CN114236023A - Porous carbon carrier, preparation method thereof and application thereof in ligand fishing - Google Patents

Porous carbon carrier, preparation method thereof and application thereof in ligand fishing Download PDF

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CN114236023A
CN114236023A CN202111446040.5A CN202111446040A CN114236023A CN 114236023 A CN114236023 A CN 114236023A CN 202111446040 A CN202111446040 A CN 202111446040A CN 114236023 A CN114236023 A CN 114236023A
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porous carbon
mobile phase
hpc
carbon carrier
ligand
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CN114236023B (en
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张伟
姜志宏
周明月
吴璇
王彩云
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Macau University of Science and Technology
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    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
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    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
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Abstract

The invention belongs to the technical field of ligand fishing, and discloses a porous carbon carrier, a preparation method thereof and application thereof in ligand fishing. The preparation method of the porous carbon carrier comprises the following steps: (1) dissolving Zn salt and polyacrylate in water to obtain a mixture; (2) and freeze-drying the mixture, and then carbonizing the mixture in inert gas to obtain the porous carbon carrier. The porous carbon carrier has good protein loading and fixing capacity, can be used for ligand fishing technology, shows good stability and repeatability, and can quickly, efficiently and accurately screen natural plant components to obtain target active substances.

Description

Porous carbon carrier, preparation method thereof and application thereof in ligand fishing
Technical Field
The invention belongs to the technical field of ligand fishing, and particularly relates to a porous carbon carrier, a preparation method thereof and application thereof in ligand fishing.
Background
Ligand fishing (Ligand fishing) is a Ligand and a receptor which are based on the affinity interaction between molecules to identify the interaction, and a new way is opened up for researching the interaction between biological macromolecules and ligands by combining with a modern organic analysis means. In short, ligand fishing is based on the interaction between a drug target and an active ligand, which is "fished" out of a complex sample system. The ligand fishing strategy with high sensitivity and high-throughput determination characteristics has a wide prospect in the aspect of screening active compounds, and the current research results show that the ligand fishing technology can realize the rapid screening of active products from complex extract components, and is a preferred strategy for carrying out the directional separation of natural active molecules. Since the traditional identification of biologically active compounds in natural sources involves repeated isolation and activity testing steps, these steps are time consuming, laborious and inefficient. And ligand fishing by selecting ligands from complex biological samples based on the fixation of target biomolecules on the micro-nano material can be a feasible and convenient method.
However, the micro-nano material for fixing biomolecules in the existing ligand fishing method has the defects of limited load rate, insufficient stability and the like, and the development and application of the ligand fishing method are limited to a certain extent. Based on this, the present invention is expected to provide a carrier material with better loading rate and stability, so as to better meet the requirements of ligand fishing technology in screening bioactive compounds in natural sources.
Disclosure of Invention
The present invention is directed to solving at least one of the problems of the prior art described above. Therefore, the porous carbon carrier (SAZn-HPC) has good protein loading and fixing capacity, can be used for ligand fishing technology, shows good stability and repeatability, and can be used for quickly, efficiently and accurately screening target active substances from natural plant components.
The invention provides a preparation method of a porous carbon carrier (SAZn-HPC), which comprises the following steps:
(1) dissolving Zn salt and polyacrylate in water to obtain a mixture;
(2) and freeze-drying the mixture, and then carbonizing the mixture in inert gas to obtain the porous carbon carrier.
The porous carbon carrier (SAZn-HPC) prepared by the method has good load capacity on biological macromolecules such as protein, nucleic acid and the like, so that the porous carbon carrier can be applied as a biological macromolecule fixing material and shows good stability and reproducibility.
The freeze drying employed in the present invention may provide better protection of the mixture than other drying means. Because the drying is carried out in a frozen state, the volume is almost unchanged, the original structure is kept, the condensation phenomenon cannot occur, and some substances which are easy to oxidize are protected. The freeze drying can remove more than 95-99% of water, so that the dried product can be stored for a long time without deterioration.
Preferably, the Zn salt in the step (1) is ZnCl2。
Preferably, the sodium polyacrylate in step (1).
Preferably, in step (1), the Zn salt and the polyacrylate salt are dissolved in water under ultrasonic agitation.
Preferably, in step (2), the freeze-drying is carried out when a snowflake appearance of significant volume expansion appears in the mixture.
