CN105399915A - Aesculin sustained and controlled release molecular imprinting skeletal material, and preparation method thereof - Google Patents

Aesculin sustained and controlled release molecular imprinting skeletal material, and preparation method thereof Download PDF

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CN105399915A
CN105399915A CN201510951751.6A CN201510951751A CN105399915A CN 105399915 A CN105399915 A CN 105399915A CN 201510951751 A CN201510951751 A CN 201510951751A CN 105399915 A CN105399915 A CN 105399915A
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aesculin
imprinted polymer
release
cyclodextrin
controlled release
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CN105399915B (en
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黄艳萍
马丽
刘照胜
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Tianjin Medical University
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
    • C08G18/6484—Polysaccharides and derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/40—Cyclodextrins; Derivatives thereof
    • 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
    • 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
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes

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  • Medicinal Chemistry (AREA)
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Abstract

The invention relates to an aesculin sustained and controlled release molecular imprinting skeletal material, and a preparation method thereof, and more specifically relates to an aesculin controlled-release molecularly-imprinted polymer material taking beta-cyclodextrin as a monomer, and [BMIM]BF4 as a pore-foaming agent, and a preparation method thereof. The aesculin controlled-release molecularly-imprinted polymer material comprises, by mass, 0.16 to 0.23% of aesculin, 6.3 to 6.4% of beta-cyclodextrin, 13 to 27% of hexamethylene diisocyanate, 20 to 36% of dimethyl sulfoxide, and 35 to 52% of a 1-butyl-3-methylimidazolium tetrafluoroborate, wherein volume ratio of dimethyl sulfoxide to [BMIM]BF4 is 3:2. MIP carrier sustained and controlled release effect of the aesculin controlled-release molecularly-imprinted polymer material is excellent, drug release time of non imprinted polymers is 6h, and stable levofloxacin release time of the aesculin controlled-release molecularly-imprinted polymer material can be 16h or longer. Physical and chemical characteristics of the aesculin controlled-release molecularly-imprinted polymer material are stable, so that foundation is provided for application of molecular imprinting in drug delivery systems.

