless otherwise specified.
Example 1
A polymer and a polymerization method thereof.
The water-soluble polymer (SP 1) is prepared by means of free radical polymerization, and the monomer structures (A), (B), (C) and the polymerization reaction formula are as follows:
2000mg of the (A) monomer and 58mg of the (C) monomer were dissolved in 85ml of pure water to prepare Mix1-1, 1447mg of the (B) monomer was dissolved in 15ml of DMF to prepare Mix1-2, and 85ml of Mix1-1 and 15ml of Mix1-2 were mixed to prepare Mix1-3, which were thoroughly mixed on a vortex mixer. The mixture Mix1-3 was filtered using a 0.22um filter membrane to filter out insoluble materials. 100mg KPS was dissolved in 2ml of purified water to form a 50mg/ml KSP solution. The mixture Mix1-3 was transferred to a 250ml three-way round bottom flask, in which a stirring magnet was placed, and fixed in a constant temperature oil bath with a heated magnetic stirrer, the temperature was set at 25℃and the rotational speed was 300rpm. The mixture Mix1-3 min was purged with nitrogen by bottom blowing nitrogen, 1.5ml of KSP solution was added, and after mixing, 100ul of TEMED reagent was added. The mixture was purged with nitrogen for 5min, the nitrogen purge was removed, the three-way round bottom flask was sealed, and the reaction was carried out at 50℃for 2h. After the reaction is finished, the oil bath device is removed, the airtight device is opened to allow air to flow in, and stirring is continued for 15min to terminate the reaction. The reaction was precipitated using 10 volumes of absolute ethanol, repeated 1 time for 2 times total, and finally dried under vacuum to obtain 2912mg of white polymer (SP 1).
Example 2
A polymer and a polymerization method thereof.
The water-soluble polymer (SP 2) is prepared by means of free radical polymerization, and the monomer structures (A) (B) and the polymerization reaction formula are as follows:
2000mg of (A) monomer was dissolved in 85ml of pure water to prepare Mix2-1, 1447mg of (B) monomer was dissolved in 15ml of DMF to prepare Mix2-2, 85ml of Mix2-1 and 15ml of Mix2-2 were mixed to prepare Mix2-3, and the mixture was thoroughly mixed on a vortex mixer. The mixture Mix2-3 was filtered using a 0.22um filter membrane to filter out insoluble materials. 50mg KPS was dissolved in 1ml of purified water to form a 50mg/ml KSP solution. The mixture Mix2-3 was transferred to a 250ml three-way round bottom flask, in which a stirring magnet was placed, and fixed in a constant temperature oil bath with a heated magnetic stirrer, the temperature was set at 25℃and the rotational speed was 300rpm. The mixture Mix2-3 min was purged with nitrogen by bottom blowing, 750ul of KSP solution was added, and after mixing, 100ul of TEMED reagent was added. The mixture was purged with nitrogen for 5min, the nitrogen purge was removed, the three-way round bottom flask was sealed, and the temperature was set to 30℃for 2h of reaction. After the reaction is finished, the oil bath device is removed, the airtight device is opened to allow air to flow in, and stirring is continued for 15min to terminate the reaction. The reaction was precipitated using 10 volumes of absolute ethanol, repeated 1 time for 2 times total, and finally dried under vacuum to obtain 3200mg of white polymer (SP 2).
Example 3
A polymer and a polymerization method thereof.
