CN1239210C - Endotoxin absorbing agent for blood perfusion and its preparation method - Google Patents
Endotoxin absorbing agent for blood perfusion and its preparation method Download PDFInfo
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Abstract
本发明涉及一种血液灌流用内毒素吸附剂及其制备方法。本发明是以球形琼脂凝胶为载体，固定有效量的亲和配基，粒度为0.45-1.0mm，吸附剂的胺基含量为40-100μmol/g吸附剂。以琼脂为原料，采取向甲苯-四氯化碳混合液中加琼脂水溶液的方法，得到球状琼脂，经碱性条件下环氧氯丙烷活化后与二胺反应，产物经与戊二醛反应，产生部分交联，得到强度较好的珠状琼脂作为吸附剂载体。载体与多粘菌素B等含胺基的配基反应后，经NaBH4还原，即得到内毒素吸附剂。本发明得到的吸附剂具有良好的血液相容性，可通过血液灌流的方法，高效吸附患者血液中的内毒素，属于新一代产品。The invention relates to an endotoxin adsorbent for hemoperfusion and a preparation method thereof. The invention uses the spherical agar gel as a carrier to immobilize an effective amount of affinity ligand, the particle size is 0.45-1.0mm, and the amine group content of the adsorbent is 40-100μmol/g adsorbent. Using agar as raw material, the method of adding agar aqueous solution to the toluene-carbon tetrachloride mixed solution is adopted to obtain spherical agar, which is activated by epichlorohydrin under alkaline conditions and reacts with diamine, and the product is reacted with glutaraldehyde. Partial cross-linking occurs, and the beaded agar with better strength is obtained as the adsorbent carrier. After the carrier reacts with polymyxin B and other amine-containing ligands, it is reduced by NaBH 4 to obtain the endotoxin adsorbent. The adsorbent obtained in the present invention has good blood compatibility, can efficiently adsorb endotoxin in patient's blood through the method of hemoperfusion, and belongs to a new generation product.
Description
Technical field
The present invention relates to biomedical materials field, particularly a kind of hemoperfusion is with endotoxin absorbent and preparation method.
Background technology
Endotoxemia is one of clinical modal deadly disease, and mortality rate can reach 40%-90%, all has every year 100000 people of surpassing to die from this disease [Skelter et al in the U.S., Arch.Microbiol.1995,164,383-389.], still do not have effective Therapeutic Method clinically.Endotoxemia is to cause owing to the endotoxin on the outer cell wall of gram negative bacteria is discharged in the blood.Endotoxin causes that series reaction finally causes organ necrosis, irreversible shock and death after entering blood.How accomplishing to remove in time, effectively or the intravital endotoxin of destruction patient, is the key issue of treatment endotoxemia.Developed the molecular biology preparation of multiple anti-endotoxin in recent years abroad, but because the complex manufacturing of antibody, the medicine source is few, cost is high, price is very expensive, and still do not have up to now a kind of can pass through III phase clinical experiment [Yao Yongming etc. Chinese critical illness emergency medicine, 1999,11:456].
To some great difficult sexually transmitted disease (STD) diseases, the blood purification therapy has unique curative effect, even miracle as " coming back to life " can appear, it is the indispensable important means of clinical treatment, wherein the hemoperfusion therapy is to rely on adsorbent directly to adsorb toxic substance or the morbid substance of removing in the blood, reaches the purpose that purifies the blood, alleviates and treat disease.In recent years, the whole blood perfusion therapy receives unprecedented in the world concern owing to its expense is low, thinks that it is blood purification main development tendency [James F.et al., Blood Purif.2002,20:81-86].This therapy has been used for treatment of diseases such as lupus erythematosus, serious symptom poisoning with hypnotic, rheumatoid, receives curative effect preferably.The method treatment endotoxemia that the foreign study person has begun one's study and utilized blood purification, the research worker of Japan is coated on polymyxin B on the inwall of blood filter doughnut, can remove endotoxin [the Tani T in the blood plasma preferably, et al., Atificial Organs 22 (12): 1038-1044 (1998)].The research worker of University of Vienna is utilized self-designed MDS system, and polymine is connected on the enterprising action thing experiment of cellulose, removes endotoxin effect also better [K.von Appen, et al., Atif.Organs, 20 (5): 420-425 (1996)].But above-mentioned two kinds of methods need be carried out plasma perfusion with blood plasma with after blood cell separates, and expense is very expensive, is not suitable for promoting at home.The domestic activated carbon whole blood perfusion method of only utilizing is adsorbed endotoxic zoopery report, and show with the activated carbon perfusion and can directly adsorb endotoxin in the blood, but DeGrain [Wang Jinda. Chinese critical illness emergency medicine, 1998,10:578].With spherical agar is that the hemoperfusion of carrier does not appear in the newspapers with endotoxin absorbent.