Description

Aesculin delays controlled release molecular imprinting framework material and preparation method thereof
Technical field
The present invention relates to a kind of aesculin and delay controlled release molecular imprinting framework material and preparation method thereof, specifically with beta-cyclodextrin (β-Cyclodextrin, β-CD) be monomer, ionic liquid 1-butyl-3-methyl imidazolium a tetrafluoro borate (1-Butyl-3-methylimidazoliumterafluoroborate, [BMIM] BF 4) be aesculin (6-O-B-D-glucosyl group-umbelliferone, Esculin) the controlled release molecularly imprinted polymer material of pore-creating agent, this polymkeric substance has specific adsorption performance in dehydrated alcohol, and pharmaceutical release time can reach 16h.
Background technology
Aesculin, has another name called Cichorigenin or esculetin, is poly-hydroxy coumarins times semihydrate, water-soluble good and fat-soluble poor, in rat body Plasma Concentration and bioavailability lower, its structure is as follows:
Prepare aesculin controlled-release material and can extend aesculin time of releasing, the selection of conventional drug carrier material adopts degradable biological, medical macromolecular materials more, as protein has albumin, gelatin; Phospholipid is if liposome, polyose are as dextran, chitosan, starch, synthetic macromolecule class, as poly(lactic acid), polyoxyethylene glycol, polyglycolic acid etc. [China. the research of Zorubicin/hydroxypropyl-beta-cyclodextrin bag and thing and the application [C] at magnetic conductance target administration. Northwest University, 2008.].Framework material conventional at present has cyclodextrin (Cyclodextrin, CD), cyclodextrin is described as the s-generation supramolecule after crown ether, is widely used in the fields such as molecular recognition, chromatographic separation, drug release, chemical sensor, mimetic enzyme catalysis.Wherein, beta-cyclodextrin molecular size is moderate and become round table-like, hydrophilic and inner side is hydrophobic outside cavity, can inclusion multiple compounds, be most widely used [Jin Zhengyu, Xu Xueming, Chen Hanqing, Deng. Cyclodextrin Chemistry-preparation and application [M]. Beijing: Chemical Industry Press, 2009:1-17.].Cyclodextrin is combined with molecular imprinting, contributes to the intelligent host molecule required for synthetic, effectively can promote the development of molecular imprinting.
Aesculin is one of principle active component of dimension medicine saussurea intybus, there is the coumarin kind compound [Dou Guifang of the effects such as heat-clearing and damp-drying drug, diffusing impediment and relieving pain, anti-inflammation detumescence, Lou Yaqing, the .8-chlorine adenosines such as Anqing are in the qualification [J] of rat passway of metabolism and meta-bolites thereof. Chinese pharmacy and toxicology magazine, 1999,13 (2): 141-144.].Through rat experiment checking, there is significant diuretic properties to mouse, suppress the aldose reductase of rat crystalline lens, be the growth inhibitor of Bacillus subtilus, also have restraining effect to chemical is carcinogenic simultaneously.
Molecular imprinting (Molecularimprintingtechnique, MIT) also known as molecular imprinting technique, be the technology that the synthesis grown up on the basis of enzyme-substrate and receptor-antibody effect in simulating nature circle has preselected property stationary phase.A frontier of molecularly imprinted polymer application is exactly as drug delivery system.Control slow release molecules imprinted polymer is as the carrier of medicine, and can be used for the research of drug delivery system as a kind of exotic materials, it both can delay the dispose procedure of medicine, had again the advantage of the highly selective of molecularly imprinted polymer, had wide range of applications.
Ionic liquid (Ionicliquids, ILs) is primarily of the positively charged ion (mainly glyoxaline cation) of comparatively large vol and different types of negatively charged ion (Cl -, BF 4-, PF 6-) composition, at room temperature or the material that is in a liquid state under closing on room temperature.Ionic liquid has the characteristics such as wide, the good dissolving power of liquid state range, good conductivity, be widely used in the fields such as extraction, organic synthesis, electrochemistry, analytical chemistry, be considered to green solvent [XiuYuanLi, XiuXiuChen, DanDanZhong, etal.Synthesisofimprintedmonolithiccolumnwithhighcontent ofmonomersinionicliquid [J] .RSCAdv., 2014,4,50662.].
Summary of the invention
The object of this invention is to provide a kind of aesculin and delay controlled release molecular imprinting framework material and preparation method thereof, it take beta-cyclodextrin as monomer, ionic liquid [BMIM] BF 4for the aesculin controlled release molecularly imprinted polymer material of pore-creating agent.Polymerization is adopted to be dissolved in dimethyl sulfoxide (DMSO) by aesculin and beta-cyclodextrin, mix with prepolymerized solution again, obtain the molecularly imprinted polymer with specific adsorption and medicine control sustained release performance after heating, the controlled release period of the imprinted polymer obtained can reach 16h.Apply the pore-creating agent of ionic liquid as organic synthesis in the present invention, preparing with beta-cyclodextrin is the aesculin controlled release molecularly imprinted polymer material of monomer, environmentally safe.
A kind of aesculin provided by the invention delays the mass percent composition of the raw material of controlled release molecular imprinting (polymkeric substance) framework material:
Aesculin 0.16 – 0.23%
Beta-cyclodextrin 6.3 – 6.4%
Hexamethylene diisocyanate 13 – 27%
Dimethyl sulfoxide (DMSO) 20 – 36%
