CN105732892A - Taxol-10-deacetylbaccatine III bi-molecular metal-coordination imprinted material and preparation method and application thereof - Google Patents
Taxol-10-deacetylbaccatine III bi-molecular metal-coordination imprinted material and preparation method and application thereof Download PDFInfo
- Publication number
- CN105732892A CN105732892A CN201610244124.3A CN201610244124A CN105732892A CN 105732892 A CN105732892 A CN 105732892A CN 201610244124 A CN201610244124 A CN 201610244124A CN 105732892 A CN105732892 A CN 105732892A
- Authority
- CN
- China
- Prior art keywords
- paclitaxel
- baccatin iii
- taxol
- deacetylation baccatin
- polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/268—Polymers created by use of a template, e.g. molecularly imprinted polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/26—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a solid phase from a macromolecular composition or article, e.g. leaching out
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/44—Materials comprising a mixture of organic materials
- B01J2220/445—Materials comprising a mixture of organic materials comprising a mixture of polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/48—Sorbents characterised by the starting material used for their preparation
- B01J2220/4806—Sorbents characterised by the starting material used for their preparation the starting material being of inorganic character
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/40—Aspects relating to the composition of sorbent or filter aid materials
- B01J2220/48—Sorbents characterised by the starting material used for their preparation
- B01J2220/4812—Sorbents characterised by the starting material used for their preparation the starting material being of organic character
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2339/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Derivatives of such polymers
- C08J2339/04—Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Analytical Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
Abstract
The invention discloses a taxol-10-deacetylbaccatine III bi-molecular metal-coordination imprinted material and a preparation method and application thereof.With a Co2+ -taxol-10- deacetylbaccatine III coordination compound being a template molecule, the amount-of-substance ratio of taxol-10-deacetylbaccatine III is controlled, the usage amount ratio of metal ions, ligand, functional monomers and a cross-linking agent in a pre-reaction mixed liquor is adjusted, and therefore bi-template-molecule imprinted polymer is successfully prepared.The obtained imprinted polymer has rapid adsorption kinetics for taxol and 10-deacetylbaccatine III; with the molecule imprinted polymer being an adsorption medium, the two compounds of taxol and 10-deacetylbaccatine III can be separated well from taxus chinensis rough extract through solid-phase extraction, and the total recovery rates are 90.38% and 93.60% respectively.The new material and the new application method are provided for gathering and separating of a natural product and trace active compounds in Chinese herbs.
Description
Technical field
The present invention relates to a kind of paclitaxel-10-deacetylation baccatin III bimolecular metal-complexing imprinted material and preparation method thereof and purposes.
Background technology
Molecularly imprinted polymer is a kind of novel high polymer material that specific target molecules has high special Sexual behavior mode prepared by molecular imprinting.It has structure effect precordainment, specific recognition ability and extensive this three big feature of practicality, has therefore obtained high development in recent decades.Simultaneously, owing to it is to use chemical method synthetic, so having strong alkali-acid resistance, corrosion-resistant, anti-adverse environment, easily storage, the repeat usage advantage not available for natural molecule identification system such as high, cheap, it is widely used in environment, food, biological with various fields such as pharmaceutical engineerings.
Ramulus et folium taxi cuspidatae has another name called yew, have the title of " plant gold ".It has good curative effect in removing food stagnancy, diuresis, antiinflammatory and the aspect such as stimulate the menstrual flow.It has been investigated that, active component main in Ramulus et folium taxi cuspidatae is Taxane diterpenes compounds, and its main representative compound has paclitaxel and 10-deacetylation baccatin III.Wherein, paclitaxel is described as " Star of Anticancer today ", and it is respectively provided with good curative effect to ovarian cancer, uterus carcinoma and breast carcinoma.And 10-deacetylation baccatin III is the intermediate of paclitaxel, and the content in Chinese yew genus plants is the highest, therefore has technique with it for precursor taxol biosynthesis simple, lower-cost advantage.At present, molecular design method is the main method solving paclitaxel resource scarcity problem.At present, the method extracting paclitaxel and 10-deacetylation baccatin III is numerous, but traditional extracting method is not only wasted time and energy, and is difficult to extract while two kinds of compounds.
