CN102350309A - Endotoxin adsorption medium based on magnetic chitosan microballoon and its application method - Google Patents
Endotoxin adsorption medium based on magnetic chitosan microballoon and its application method Download PDFInfo
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Abstract
The invention discloses an endotoxin adsorption medium based on magnetic chitosan microballoon and an application method, wherein the preparation method of endotoxin adsorption medium comprises the following steps: (1) dispersing a magnetic material in an acetic acid solution, adding chitosan to prepare water phase I, transferring water phase I to liquid paraffin containing span 80, taking glutaraldehyde as a cross-linking agent, preparing chitosan microballoon by using an anti-phase suspension method; (2) dispersing magnetic chitosan microballoon in a mixed solution of dimethyl sulfoxide and sodium hydroxide, adding chloropropylene oxide for activating, washing by deionized water till neutralizing to obtain an activated product; (3) placing the activated product in an endotoxin affinity ligand solution for immobilizing to obtain the endotoxin adsorption medium based on the magnetic chitosan microballoon. The endotoxin adsorption medium of the present invention has high selectivity of endotoxin and simple operation, and can be used for removing the endotoxin in a plurality of biological products.
Description
One, technical field
The present invention relates to field of biomedical materials, particularly relate to a kind of preparation and method for using thereof of external endotoxin adsorbing medium.
Two, background technology
Peculiar structure on endotoxin (Endotoxin) the cell membrane adventitia that to be Gram-negative bacteria discharge when growth, division or cracking is come out when dead.Because Gram-negative bacteria is very obstinate, in water, only need few nutrient to survive, thereby endotoxin extensively is present on the wall that reaches contact with water solution in drinking water, food, the biological medicine preparation; In the higher organism body, the Gram-negative Pseudomonas of intestines and stomach lower end is the endotoxic main source of organism, and the endotoxin that discharges after the bacterial death can get into blood circulation and cause a series of pathological changes.Hospital clinical when using the medicine injection if contain bacterial endotoxin greater than 1EU/mL; Then patient can produce that shiver with cold, heating, vomiting, the colour of skin are greyish white, heat source response such as shock even death; Therefore NF has strict regulations to bacterial endotoxin index in the injection article, and its limit level is per unit body weight 5EU.
The endotoxic method of removal at present commonly used has charcoal absorption, ultrafiltration, extraction, affinity chromatography etc., but first three methods only is suitable for from more stable relatively small-molecule substance, removing endotoxin, and loss of effective components is bigger; Though the affinity chromatography selectivity is better, also have steps consuming time such as dressing post, preliminary treatment, and treating capacity is less.
Three, summary of the invention
The technical problem that the present invention will solve provides a kind of endotoxin adsorbing medium and method for using thereof, and this endotoxin adsorbing medium not only has higher selectivity for endotoxin, and easy to use, is suitable for endotoxic removal in the large number of biological goods.
For solving the problems of the technologies described above, the present invention adopts following technical scheme:
A kind of endotoxin adsorbing medium based on chitosan magnetic micro-sphere, its preparation method comprises the steps:
(1) elder generation is dispersed in magnetic material and contains in the acetic acid solution, adds shitosan and obtains water I, this water I is transferred in the atoleine that contains sorbester p17 again, with glutaraldehyde as cross linker, adopts inverse suspension method to make chitosan magnetic micro-sphere; Described magnetisable material is tri-iron tetroxide or iron;
(2) chitosan magnetic micro-sphere is distributed in the mixed solution of dimethyl sulfoxide (DMSO) and NaOH, adds the epoxychloropropane activation again, the deionized water washing obtains activating afterproduct to neutral;
(3) will activate afterproduct and place endotoxin affinity ligand solution immobilized, promptly obtain described endotoxin adsorbing medium based on chitosan magnetic micro-sphere; Described endotoxin affinity ligand is histidine, arginine, poly-D-lysine, PB or TEPA.