Preferably, the inert gas in the step (2) is Ar gas.
Preferably, after the carbonization in the step (2), the operations of grinding, washing and drying are also performed.
The invention also provides a porous carbon carrier (SAZn-HPC), which is hierarchical porous carbon with monoatomic Zn sites and is prepared by the preparation method.
The invention also provides application of the porous carbon carrier in ligand fishing.
The invention also provides application of the porous carbon carrier in screening of active ingredients of natural plants. The porous carbon carrier is combined with ligand for fishing, and can be used for screening active ingredients of natural plants.
The invention also provides a ligand screening system which comprises the porous carbon carrier and biological macromolecules, wherein the biological macromolecules are fixed on the porous carbon carrier. According to the principle of affinity, the ligand screening system can be used for screening corresponding active ligands (ligand fishing) which can be specifically combined with biological macromolecules from a mixture to be screened.
Preferably, the biomacromolecule is amyloid beta (a β).
The invention also provides a method for screening the potential inhibitor of the A beta from the curcuma extract, which comprises the following steps:
s1, diluting Abeta with a buffer solution, mixing the Abeta with the porous carbon carrier, oscillating and washing to prepare Abeta @ SAZn-HPC;
s2, mixing the Abeta @ SAZn-HPC and the turmeric extract in a vortex manner, removing supernatant, incubating, washing, mixing with methanol in a vortex manner, and performing mass spectrum detection on the obtained solution;
the condition parameters of the mass spectrum detection comprise:
mobile phase composition:
mobile phase A: 0.1% (v/v) aqueous formic acid; mobile phase B: acetonitrile;
gradient elution conditions:
0-25 min: 25% -70% of mobile phase B, and the balance of mobile phase A;
25-40 min: 70-95% of mobile phase B, and the balance of mobile phase A;
40-50 min: 95-25% of mobile phase B and the balance of mobile phase A.
The turmeric is a commonly used traditional Chinese medicine in China, has the effects of promoting qi circulation, removing blood stasis, dredging channels and relieving pain, and is mainly used for treating chest and abdomen distending pain, shoulder and arm pain, intolerable heart pain, postpartum hematodynia, initial onset of sore and tinea, irregular menstruation, amenorrhea and traumatic injury. Curcuma rhizome carried by the 'Chinese pharmacopoeia' of 2020 edition is dried rhizome of Curcuma rhizome Curcuma Longa L. Modern pharmacological research shows that the turmeric has multiple biological activities of resisting inflammation, resisting cancer, protecting liver, reducing blood pressure or blood fat and the like. Among them, chemical components such as curcumin have shown a remarkable effect of preventing or treating Alzheimer Disease (AD). However, since there are many ingredients in turmeric, there is little information about the active ingredient and mechanism. The porous carbon carrier is adopted to fix amyloid beta-protein (A beta), so that the purpose of screening potential inhibitors of amyloid beta-protein (A beta) in turmeric extract can be effectively realized.
Preferably, the buffer solution in step S1 is PBS buffer solution.
Preferably, the washing is performed using PBS buffer in step S1.
Preferably, the preparation method of the turmeric extract in step S2 is: pulverizing Curcuma rhizome, adding 75% ethanol, reflux-extracting, and evaporating the filtrate under reduced pressure to remove solvent by rotary evaporator to obtain Curcuma rhizome extract.
Preferably, the condition parameters for mass spectrometry detection in step S2 further include: the collection time is about 55 min; the flow rate of the mobile phase is about 300 mu L/min; the column was Agilent ZORBAX SB-C18 (2.1X 100mm, 3.5 μm); the column temperature is 30-35 ℃; the sample size is about 10 muL; setting the voltage of an ion source to be 4.0kV, and detecting in a positive detection mode; taking nitrogen as a sheath gas and helium as an auxiliary gas, wherein the flow rates are respectively 10CFM and 0; the capillary temperature was 275 ℃; detecting in the range of m/z of 100-; the resolution is 30000; the normalized collision energy was 35% and the Q value was 0.25.
Preferably, the incubation temperature in step S2 is 35-37 deg.C, and the incubation time is 25-35 min.
Compared with the prior art, the invention has the following beneficial effects:
(1) the porous carbon carrier has good protein loading and fixing capacity, can be used for ligand fishing technology, shows good stability and repeatability, and can quickly, efficiently and accurately screen natural plant components to obtain target active substances.