Summary of the invention
For overcoming the deficiencies in the prior art; we use molecular imprinting; double-template molecularly imprinted polymer is prepared collectively as template molecule with paclitaxel and 10-deacetylation baccatin III; and investigate imprinted material to slective extraction ability while paclitaxel in Ramulus et folium taxi cuspidatae and 10-deacetylation baccatin III, to realizing being enriched with while various taxanes diterpene-kind compound in plant and separating analysis.Meanwhile, enrichment and separation for the trace active compound in natural product and Chinese herbal medicine provide a kind of new material and methods for using them.
For obtaining paclitaxel-10-deacetylation baccatin III bimolecular metal-complexing imprinted material, the present invention takes following processing step:
Accurately weigh 0.1 mmol template molecule, 0.1 mmol nickel acetate is dissolved in 4.0 mL acetonitriles-dimethyl sulfoxide (3/1, v/v) mixed solution and shakes 10 min, adds the mixed function each 0.4mmol of monomer 4-VP and 2-VP, shake 30 min, make it fully act on function monomer, add the initiator A IBN of 3.0 mmol cross-linking agent EDMA and 30.0 mg, after being sufficiently mixed, proceed to round-bottomed flask, ultrasonic degassing 15 min, is passed through argon 15 min, seals bottle；Round-bottomed flask is put into polyreaction 24 h in 60 DEG C of thermostat water baths；The bulk polymer of gained is pulverized, after crossing 200 mesh sieves, settles 3 times with acetone, each 30 min, discard the turbid liquid in upper strata, to remove particle meticulous in polymer, lower sediment is vacuum dried；The polymer the obtained EDTA solution of 0.1 mmol/L washes away metal ion unnecessary in polymer, then the EDTA solution of residual it is washed with deionized water, again polymer is put in apparatus,Soxhlet's, with methanol-acetic acid (9/1, v/v) eluant solution removes template molecule, and again with methanol is washed for several times, is finally putting into vacuum drying oven and is dried 24 h in 60 DEG C, i.e. obtain imprinted polymer used, be put in drying baker standby.
The present invention is (3/1, v/v) with acetonitrile-dimethyl sulfoxide as mixed solvent, and paclitaxel and 10-deacetylation baccatin III, collectively as template, use metal-chelating method to be prepared for bimolecular coordination imprinted polymer.
Fixed form molecule total amount, metal complex consumption, two kinds of function monomers and dosage of crosslinking agent are respectively 0.1,0.1,0.4 and 3 mmol, change amount ratio respectively 1:1,1:4 and 4:1 of two kinds of template molecules, be prepared for molecularly imprinted polymer MIP1, MIP2 and MIP3.By comparing three kinds of molecularly imprinted polymers adsorbance to two kinds of templates, MIP2, to the most maximum to the adsorbance of two kinds of template compounds, is respectively 52.99 mg/g and 61.80 mg/g to the adsorbance of paclitaxel and 10-DAB.And also have found that while that in polymer, the consumption of paclitaxel is higher than 10-deacetylation baccatin III; but imprinted polymer remains above paclitaxel to the adsorbance of 10-deacetylation baccatin III; this is likely due to, and the relative molecular mass of two kinds of template molecule compounds is big, functional group is many and stereochemical structure is complicated; 10-deacetylation baccatin III is the precursor of paclitaxel simultaneously, and its molecular structure is compared the structure of paclitaxel and lacked a benzene isoerine side chain.
Therefore, 10-deacetylation baccatin III can be shown high selection combination with the imprinted cavity that 10-deacetylation baccatin III is formed as template, and low to the selectivity of paclitaxel；Equally, the imprinted cavity formed with paclitaxel for template also can produce good combination to 10-deacetylation baccatin III molecule.
Based on MIP2, two kinds of template molecules are respectively provided with higher absorption property, therefore select it to carry out absorption below and applied research.Investigate the application molecularly imprinted polymer target compound to adding in target sample solution and carry out Solid-Phase Extraction; HPLC measurement result shows: paclitaxel and 10-deacetylation baccatin III have obtained selective separation and enrichment by molecular engram solid phase extraction technology, and the response rate is respectively 90.38% and 93.60%.This shows MIP-SPE post can realize while paclitaxel in Ramulus et folium taxi cuspidatae sample extracting solution and 10-deacetylation baccatin III to separate, analyze and detect.