Further; Recommendation step of the present invention (1) is specifically according to carrying out as follows: be distributed in the acetic acid solution magnetic material is ultrasonic; Stir behind the adding shitosan and obtain water I; The concentration of shitosan is 10～40g/L among the water I; Acetic acid concentration is 10～50mL/L, and the mass ratio that feeds intake of magnetic material and shitosan is 0.2～1: 1; Then water I is joined in the atoleine that contains 0.1～2vol% sorbester p17, water I is 1: 1～5 with the mixed volume ratio of the atoleine that contains 0.1～2vol% sorbester p17; Add glutaraldehyde behind the mixing; The glutaraldehyde that is added and the mol ratio of amino of chitosan are 1: 0.1～6; Finish adjustment temperature to 25～50 ℃ reaction 1～3 hour; Adjust system pH to 10～13 then; Be warming up to 50～80 ℃; Continue stirring reaction, fully reaction back separated product obtains chitosan magnetic micro-sphere through washing, drying.
Further, in the above-mentioned steps (1), preferable chitosan concentration is 30～40g/L; The mol ratio of glutaraldehyde and amino of chitosan is preferably 1: 1～and 2; PH transfers to after 10～13 temperature and rises to 70 ℃ of reactions and be advisable in 2～3 hours.
Further; The present invention recommends described step (2) specifically according to carrying out as follows: chitosan magnetic micro-sphere is distributed in methyl-sulfoxide/NaOH mixed solution; Add epoxychloropropane then and down carry out priming reaction in 25～50 ℃ in vibration, fully filter the reaction back, washing to neutrality, drying obtain described activation afterproduct; Said methyl-sulfoxide/NaOH mixed solution is obtained according to volume ratio 1: 0.25～5 preparations by the sodium hydrate aqueous solution of methyl-sulfoxide and 0.1～2mol/L; The volume ratio that feeds intake of said epoxychloropropane and methyl-sulfoxide/NaOH mixed solution is 1～50: 100, and the mass volume ratio that feeds intake of chitosan magnetic micro-sphere and epoxychloropropane is 1g/1～10mL.
Further, in the above-mentioned steps (2), the NaOH final concentration is controlled at 0.5～1mol/L and is advisable in methyl-sulfoxide/NaOH mixed solution.
The present invention recommends described step (3) specifically according to carrying out as follows: will activate afterproduct and place 0.1～0.5mol/L endotoxin affinity ligand solution; Regulate pH to 10～12; Spend the night in 20～50 ℃ of oscillating reactions, reaction finishes, and filter the back, washing is extremely neutral, be drying to obtain described endotoxin adsorbing medium.
Further, the mass volume ratio of activation afterproduct and 0.1～0.5mol/L endotoxin affinity ligand solution is 0.1～1g/10mL.
The present invention also provides the method for using of described endotoxin adsorbing medium based on chitosan magnetic micro-sphere; Said method for using is specially: get the endotoxin adsorbing medium and wash with deoxycholic acid sodium water solution (the deoxycholic acid sodium water solution of preferred mass concentration 0.5～1.0%); Fully wash with apirogen water again; Be distributed to after the drying and contain in the endotoxic pending solution; Fully vibration or stirring; Externally-applied magnetic field takes out supernatant and is processing back solution then.
Compared with prior art; Beneficial effect of the present invention is: endotoxin adsorbing medium of the present invention not only has higher selectivity for endotoxin; And owing to introduced magnetisable material; Also need not adorn post during absorption handles; Externally-applied magnetic field can be with adsorbing medium and sample separation after treating adsorption equilibrium; Easy and simple to handle, can be used for endotoxic removal in the large number of biological goods.
Four, description of drawings
Fig. 1 is the sem photograph of embodiment 1 gained adsorbing medium;
Fig. 2 is the particle diameter distribution map of embodiment 1 gained adsorbing medium;
Fig. 3 is that the magnetic hysteresis of embodiment 1 gained adsorbing medium returns line chart;
Fig. 4 is embodiment 1 chitosan magnetic micro-sphere-histidine (MCM-His) curve of adsorption kinetics;
Fig. 5 is embodiment 1 and the adsorption effect figure of the different endotoxin adsorbing mediums of embodiment 2 gained.
