CN108948230B - Water-soluble beta-cyclodextrin amidated derivative, synthetic method and application in oxidation resistance and antibiosis - Google Patents
Water-soluble beta-cyclodextrin amidated derivative, synthetic method and application in oxidation resistance and antibiosis Download PDFInfo
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Abstract
The invention discloses a water-soluble beta-cyclodextrin amidated derivative, a synthetic method and application thereof in oxidation resistance and antibiosis, wherein the structural formula of the derivative is
In the formula R1、R2、R3、R4、R5Each independently represents H, OH, C1～C2Alkoxy radical, C1～C3Any one of alkyl, at least one of which is OH;
represents 6-dehydroxy beta-cyclodextrin. The cinnamic acid derivative is prepared from cinnamic acid derivatives, beta-cyclodextrin, p-toluenesulfonyl chloride, ethylenediamine and the like serving as raw materials through sulfonylation reaction, amination reaction and amidation reaction. The synthetic method has the advantages of cheap and easily-obtained raw materials, simple operation and mild conditions, and the synthesized beta-cyclodextrin amidated derivative has high purity and good water solubility. In addition, the synthesized beta-cyclodextrin amidation derivative has excellent antioxidant and antibacterial performance without inclusion of functional guest molecules.
Description
Technical Field
The invention belongs to the technical field of organic synthesis and fine chemical engineering, and particularly relates to a water-soluble beta-cyclodextrin amidated derivative, a synthetic method of the compound and application of the compound in oxidation resistance and antibiosis.
Background
Cyclodextrins (CDs) are primarily degradation products of starch by the action of cyclodextrin glycosyltransferases. Cyclodextrin is a typical renewable, nontoxic and biodegradable resource, has special structures and properties of 'inner cavity hydrophobic and outer wall hydrophilic', and becomes an excellent structural unit for constructing various functional materials, wherein beta-cyclodextrin is cheap and easy to obtain and is most widely applied.
The cyclodextrin has extremely low solubility in water, so that the identification of a drug guest molecule is hindered, and the application of the cyclodextrin in the field of pharmacology is limited, so that the synthesis of beta-cyclodextrin derivatives is more and more favored by people. The solubility of the beta-cyclodextrin derivative in water is remarkably enhanced, so that the size of the cavity can be increased, and the enveloping effect of the beta-cyclodextrin derivative and the guest drug is enhanced.
There are two main ways to modify cyclodextrin at home and abroad: chemical methods and enzyme engineering methods. The chemical method is a main modification method, in which alcoholic hydroxyl groups on the surfaces of cyclodextrin molecules undergo various chemical reactions, such as esterification, oxidation, etherification, crosslinking and the like, so that the molecular surfaces of cyclodextrin molecules are connected with new functional groups to obtain cyclodextrin derivatives with different properties. The cyclodextrin derivative obtained by modifying natural cyclodextrin has different characteristics from parent cyclodextrin, and particularly the derivative obtained by substituting 6-position hydroxyl of cyclodextrin has stronger binding capacity with guest molecules. The enzyme engineering method is a method for preparing branched cyclodextrin, namely, monosaccharide or oligosaccharide is combined on cyclodextrin under the action of cyclodextrin glucosyltransferase or pullulanase to form the required branched cyclodextrin. The cyclodextrin derivative has low cost and good intermiscibility, expands the application range, develops new application, and can be well applied to various aspects of pharmacy, analysis, separation, catalysis and the like. Therefore, it is necessary to study cyclodextrin derivatives.
Disclosure of Invention
The invention aims to provide a water-soluble beta-cyclodextrin amidated derivative with antioxidant and antibacterial properties, and a synthetic method and application of the compound.
The structural formula of the water-soluble beta-cyclodextrin amidation derivative for solving the technical problems is shown as follows:
in the formula R1、R2、R3、R4、R5Each independently represents H, OH, C1～C2Alkoxy radical, C1～C3Any one of alkyl, at least one of which is OH;
represents 6-dehydroxy beta-cyclodextrin.