Compared with prior art, the beneficial effects of the present invention is:
With Co2+-paclitaxel-10-deacetylation baccatin III coordination compound is template molecule; control the amount ratio of paclitaxel-10-deacetylation baccatin III material for 1:4; in regulation pre-reaction mixed liquor, metal ion, double part, complex function monomer and dosage of crosslinking agent are than the amount ratio for 1:1:8:30(material), it is successfully prepared double-template molecularly imprinted polymer.Gained imprinted polymer is respectively provided with adsorption dynamics adsorption kinetics faster to paclitaxel and 10-deacetylation baccatin III, and equilibrium adsorption capacity reaches 53.02 and 61.90 mg/g respectively.Scatchard analyzes the affine binding site of height showing to exist the binding site of four class different performances, respectively paclitaxel and 10-deacetylation baccatin III in molecularly imprinted polymer matrix and the nonselective linkages site to two kinds of compounds.Isothermal adsorption is carried out Langmuir and Freundlich matching, finds that molecularly imprinted polymer more meets Langmuir adsorption isotherm model of fit to the absorption of two kinds of target molecules.
In the mixture simulated system of different templates ratio, molecularly imprinted polymer Relative distribution coefficient (k=K to 10-deacetylation baccatin IIId (10-DAB)/Kd (PAX)) it is all higher than 1.0, and when in simulation mixture, 10-deacetylation baccatin III concentration is higher, Relative distribution coefficient and separation factor (α=qe (10-DAB)/qe (PAX)) it is up to 5.04 and 3.24 respectively, show that molecularly imprinted polymer is higher to the selection bonding action of 10-deacetylation baccatin III.With molecularly imprinted polymer as adsorbing medium, by Solid-Phase Extraction can from Ramulus et folium taxi cuspidatae extract preferable isolation of taxol and two kinds of compounds of 10-deacetylation baccatin III, overall recovery is respectively 90.38 and 93.60%.
Detailed description of the invention
Hereinafter paclitaxel-10-deacetylation baccatin III bimolecular metal-complexing imprinted material and preparation method thereof are described in detail with purposes.
Accurately weigh 0.1 mmol template molecule, 0.1 mmol nickel acetate is dissolved in 4.0 mL acetonitriles-dimethyl sulfoxide (3/1, v/v) mixed solution and shakes 10 min, adds the mixed function each 0.4mmol of monomer 4-VP and 2-VP, shake 30 min, make it fully act on function monomer, add the initiator A IBN of 3.0 mmol cross-linking agent EDMA and 30.0 mg, after being sufficiently mixed, proceed to round-bottomed flask, ultrasonic degassing 15 min, is passed through argon 15 min, seals bottle；Round-bottomed flask is put into polyreaction 24 h in 60 DEG C of thermostat water baths；The bulk polymer of gained is pulverized, after crossing 200 mesh sieves, settles 3 times with acetone, each 30 min, discard the turbid liquid in upper strata, to remove particle meticulous in polymer, lower sediment is vacuum dried；The polymer the obtained EDTA solution of 0.1 mmol/L washes away metal ion unnecessary in polymer, then the EDTA solution of residual it is washed with deionized water, again polymer is put in apparatus,Soxhlet's, with methanol-acetic acid (9/1, v/v) eluant solution removes template molecule, and again with methanol is washed for several times, is finally putting into vacuum drying oven and is dried 24 h in 60 DEG C, i.e. obtain imprinted polymer used, be put in drying baker standby.
Fixed form molecule total amount, metal complex consumption, two kinds of function monomers and dosage of crosslinking agent are respectively 0.1,0.1,0.4 and 3 mmol, change amount ratio respectively 1:1,1:4 and 4:1 of two kinds of template molecules, be prepared for molecularly imprinted polymer MIP1, MIP2 and MIP3.By comparing three kinds of molecularly imprinted polymers adsorbance to two kinds of templates, MIP2, to the most maximum to the adsorbance of two kinds of template compounds, is respectively 52.99 mg/g and 61.80 mg/g to the adsorbance of paclitaxel and 10-DAB.And also have found that while that in polymer, the consumption of paclitaxel is higher than 10-deacetylation baccatin III; but imprinted polymer remains above paclitaxel to the adsorbance of 10-deacetylation baccatin III; this is likely due to, and the relative molecular mass of two kinds of template molecule compounds is big, functional group is many and stereochemical structure is complicated; 10-deacetylation baccatin III is the precursor of paclitaxel simultaneously, and its molecular structure is compared the structure of paclitaxel and lacked a benzene isoerine side chain.