Five, the specific embodiment
With specific embodiment technical scheme of the present invention is further specified below, but protection scope of the present invention is not limited thereto:
Embodiment 1: the preparation of shitosan-histidine endotoxin adsorbing medium (MCM-His)
(1) be in 2% the acetic acid solution with the ultrasonic 100mL of the being dispersed in volume fraction of 1.5g tri-iron tetroxide; (Ao Xing company produces to add the 3g shitosan; Molecular weight 300,000; Deacetylation 95%; Be that amino density is 5833 μ mol/g) be distributed to 100mL after it is dissolved fully and contain in the atoleine of 1mL sorbester p17; Dropping 3mL volume fraction is 25% glutaraldehyde solution behind the stirring 30min; 40 ℃ of reaction 2h; Using mass fraction is about 10% NaOH solution adjustment pH to 12; Be warming up to 70 ℃ simultaneously; Continue stirring reaction 2h; Product is dry through benzinum and hot ethanol washing final vacuum; Promptly get chitosan magnetic micro-sphere (MCM); Adopt its amino density of determination of acid-basetitration: get in the hydrochloric acid solution that microballoon 50mg is dispersed to 20ml 10mmol/L, oscillating reactions 1h, externally-applied magnetic field holds microballoon; Get clear liquid 15ml with the titration of 10mmol/L sodium hydroxide solution, calculate the back result and see table 1.
(2) step (1) gained chitosan magnetic micro-sphere 1.0g is distributed to the mixed solution (volume ratio 1: 1 of 20mL methyl-sulfoxide and NaOH; Naoh concentration is 1mol/L) in; Add the 3mL epoxychloropropane, spend deionised water behind 40 ℃ of oscillating reactions 4h to neutral, dry.
(3) step (2) products therefrom 0.5g is transferred in the 10mL 0.1mol/L histidine solution; With the 0.5M sodium hydroxide solution pH is adjusted to about 11; 40 ℃ of water-bath shaken overnight; Spend deionised water to neutral back kept dry and promptly get chitosan magnetic-histidine endotoxin adsorbing medium (MCM-His); Its amino density is seen table 1, and its sem photograph, particle diameter distribution map, magnetic hysteresis return line chart respectively like Fig. 1, Fig. 2, shown in Figure 3.
Embodiment 2: the preparation of shitosan-TEPA endotoxin adsorbing medium (MCM-TEPA)
(1) be in 5% the acetic acid solution with the ultrasonic 100mL of the being dispersed in volume fraction of 2.0g tri-iron tetroxide; (Ao Xing company produces to add the 4g shitosan; Molecular weight 300,000; Deacetylation 95%; Be that amino density is 5833 μ mol/g) be distributed to 200mL after it is dissolved fully and contain in the atoleine of 3mL sorbester p17; Dropping 4mL volume fraction is 25% glutaraldehyde solution behind the stirring 30min; 40 ℃ of reaction 1h; With mass fraction is about 10% NaOH solution adjustment pH to 12; Be warming up to 70 ℃ simultaneously; Continue stirring reaction 3h, product is dry through benzinum and hot ethanol washing final vacuum, promptly gets chitosan magnetic micro-sphere.
(2) step (1) gained chitosan magnetic micro-sphere 0.5g is distributed to the mixed solution (volume ratio 1: 1 of 10mL methyl-sulfoxide and NaOH; Naoh concentration is 1mol/L) in; Add the 3mL epoxychloropropane, spend deionised water behind 40 ℃ of oscillating reactions 4h to neutral, dry.
(3) step (2) products therefrom 0.5g is transferred in the 10mL 0.2mol/L TEPA solution; With the 0.5M sodium hydroxide solution pH is adjusted to about 11; 40 ℃ of water-bath shaken overnight; Spend deionised water to neutral back kept dry and promptly get chitosan magnetic-TEPA endotoxin adsorbing medium (MCM-TEPA), its amino density is seen table 1.