Summary of the invention
The invention provides a kind of endotoxin absorbent that is used for hemoperfusion, it has good blood compatibility, can efficiently adsorb the endotoxin in the blood samples of patients by the method for hemoperfusion, can be used for whole blood perfusion, also can be used for plasma perfusion.
The present invention is to be carrier with spherical agar gel, and fixedly the affinity ligand of effective dose constitutes, and granularity is 0.45-1.0mm, and the amido content of adsorbent is 40-100 μ mol/g adsorbent.
Described affinity ligand is polymyxin B, arginine, lysine, histidine or polylysine.。
The molecular weight of described polylysine is 1.0-4.0 ten thousand.
Described hemoperfusion comprises the steps: with the preparation method of endotoxin absorbent
(1) the spherical agar carrier of preparation:
Aqueous agar solution heat fused with 2～10%, pour in toluene-carbon tetrachloride system, add Tween 80, stir, make agar solution in organic facies, be dispersed into drop, 60～90 ℃ were reacted 2-4 hour, after the cooling, topple over and the upper strata organic solvent, the agar ball of screening 0.45-1.0mm, behind the water thorough washing, as adsorbing agent carrier.
(2) epoxychloropropane activated carrier:
Carrier is in 2M NaOH solution, and 30-50 ℃ is descended and epichlorohydrin reaction 1-4 hour, washes with water to neutrality, removes unreacted epoxychloropropane, obtains the carrier that epoxychloropropane is modified.
(3) aminolysis reaction
The carrier that epoxychloropropane is modified in the aqueous solution of pH 9～12 under 50-70 ℃, with diamine reactant 1-4 hour.Add ethanolamine solutions and at room temperature react 1-6h with sealing unreacted epoxy groups group.
(4) cross-linking reaction
The gel ball that adds aminolysis in the phosphate buffer solution of pH7.4, add 25% glutaraldehyde, room temperature vibration 1-4 hour, 30% amido and glutaraldehyde cross-linking in the aminolysis carrier, to increase the intensity of carrier, 70% amido links to each other with glutaraldehyde, leaves the suspension aldehyde radical, can generate western Buddhist alkali with the primary amine groups in the part, aglucon is incorporated on the carrier.The aglucon content of method introducing is higher thus.Final rinse water.
(5) immobilized aglucon
Agar ball after crosslinked was reacted 1-2 hour with aglucon under pH9-12, make the primary amine groups that hangs in aldehyde radical and the aglucon generate western Buddhist alkali, the NaCl with 1M washes to neutrality then.
(6) reduction: the gel ball behind the immobilized aglucon adds sodium borohydride in the phosphate buffer solution of pH7.4, and room temperature was vibrated 2～6 hours, and the reaction back is extremely neutral with sodium chloride and the water flushing of 1M.
Described hemoperfusion with the material proportion of each step of preparation method of endotoxin absorbent is:
Toluene: carbon tetrachloride is 1～4: 1, v/v; The NaOH of agar ball: 2M: epoxychloropropane is 1: 1～4: 0.5～2, w/v/v; The agar ball: diamidogen is 5: 0.1～0.5, w/w; The consumption of 25% glutaraldehyde is the 25%-150% of amination agar ball, v/w; NaBH
4: the agar ball is 0.1～0.5: 5, w/w.
Described diamidogen is ethylenediamine, propane diamine, butanediamine, pentanediamine or hexamethylene diamine.
Described hemoperfusion is used for clinical whole blood perfusion with endotoxin absorbent and removes the blood endotoxin, diseases such as treatment endotoxemia.
Use described adsorbent to carry out the method for hemoperfusion, comprise the steps: under the room temperature, get adsorbent and pack in the perfusion post endotoxemia patient's whole blood into, with the flow velocity perfusion of 15ml/min 2 hours, adopt azo development process to detect endotoxin concns before and after the absorption; Or under the room temperature, adsorbent is contained in the endotoxic blood plasma direct the adding, static adsorption 20 minutes, adsorbent: serum is 1: 20, w/v.