Based on MIP2, two kinds of template molecules are respectively provided with higher absorption property, therefore select it to carry out absorption below and applied research.Investigate the application molecularly imprinted polymer target compound to adding in target sample solution and carry out Solid-Phase Extraction; HPLC measurement result shows: paclitaxel and 10-deacetylation baccatin III have obtained selective separation and enrichment by molecular engram solid phase extraction technology, and the response rate is respectively 90.38% and 93.60%.This shows MIP-SPE post can realize while paclitaxel in Ramulus et folium taxi cuspidatae sample extracting solution and 10-deacetylation baccatin III to separate, analyze and detect.
The present invention is not made any pro forma restriction by above-described embodiment, any those of ordinary skill in the art, in the case of without departing from technical solution of the present invention scope, technical solution of the present invention is made many possible variations and modification by the technology contents that all may utilize the disclosure above, or is revised as the Equivalent embodiments of equivalent variations.Therefore, every content without departing from technical solution of the present invention, according to the technology of the present invention essence to any simple modification made for any of the above embodiments, equivalent variations and modification, all should fall in the range of technical solution of the present invention is protected.
Claims (4)
1. the preparation method of a paclitaxel-10-deacetylation baccatin III bimolecular metal-complexing imprinted material, it is characterised in that: accurately weigh 0.1
Mmol template molecule, 0.1 mmol nickel acetate is dissolved in 4.0 mL acetonitriles-dimethyl sulfoxide (3/1, v/v) mixed solution and shakes 10 min, adds the mixed function each 0.4mmol of monomer 4-VP and 2-VP, shake 30 min, make it fully act on function monomer, add the initiator A IBN of 3.0 mmol cross-linking agent EDMA and 30.0 mg, after being sufficiently mixed, proceed to round-bottomed flask, ultrasonic degassing 15 min, is passed through argon 15 min, seals bottle；Round-bottomed flask is put into polyreaction 24 h in 60 DEG C of thermostat water baths；The bulk polymer of gained is pulverized, after crossing 200 mesh sieves, settles 3 times with acetone, each 30 min, discard the turbid liquid in upper strata, to remove particle meticulous in polymer, lower sediment is vacuum dried；The polymer the obtained EDTA solution of 0.1 mmol/L washes away metal ion unnecessary in polymer, then the EDTA solution of residual it is washed with deionized water, again polymer is put in apparatus,Soxhlet's, with methanol-acetic acid (9/1, v/v) eluant solution removes template molecule, again with methanol is washed for several times, is finally putting into vacuum drying oven and is dried 24 h in 60 DEG C, to obtain final product.
The preparation method of paclitaxel-10-deacetylation baccatin III bimolecular metal-complexing imprinted material the most according to claim 1, it is characterised in that: in template molecule, paclitaxel and the amount of 10-deacetylation baccatin III material are than respectively 1:1,1:4 and 4:1.
Paclitaxel-10-deacetylation baccatin III bimolecular metal-complexing the imprinted material that method the most according to claim 1 or claim 2 obtains.