1-butyl-3-methyl imidazolium tetrafluoroborate 35 – 52%
The quality composition sum of above-mentioned each raw material is 100%.Pore-creating agent is ionic liquid [BMIM] BF 4, wherein [BMIM] BF 4be 3:2 with the volume ratio of solvent dimethyl sulfoxide (DMSO).
The preparation method of above-mentioned aesculin controlled release molecularly imprinted polymer framework material provided by the invention, adopts polymerization preparation, specifically through the following step:
1) proceed in ampoule by the dimethyl sulphoxide solution of template molecule aesculin, function monomer beta-cyclodextrin, linking agent hexamethylene diisocyanate respectively by metering, excusing from death adds pore-creating agent [BMIM] BF after dissolving 4, excusing from death mixing, the oxygen in removing reaction solution, sealing, reacts 2-3h in 50-60 DEG C of water-bath;
2) molecularly imprinted polymer obtained above porphyrize in mortar, first use methyl alcohol: acetic acid (v/v, 9:1) surname extraction 48-72 hour, removes unreacted residual impurity and rinses removing aesculin, until can't detect aesculin by ultraviolet spectrophotometry.Use methyl alcohol surname extraction 24-48 hour again, the acetic acid that wash-out is residual; The aesculin molecularly imprinted polymer obtained, dries under room temperature.
The synthesis of non-imprinted polymer is not except adding template molecule aesculin, and all the other steps are the same.
The invention provides a kind of be monomer with cyclodextrin, ionic liquid is pore-creating agent molecular imprinting controlled release drug carrier and preparation method thereof, is specifically monomer, ionic liquid [BMIM] BF with beta-cyclodextrin 4for the aesculin controlled release molecularly imprinted polymer material of pore-creating agent.First with ionic liquid [BMIM] BF 4as the pore-creating agent of beta-cyclodextrin molecularly imprinted polymer, synthesis has predetermined selectivity aesculin molecularly imprinted polymer, by regulating [BMIM] BF 4with the volume ratio of dimethyl sulfoxide (DMSO), template and the ratio of monomer, the consumption of linking agent, synthesis has the aesculin molecularly imprinted polymer of specific recognition performance.The reagent quoted in this preparation method is less, easily operates, and preparation process is simple.The aesculin molecularly imprinted polymer of preparation has specific recognition performance in dehydrated alcohol, shown by the equilibrium adsorption experiment of aesculin molecularly imprinted polymer to aesculin, the aesculin molecularly imprinted polymer of synthesis has specific adsorption and obvious imprinting effect (imprinting factor=2.23) to aesculin; Shown by the outer release experiment of aesculin, aesculin molecularly imprinted polymer has good controlled release properties, compare the time (6h) of non-imprinted polymer drug release, its Stable Release aesculin can reach more than 16h, and releasing theory comparatively meets Zero order release model.Physics and chemistry stable in properties of the present invention, is applicable to the research of drug delivery system as a kind of special drug carrier material.
Accompanying drawing explanation
That Fig. 1 is prepared by the present invention take beta-cyclodextrin as monomer, ionic liquid [BMIM] BF 4aesculin controlled release molecularly imprinted polymer MIP for pore-creating agent and the non-imprinted polymer NIP N2 adsorption-desorption thermoisopleth comparison diagram without aesculin.
Fig. 2 is the absorption figure that the present invention prepares aesculin molecularly imprinted polymer MIP and balances without the non-imprinted polymer NIP of aesculin.
Fig. 3 is the releasing curve diagram that the present invention prepares the external drug release experiment of aesculin molecularly imprinted polymer.
Embodiment
Below in conjunction with specific embodiment, elaborate the present invention further.The experimental technique of unreceipted actual conditions in embodiment, usually conveniently condition and the condition described in handbook, or according to the condition that manufacturer advises; General-purpose equipment used, material, reagent etc., if no special instructions, all can obtain from commercial channels.
Embodiment 1
Be monomer, ionic liquid [BMIM] BF to characterize with beta-cyclodextrin 4for the morphological characteristic of the aesculin controlled release molecularly imprinted polymer of pore-creating agent, we have prepared with aesculin molecularly imprinted polymer MIP and the non-imprinted polymer NIP without aesculin, and N2 adsorption-parsing Fufen has been carried out to two kinds of polymkeric substance analyse, concrete operation step is as follows:
Take beta-cyclodextrin as monomer, ionic liquid [BMIM] BF 4aesculin controlled release molecularly imprinted polymer preparation method for pore-creating agent:
A. by template molecule aesculin 0.23% (being mass percent), function monomer beta-cyclodextrin 6.50%, linking agent hexamethylene diisocyanate 28.87%, being dissolved in mass percent is in the dimethyl sulfoxide (DMSO) of 22.91%; Add massfraction 41.58% pore-creating agent [BMIM] BF 4.Ultrasonic 10min(300W under room temperature), make it to dissolve, clarify, oxygen in removing mixed reaction solution, sealing, reacts 2h in 60 DEG C of water-baths;
B. molecularly imprinted polymer obtained above porphyrize in mortar, first use methyl alcohol: acetic acid (v/v, 9:1) surname extraction 48 hours, removes unreacted residual impurity and rinses removing aesculin, until can't detect aesculin by ultraviolet spectrophotometry.Use methyl alcohol surname extraction again 24 hours, the acetic acid that wash-out is residual; The aesculin molecularly imprinted polymer obtained, dries under room temperature.