(2) The method for screening the A beta potential inhibitor from the curcuma extract has the characteristics of high specificity, high screening efficiency, low labor and time cost, low requirement on sample pretreatment and the like.
Drawings
FIG. 1 is a morphological feature diagram of a porous carbon support (SAZn-HPC) in example 1 of the present invention;
FIG. 2 shows the results of the performance test of A β @ SAZn-HPC and the results of the screening for active compounds in turmeric extract in example 2 of the present invention;
FIG. 3 shows the results of biological assays performed on the active compounds screened in example 3 of the present invention.
Detailed Description
In order to make the technical solutions of the present invention more apparent to those skilled in the art, the following examples are given for illustration. It should be noted that the following examples are only preferred embodiments of the present invention, and the claimed protection scope is not limited thereto, and any modification, substitution, combination made without departing from the spirit and principle of the present invention are included in the protection scope of the present invention.
The starting materials, reagents or apparatuses used in the following examples are conventionally commercially available or can be obtained by conventionally known methods, unless otherwise specified.
Example 1
This example provides a porous carbon support, a hierarchical porous carbon with monoatomic Zn sites, named SAZn-HPC, prepared by a method comprising the steps of:
(1) reacting ZnCl2Dissolving the mixture and sodium polyacrylate in deionized water under ultrasonic stirring to obtain a mixture;
(2) freeze-drying the mixture prepared in the step (1), and then carbonizing the mixture in Ar gas to obtain a primary product;
(3) and (3) grinding, washing and drying the primary product prepared in the step (2) to prepare the porous carbon carrier SAZn-HPC.
FIG. 1 shows the morphological characteristics of the porous carbon support (SAZn-HPC), as can be seen from FIG. 1: a broad peak at 23 ℃ pointing to the (002) peak of amorphous carbon (JCPDS No.41-1487) was observed in SAZn-HPC, indicating the presence of a random combination of graphitic and turbostratic stacking (shown in FIG. 1A); from Scanning Electron Microscopy (SEM) and Transmission Electron Microscopy (TEM), SAZn-HPC shows a typical layered porous structure, including the formation of large pores with long-range orderAnd having sidewalls (shown as B and C in fig. 1) interconnecting the mesopores/micropores; the raman spectrum of SAZn-HPC (shown as D in fig. 1) exhibits typical non-graphitic carbon characteristics with strong D-bands (due to defect induction mode) and G-bands (identified as graphitic mode); EDS mapping showed that Zn elements are highly dispersed in the network of the carbon matrix (shown as E and F in fig. 1); the nitrogen adsorption-desorption isotherms and pore size distribution curves (shown as G in FIG. 1) of SAZn-HPC show typical IV isotherms, with micropores and mesopores being observed in the material, and the Brunauer-Emmett-Teller (BET) specific surface area calculation result is about 1328.8m2(ii) in terms of/g. Based on the larger mass and stronger scattering power of the Zn element, a dark field probe of AC-TEM was used, and this result confirmed the atomic dispersion of the Zn element (shown in H and I in fig. 1).
In summary, the prepared SAZn-HPC has a layered porous structure with typical hard carbon characteristics, abundant structural defects, high BET surface area and enlarged interlayer spacing (0.395nm), and Zn and C elements show uniform distribution characteristics.
Example 2
This example provides a ligand screening system comprising amyloid beta protein (A β) and the porous carbon support SAZn-HPC prepared in example 1, named A β @ SAZn-HPC. The preparation method of the ligand screening system comprises the following steps:
(1) dissolving A beta in hexafluoroisopropanol, performing ultrasonic treatment for 15min, drying in a nitrogen blowing instrument to obtain an A beta film, and storing in a refrigerator at-80 ℃ for later use. The resulting a β films were re-dissolved with DMSO and PBS, and a β was incubated at 37 ℃ for 5 days to form an aggregated form of a β for assay.
(2) A β was diluted with PBS to various concentrations (0.125mg/mL, 0.250mg/mL, 0.500mg/mL), mixed with SAZn-HPC prepared in example 1, washed three times with 4.0mL PBS overnight in a shaker at 4 ℃ and centrifuged at 1000 Xg for 10 minutes to prepare A β @ SAZn-HPC.