Blood plasma with static adsorption endotoxemia patient of the present invention can reach 70% to the endotoxin clearance rate, and visible adsorbent has higher removing ability to endotoxin.
Adsorbent of the present invention has good blood compatibility, can efficiently adsorb the endotoxin in the blood samples of patients by the method for hemoperfusion, can be used for whole blood perfusion, also can be used for plasma perfusion.The present invention is the whole blood perfusion endotoxin absorbent, by diseases such as whole blood perfusion therapy for treating endotoxemias.Do not need blood cell and blood plasma to be separated and be different from external plasma perfusion method, thereby greatly reduce the treatment cost.
Description of drawings
Fig. 1. the crosslinked front and back of agar ball carrier thermogravimetric curve.
Fig. 2. the crosslinked front and back of agar ball carrier difference quotient thermogravimetric curve.
The specific embodiment
Followingly the present invention is described, but they do not impose any restrictions to the present invention with specific embodiment.
Embodiment 1
The preparation of the spherical agar gel carrier of 1-1
The 500ml there-necked flask is placed 60 ℃ of water-baths, in bottle, add 100ml toluene, the 50ml carbon tetrachloride, the 0.5ml Tween 80 evenly stirs.
Take by weighing 4 gram agar powders and add distilled water 30ml, heat fused is poured the agar of fusing in toluene-carbon tetrachloride system into, stirs, and makes agar solution be dispersed into the drop of suitable size in organic facies.Cool to room temperature is toppled over and the upper strata organic solvent, and the agar ball of screening 0.45-1.0mm after washing with water, moves into conical flask, and 4 ℃ of hygrometric states are preserved.
The activation of 1-2 epoxychloropropane
Get agar ball 20.0 grams, the sodium hydroxide that adds 29.6 milliliters of 2M, the epoxychloropropane that adds 13.3 milliliters again, reacted 2 hours down at 40 ℃, be washed with water to neutrality, and the thorough remaining epoxychloropropane of flush away, obtaining the activatory gel ball of epoxy, the epoxy radicals supported quantity is 110.2 μ mol/g gel balls.
The 1-3 aminolysis
1-3-1 adds 1 gram 1 in the 80ml distilled water, regulating pH value is 10, adds the activatory gel ball of 20 gram epoxies, and reaction is 2 hours under 50 ℃.The water flushing of reaction back obtains the gel ball of ethylenediamineization to neutral.The ethylenediamine supported quantity is 90.6 μ mol/g gel balls.The product and the 0.1g ethanolamine solutions that obtain are at room temperature reacted 2h with sealing unreacted epoxy groups group.
1-3-2 adds 2 grams 1 in the 80ml distilled water, the 3-propane diamine, and regulating pH value is 11, adds the activatory gel ball of 20 gram epoxies, reaction is 3 hours under 60 ℃.The water flushing of reaction back obtains the gel ball of propane diamineization to neutral.The propane diamine supported quantity is 92.8 μ mol/g gel balls.The product and the 0.1g ethanolamine solutions that obtain are at room temperature reacted 3h with sealing unreacted epoxy groups group.
1-3-3 adds 2 grams 1 in the 80ml distilled water, the 4-butanediamine, and regulating pH value is 12, adds the activatory gel ball of 20 gram epoxies, reaction is 1 hour under 70 ℃.The water flushing of reaction back obtains the gel ball of butanediamineization to neutral.The butanediamine supported quantity is 91.3 μ mol/g gel balls.The product and the 0.1g ethanolamine solutions that obtain are at room temperature reacted 5h with sealing unreacted epoxy groups group.
1-3-4 adds 2 grams 1 in the 80ml distilled water, the 5-pentanediamine, and regulating pH value is 9, adds the activatory gel ball of 20 gram epoxies, reaction is 4 hours under 50 ℃.The water flushing of reaction back obtains the gel ball of pentanediamineization to neutral.The pentanediamine supported quantity is 90.9 μ mol/g gel balls.The product and the 0.1g ethanolamine solutions that obtain are at room temperature reacted 1h with sealing unreacted epoxy groups group.
1-3-5 adds 2 grams 1 in the 80ml distilled water, the 6-hexamethylene diamine, and regulating pH value is 10, adds the activatory gel ball of 20 gram epoxies, reaction is 3 hours under 50 ℃.The water flushing of reaction back obtains the gel ball of hexamethylene diamineization to neutral.The hexamethylene diamine supported quantity is 92.9 μ mol/g gel balls.The product and the 0.1g ethanolamine solutions that obtain are at room temperature reacted 3h with sealing unreacted epoxy groups group.