4. one kind concurrently separates paclitaxel and the method for 10-deacetylation baccatin III in Ramulus et folium taxi cuspidatae crude extract; it is characterized in that: with paclitaxel-10-deacetylation baccatin III bimolecular metal-complexing imprinted material described in claim 3 as adsorbing medium, by Solid phase extraction separation paclitaxel and two kinds of compounds of 10-deacetylation baccatin III.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610244124.3A CN105732892B (en) | 2016-04-19 | 2016-04-19 | The deacetylation baccatin III bimolecular metal-complexing imprinted material of taxol 10 and its preparation method and purposes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610244124.3A CN105732892B (en) | 2016-04-19 | 2016-04-19 | The deacetylation baccatin III bimolecular metal-complexing imprinted material of taxol 10 and its preparation method and purposes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105732892A true CN105732892A (en) | 2016-07-06 |
| CN105732892B CN105732892B (en) | 2018-02-02 |
Family
ID=56254707
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610244124.3A Active CN105732892B (en) | 2016-04-19 | 2016-04-19 | The deacetylation baccatin III bimolecular metal-complexing imprinted material of taxol 10 and its preparation method and purposes |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105732892B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111704693A (en) * | 2020-07-07 | 2020-09-25 | 重庆迈德凯医药有限公司 | Pseudo template molecularly imprinted polymer and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6452024B1 (en) * | 2000-02-22 | 2002-09-17 | Chaichem Pharmaceuticals International | Process for extraction and purification of paclitaxel from natural sources |
| CN103980524A (en) * | 2014-06-03 | 2014-08-13 | 吉首大学 | Preparation method and application of metal ion medium diosgenin imprinted polymer |
| CN104693353A (en) * | 2015-03-06 | 2015-06-10 | 南开大学 | Preparation method of molecularly imprinted polymer capable of enriching paclitaxel |
| CN105130793A (en) * | 2015-09-14 | 2015-12-09 | 吉首大学 | Method of simultaneously extracting caffeic acid and ferulic acid in cimicifuga rhizome |
-
2016
- 2016-04-19 CN CN201610244124.3A patent/CN105732892B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6452024B1 (en) * | 2000-02-22 | 2002-09-17 | Chaichem Pharmaceuticals International | Process for extraction and purification of paclitaxel from natural sources |
| CN103980524A (en) * | 2014-06-03 | 2014-08-13 | 吉首大学 | Preparation method and application of metal ion medium diosgenin imprinted polymer |
| CN104693353A (en) * | 2015-03-06 | 2015-06-10 | 南开大学 | Preparation method of molecularly imprinted polymer capable of enriching paclitaxel |
| CN105130793A (en) * | 2015-09-14 | 2015-12-09 | 吉首大学 | Method of simultaneously extracting caffeic acid and ferulic acid in cimicifuga rhizome |
Non-Patent Citations (9)
| Title |
|---|
| JIE-PING FAN，等: "Preparation and characterization of molecular imprinted polymer functionalized with core/shell magnetic particles (Fe3O4@SiO2@MIP) for the simultaneous recognition and enrichment of four taxoids in Taxus x media", 《CHEMICAL ENGINEERING JOURNAL》 * |
| 吴殿星，等: "《植物组织培养》", 31 August 2004, 上海交通大学出版社 * |
| 徐任生，等: "《天然产物化学》", 30 September 2004, 科学出版社 * |
| 方大树，等: "紫杉烷二萜类化合物10-DABⅢ的分离纯化", 《中国药房》 * |
| 曾戎等: "《生物医用仿生高分子材料》", 31 October 2010, 华南理工大学出版社 * |
| 王素素，等: "Zn2+配位双模板印迹聚合物的制备表征及同时萃取升麻中的阿魏酸和咖啡酸", 《化工进展》 * |
| 陆敏，等: "《化学制药工艺与反应器》", 30 June 2005, 化学工业出版社，教材出版中心 * |
| 陈守文，等: "《酶工程》", 28 February 2008, 科学出版社 * |
| 陈方方，等: "分子印迹固相萃取技术在天然产物有效成分分离分析中的应用进展", 《色谱》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111704693A (en) * | 2020-07-07 | 2020-09-25 | 重庆迈德凯医药有限公司 | Pseudo template molecularly imprinted polymer and application thereof |
| CN111704693B (en) * | 2020-07-07 | 2022-03-18 | 重庆迈德凯医药有限公司 | Pseudo template molecularly imprinted polymer and application thereof |
| CN114292360A (en) * | 2020-07-07 | 2022-04-08 | 重庆迈德凯医药有限公司 | Pseudo template molecularly imprinted polymer and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105732892B (en) | 2018-02-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wan et al. | Novel dual functional monomers based molecularly imprinted polymers for selective extraction of myricetin from herbal medicines | |