The water-soluble polymer (SP 3) is prepared by means of free radical polymerization, and the monomer structures (A) (D) and the polymerization reaction formula are as follows:
2000mg of (A) monomer was dissolved in 85ml of pure water to prepare Mix3-1, 1215mg of (D) monomer was dissolved in 15ml of DMF to prepare Mix3-2, 85ml of Mix3-1 and 15ml of Mix3-2 were mixed to prepare Mix3-3, and the mixture was thoroughly mixed on a vortex mixer. The mixture Mix3-3 was filtered using a 0.22um filter membrane to filter out insoluble materials. 50mg KPS was dissolved in 1ml of purified water to form a 50mg/ml KSP solution. The mixture Mix3-3 was transferred to a 250ml three-way round bottom flask, in which a stirring magnet was placed, and fixed in a constant temperature oil bath with a heated magnetic stirrer, the temperature was set at 25℃and the rotational speed was 300rpm. The mixture Mix3-3 min was purged with nitrogen by bottom blowing, 750ul of KSP solution was added, and after mixing, 100ul of TEMED reagent was added. The mixture was purged with nitrogen for 5min, the nitrogen purge was removed, the three-way round bottom flask was sealed, and the temperature was set to 30℃for 2h of reaction. After the reaction is finished, the oil bath device is removed, the airtight device is opened to allow air to flow in, and stirring is continued for 15min to terminate the reaction. The reaction was precipitated using 10 volumes of absolute ethanol, repeated 1 time for 2 times total, and finally dried under vacuum to obtain 3218mg of white polymer (SP 3).
Detection result:
as a result of measurement of SP1, SP2 and SP3 by GPC, as shown in FIG. 1, as is apparent from FIG. 1 (a), the average molecular weight Mw of the polymer SP1 is 32565; as can be seen from FIG. 1 (b), the average molecular weight Mw of the polymer SP2 is 210320; as can be seen from FIG. 1 (c), the average molecular weight Mw of the polymer SP3 was 178859.
Example 4
A chip and its preparation method are provided.
1. Preparation of a chip substrate:
and (3) carrying out surface coating by using a glass substrate and adopting a chemical gas sedimentation mode. And respectively using absolute ethyl alcohol and 1M NaOH solution for the glass substrate, carrying out ultrasonic treatment on pure water at 55 ℃ for 15min, drying the surface of the glass by using a nitrogen source after ultrasonic treatment, placing the glass substrate into a Plasma instrument, and carrying out Plasma treatment for 5min at 150W power. The vacuum chamber was pumped to a pressure below 10bar with a vacuum pump, replaced 3 times with nitrogen, and then placed in a 50ml centrifuge tube lid to which was added 50ul of allyltrimethoxysilane. And (3) transferring the plasma treated glass into the vacuum cavity, closing a vacuum cavity door, using a vacuum pump to reach the pressure of 1bar, setting the temperature of 80 ℃, and setting the temperature of 25 ℃ after reacting for 2 hours. And taking out the glass sheet after cooling to obtain the glass surface coated with the alkenyl active groups. Immersing the glass sheet coated with the alkenyl groups in 0.1% (m/v) SP1 aqueous solution, immersing at 60 ℃ for 1.5 hours, taking out, and cleaning with pure water to obtain the surface modified with the (SP 1) polymer. The surface modified with (SP 1) polymer was reacted with 50uM of 3XSSC solution of DBCO-CY5 at 60℃for 1 hour, and scanning photographing was performed under Salus Pro instrument using 640nm laser band, and the result is shown in FIG. 2 (a).
2. Preparation of the chip:
reacting the nucleic acid sequence modified with a DBCO group with a 5-prime with a surface modified with a (SP 1) polymer, grafting the nucleic acid sequence to the glass surface: the surface of the modified SP1 polymer was reacted with 3XSSC solution of 3uM DBCO-space6-A30 at 60℃for 2 hours, and after the reaction was completed, the biochip modified with the nucleic acid sequence was obtained by washing with pure water. Biochip hybridization characterization using T30-CY 5: hybridization was performed using 3XSSC solution of 3uM T30-CY5 at 37℃for 15min, scanning photographing was performed using a 640nm laser band under Salus pro instrument, and the average brightness of the pictures was analyzed by imageJ software, and the results are shown in FIG. 3 (a).
Example 5
A chip and its preparation method are provided.