Comparative example 1
The SAZn-HPC prepared in example 1 was vortexed in 0.5mM HCl to remove Zn single atoms, and the resulting sample was designated as HPC. The same preparation method as in example 2 was used to prepare the corresponding ligand screening system a β @ HPC, using the HPC obtained as the material.
Load performance, stability and reproducibility testing
The content of A β @ SAZn-HPC in example 2 and the content of A β @ HPC supported by A β @ HPC in comparative example 1 were measured using the BCA kit, and the results are shown in A of FIG. 2. In the presence of a certain amount of a β, the loading capacity of SAZn-HPC and HPC increases with increasing a β concentration until the final loading capacity is reached. However, at the same A β concentration, the maximum adsorption capacity of SAZn-HPC for A β is significantly higher than that of HPC. The results indicate that SAZn-HPC has better loading capacity and higher adsorption capacity than HPC.
And B in FIG. 2 is the stability results of A β @ SAZn-HPC and A β @ HPC, the amount of SAZn-HPC immobilized protein decreased rapidly in the first two days, slowly in the third to sixth days, and the amount of HPC immobilized protein decreased continuously in six days after storage at 4 ℃. This result indicates that a β can be more effectively immobilized on SAZn-HPC by the interaction between atomically dispersed Zn sites and amino acid residues of a β.
In addition, the reproducibility between batches was evaluated by fixing the content of a β protein, and the test results are shown in table 1. The results show that both SAZn-HPC and HPC have good reproducibility with RSD values less than 2.0%.
TABLE 1 reproducibility test results
RSD(％) Intra-day(n＝3) Inter-day(n＝3)
SAZn-HPC 1.87 1.89
HPC 1.7 1.47
Example 3
This example provides a method for screening for potential inhibitors of a β from turmeric extract comprising the steps of:
(1) pulverizing Curcuma rhizome, extracting with 75% (v/v) ethanol under reflux for 2 hr, evaporating the filtrate under reduced pressure in rotary evaporator, and storing at 4 deg.C;
(2) vortex mixing the a β @ SAZn-HPC prepared in example 2 with the turmeric extract of step (1), removing the supernatant, incubating at 37 ℃ for 30min, washing 3 times with PBS, vortex mixing with 70% methanol, and subjecting the resulting solution to mass spectrometric detection analysis; control experiments were also performed using PBS instead of turmeric extract.
The condition parameters of mass spectrum detection comprise:
mobile phase composition:
mobile phase A: 0.1% (v/v) aqueous formic acid; mobile phase B: acetonitrile;
gradient elution conditions:
0-25 min: 25% -70% of mobile phase B, and the balance of mobile phase A;
25-40 min: 70-95% of mobile phase B, and the balance of mobile phase A;
40-50 min: 95-25% of mobile phase B and the balance of mobile phase A.
The collection time was 55min, and the column chromatography was Agilent ZORBAX SB-C18 (2.1X 100mm, 3.5 μm); the flow rate of the mobile phase is 300 muL/min, the column temperature is 35 ℃, and the sample injection amount is 10 muL. The ion source voltage was set to 4.0kV and detection was performed in the positive detection mode. Nitrogen as the sheath gas and helium as the auxiliary gas, at flow rates of 10CFM and 0, respectively. The capillary temperature was 275 ℃, measured in the range of m/z of 100-.
The turmeric extract was analyzed by the above method, 64 compounds were determined according to the exact mass number and fragment number, as shown in fig. 2C to I, and 5 compounds having strong affinity to Α β @ SAZn-HPC, including curcumenol (56), curcumenol (33), demethoxycurcumin (38), bisdemethoxycurcumin (36) and curcumin (42), were selected according to the peak area, and curcumenol (37), which is a less affinity compound, was selected as a negative control.
Biological verification: a.beta.was diluted with PBS and incubated at 37 ℃ for 7 days. The sample solution was diluted in a solution of thioflavin-T (ThT) to a final concentration of 20. mu.M. 190. mu.L of ThT solution and 10. mu. L A. beta. were mixed into a 96-well plate and incubated for 1 h. Fluorescence measurements were performed using a microtiter plate reader at 450 and 490nm excitation. ThT can be used to further monitor and confirm inhibition of a β fibril formation in vitro. Fluorescence intensity indicated that the concentration of a β fibrils increased after treatment with dimethyl sulfoxide (DMSO) and curcumol, indicating no effect in resisting a β fibril formation (shown in fig. 3 a). The fluorescence intensity is proportional to the formation of a β fibrils. The stronger the fluorescence, the more a β fibrils are formed. The experimental result shows that the anti-A beta fibril formation function is curcumin > bisdemethoxycurcumin > baicalein > demethoxycurcumin > curcumenone > curcumenodiene > curcumenol alcohol in sequence.