| CN102167777B (en) | Preparation method and application of molecularly imprinted polymer | |
| CN105348440B (en) | Oblongifolin C molecularly imprinted polymers and its preparation method and application | |
| CN104693353B (en) | A kind of preparation method of the molecularly imprinted polymer being enriched with paclitaxel | |
| CN103254354A (en) | Cadmium ion imprinted adsorbent, and preparation method and application thereof | |
| CN102174148A (en) | Preparation of triazine phytocide molecular imprinting solid phase extracting material | |
| Li et al. | Theoretical design, preparation, and evaluation of Ginkgolide B molecularly imprinted polymers | |
| CN103055831A (en) | Preparation method of inorganic core-shell type quercetin molecularly imprinted polymer microsphere | |
| CN103554363A (en) | Preparation and application of nano silica-based doxycycline molecularly imprinted polymer | |
| CN108159124A (en) | A kind of preparation method of Corydalis P.E and its application in analgesic | |
| CN105130793B (en) | Method of simultaneously extracting caffeic acid and ferulic acid in cimicifuga rhizome | |
| Dursun et al. | Synthesis of novel monolithic cartridges with specific recognition sites for extraction of melamine | |
| CN103980524A (en) | Preparation method and application of metal ion medium diosgenin imprinted polymer | |
| CN105732892A (en) | Taxol-10-deacetylbaccatine III bi-molecular metal-coordination imprinted material and preparation method and application thereof | |
| CN104189026B (en) | A kind of method for removing from Ginkgo Biloba Extract and being enriched with ginkgoic acid | |
| Ma et al. | Molecularly imprinted polymer-specific solid-phase extraction for the determination of 4-hydroxy-2 (3H) benzoxazolone isolated from Acanthus ilicifolius Linnaeus using high-performance liquid chromatography-tandem mass spectrometry | |
| CN105854844B (en) | Arteannuic acid magnetic blotting microballoon and its preparation method and application | |
| CN106279488B (en) | The preparation for the molecularly imprinted polymer that three kinds of alkaloids of sandliving sophora seed extract at the same time and extracting process | |
| CN105254692A (en) | Method for extracting aucubin and geniposide from eucommia ulmoides peel at same time | |
| Wu et al. | Fabrication and evaluation of molecularly imprinted regenerated cellulose composite membranes via atom transfer radical polymerization | |
| CN105646781B (en) | The preparation method and application of the simulation magnetic molecularly imprinted material of amantadine | |
| CN105289532B (en) | A kind of vitamin B12 molecular engram solid phase extraction magnetic material and its preparation method and application | |
| CN102936315B (en) | Preparation method of molecularly imprinted polymer capable of enriching hispidin | |
| CN106117386A (en) | The method that molecular engram extracts ganoderan with ultrasonic coupling | |
| CN106589190B (en) | A kind of preparation method and application of Superhydrophilic molecularly imprinted polymer |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20200109 Address after: 116000 part of 29 / F, building a, Maritime Science and technology building, No. 523, Huangpu Road, Dalian hi tech Industrial Park, Liaoning Province (room number, 2908-1-20) Patentee after: DALIAN YIKE BIOTECHNOLOGY Co.,Ltd. Address before: 416000 Hunan, Xiangxi Tujia and Miao Autonomous Prefecture, Jishou City People's road, No. 120 Patentee before: Jishou University |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20230601 Address after: 3-11-1, No. 8, Xianling Street, Ganjingzi District, Dalian City, Liaoning Province, 116033 Patentee after: Tian Xin Address before: Part of the area on the 29th floor of Block A, Maritime Science and Technology Building, 523 Huangpu Road, High and New Technology Industrial Park, Dalian, Liaoning Province, 116000 (room number, 2908-1-20) Patentee before: DALIAN YIKE BIOTECHNOLOGY Co.,Ltd. |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20230915 Address after: Room 312, 3rd Floor, Zone B, Office Building 201 Huangpu Road, Shahekou District, Dalian City, Liaoning Province, 116000 Patentee after: Liaoning Xinhaofeng Biotechnology Co.,Ltd. Address before: 3-11-1, No. 8, Xianling Street, Ganjingzi District, Dalian City, Liaoning Province, 116033 Patentee before: Tian Xin |
|
| TR01 | Transfer of patent right |