CN103724655B - A kind of method adopting hybrid template to prepare ebormycine molecular imprinted polymer membrane - Google Patents
A kind of method adopting hybrid template to prepare ebormycine molecular imprinted polymer membrane Download PDFInfo
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Abstract
The invention discloses a kind of method adopting hybrid template to prepare ebormycine molecular imprinted polymer membrane, belong to molecular imprinting field, comprise the following steps: after 1) template molecule epothilone B being mixed with Epothilone D, add function monomer and linking agent, abundant mixing, forms mixture; This mixture is added in pore-creating agent, under ultrasound condition after mixing, left at room temperature, then add initiator, mixing obtains mixed solution; 2) base film is immersed after soaking in mixed solution, take out and be placed between two sheet glass, put into sealing bag after getting rid of bubble, seal after passing into nitrogen, after ultra violet lamp, sheet glass is separated, obtains ebormycine molecular imprinted polymer membrane.Processing ease of the present invention, easy control of reaction conditions, preparation cost is cheap, and this film is easy to adsorb and wash-out again, and repeating utilization factor is high, has both overcome the shortcoming of rodlike molecule imprinted polymer polymerization time length and needs screening, has shortened elution time again.
Description
Technical field
The invention belongs to molecular imprinting field, be specifically related to a kind of method adopting hybrid template to prepare ebormycine molecular imprinted polymer membrane.
Background technology
Ebormycine is the class macrolides compound produced by sorangium cellulosum (Sorangiumcellulosum), there is multiple natural derivative, with taxol, there is the mechanism of action that identical inhibition tumor cell grows, and powerful antitumour activity is all showed to the tumour cell of multidrug resistant tumour cell and resistance to taxol, along with going deep into of research, ebormycine is played a great role at last in treating human cancer.
Have the correlative study in some fermentative production about ebormycine and separation and Extraction at present, the problems such as but existing fermentation method for producing ubiquity output is unstable and its output is on the low side, and separation and Extraction complex steps, separation efficiency is low, with an organic solvent more, cause cost higher.Therefore exploitation can the sorbent material of specific adsorption epothilones be used for greatly reducing the production cost of ebormycine medicine in its fermentative production and separation and Extraction, and this will be particularly important.
Molecular engram film is a kind of emerging technology having molecular imprinting and membrane separation technique advantage concurrently, compared with common separatory membrane, there is the feature high to specific molecular selectivity, compared with traditional imprinted polymer, have without the need to pulverizing process of lapping, trace hole retention rate is high, the feature that molecular recognition performance is strong, is the study hotspot of functionalization separatory membrane.On organic polymer thin film matrix, in-situ polymerization prepares molecular engram film, and not only method is easy, cost is low, favorable reproducibility, and the molecular engram film obtained has the advantages such as selectivity is good, mass transfer is fast.The research of molecular engram film will be the once breakthrough to traditional membrane separation technique undoubtedly.
At present, the preparation applying it in fermentative production and separation and Extraction process of ebormycine molecular imprinted polymer membrane have not been reported.
Summary of the invention
A kind of employing hybrid template to ebormycine high-selectivity adsorption is the object of the present invention is to provide to prepare the method for ebormycine molecular imprinted polymer membrane.
The present invention is achieved through the following technical solutions:
Adopt hybrid template to prepare a method for ebormycine molecular imprinted polymer membrane, comprise the following steps:
1) epothilone B and Epothilone D are pressed (0.5 ~ 2): after the mixed in molar ratio of (1 ~ 2), obtain template molecule, in template molecule, add function monomer, obtain title complex, then add linking agent in title complex, fully mix, form mixture; Add in pore-creating agent by this mixture, under ultrasound condition after mixing, at room temperature leave standstill 1 ~ 3h, then add initiator, mixing obtains mixed solution;
Wherein, described function monomer is vinylformic acid, methacrylic acid, methyl methacrylate, Styrene and its derivatives, vinyl pyridine, vinyl pyrrolidone or trimethylallylammonium chloride;
In described mixture, the mol ratio of template molecule, function monomer and linking agent is 1:(2 ~ 6): (10 ~ 30); The consumption of described pore-creating agent is 20 ~ 25mL/1mmol template molecule, and the consumption of initiator is 10 ~ 15mg/1mmol template molecule;
2) base film is immersed after soaking 20 ~ 30min in mixed solution, take out and be placed between two sheet glass, after getting rid of bubble, put into sealing bag, seal after passing into nitrogen 10 ~ 15min, carry out uv irradiating again, then sheet glass is separated, obtains ebormycine molecular imprinted polymer membrane.