1. Preparation of a chip substrate:
and (3) carrying out surface coating by using a glass substrate and adopting a chemical gas sedimentation mode. And respectively using absolute ethyl alcohol and 1M NaOH solution for the glass substrate, carrying out ultrasonic treatment on pure water at 55 ℃ for 15min, drying the surface of the glass by using a nitrogen source after ultrasonic treatment, placing the glass substrate into a Plasma instrument, and carrying out Plasma treatment for 5min at 150W power. The vacuum chamber was pumped to a pressure below 10bar with a vacuum pump, replaced 3 times with nitrogen, then placed in a 50ml centrifuge tube lid and 50ul of 2-propynyl [3- (triethoxysilyl) propyl ] carbamate was added to the lid. And (3) transferring the plasma treated glass into the vacuum cavity, closing a vacuum cavity door, using a vacuum pump to reach the pressure of 1bar, setting the temperature of 80 ℃, and setting the temperature of 25 ℃ after reacting for 2 hours. And taking out the glass sheet after cooling to obtain the glass surface coated with the alkynyl active groups. Immersing the glass sheet coated with the alkynyl in (SP 2) aqueous solution with the concentration of 0.1% (m/v), immersing for 1h and 30min at 60 ℃, taking out, and cleaning with pure water to obtain the surface modified with (SP 2) polymer. The surface modified with (SP 2) polymer was reacted with 50uM of 3XSSC solution of DBCO-CY5 at 60℃for 1 hour, and scan-photographed under Salus pro instrument using 640nm laser band, and the result is shown in FIG. 2 (b).
2. Preparation of the chip:
reacting the nucleic acid sequence modified with a DBCO group with a 5-prime with a surface modified with a (SP 2) polymer, grafting the nucleic acid sequence to the glass surface: the surface of the modified (SP 2) polymer was reacted with 3XSSC solution of 3uM DBCO-space6-A30 at 60℃for 2 hours, and after the reaction was completed, the biochip modified with the nucleic acid sequence was obtained by washing with pure water. Biochip hybridization characterization using T30-CY 5: hybridization was performed using a 3XSSC solution of 3uM T30-CY5 at 37℃for 15min, scanning photographs were performed under a Salus Pro instrument using a 640nm laser band, and the average brightness of the pictures was analyzed by imageJ software, and the results are shown in FIG. 3 (b).
Example 6
A chip and its preparation method are provided.
1. Preparation of a chip substrate:
and (3) carrying out surface coating by using a glass substrate and adopting a chemical gas sedimentation mode. And respectively using absolute ethyl alcohol and 1M NaOH solution for the glass substrate, carrying out ultrasonic treatment on pure water at 55 ℃ for 15min, drying the surface of the glass by using a nitrogen source after ultrasonic treatment, placing the glass substrate into a Plasma instrument, and carrying out Plasma treatment for 5min at 150W power. The vacuum chamber was pumped to a pressure below 10bar with a vacuum pump, replaced 3 times with nitrogen, then placed in a 50ml centrifuge tube lid and 50ul of gamma- (2, 3-glycidoxy) propyltrimethoxysilane was added to the lid. And (3) transferring the plasma treated glass into the vacuum cavity, closing a vacuum cavity door, using a vacuum pump to reach the pressure of 1bar, setting the temperature of 80 ℃, and setting the temperature of 25 ℃ after reacting for 2 hours. And taking out the glass sheet after cooling to obtain the glass surface coated with the epoxy group active group. The glass sheet coated with the epoxy group was immersed in (SP 3) carbonate buffer solution (ph=9.2) having a concentration of 0.1% (m/v), immersed at 37 ℃ for 8 hours, taken out, and washed with pure water to obtain a surface modified with (SP 3) polymer. The reaction was carried out with 50uM of NHS-CY5 carbonate buffer (ph=9.2) with the (SP 3) polymer-modified surface at room temperature for 30min, and scanning photographing was carried out under a Salus Pro instrument using a 640nm laser band, and the results are shown in fig. 2 (c).