The synthetic route and the specific synthetic method of the water-soluble beta-cyclodextrin amidation derivative are as follows:
1. synthesis of beta-cyclodextrin sulfonylated derivatives
Using sodium hydroxide aqueous solution as a solvent, reacting beta-cyclodextrin and p-toluenesulfonyl chloride for 3 hours at room temperature according to the molar ratio of 0.6:1, then carrying out suction filtration, adjusting the pH of filtrate to 2 by using hydrochloric acid, and separating and purifying a product to obtain the beta-cyclodextrin sulfonylation derivative shown in the formula I.
2. Synthesis of beta-cyclodextrin aminated derivatives
And (2) taking absolute ethyl alcohol as a solvent, reacting the beta-cyclodextrin sulfonylation derivative with ethylenediamine according to the molar ratio of 1: 290-300 at 80 ℃ for 4 hours, and separating and purifying a product to obtain the beta-cyclodextrin amination derivative shown in the formula II.
3. Synthesis of water-soluble beta-cyclodextrin amidated derivatives
Activating the cinnamic acid derivative shown in the formula III by using N, N-dimethylformamide as a solvent and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 1-hydroxybenzotriazole as condensing agents, adding a beta-cyclodextrin amination derivative, reacting at room temperature, and separating and purifying a product after the reaction is finished to obtain the beta-cyclodextrin amidation derivative.
In the step 3, the molar ratio of the cinnamic acid derivative to the 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, the 1-hydroxybenzotriazole and the beta-cyclodextrin amination derivative is 1: 0.9-1: 0.6-1.
The water-soluble beta-cyclodextrin amidated derivative is applied to oxidation resistance as an antioxidant.
The water-soluble beta-cyclodextrin amidated derivative of the present invention is used as antibacterial agent in antibacterial application.
Compared with the prior art, the invention has the following beneficial effects:
1. the synthetic method of the water-soluble beta-cyclodextrin amidation derivative has the advantages of cheap and easily-obtained raw materials, simple operation and mild conditions, and the synthesized beta-cyclodextrin amidation derivative has high purity.
2. The water solubility of the beta-cyclodextrin amidated derivative is quite good and is more than 600mg/mL, while the water solubility of a beta-cyclodextrin parent body is only 18.5 mg/mL.
3. The cinnamic acid derivative modified beta-cyclodextrin is adopted to improve the water solubility of a cyclodextrin matrix, and simultaneously, the multifunctional effect can be realized, and the beta-cyclodextrin amidated derivative body has good oxidation resistance and antibacterial performance. However, the general cyclodextrin derivative host requires inclusion of a functional guest molecule to have additional functions. The beta-cyclodextrin amidated derivative of the present invention has wide application range, new use and other application.
Drawings
FIG. 1 is a mass spectrum of a β -cyclodextrin sulfonylated derivative prepared in example 1.
FIG. 2 is a NMR chart of a sulfonylated derivative of β -cyclodextrin prepared in example 1.
FIG. 3 is a mass spectrum of the β -cyclodextrin aminated derivative prepared in example 1.
FIG. 4 is a NMR chart of β -cyclodextrin aminated derivative prepared in example 1.
FIG. 5 is a mass spectrum of β -cyclodextrin amidated derivative prepared in example 1.
FIG. 6 is a NMR spectrum of β -cyclodextrin amidated derivative prepared in example 1.
FIG. 7 is a mass spectrum of β -cyclodextrin amidated derivative prepared in example 2.
FIG. 8 is a NMR spectrum of β -cyclodextrin amidated derivative prepared in example 2.
FIG. 9 is a mass spectrum of β -cyclodextrin amidated derivative prepared in example 3.
FIG. 10 is a NMR spectrum of β -cyclodextrin amidated derivative prepared in example 3.
FIG. 11 is an absorbance curve of different concentrations of β -cyclodextrin amidated derivatives prepared in example 1 with the same concentration of DPPH added.
FIG. 12 is an absorbance curve of different concentrations of β -cyclodextrin amidated derivatives prepared in example 2 with the same concentration of DPPH added.
FIG. 13 is an absorbance curve of different concentrations of β -cyclodextrin amidated derivatives prepared in example 3 with the same concentration of DPPH added.
FIG. 14 is an absorbance curve of β -cyclodextrin amidated derivatives prepared in examples 1 to 3 with the same concentration of DPPH added thereto.