Also comprise the purification process to ebormycine molecular imprinted polymer membrane, be specially: by obtained ebormycine molecular imprinted polymer membrane at acetic acid: the volume ratio of methyl alcohol is 2:(6 ~ 9) mixed solution in soxhlet's extraction for several times, again with after methanol extraction several, drying, obtains pure ebormycine molecular imprinted polymer membrane.
Described soxhlet extraction number of times is 3 ~ 5 times, each 8 ~ 12 hours; Methanol extraction 1 ~ 2 time; Described drying is at 40 ~ 60 DEG C, dried in vacuo overnight.
Linking agent described in step 1) is ethylene glycol dimethacrylate, methylene-bisacrylamide, divinyl toluene or trimethyl propane trimethacrylate.
Pore-creating agent described in step 1) is acetonitrile, chloroform, Virahol, polyacrylamide, toluene, paraffin, gelatin or tetracol phenixin.
Initiator described in step 1) is Diisopropyl azodicarboxylate or ammonium persulphate.
Supersound process described in step 1) is under ultrasonic frequency is 20000 ~ 60000Hz, process 10 ~ 30min.
Step 2) described in base film be polyethylene film, polypropylene screen, cellulose acetate membrane, polyacrylonitrile film, nylon membrane, polyvinylidene fluoride film or polychloroethylene film.
Step 2) described in ultra violet lamp be adopt the ultra violet lamp 10 ~ 16h of 400W.
Step 2) described in base film before use through pre-treatment, be specially: be the N of 30 ~ 90%, N by base film in volumetric concentration, N ', soak 0.5 ~ 1.5h in N '-Tetramethyl Ethylene Diamine aqueous solution, take out and be placed in 30 ~ 70 DEG C of vacuum drying ovens, dry 2 ~ 4h.
Compared with prior art, the present invention has following useful technique effect:
The present invention is using the mixture of epothilone B and Epothilone D as template molecule, choose the base film of appropriate well structure and film layer structure as supporting layer, UV-light is utilized to cause home position polymerization reaction grafting molecules imprinted polymer and obtained ebormycine molecular imprinted polymer membrane on base film, the feature of the Selective recognition of the imprinted polymer that thus made it existing, there is again the stability of film, thus there is the feature of highly selective and large flux.This blotting membrane can make template molecule ebormycine be delivered to the opposite side of film by the side continuously from film, but not template molecule then can not pass through, and achieves the object of separating-purifying ebormycine from mixture.It is simple that preparation method of the present invention has process, processing ease, easy control of reaction conditions, the advantages such as preparation cost is cheap, and this film is easy to adsorb and wash-out again, repeating utilization factor is high, has both overcome the shortcoming of rodlike molecule imprinted polymer polymerization time length and needs screening, has shortened elution time again.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail, and the explanation of the invention is not limited.