1-4 introduces glutaraldehyde arm and partial cross-linked reaction
1-4-1 adds the 20 two aminating carriers of restraining oneself in the phosphate buffer solution of 50 milliliters of 0.05M pH=7.4, drip 15 milliliter 25% glutaraldehyde under stirring condition, room temperature vibration 2 hours.The residue aldehyde radical is 74.3 μ mol/ grams on the agar ball.The reaction back is washed with 0.1M phosphate buffer solution and water.
1-4-2 changes hexamethylene diamine into pentanediamine under the 1-4-1 condition, vibrated 1 hour, and the residue aldehyde radical is 70.3 μ mol/ grams on the agar ball.
1-4-3 changes hexamethylene diamine into butanediamine under the 1-4-1 condition, vibrated 1 hour, and the residue aldehyde radical is 68.3 μ mol/ grams on the agar ball.
1-4-4 changes hexamethylene diamine into propane diamine under the 1-4-1 condition, vibrated 4 hours, and the residue aldehyde radical is 74.3 μ mol/ grams on the agar ball.
1-4-5 changes hexamethylene diamine into ethylenediamine under the 1-4-1 condition, vibrated 1 hour, and the residue aldehyde radical is 78.3 μ mol/ grams on the agar ball.
The immobilized aglucon of 1-5
1-5-1 adds 0.2 gram polymyxin B in the aqueous solution of 20 milliliters of pH11, adds 1-4-2 agar ball 5 grams after crosslinked, room temperature vibration 2 hours, and the sodium chloride with 1M washes then.Adsorbent amido supported quantity is 44.8 μ mol amido/g.
1-5-2 adds 0.2 gram arginine in the aqueous solution of 20 milliliters of pH9, adds 1-4-3 agar ball 5 grams after crosslinked, room temperature vibration 1 hour, and the sodium chloride with 1M washes then.Adsorbent amido supported quantity is 69.5 μ mol amido/g.
1-5-3 adds 0.2 gram lysine in the aqueous solution of 20 milliliters of pH10, adds 1-4-4 agar ball 5 grams after crosslinked, room temperature vibration 1 hour, and the sodium chloride with 1M washes then.Adsorbent amido supported quantity is 87.6 μ mol amido/g.
1-5-4 adds 0.2 gram polylysine in the aqueous solution of 20 milliliters of pH12, adds 1-4-1 agar ball 5 grams after crosslinked, room temperature vibration 2 hours, and the sodium chloride with 1M washes then.Adsorbent amido supported quantity is 74.5 μ mol amido/g.
1-5-5 adds 0.2 gram histidine in the aqueous solution of 20 milliliters of pH9, adds 1-4-5 agar ball 5 grams after crosslinked, room temperature vibration 2 hours, and the sodium chloride with 1M washes then.Adsorbent amido supported quantity is 94.5 μ mol amido/g.
The 1-6 reduction
1-6-1 adds the sodium borohydride of 0.3g in the phosphate buffer solution of 10 milliliters of 0.1M pH7.4, the 1-5-4 gel ball behind the immobilized aglucon of adding 5g, and room temperature vibration 4 hours, the reaction back is washed to neutral with sodium chloride and the water of 1M.Obtain endotoxin absorbent.
Under these conditions, change 1-5-4 into 1-5-1 respectively, 1-5-2,1-5-3,1-5-5 carries out sodium borohydride reduction, obtains serial endotoxin absorbent.
Glutaraldehyde cross-linking is to the influence of agar ball carrier character
2-1 gets before the 50mg glutaraldehyde cross-linking 1-4 agar ball behind the 1-1 and glutaraldehyde cross-linking respectively, cleans, and grinds behind the vacuum drying.Adopt the TG209 thermogravimetric analyzer to measure the thermogravimetric curve of carrier ball, 14.0 ℃/min of programming rate, 20～620 ℃ of intensification scopes.After crosslinked, the peak value of thermal weight loss is increased to 295.8 ℃ from 277.4 ℃, the heat stability of this crosslinked back of explanation agar ball be improved (seeing Fig. 1,2).Fig. 1. the crosslinked front and back of agar ball carrier thermogravimetric curve.Fig. 2. the crosslinked front and back of agar ball carrier difference quotient thermogravimetric curve.