The synthesis of non-imprinted polymer is not except adding template molecule aesculin, and all the other steps are the same.
N2 adsorption is tested:
By synthesis take beta-cyclodextrin as monomer, ionic liquid [BMIM] BF 4aesculin controlled release molecularly imprinted polymer MIP for pore-creating agent and the non-imprinted polymer NIP without aesculin puts 60oC vacuum stripping (10 3torr) 4 hours, get dried particle and put in ASAP-2020 microparticle surfaces sum lacunarity analysis instrument and carry out, process is carried out to the data obtained and obtains aesculin molecularly imprinted polymer N2 adsorption-desorption thermoisopleth and specific surface area.
Being shown by N2 adsorption test result, take beta-cyclodextrin as monomer, ionic liquid [BMIM] BF 4for the aesculin controlled release molecularly imprinted polymer MIP of pore-creating agent has larger specific surface area relative to NIP, Brunauer-Emmett-Teller (BET) specific surface area is 0.32m 2/ g, adsorptive capacity (STP) is 18.3cm 3/ g, the specific surface area of non-imprinted polymer is 0.24m 2/ g, adsorptive capacity (STP) is 7.9cm 3/ g(Fig. 1).
Embodiment 2
The research of aesculin equilibrium adsorption experiment is monomer, ionic liquid [BMIM] BF with beta-cyclodextrin 4for the aesculin molecularly imprinted polymer of pore-creating agent is to the specific adsorption performance of trace aesculin, in order to investigate the specific recognition capability to aesculin of imprinted polymer, determine aesculin imprinted polymer and the adsorption isothermal line of non-imprinted polymer within the scope of 0 ~ 10mmol/L.Concrete operation step is as follows:
A. same aforesaid method (embodiment 1) synthesis beta-cyclodextrin is monomer, ionic liquid [BMIM] BF 4for the aesculin molecularly imprinted polymer MIP of pore-creating agent, the synthesis of non-imprinted polymer NIP is not except adding template aesculin, and all the other steps are with the synthesis of aesculin molecularly imprinted polymer.
B. the aesculin molecularly imprinted polymer and the non-imprinted polymer 10.0mg that take drying respectively put into 5mL centrifuge tube, add the aesculin ethanol solution of 2.0mL concentration at 0 ~ 10mmol/L, put into vibrator (power 100W), vibrate under room temperature 24h, then mixed solution is proceeded in supercentrifuge with the centrifugal 10min of 8000r/min, get the centrifuged supernatant of 100 μ L, be diluted with water to 10mL, under 335nm wavelength, measure the equilibrium concentration of aesculin with spectrophotometry.
According to before and after combining in solution the change calculations of aesculin concentration be monomer, ionic liquid [BMIM] BF with beta-cyclodextrin 4for the aesculin molecularly imprinted polymer of pore-creating agent and non-imprinted polymer to aesculin in conjunction with adsorptive capacity Q e, calculation formula is:
q e (mmol/g) be the amount of Polymer adsorption aesculin, c o , c e (mmol/l) concentration when being respectively the starting point concentration of aesculin solution and reaching balance, vfor the volume of absorption mother liquor added, mfor the quality of MIP and NIP of use in experiment.Replicate(determination) 3 times, averages.
With qeright ceto map to obtain aesculin molecularly imprinted polymer adsorption isothermal line.
Result shows, along with absorption mother liquor c o the increase of concentration, aesculin molecularly imprinted polymer and the adsorptive capacity of non-imprinted polymer to aesculin rise gradually, and imprinted polymer is obviously greater than non-imprinted polymer (Fig. 2) for the adsorptive capacity of aesculin.Illustrate with beta-cyclodextrin to be monomer, ionic liquid [BMIM] BF 4for the aesculin molecularly imprinted polymer of pore-creating agent has specific adsorption and obvious imprinting effect (imprinting factor=2.23) to template molecule aesculin
Embodiment 3
Dynamic (dynamical) model of drug release experiment research aesculin molecularly imprinted polymer release medicine.In order to investigate the releasing theory of medicine, determine the medicine total amount of aesculin molecularly imprinted polymer and the release within a certain period of time of non-imprinted polymer.Concrete operation step is as follows:
A. same aforesaid method (embodiment 1) synthesis is monomer, ionic liquid [BMIM] BF with beta-cyclodextrin 4for the aesculin controlled release molecularly imprinted polymer of pore-creating agent, the synthesis of non-imprinted polymer is not except adding template molecule aesculin, and all the other steps are with the synthesis of aesculin molecularly imprinted polymer.
B. the dimethyl sulphoxide solution synthetic aesculin molecularly imprinted polymer and non-imprinted polymer being placed in aesculin soaks three days, dries 24h, then washes twice with dehydrated alcohol, dry under room temperature under room temperature; The aesculin molecularly imprinted polymer and the non-imprinted polymer that accurately take medicine carrying are placed in 10% methanol/water solution, stirred at ambient temperature, 50rp/min respectively; Certain hour interval, gets 3.00mL working sample, and with Uv-vis spectrophotometric determination release amount of medicine, the sample of taking-up is refunded in release medium again.
With the dose of cumulative release, the time is mapped, draw the release profiles of medicine, drug release model compares and meets Zero order release model, molecularly imprinted polymer carrier controlled-release effect is good, compare the time (6h) of non-imprinted polymer drug release, its Stable Release aesculin can reach more than 16h (Fig. 3).Prove with beta-cyclodextrin to be monomer, ionic liquid [BMIM] BF 4for the aesculin controlled release molecularly imprinted polymer of pore-creating agent has good controlled-release effect to aesculin.