Embodiment 1
Adopt hybrid template to prepare the method for ebormycine molecular imprinted polymer membrane, comprise the following steps:
1) template molecule 1.0mmol epothilone B is mixed with 1.0mmol Epothilone D, add 4mmol function monomer vinylformic acid (AA) to make it to form host-guest coordination compound, add 20mmol linking agent ethylene glycol dimethacrylate (EGDMA) again, abundant mixing, form mixture, this mixture is dissolved in 40mL pore-creating agent acetonitrile, under ultrasonic frequency is 60000Hz, supersound process 10min makes it mix, in left at room temperature 1h, then add 20mg initiator Diisopropyl azodicarboxylate, mixing obtains mixed solution;
2) by cellulose acetate membrane in volumetric concentration be 30% the N,N,N′,N′ tetramethylethylene diamine aqueous solution in soak 0.5h, then take out be placed in 30 DEG C of dry 4h of vacuum drying oven, for subsequent use;
3) by step 2) cellulose acetate membrane that processed puts into after the obtained mixed solution of step 1) soaks 20min, taking-up is placed between two sheet glass, after firmly bubble is got rid of in extruding, put into sealing bag, pass into nitrogen 10min, sealing and after irradiating 10h with 400W ultraviolet lamp (365nm), sheet glass is separated, with acetic acid: methyl alcohol volume ratio is the solution lixiviate 3 times of 2:6, each 8 hours, removing template molecule, finally remove molecular acid 1 time by methanol-eluted fractions, then in 50 DEG C of dried in vacuo overnight, obtaining take cellulose acetate membrane as the molecular imprinted polymer membrane of propping material.
Embodiment 2
Adopt hybrid template to prepare the method for ebormycine molecular imprinted polymer membrane, comprise the following steps:
1) template molecule 1.0mmol epothilone B is mixed with 1.5mmol Epothilone D, add 7.5mmol function monomer methyl methacrylate (MA) to make it to form host-guest coordination compound, add 25mmol linking agent methylene-bisacrylamide again, fully mix, form mixture; Be dissolved in by this mixture in 50mL pore-creating agent chloroform, under ultrasonic frequency is 50000Hz, supersound process 15min makes it mix, and in left at room temperature 2h, then adds 30mg initiator Diisopropyl azodicarboxylate, and mixing obtains mixed solution;
2) be 40%(v/v by polyethylene film in concentration) the N,N,N′,N′ tetramethylethylene diamine aqueous solution in soak 1h, then take out and be placed in 40 DEG C of dry 3h of vacuum drying oven, for subsequent use;
3) then by step 2) polyethylene film that processed puts into after the obtained mixed solution of step 1) soaks 20min, taking-up is placed between two sheet glass, after firmly bubble is got rid of in extruding, put into sealing bag, pass into nitrogen 12min, sealing and after irradiating 12h with 400W ultraviolet lamp (365nm); Sheet glass is separated, with acetic acid: methyl alcohol volume ratio is the solution lixiviate 4 times of 2:7, each 8 hours, removing template molecule, finally remove molecular acid by methanol-eluted fractions 1 time, then in 50 DEG C of dried in vacuo overnight, obtaining take polyethylene film as the molecular imprinted polymer membrane of propping material.
Embodiment 3
Adopt hybrid template to prepare the method for ebormycine molecular imprinted polymer membrane, comprise the following steps:
1) template molecule 1.0mmol epothilone B is mixed with 2.0mmol Epothilone D, add 9mmol function monomer vinylbenzene to make it to form host-guest coordination compound, add 60mmol linking agent trimethyl propane trimethacrylate (TRIM) again, fully mix, form mixture; Be dissolved in by this mixture in 66mL pore-creating agent tetracol phenixin, under ultrasonic frequency is 30000Hz, supersound process 20min makes it mix, and in left at room temperature 1h, then adds 35mg initiator Diisopropyl azodicarboxylate, and mixing obtains mixed solution;
2) be 50%(v/v by nylon membrane in concentration) the N,N,N′,N′ tetramethylethylene diamine aqueous solution in soak 1h, then take out and be placed in 50 DEG C of dry 2.5h of vacuum drying oven, for subsequent use;
3) just step 2) nylon membrane that processed puts into step 1) and obtains after mixed solution soaks 25min, taking-up is placed between two sheet glass, after firmly bubble is got rid of in extruding, puts into sealing bag, pass into nitrogen 12min, sealing and after irradiating 13h with 400W ultraviolet lamp (365nm); Sheet glass is separated, with acetic acid: methyl alcohol volume ratio is the solution lixiviate 5 times of 2:8, each 8 hours, removing template molecule, finally remove molecular acids by methanol-eluted fractions 2 times, then in 50 DEG C of dried in vacuo overnight, obtaining take nylon membrane as the molecular imprinted polymer membrane of propping material.