FIG. 15 is a graph showing the bactericidal activity against Staphylococcus aureus of the β -cyclodextrin amidated derivatives prepared in examples 1 to 3.
Detailed Description
The invention will be further described in detail with reference to the following figures and examples, but the scope of the invention is not limited to these examples.
Example 1
Synthesizing beta-cyclodextrin amidated derivative with the structural formula
1. Synthesis of beta-cyclodextrin sulfonylated derivatives
Dissolving 17.22g (0.015mol) of beta-cyclodextrin in 200mL of 0.25mol/L aqueous sodium hydroxide solution, dropwise adding 16.5mL of acetonitrile solution in which 4.35g (0.023mol) of p-toluenesulfonyl chloride is dissolved into the solution, reacting at room temperature for 3 hours, carrying out suction filtration, adjusting the pH of filtrate to 2 by using hydrochloric acid, standing overnight at 4 ℃, separating out a large amount of white solid, carrying out suction filtration, recrystallizing by using deionized water, and carrying out vacuum drying at 40 ℃ for 5 hours to obtain a white powdery product beta-CD-6-OTs.
The obtained beta-CD-6-OTs are characterized by a mass spectrometer and a nuclear magnetic resonance spectrometer, and the results are shown in figures 1 and 2. The relative molecular weight of the compound is 1310.3606, as can be seen from figure 1, the molecular ion peak of the mass spectrum is 1311.3664, and the corresponding ion peak is M+(ii) a In fig. 2, each hydrogen in the compound can be in one-to-one correspondence with the chemical shift and integral on the hydrogen spectrum, and the specific data are as follows:1H NMR(400MHz,DMSO)::2.41(s,3H,CH3),3.24-3.80(m,42H,CH)，4.47-4.55(m，6H,OH),4.80-4.84(m,7H,CH),5.62-5.83(m,14H,OH),7.42(d,2H,PhH),7.74(d,2H,PhH).
2. synthesis of beta-cyclodextrin aminated derivatives
3g (0.0023mol) of beta-CD-6-OTs are added into an ethanol solution dissolved with 45mL (0.675mol) of ethylenediamine, stirred and dissolved, heated to 80 ℃, reacted for 4 hours, and decompressed and distilled to remove the solvent. The solid obtained was dissolved in a small amount of hot water, washed with 300mL of acetone and filtered with suction. And (3) repeating the purification for 3 times, and performing vacuum drying for 5 hours at the temperature of 40 ℃ to obtain a white powdery product beta-CD-6-EDA.
The structure of the obtained beta-CD-6-EDA is characterized by a mass spectrometer and a nuclear magnetic resonance spectrometer, and the results are shown in figures 3 and 4. The compound has a relative molecular weight of 1176.4279, as can be seen from FIG. 3The molecular ion peak of the mass spectrum is 1177.4312, and the corresponding ion peak is M+(ii) a In fig. 4, each hydrogen in the compound can be in one-to-one correspondence with the chemical shift and integral on the hydrogen spectrum, and the specific data are as follows:1H NMR(400MHz,DMSO)::2.09-2.01(m,1H,NH),2.32-2.34(m,2H,CH2),2.43-2.45(m,2H,CH2),3.24-3.80(m,42H,CH)，4.47-4.55(m,6H,OH),4.80-4.84(m,7H,CH),5.62-5.83(m,14H,OH),8.20(t,2H,NH2).
3. synthesis of beta-cyclodextrin amidated derivatives
0.29g (0.15mmol) of Ferulic Acid (FA), 0.25g (0.13mmol) of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 0.176g (0.13mmol) of 1-hydroxybenzotriazole were added to N, N-dimethylformamide in which 865. mu.L (0.68mmol) of triethylamine was dissolved, and the mixture was reacted for 2 hours under ice-bath conditions. After the reaction, 10mL of an anhydrous N, N-dimethylformamide solution containing 1.35g (0.10mmol) of β -CD-6-EDA dissolved therein was slowly added, reacted at room temperature for 5 days, washed with acetone, and separated by column chromatography (eluent was a mixture of N-propanol: ethanol: water: aqueous ammonia: 12:2:4: 1) to obtain β -cyclodextrin amidated derivative, which was designated as β -CD-6-FA, with a yield of 56.58%.