2. Preparation of the chip:
reacting the 5-prime epoxy-modified nucleic acid sequence with a surface modified with a (SP 3) polymer to graft the nucleic acid sequence to the glass surface: the surface of the modified (SP 3) polymer was reacted with a carbonate buffer (ph=9.2) of 3uM epoxy-space 6-a30 at 37 ℃ for 8 hours, and after the reaction was completed, the biochip modified with a nucleic acid sequence was obtained by washing with pure water. Biochip hybridization characterization using T30-CY 5: hybridization was performed using a 3XSSC solution of 3uM T30-CY5 at 37℃for 15min, scanning photographs were performed using a 640nm laser band under a Salus Pro instrument, and the average brightness of the pictures was analyzed by imageJ software, and the results are shown in FIG. 3 (c).
As can be seen from FIG. 2, the average brightness value of the pictures in FIG. 2 (a) and FIG. 2 (b) is increased because CY5 fluorophores are too dense, and a "quenching" phenomenon occurs, indicating that very dense N exists on the substrate surface 3 A group; the average brightness value of the picture in FIG. 2 (c) increases because the CY5 fluorophores are "quenched" due to too close a pattern, indicating very dense NH on the substrate surface 2 A group.
As can be seen from FIG. 3, the SP1, SP2 and SP3 modified surfaces after T30-CY5 hybridization all have uniform and stronger fluorescent signals under Salus Pro photographing, which indicates that the SP1, SP2 and SP3 modified surfaces can successfully covalently link the oligonucleotide chains, and the linked oligonucleotide chains are uniformly distributed and have higher density.
Effect detection of examples 4-6 chip:
the DNA clusters on the chips of examples 4-6 were generated and characterized.
1. The generation of DNA clusters was performed using isothermal amplification techniques.
2. The P1 skim-cy 5 hybridized P1 region was used to characterize cluster generation: a3 XSSC solution of 1uM P1 prime-cy 5 was hybridized at 55℃for 15min, and a scanning photograph was taken under a Salus Pro instrument using a 640nm laser band, and the results are shown in FIG. 4. Fig. 4 (a) shows an SP1 modified chip, fig. 4 (b) shows an SP2 modified chip, and fig. 4 (c) shows an SP3 modified chip, as can be seen from fig. 4, the 3 chips can well complete amplification, and the substrate surface adsorption after amplification is low and the signal to noise ratio is high.
The foregoing describes in detail preferred embodiments of the present invention. It should be understood that numerous modifications and variations can be made in accordance with the concepts of the invention by one of ordinary skill in the art without undue burden. Therefore, any modification, equivalent replacement, improvement or the like of the prior art through logic analysis, reasoning or limited experiments according to the present invention will be within the scope of protection defined by the claims.
Claims (5)
1. A polymer, wherein the polymer comprises:
or->Or->；
x, y and z are positive integers;
x is 0-12000; y is 5-6000; z is 0-500, and x, z are not 0;
the molar ratio of x to y is 1-30:1.
2. a chip comprising a substrate and the polymer of claim 1 grafted to the surface of the substrate.
3. The chip of claim 2, wherein the chip further comprises a biological component; the biological component includes a reactive group.
4. A method of manufacturing a chip as claimed in any one of claims 2 to 3, comprising the steps of:
(1) Firstly, carrying out chemical reaction on active groups on the biological components and active groups on the surface of a polymer to form covalent connection, and preparing a semi-finished product;
(2) And grafting the semi-finished product on the surface of a substrate, wherein the grafting mode is covalent connection and/or non-covalent connection, so as to prepare the chip.
5. Use of a chip according to any one of claims 2-3 for amplifying DNA clusters.
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| CN115677922A (en) * | 2022-09-28 | 2023-02-03 | 深圳市曙芯生物科技有限公司 | Difunctional polymer and modification method |
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