Embodiment 4
Adopt hybrid template to prepare the method for ebormycine molecular imprinted polymer membrane, comprise the following steps:
1) template molecule 1.5mmol epothilone B is mixed with 1.0mmol Epothilone D, add 10mmol function monomer methacrylic acid (MAA) to make it to form host-guest coordination compound, add 30mmol linking agent divinyl toluene again, fully mix, form mixture, this mixture is dissolved in 50mL pore-creating agent Virahol, under ultrasonic frequency is 30000Hz, supersound process 20min makes it mix, in left at room temperature 3h, then add 30mg initiator ammonium persulfate, mixing obtains mixed solution;
2) be 60%(v/v by polyacrylonitrile film in concentration) the N,N,N′,N′ tetramethylethylene diamine aqueous solution in soak 1.5h, then take out and be placed in 50 DEG C of dry 3h of vacuum drying oven, for subsequent use;
3) treated polyacrylonitrile film is put into after the obtained mixed solution of step 1) soaks 20min, taking-up is placed between two sheet glass, after firmly bubble is got rid of in extruding, put into sealing bag, pass into nitrogen 15min, sealing and after irradiating 10h with 400W ultraviolet lamp (365nm), sheet glass is separated, with acetic acid: methyl alcohol volume ratio is the solution lixiviate 5 times of 2:8, each 10 hours, removing template molecule, finally remove molecular acid 2 times by methanol-eluted fractions, then in 50 DEG C of dried in vacuo overnight, obtaining take polyacrylonitrile film as the molecular imprinted polymer membrane of propping material.
Embodiment 5
Adopt hybrid template to prepare the method for ebormycine molecular imprinted polymer membrane, comprise the following steps:
1) template molecule 2.0mmol epothilone B is mixed with 1.0mmol Epothilone D, add 15mmol function monomer vinyl pyridine to make it to form host-guest coordination compound, add 30mmol linking agent trimethyl propane trimethacrylate again, abundant mixing, form mixture, this mixture is dissolved in 75mL pore-creating agent polyacrylamide, under ultrasonic frequency is 25000Hz, supersound process 25min makes it mix, in left at room temperature 1h, then add 45mg initiator ammonium persulfate, mixing obtains mixed solution;
2) be 70%(v/v by polychloroethylene film in concentration) the N,N,N′,N′ tetramethylethylene diamine aqueous solution in soak 1.5h, then take out and be placed in 60 DEG C of dry 2.5h of vacuum drying oven, for subsequent use;
3) by step 2) polychloroethylene film that processed puts into after the obtained mixed solution of step 1) soaks 30min, taking-up is placed between two sheet glass, after firmly bubble is got rid of in extruding, put into sealing bag, pass into nitrogen 14min, sealing and after irradiating 15h with 400W ultraviolet lamp (365nm), sheet glass is separated, with acetic acid: methyl alcohol volume ratio is the solution lixiviate 5 times of 2:8, each 12 hours, removing template molecule, finally remove molecular acid 2 times by methanol-eluted fractions, then in 50 DEG C of dried in vacuo overnight, obtaining take polychloroethylene film as the molecular imprinted polymer membrane of propping material.
Embodiment 6
Adopt hybrid template to prepare the method for ebormycine molecular imprinted polymer membrane, comprise the following steps:
1) template molecule 0.5mmol epothilone B is mixed with 1.0mmol Epothilone D, add 9mmol function monomer trimethylallylammonium chloride to make it to form host-guest coordination compound, add 45mmol linking agent trimethyl propane trimethacrylate again, abundant mixing, form mixture, this mixture is dissolved in 30mL pore-creating agent gelatin, under ultrasonic frequency is 20000Hz, supersound process 30min makes it mix, in left at room temperature 1h, then add 20mg initiator ammonium persulfate, mixing obtains mixed solution;
2) be 90%(v/v by polyvinylidene fluoride film in concentration) the N,N,N′,N′ tetramethylethylene diamine aqueous solution in soak 1.5h, then take out and be placed in 70 DEG C of dry 2h of vacuum drying oven, for subsequent use;
3) by step 2) polyvinylidene fluoride film that processed puts into after the obtained mixed solution of step 1) soaks 30min, taking-up is placed between two sheet glass, after firmly bubble is got rid of in extruding, puts into sealing bag, pass into nitrogen 15min, seal and irradiate 16h with 400W ultraviolet lamp (365nm); Sheet glass is separated, with acetic acid: methyl alcohol volume ratio is the solution lixiviate 5 times of 2:9, each 12 hours, removing template molecule, finally remove molecular acids by methanol-eluted fractions 2 times, then in 50 DEG C of dried in vacuo overnight, obtaining take polyvinylidene fluoride film as the molecular imprinted polymer membrane of propping material.