The structure of the obtained beta-CD-6-FA is characterized by a mass spectrometer and a nuclear magnetic resonance spectrometer, and the results are shown in FIGS. 5 and 6. The relative molecular weight of the compound is 1352.4753, as can be seen from FIG. 5, the molecular ion peak of the mass spectrum is 1353.4829, and the corresponding ion peak is M+(ii) a In fig. 6, each hydrogen in the compound can be in one-to-one correspondence with the chemical shift and integral on the hydrogen spectrum, and the specific data are as follows:1H NMR(400MHz,DMSO)::2.09-2.01(m,1H,NH),2.32-2.34(m,2H,CH2),2.43-2.45(m,2H,CH2),3.24-3.72(m,42H,CH)，3.80(s,3H,CH3)，4.47-4.55(m，6H,OH),4.80-4.84(m,7H,CH),5.62-5.83(m,14H,OH),6.46(d,1H,CH),6.81(d,1H,PhH),7.00(d,1H,PhH),7.13(s,1H,PhH),7.31(d,1H,CH),7.93(s,1H,OH),8.20(t,H,NH).
example 2
Synthesizing beta-cyclodextrin amidated derivative with the structural formula
In this example, the ferulic acid of example 1 was replaced by equimolar coumaric acid (p-CA), and the procedure was otherwise the same as in example 1, to give a yellow solid amidated derivative of β -cyclodextrin, designated as β -CD-6-p-CA, in 50.71% yield.
The structure of the obtained beta-CD-6-p-CA is characterized by a mass spectrometer and a nuclear magnetic resonance spectrometer, and the results are shown in figures 7 and 8. The relative molecular weight of the compound is 1322.4720, and as can be seen from FIG. 7, the molecular ion peak of the mass spectrum is 1323.4710, and the corresponding ion peak is M+(ii) a In fig. 8, each hydrogen in the compound can be in one-to-one correspondence with the chemical shift and integral on the hydrogen spectrum, and the specific data are as follows:1H NMR(400MHz,DMSO)::2.09-2.01(m,1H,NH),2.32-2.34(m,2H,CH2),2.43-2.45(m,2H,CH2),3.24-3.80(m,42H,CH)，4.47-4.55(m，6H,OH),4.80-4.84(m,7H,CH),5.62-5.83(m,14H,OH),6.44(d,1H,CH),6.78(d,2H,PhH),7.30(d,1H,CH),7.38(d,2H,PhH),7.93(s,1H,OH),8.18(t,1H,NH).
example 3
Synthesizing beta-cyclodextrin amidated derivative with the structural formula
In this example, the ferulic acid of example 1 was replaced by equimolar Caffeic Acid (CA), and the procedure was otherwise the same as in example 1, to give a yellow solid β -cyclodextrin amidated derivative, designated β -CD-6-CA, in 60.12% yield.
The structure of the obtained beta-CD-6-CA is characterized by a mass spectrometer and a nuclear magnetic resonance spectrometer, and the results are shown in figures 9 and 10. The relative molecular weight of the compound is 1338.4669, and as can be seen from FIG. 9, the molecular ion peak of the mass spectrum is 1339.4659, and the corresponding ion peak is M+(ii) a In fig. 10, each hydrogen in the compound can be in one-to-one correspondence with the chemical shift and integral on the hydrogen spectrum, and the specific data are as follows:1H NMR(400MHz,DMSO)::2.09-2.01(m,1H,NH),2.32-2.34(m,2H,CH2),2.43-2.45(m,2H,CH2),3.24-3.80(m,42H,CH)，4.47-4.55(m，6H,OH),4.80-4.84(m,7H,CH),5.62-5.83(m,14H,OH),6.30-6.35(d,1H,CH),6.72-6.74(d,1H,PhH),6.82-6.86(d,1H,PhH),6.94(s,1H,PhH),7.20-7.23(d,1H,CH),7.94(s,1H,OH),7.98(s,1H,OH),8.20(t,1H,NH).