Claims (4)

1. aesculin delays a controlled release molecular imprinting framework material, it is characterized in that the quality composition of its raw material:
Aesculin 0.16 – 0.23%
Beta-cyclodextrin 6.3 – 6.4%
Hexamethylene diisocyanate 13 – 27%
Dimethyl sulfoxide (DMSO) 20 – 36%
1-butyl-3-methyl imidazolium tetrafluoroborate 35 – 52%
The mass percent composition sum of above-mentioned each raw material is 100%.
2. delay controlled release molecular imprinting framework material according to aesculin according to claim 1, it is characterized in that the quality composition of its raw material:
Aesculin 0.23%
Beta-cyclodextrin 6.50%
Hexamethylene diisocyanate 28.84%
Dimethyl sulfoxide (DMSO) 22.91%
1-butyl-3-methyl imidazolium tetrafluoroborate 41.52%.
3. delay controlled release molecular imprinting framework material according to aesculin according to claim 1, it is characterized in that pore-creating agent is ionic liquid 1-butyl-3-methyl imidazolium a tetrafluoro borate, the volume ratio of dimethyl sulfoxide (DMSO) and 1-butyl-3-methyl imidazolium tetrafluoroborate is 3:2.
4. aesculin according to claim 1 delays the preparation method of controlled release molecular imprinting framework material, it is characterized in that through the following step:
1) respectively the solution of the dimethyl sulfoxide (DMSO) of template molecule aesculin, function monomer beta-cyclodextrin, linking agent hexamethylene diisocyanate is proceeded in ampoule by metering, then add pore-creating agent ionic liquid [BMIM] BF 4, the oxygen in removing reaction solution, sealing, reacts 2-3h in 50-60 DEG C of water-bath;
2) molecularly imprinted polymer obtained above porphyrize in mortar, be first that the methyl alcohol of 9:1 and acetic acid carry out surname extraction 48-72 hour by volume ratio, remove unreacted residual impurity and rinse removing aesculin, use methyl alcohol surname extraction 24-48 hour again, the acetic acid that wash-out is residual, the aesculin imprinted polymer obtained, dries under room temperature.
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CN114426698A (en) * 2022-03-11 2022-05-03 北京科技大学 Ultralow dielectric porous polyimide film and preparation method thereof

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