DTG is an a kind of most important method of estimating the macromolecular material heat stability.。From the thermogravimetric curve of Fig. 1 as can be seen, the ratio of crosslinked back thermal weight loss reduces to 48.05% by 67.06%, and this explanation has reduced through cross-linked gel ball thermal dehydration amount; On the other hand, from the difference quotient thermogravimetric curve of Fig. 2 as can be seen, crosslinked after the peak value of thermal weight loss be increased to 295.8 ℃ from 277.4 ℃, this heat stability that crosslinked back gel ball also is described has improved.
2-2 is accurately measured the agar ball of the crosslinked front and back of 30ml, and the diameter 1cm bottom of packing into has in the glass column of frosted plate, and the top adding distilled water from post keeps distilled water steady flow in post, measures the rate of outflow of distilled water with stopwatch.Flowing velocity before crosslinked is 38.4 ml/min, is 66.8 ml/min after crosslinked.After crosslinked, the flowing velocity of water in post obviously accelerated, and illustrates that the hardness of crosslinked back agar ball is improved significantly.
Embodiment 3
The blood compatibility experiment
Get 2 milliliters of the adsorbents of embodiment 1 preparation, in normal saline, soak in the perfusion post of packing into after 12 hours, inject 5 milliliters of rabbit whole bloods that are mixed with anticoagulant, with the flow velocity perfusion of 15ml/min 2 hours with syringe.Simultaneously with empty perfusion post post in contrast.Measure the variation of perfusion front and back each composition of blood by the MEK-6318K cellanalyzer.The result shows that before and after the perfusion, various blood constituents change little, and the percentage number average of decline is in 5%, and this shows that this series adsorbent has blood compatibility preferably, can be used for whole blood perfusion.
Embodiment 4
Endotoxic adsorption experiment in the animal blood slurry
4-1 gets 0.05 and restrains reduction back 1-5-3 adsorbent, adds the blood plasma of 1 milliliter of endotoxemia model rat, room temperature vibration 20 minutes, endotoxin concns before and after the employing azo development process detection absorption.Endotoxin concns 0.635 EU/ml (EU is an endotoxin unit) in the blood plasma before the absorption, absorption back 0.220EU/ml, and endotoxin concns is 0.18～0.22 EU/ml in the normal rat blood plasma.
4-2 gets 0.05 and restrains reduction back 1-5-5 adsorbent, adds the blood plasma of 1 milliliter of endotoxemia model rat, room temperature vibration 20 minutes, endotoxin concns before and after the employing azo development process detection absorption.Endotoxin concns 0.635 EU/ml in the blood plasma before the absorption, absorption back 0.380EU/ml.
4-3 gets 1ml reduction back 1-5-4 adsorbent and packs in 1 * 5ml perfusion device, and with the medical alcohol washing of flowing repeatedly, the washing of flowing repeatedly of reuse distilled water, redistilled water, normal saline is flowed with no heat source water 100ml at last and washed.With crossing current pump control flow velocity 15ml/min, with 20 ml endotoxin model rabbit whole bloods (in add anticoagulant) perfusion 2 hours.Adopt azo development process to detect perfusion front and back endotoxin concns.Plasma endotoxin content 0.685EU/ml before the perfusion, blood plasma endotoxin content 0.122EU/ml behind the perfusion.Normal rabbit plasma endotoxin content 0.067-0.135Eu/ml.
Endotoxic adsorption experiment in the human plasma
4-4 gets 0.05 gram reduction back 1-5-4 adsorbent, 1 milliliter of endotoxemia patient's of adding blood plasma, and room temperature vibration 20 minutes adopts azo development process to detect absorption front and back endotoxin concns.Endotoxin concns 0.683EU/ml in the blood plasma before the absorption, absorption back 0.200EU/ml, and endotoxin concns is 0.18～0.22EU/ml among the human normal plasma, this illustrates that this adsorbent has strong absorbability to endotoxin.
4-5 gets 0.05 gram reduction back 1-5-1 adsorbent, 1 milliliter of endotoxemia patient's of adding blood plasma, and room temperature vibration 20 minutes adopts azo development process to detect absorption front and back endotoxin concns.Endotoxin concns 0.523EU/ml in the blood plasma before the absorption, absorption back 0.300EU/ml.
4-6 gets 0.05 gram reduction back 1-5-2 adsorbent, 1 milliliter of endotoxemia patient's of adding blood plasma, and room temperature vibration 20 minutes adopts azo development process to detect absorption front and back endotoxin concns.Endotoxin concns 0.523EU/ml in the blood plasma before the absorption, absorption back 0.324EU/ml.
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