example 4
Application of beta-cyclodextrin amidated derivative prepared in examples 1 to 3 as antioxidant
Taking 7.20mg of DPPH, using ethanol to fix the DPPH in a 100mL volumetric flask, after ultrasonic dissolution, respectively transferring 5mL of DPPH to dissolve in a colorimetric tube, then respectively adding 0, 0.2, 0.4, 0.6, 0.8 and 1mL of 1mmol/L beta-cyclodextrin amidated derivative aqueous solution, and using a mixed solution with the volume ratio of ethanol and water being 1:1 to fix the volume to 6mL, wherein the concentration of the beta-cyclodextrin amidated derivative in the system is 0, 33, 66, 99, 132 and 165 mu mol/L from small to large according to the added volume. Standing for 30 minutes in dark place, and testing UV-Vis, wherein the result is shown in figures 11-14.
As can be seen from FIGS. 11 to 13, the absorbance of DPPH at 517nm gradually decreases with the increase of the concentration of the β -cyclodextrin amidated derivative, and the change of the absorbance at 517nm shows a better linear relationship. As can be seen from FIG. 14, the DPPH radical clearance rate of 33. mu. mol/L beta-CD-6-FA is 26.38%, the DPPH radical clearance rate of 33. mu. mol/L beta-CD-6-p-CA is 8.96%, and the DPPH radical clearance rate of 33. mu. mol/L beta-CD-6-CA is 99.91%, indicating that the antioxidant property of beta-CD-6-CA is the best at the same concentration. And when the concentration of the beta-CD-6-FA is 198 mu mol/L and the concentration of the beta-CD-6-p-CA is 330 mu mol/L, the highest clearance rate to DPPH free radicals can reach more than 99.00 percent.
Example 5
Application of beta-cyclodextrin amidated derivative prepared in examples 1 to 3 as antibacterial agent
Taking 1mL of staphylococcus aureus bacterial suspension, centrifuging for 5 minutes, washing out the culture medium nutrient solution by using a PBS buffer solution, and repeating the process for 3 times; the centrifuged cell suspension was diluted to a concentration of 1X 10 with PBS buffer6CFU/mL; 1mL of amidated derivative containing 5.12mmol/L of beta-cyclodextrin, 1X 106The mixture of CFU/mL Staphylococcus aureus (S.aureus, positive bacteria) was incubated at 37 ℃ for 3 hours, and then gradually diluted with PBS buffer to1×104CFU/mL; 100 μ L of the bacterial suspension was inoculated onto LB agar plates and spread evenly, incubated at 37 ℃ for 24 hours, and the number of colonies was recorded. During this experiment, each sample was assayed in triplicate and the results are shown in FIG. 15.
Bactericidal rate (CFU)Blank space–CFUSample (I))/(CFUBlank space)×100％
As can be seen from FIG. 15, the sterilization rate of beta-CD-6-FA on Staphylococcus aureus can reach 28.70%, the sterilization rate of beta-CD-6-p-CA on Staphylococcus aureus can reach 76.86%, and the sterilization rate of beta-CD-6-CA on Staphylococcus aureus can reach 84.14%, which indicates that the beta-cyclodextrin amidation derivative of the present invention has good antibacterial performance.
Claims (4)
1. A water-soluble beta-cyclodextrin amidated derivative is characterized in that the structural formula of the compound is as follows:
in the formula
Represents 6-dehydroxy beta-cyclodextrin.
2. A method for synthesizing the water-soluble β -cyclodextrin amidated derivative of claim 1, wherein:
(1) synthesis of beta-cyclodextrin sulfonylated derivatives
Taking a sodium hydroxide aqueous solution as a solvent, reacting beta-cyclodextrin and p-toluenesulfonyl chloride for 3 hours at room temperature according to the molar ratio of 0.6:1, then carrying out suction filtration, adjusting the pH of the filtrate to 2 by using hydrochloric acid, and separating and purifying a product to obtain a beta-cyclodextrin sulfonylated derivative shown in a formula I;
(2) synthesis of beta-cyclodextrin aminated derivatives
Reacting beta-cyclodextrin sulfonylation derivatives with ethylenediamine according to a molar ratio of 1: 290-300 at 80 ℃ for 4 hours by using absolute ethyl alcohol as a solvent, and separating and purifying the product to obtain beta-cyclodextrin amination derivatives shown in a formula II;
(3) synthesis of water-soluble beta-cyclodextrin amidated derivatives
Activating a cinnamic acid derivative shown in a formula III by using N, N-dimethylformamide as a solvent and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride and 1-hydroxybenzotriazole as condensing agents, adding a beta-cyclodextrin amination derivative, reacting at room temperature, and separating and purifying a product after the reaction is finished to obtain a beta-cyclodextrin amidation derivative;
the molar ratio of the cinnamic acid derivative to the 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole and beta-cyclodextrin amination derivative is 1: 0.9-1: 0.6-1.