The amino density of the different adsorbing mediums of table 1
Embodiment 3: the use of adsorbing medium
Getting chitosan magnetic micro-sphere (MCM that embodiment 1 makes), chitosan magnetic micro-sphere-histidine (MCM-His that embodiment 1 makes) and chitosan magnetic micro-sphere-TEPA (MCM-TEPA that embodiment 2 makes) 50mg use mass fraction respectively is that separate three times in 1% NaTDC solution washing suction filtration or magnetic field; Again with apirogen water washing three times; Being distributed to 2mL after the drying contains in the endotoxic solution (running water); Vibration absorption 30min; Use the magnet attracts adsorbing medium, take out supernatant and measure endotoxin content.
Endotoxin content is measured the TAL colour developing matrix method that adopts; Chitosan magnetic micro-sphere-histidine (MCM-His) to endotoxic curve of adsorption kinetics as shown in Figure 4; The adsorption effect of different adsorbing mediums as shown in Figure 5; The adsorption equilibrium time of this adsorbing medium is shorter as can be seen from Figure 4; Within 10min, can efficiently go endotoxin to handle to sample fast.As can be seen from Figure 5; Also there is certain suction-operated in chitosan magnetic micro-sphere (MCM) itself to endotoxin; Because though glutaraldehyde and chitosan crosslinked reaction occur in aldehyde radical with amino, can not be fully, the gel pore of adding microballoon itself all can produce certain suction-operated to endotoxin.Adsorption capacity through histidine and the immobilized back of TEPA adsorbing medium is improved, and wherein is that the adsorption capacity of the adsorbing medium (MCM-TEPA) of aglucon has been brought up to 554.1EU/g with the TEPA.
Claims (10)
1. endotoxin adsorbing medium based on chitosan magnetic micro-sphere, it is characterized in that: the preparation method of described endotoxin adsorbing medium comprises the steps:
(1) earlier magnetic material is dispersed in the acetic acid solution, adds shitosan and be made into water I, again this water I is transferred in the atoleine that contains sorbester p17,, adopt inverse suspension method to make chitosan magnetic micro-sphere with glutaraldehyde as cross linker; Described magnetisable material is tri-iron tetroxide or iron;
(2) chitosan magnetic micro-sphere is distributed in the mixed solution of dimethyl sulfoxide (DMSO) and NaOH, adds the epoxychloropropane activation again, the deionized water washing obtains activating afterproduct to neutral;
(3) will activate afterproduct and place endotoxin affinity ligand solution immobilized, promptly obtain described endotoxin adsorbing medium based on chitosan magnetic micro-sphere; Described endotoxin affinity ligand is histidine, arginine, poly-D-lysine, PB or TEPA.
2. the endotoxin adsorbing medium based on chitosan magnetic micro-sphere as claimed in claim 1; It is characterized in that: described step (1) is specifically according to carrying out as follows: be distributed in the acetic acid solution magnetic material is ultrasonic; Stir behind the adding shitosan and obtain water I; The concentration of shitosan is 10～40g/L among the water I; Acetic acid concentration is 10～50mL/L, and the mass ratio that feeds intake of magnetic material and shitosan is 0.2～1: 1; Then water I is joined in the atoleine that contains 0.1～2vol% sorbester p17, water I is 1: 1～5 with the mixed volume ratio of the atoleine that contains 0.1～2vol% sorbester p17; Add glutaraldehyde behind the mixing; The glutaraldehyde that is added and the mol ratio of amino of chitosan are 1: 0.1～6; Finish adjustment temperature to 25～50 ℃ reaction 1～3 hour; Adjust system pH to 10～13 then; Be warming up to 50～80 ℃ simultaneously; Continued stirring reaction 1～3 hour, fully reaction back separated product obtains chitosan magnetic micro-sphere through washing, drying.
3. the endotoxin adsorbing medium based on chitosan magnetic micro-sphere as claimed in claim 2 is characterized in that: in the said step (1), chitosan concentration is 30～40g/L among the water I.