Embodiment 7
Adopt hybrid template to prepare the method for ebormycine molecular imprinted polymer membrane, comprise the following steps:
1) template molecule 0.5mmol epothilone B is mixed with 1.5mmol Epothilone D, add 10mmol function monomer vinyl pyrrolidone to make it to form host-guest coordination compound, add 45mmol linking agent trimethyl propane trimethacrylate again, abundant mixing, form mixture, this mixture is dissolved in 30mL pore-creating agent paraffin, under ultrasonic frequency is 25000Hz, supersound process 30min makes it mix, in left at room temperature 2h, then add 20mg initiator ammonium persulfate, mixing obtains mixed solution;
2) be 90%(v/v by polypropylene screen in concentration) the N,N,N′,N′ tetramethylethylene diamine aqueous solution in soak 1.5h, then take out and be placed in 70 DEG C of dry 2h of vacuum drying oven, for subsequent use;
3) by step 2) polypropylene screen that processed puts into after the obtained mixed solution of step 1) soaks 30min, taking-up is placed between two sheet glass, after firmly bubble is got rid of in extruding, puts into sealing bag, pass into nitrogen 15min, seal and irradiate 16h with 400W ultraviolet lamp (365nm); Sheet glass is separated, with acetic acid: methyl alcohol volume ratio is the solution lixiviate 5 times of 2:7, each 12 hours, removing template molecule, finally remove molecular acids by methanol-eluted fractions 2 times, then in 45 DEG C of dried in vacuo overnight, obtaining take polypropylene screen as the molecular imprinted polymer membrane of propping material.
Claims (9)
1. adopt hybrid template to prepare a method for ebormycine molecular imprinted polymer membrane, it is characterized in that, comprise the following steps:
1) epothilone B and Epothilone D are pressed (0.5 ~ 2): after the mixed in molar ratio of (1 ~ 2), obtain template molecule, in template molecule, add function monomer, obtain title complex, in title complex, add linking agent again, fully mix, form mixture; Add in pore-creating agent by this mixture, under ultrasound condition after mixing, at room temperature leave standstill 1 ~ 3h, then add initiator, mixing obtains mixed solution;
Wherein, described function monomer is vinylformic acid, methacrylic acid, methyl methacrylate, Styrene and its derivatives, vinyl pyridine, vinyl pyrrolidone or trimethylallylammonium chloride;
Described linking agent is ethylene glycol dimethacrylate, methylene-bisacrylamide, trimethyl propane trimethacrylate or divinyl toluene;
In described mixture, the mol ratio of template molecule, function monomer and linking agent is 1:(2 ~ 6): (10 ~ 30); The consumption of described pore-creating agent is 20 ~ 25mL/1mmol template molecule, and the consumption of initiator is 10 ~ 15mg/1mmol template molecule;
2) base film is immersed after soaking 20 ~ 30min in mixed solution, take out and be placed between two sheet glass, after getting rid of bubble, put into sealing bag, seal after passing into nitrogen 10 ~ 15min, carry out uv irradiating again, then sheet glass is separated, obtains ebormycine molecular imprinted polymer membrane.