EZ-Link NHS-LC-LC-biotin was dissolved in DMSO to a concentration of 10 mM. A β was biotinylated with biotin reagents in a molar ratio of 1:0.5 and incubated at room temperature for 30min before being added to a 96-well plate and the biotinylation was determined by loading the mixture onto a Super Streptavidin (SSA) volumetric pipette and detecting by Forte BIO Octet Red instrument. The screened compounds were dissolved in DMSO, diluted with PBS to the appropriate concentration to a final volume of 200. mu.L/well and an equivalent amount of D MSO was added to the control wells. Consists of a repeating cycle of four main steps: wash (300s), baseline (120s), bind (120s) and dissociate (120 s). Results including association and dissociation patterns and kinetic constants were analyzed using Forte. BIO data analysis software. The results showed that the KD values of curcumin, bisdemethoxyucucumin, baicalein, demethoxyucumin, furadodine, curcumenol and curcumol were 2.52, 4.44, 13.1, 17.5, 32.9, 44.6 and 232 μ M, which respectively showed direct and reversible interactions with a β (shown in fig. 3 as B to H).
According to the invention, SAZn-HPC is adopted to screen out active ingredients for inhibiting A beta aggregation in the curcuma extract, and Tht and biolayer interferometry are adopted to verify, so that the accuracy of the established ligand fishing system is ensured.
The embodiments of the present application have been described in detail with reference to the drawings, but the present application is not limited to the embodiments, and various changes can be made within the knowledge of those skilled in the art without departing from the gist of the present application. Furthermore, the embodiments and features of the embodiments of the present application may be combined with each other without conflict.

Claims (10)

1. A method for preparing a porous carbon support, comprising the steps of:
(1) dissolving Zn salt and polyacrylate in water to obtain a mixture;
(2) and freeze-drying the mixture, and then carbonizing the mixture in inert gas to obtain the porous carbon carrier.
2. The method according to claim 1, wherein the Zn salt and the polyacrylate salt are dissolved in water under ultrasonic agitation in step (1).
3. A porous carbon support, characterized by being hierarchical porous carbon having monoatomic Zn sites, which is produced by the production method according to any one of claims 1 to 2.
4. Use of the porous carbon support of claim 3 in ligand fishing.
5. Use of a porous carbon support according to claim 3 in the screening of natural plant active ingredients.
6. A ligand screening system comprising a biological macromolecule and the porous carbon support of claim 3, said biological macromolecule being immobilized on said porous carbon support.
7. The ligand screening system of claim 6, wherein the biomacromolecule is a β.
8. A method for screening potential inhibitors of A beta from turmeric extract, comprising the steps of:
s1, diluting A beta with a buffer solution, mixing the A beta with the porous carbon carrier of claim 3, and oscillating and washing to prepare A beta @ SAZn-HPC;
s2, mixing the Abeta @ SAZn-HPC and the turmeric extract in a vortex manner, removing supernatant, incubating, washing, mixing with methanol in a vortex manner, and performing mass spectrum detection on the obtained solution;
the condition parameters of the mass spectrum detection comprise:
mobile phase composition:
mobile phase A: 0.1% aqueous formic acid; mobile phase B: acetonitrile;
gradient elution conditions:
0-25 min: 25% -70% of mobile phase B, and the balance of mobile phase A;
25-40 min: 70-95% of mobile phase B, and the balance of mobile phase A;
40-50 min: 95-25% of mobile phase B and the balance of mobile phase A.
9. The method of claim 8, wherein the turmeric extract of step S2 is prepared by: pulverizing Curcuma rhizome, adding 75% ethanol, reflux-extracting, and evaporating the filtrate under reduced pressure to remove solvent by rotary evaporator to obtain Curcuma rhizome extract.
10. The method according to claim 8, wherein the incubation in step S2 is performed at a temperature of 35-37 ℃ for a period of 25-35 min.
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