4. the endotoxin adsorbing medium based on chitosan magnetic micro-sphere as claimed in claim 2 is characterized in that: in the said step (1), the mol ratio of glutaraldehyde and amino of chitosan is 1: 1～2.
5. the endotoxin adsorbing medium based on chitosan magnetic micro-sphere as claimed in claim 2 is characterized in that: in the said step (1), adjustment system pH transfers to after 10～13, is warming up to 70 ℃ of reactions 2～3 hours.
6. the endotoxin adsorbing medium based on chitosan magnetic micro-sphere as claimed in claim 1; It is characterized in that: described step (2) is specifically according to carrying out as follows: chitosan magnetic micro-sphere is distributed in methyl-sulfoxide/NaOH mixed solution; Add epoxychloropropane then and down carry out priming reaction in 25～50 ℃ in vibration, fully filter the reaction back, washing to neutrality, drying obtain described activation afterproduct; Said methyl-sulfoxide/NaOH mixed solution is obtained according to volume ratio 1: 0.25～5 preparations by the sodium hydrate aqueous solution of methyl-sulfoxide and 0.1～2mol/L; The volume ratio that feeds intake of said epoxychloropropane and methyl-sulfoxide/NaOH mixed solution is 1～50: 100, and the mass volume ratio that feeds intake of chitosan magnetic micro-sphere and epoxychloropropane is 1g/1～10mL.
7. the endotoxin adsorbing medium based on chitosan magnetic micro-sphere as claimed in claim 6 is characterized in that: in the described step (2), the NaOH final concentration is at 0.8～1mol/L in control methyl-sulfoxide/NaOH mixed solution.
8. the endotoxin adsorbing medium based on chitosan magnetic micro-sphere as claimed in claim 1; It is characterized in that: described step (3) is specifically according to carrying out as follows: will activate afterproduct and place 0.1～0.5mol/L endotoxin affinity ligand solution; Regulate pH to 10～12; Spend the night in 20～50 ℃ of oscillating reactions, reaction finishes, and filter the back, washing is extremely neutral, be drying to obtain described endotoxin adsorbing medium.
9. the endotoxin adsorbing medium based on chitosan magnetic micro-sphere as claimed in claim 8 is characterized in that: in the described step (3), the mass volume ratio of said activation afterproduct and 0.1～0.5mol/L endotoxin affinity ligand solution is 0.1～1g/10mL.
10. the method for using of the endotoxin adsorbing medium based on chitosan magnetic micro-sphere as claimed in claim 1; Specifically carry out: get endotoxin adsorbing medium NaTDC solution washing according to following method; Fully wash with apirogen water again; Be distributed to after the drying and contain in the endotoxic pending solution; Fully vibration or stirring; Externally-applied magnetic field holds adsorbing medium then, takes out supernatant and is processing back solution.