2. a kind of method adopting hybrid template to prepare ebormycine molecular imprinted polymer membrane according to claim 1, it is characterized in that, also comprise the purification process to ebormycine molecular imprinted polymer membrane, be specially: by obtained ebormycine molecular imprinted polymer membrane at acetic acid: the volume ratio of methyl alcohol is 2:(6 ~ 9) mixed solution in soxhlet's extraction for several times, again with after methanol extraction several, drying, obtains pure ebormycine molecular imprinted polymer membrane.
3. a kind of method adopting hybrid template to prepare ebormycine molecular imprinted polymer membrane according to claim 2, it is characterized in that, described soxhlet extraction number of times is 3 ~ 5 times, each 8 ~ 12 hours; Methanol extraction 1 ~ 2 time; Described drying is at 40 ~ 60 DEG C, dried in vacuo overnight.
4. according to a kind of method adopting hybrid template to prepare ebormycine molecular imprinted polymer membrane in claims 1 to 3 described in any one, it is characterized in that, step 1) described in pore-creating agent be acetonitrile, chloroform, Virahol, polyacrylamide, toluene, paraffin, gelatin or tetracol phenixin.
5., according to a kind of method adopting hybrid template to prepare ebormycine molecular imprinted polymer membrane in claims 1 to 3 described in any one, it is characterized in that, step 1) described in initiator be Diisopropyl azodicarboxylate or ammonium persulphate.
6. according to a kind of method adopting hybrid template to prepare ebormycine molecular imprinted polymer membrane in claims 1 to 3 described in any one, it is characterized in that, it is characterized in that, step 1) described in supersound process be under ultrasonic frequency is 20000 ~ 60000Hz, process 10 ~ 30min.
7. according to a kind of method adopting hybrid template to prepare ebormycine molecular imprinted polymer membrane in claims 1 to 3 described in any one, it is characterized in that, step 2) described in base film be polyethylene film, polypropylene screen, cellulose acetate membrane, polyacrylonitrile film, nylon membrane, polyvinylidene fluoride film or polychloroethylene film.
8. according to a kind of method adopting hybrid template to prepare ebormycine molecular imprinted polymer membrane in claims 1 to 3 described in any one, step 2) described in ultra violet lamp be the ultra violet lamp 10 ~ 16h adopting 400W.
9. according to a kind of method adopting hybrid template to prepare ebormycine molecular imprinted polymer membrane in claims 1 to 3 described in any one, it is characterized in that, step 2) described in base film before use through pre-treatment, be specially: be the N of 30 ~ 90% by base film in volumetric concentration, N, N ', soak 0.5 ~ 1.5h in N '-Tetramethyl Ethylene Diamine aqueous solution, taking-up is placed in 30 ~ 70 DEG C of vacuum drying ovens, dry 2 ~ 4h.
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| CN103937852A (en) * | 2014-04-23 | 2014-07-23 | 陕西科技大学 | Method for preparing epothilone B based on coupling of separation and fermentation of molecularly imprinted membrane |
| CN104151596A (en) * | 2014-08-12 | 2014-11-19 | 河北科技大学 | Preparation method and application of dual-template molecularly imprinted solid phase extraction membrane |
| CN104297043B (en) * | 2014-09-29 | 2017-07-04 | 宁波大学 | The membrane extraction method of pyrethroid pesticide is remained in a kind of complex sample |
| CN104311744B (en) * | 2014-09-29 | 2017-01-11 | 宁波大学 | Preparation method of pyrethroid pesticide type molecularly imprinted membrane |
| CN109351344A (en) * | 2018-09-26 | 2019-02-19 | 长安大学 | Ochracin adsorbent material, preparation method and applications in a kind of corn |
| CN109254044B (en) * | 2018-11-05 | 2021-01-08 | 济南大学 | Preparation method and application of macrolide antibiotic sensor based on FeN |
| CN114887597B (en) * | 2022-03-25 | 2023-08-22 | 西安交通大学 | Aflatoxin surface molecularly imprinted nanofiber membrane adsorbent and preparation method and application thereof |
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| CN102977403A (en) * | 2012-12-24 | 2013-03-20 | 重庆大学 | Molecularly imprinted membrane based on porphyrin and acrylic monomers for organophosphorus pesticide and application thereof |
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