3. Use of the water-soluble β -cyclodextrin amidated derivative of claim 1 to prepare an antioxidant.
4. Use of the water-soluble β -cyclodextrin amidated derivative of claim 1 to prepare an antibacterial agent.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06199733A (en) * | 1993-01-04 | 1994-07-19 | Sansho Seiyaku Co Ltd | New clathrate compound and use thereof |
| JPH07313129A (en) * | 1994-05-23 | 1995-12-05 | Ensuiko Sugar Refining Co Ltd | Freshness preservative for food |
| CN103524751A (en) * | 2013-09-11 | 2014-01-22 | 江南大学 | Preparation method of double-sensitivity cyclodextrin supermolecule aggregate |
| CN106902356A (en) * | 2015-12-18 | 2017-06-30 | 南京理工大学 | A kind of double-response multi-medicament Transmission system based on cyclodextrin |
| CN109867734A (en) * | 2017-12-05 | 2019-06-11 | 天津工业大学 | The cyclodextrine derivatives and preparation method thereof of a kind of caffeic acid modification |
| CN109867733A (en) * | 2017-12-05 | 2019-06-11 | 天津工业大学 | The cyclodextrine derivatives and preparation method thereof of a kind of ferulic acid modification |
-
2018
- 2018-08-01 CN CN201810865494.8A patent/CN108948230B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06199733A (en) * | 1993-01-04 | 1994-07-19 | Sansho Seiyaku Co Ltd | New clathrate compound and use thereof |
| JPH07313129A (en) * | 1994-05-23 | 1995-12-05 | Ensuiko Sugar Refining Co Ltd | Freshness preservative for food |
| CN103524751A (en) * | 2013-09-11 | 2014-01-22 | 江南大学 | Preparation method of double-sensitivity cyclodextrin supermolecule aggregate |
| CN106902356A (en) * | 2015-12-18 | 2017-06-30 | 南京理工大学 | A kind of double-response multi-medicament Transmission system based on cyclodextrin |
| CN109867734A (en) * | 2017-12-05 | 2019-06-11 | 天津工业大学 | The cyclodextrine derivatives and preparation method thereof of a kind of caffeic acid modification |
| CN109867733A (en) * | 2017-12-05 | 2019-06-11 | 天津工业大学 | The cyclodextrine derivatives and preparation method thereof of a kind of ferulic acid modification |
Non-Patent Citations (5)
| Title |
|---|
| "A Cyclodextrin-Based Photoresponsive Molecular Gate that Functions Independently of Either Solvent or Potentially Competitive Guests";Ka-Heng Loh等;《Chem. Asian J.》;20150828;第10卷;第2328-2332页 * |
| "Formation of Supramolecular Polymers Constructed by Cyclodextrins with Cinnamamide";MASAHIKO MIYAUCHI等;《Journal of Inclusion Phenomena and Macrocyclic Chemistry》;20041031;第50卷;第57-62页 * |
| "Molecular Binding Ability and Selectivity of Natural α-, β-, γ-Cyclodextrins and Oligo(ethylenediamino) Modified β-Cyclodextrins with Chinese Traditional Medicines";AI-DI QI等;《Journal of Inclusion Phenomena and Macrocyclic Chemistry》;20030228;第45卷;第69–72页 * |
| "Synthesis and molecular recoginition properties of a novel chemical modified β-cyclodextrin";Xie Hongzhi等;《PROGRESS IN NATURAL SCIENCE》;20000110;第10卷(第1期);第27-32页 * |
| "基于环糊精主客体包合作用构筑的聚合物";王丹等;《化学通报》;20130918;第76卷(第9期);第806-810页 * |
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