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106397552A (en) * | 2016-09-06 | 2017-02-15 | 湖北中创医疗用品有限公司 | Method for removing endotoxin in recombinant protein A solution |
| CN106512968A (en) * | 2016-10-21 | 2017-03-22 | 浙江工业大学 | Magnetic imprinting material as well as preparation method and application thereof |
| CN106914219A (en) * | 2017-04-07 | 2017-07-04 | 安徽工业大学 | A kind of application of magnetic carbosphere Cr VI in waste water is removed |
| CN107308911A (en) * | 2016-04-27 | 2017-11-03 | 中国科学院城市环境研究所 | It is a kind of go water removal in pyrogenic substances new method |
| CN108579699A (en) * | 2018-04-17 | 2018-09-28 | 北京科技大学 | Adsorb the three-dimensional manometer fiber sponge sorbing material and preparation method of bacterial endotoxin |
| CN108982623A (en) * | 2018-05-23 | 2018-12-11 | 浙江工业大学 | A kind of aptamer biosensor and its preparation and application |
| CN109201016A (en) * | 2018-11-21 | 2019-01-15 | 淄博康贝医疗器械有限公司 | For adsorbing endotoxic Magnetic Microspheres-Carrier and preparation method thereof |
| CN109225146A (en) * | 2018-09-05 | 2019-01-18 | 桂林航天工业学院 | Chitosan-based compound emergency material of one kind and its preparation method and application |
| CN110170305A (en) * | 2019-04-30 | 2019-08-27 | 浙江工业大学 | A kind of separating technology of polylysine |
| CN111534644A (en) * | 2020-05-26 | 2020-08-14 | 广西大学 | Method for removing alkaline degradation pigments of sugar beet sugar-making dilute juice hexose |
| CN113000039A (en) * | 2021-03-19 | 2021-06-22 | 北京石油化工学院 | Preparation method of chromatography medium for removing endotoxin in biological nanoparticles |
| CN114558529A (en) * | 2022-02-28 | 2022-05-31 | 健帆生物科技集团股份有限公司 | Endotoxin latex microsphere and preparation method and application thereof |
| CN115739031A (en) * | 2021-09-02 | 2023-03-07 | 中国科学院理化技术研究所 | Application of chitosan or derivatives thereof in removing endotoxin in gelatin |
| CN116253809A (en) * | 2023-04-19 | 2023-06-13 | 广州润虹医药科技股份有限公司 | Method for removing endotoxin in chitosan |
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| CN107308911A (en) * | 2016-04-27 | 2017-11-03 | 中国科学院城市环境研究所 | It is a kind of go water removal in pyrogenic substances new method |
| CN106397552A (en) * | 2016-09-06 | 2017-02-15 | 湖北中创医疗用品有限公司 | Method for removing endotoxin in recombinant protein A solution |
| CN106512968A (en) * | 2016-10-21 | 2017-03-22 | 浙江工业大学 | Magnetic imprinting material as well as preparation method and application thereof |
| CN106914219A (en) * | 2017-04-07 | 2017-07-04 | 安徽工业大学 | A kind of application of magnetic carbosphere Cr VI in waste water is removed |
| CN108579699A (en) * | 2018-04-17 | 2018-09-28 | 北京科技大学 | Adsorb the three-dimensional manometer fiber sponge sorbing material and preparation method of bacterial endotoxin |
| CN108982623A (en) * | 2018-05-23 | 2018-12-11 | 浙江工业大学 | A kind of aptamer biosensor and its preparation and application |
| CN109225146A (en) * | 2018-09-05 | 2019-01-18 | 桂林航天工业学院 | Chitosan-based compound emergency material of one kind and its preparation method and application |
| CN109201016A (en) * | 2018-11-21 | 2019-01-15 | 淄博康贝医疗器械有限公司 | For adsorbing endotoxic Magnetic Microspheres-Carrier and preparation method thereof |
| CN110170305A (en) * | 2019-04-30 | 2019-08-27 | 浙江工业大学 | A kind of separating technology of polylysine |
| CN110170305B (en) * | 2019-04-30 | 2022-05-24 | 浙江工业大学 | Polylysine separation process |
| CN111534644A (en) * | 2020-05-26 | 2020-08-14 | 广西大学 | Method for removing alkaline degradation pigments of sugar beet sugar-making dilute juice hexose |
| CN113000039A (en) * | 2021-03-19 | 2021-06-22 | 北京石油化工学院 | Preparation method of chromatography medium for removing endotoxin in biological nanoparticles |
| CN113000039B (en) * | 2021-03-19 | 2023-07-18 | 北京石油化工学院 | Preparation method of chromatographic medium for removing endotoxin in biological nano-particles |
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| CN115739031B (en) * | 2021-09-02 | 2024-05-28 | 中国科学院理化技术研究所 | Application of chitosan or derivatives thereof in removal of endotoxin in gelatin |
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| CN116253809A (en) * | 2023-04-19 | 2023-06-13 | 广州润虹医药科技股份有限公司 | Method for removing endotoxin in chitosan |
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Application publication date: 20120215 |