WO2018053696A1 - Nanocarrier for treating endotoxemia - Google Patents
Nanocarrier for treating endotoxemia Download PDFInfo
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- WO2018053696A1 WO2018053696A1 PCT/CN2016/099518 CN2016099518W WO2018053696A1 WO 2018053696 A1 WO2018053696 A1 WO 2018053696A1 CN 2016099518 W CN2016099518 W CN 2016099518W WO 2018053696 A1 WO2018053696 A1 WO 2018053696A1
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- 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
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/282—Porous sorbents
- B01J20/285—Porous sorbents based on polymers
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- 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
- B01J20/30—Processes for preparing, regenerating, or reactivating
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/08—Styrene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/34—Monomers containing two or more unsaturated aliphatic radicals
- C08F212/36—Divinylbenzene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F218/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an acyloxy radical of a saturated carboxylic acid, of carbonic acid or of a haloformic acid
- C08F218/02—Esters of monocarboxylic acids
- C08F218/04—Vinyl esters
- C08F218/08—Vinyl acetate
Definitions
- ETM Endotoxemia in humans can be divided into two categories: exogenous and endogenous.
- Exogenous endotoxemia is mainly caused by endotoxin released by lysis of bacteria after Gram-negative bacteria infection.
- Endogenous endotoxemia is caused by abnormal metabolism of the intestinal flora or entry into the systemic circulation through an abnormal route.
- LPS lipopolysaccharide
- GNB Gram-negative bacteria
- Lipopolysaccharide has a molecular weight of more than 10,000 and consists of three parts. Similar to phospholipids, it has a hydrophilic head and a hydrophobic tail. Its fatty acyl chain is embedded in the outer membrane of the bacteria, and its sugar chain is exposed to the surface of the bacteria, and its toxic component is mainly lipidoid A.
- Lipid A is a glycolipid that constitutes endotoxin activity and is covalently linked to the heteropolysaccharide chain and released when the bacteria break. A series of reactions caused by release into the blood, eventually leading to systemic damage, irreversible shock and death. LPS interacts with proteins on cell membranes or receptors on specific cell membranes, such as endothelial cells, monocytes, macrophages, etc., causing them to release large amounts of mediators such as oxygen free radicals, arachidonic acid metabolites, platelet activating factor. , 1L-1, 1L-6, 1L-8 and TNF- ⁇ , etc. These mediators are important for the pathology of endotoxin-induced organ damage and septic shock.
- PMB Polymyxin-B immobilized fiber column
- Nanocarriers for clinical use are reported in the literature as liposomes as nanocarriers.
- Liposomes are a membrane material and phospholipids are their main constituents. Its role is to load drugs into the body to play a therapeutic role, liposomes will be ablated in the body. There is no function of adsorbing pathogenic substances to carry the human body.
- the blood perfusion device has been in clinical use for several decades as an auxiliary medical device, and the adsorbent used during the development of activated carbon to macroporous adsorption resin.
- a macroporous adsorption resin Currently widely used is a macroporous adsorption resin. Its role is to carry out the pathogenic substances in the blood out of the body through the blood purification route.
- the inventors have developed a blood perfusion device that is designed to remove blood endotoxin and treat endotoxemia in products to be marketed.
- the object of the present invention is to propose a nano-adsorbing resin carrier technical solution dedicated to endotoxemia, which provides a new therapeutic route for rapid treatment of endotoxemia.
- the nano carrier for treating endotoxemia is a powder of a micro-nano-sized particle size adsorption resin of an amphiphilic glycosylated resin having a polyvinyl acetate as a skeleton; or an amphiphilic structure based on polyvinyl acetate.
- the micro-nano-sized elemental powder of the glycosylated adsorption resin and the glycosylated styrene-divinylbenzene are mixed powders of the micro-nano-sized particle powder of the skeleton lipophilic adsorption resin.
- the elemental or mixed powder has a particle size ranging from 50 to 1000 nm.
- This embodiment can be used to prepare a powder for oral or skin application, or to be compressed into a suppository.
- Embodiment 2 of the present invention the particle size of the elemental or mixed powder ranges from 100 to 200 nm.
- This embodiment can be used for making an injection or an infusion agent for direct use in a patient's site or direct blood for rescue measures.
- the third embodiment of the present invention the powder of the present invention can be used as a single substance, and when mixed, the composition ratio of the mixed powder is 1:1.
- the nanocarrier of the present invention can be directly administered orally, or can be orally administered as a sustained release capsule, or as an injection, an infusion solution, or as a suppository.
- the powder of the present invention can be used in combination with a blood perfusion device filled with a macroporous adsorption resin of the same type of conventional particles.
- the nanocarrier film material with phospholipid as a main component in the prior art has substantial difference: the nanocarrier of the invention is a powder and does not degrade or ablate in vivo; the nanometer powder has high specific surface area and strong Surface adsorption; can penetrate human tissues including blood vessel walls and cell membranes, and has strong affinity adsorption on hydrophobic heads and hydrophilic tails of mucopolysaccharide molecules on bacterial cell walls and blood; adsorption of lipopolysaccharide on bacterial cell walls can promote bacteria The cells are inactivated and have a bactericidal effect; the nanocarrier of the invention can be quickly adsorbed from the blood and carried to carry out the mucopolysaccharide molecules, thereby avoiding binding to the receptors in the body; thereby achieving the purpose of treating endotoxemia.
- amphiphilic or lipophilic glycosylated macroporous medical resin nano-sized particle powder used in the invention has excellent blood compatibility, and has no neurotoxicity and nephrotoxicity, and is in treatment. It also does not cause a loss of a large amount of plasma protein in the blood; it overcomes the disadvantages of the polymyxin B-supported fiber column used in the prior art in Japan.
- the nano-scale carrier powder of the invention is a synthetic chemical product, which has chemical stability in the human environment, and the carrier function is the physical adsorption of Edwardian force in the surface micro-environment of the substance, and does not participate in any biochemical reaction in the body. It provides a safe, effective, fast and inexpensive clinical treatment for endotoxemia.
- the nano-materials of the present invention are capable of removing pathogenic target substances in vivo, which are lipopolysaccharides, and have similar adsorption and scavenging effects on other pathogenic substances having similar lipopolysaccharide molecules and hydrophilic substances on the other side; and other diseases caused by them Have the same therapeutic effect.
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Abstract
A nanocarrier for treating endotoxemia being a micro-nano medical polymeric adsorbent powder of an amphiphilic glycosylated resin with polyvinyl acetate backbone. Alternatively, the nanocarrier is a micro-nano amphiphilic polymeric adsorbent simple powder of an amphiphilic glycosylated resin with a polyvinyl acetate backbone and a micro-nano lipophilic polymeric adsorbent complex powder with a glycosylated styrene-divinylbenzene backbone.
Description
所属技术领域：医用材料Technical field: Medical materials
现有技术背景Prior art background
人体的内毒素血症(Endotoxemia，ETM)可分为两类：外源性和内源性。Endotoxemia (ETM) in humans can be divided into two categories: exogenous and endogenous.
外源性内毒素血症主要是由革兰氏阴性菌感染后菌体裂解所释放出的内毒素引起。Exogenous endotoxemia is mainly caused by endotoxin released by lysis of bacteria after Gram-negative bacteria infection.
内源性内毒素血症是由于肠道菌群代谢功能异常或通过非正常途径进入体循环所致。Endogenous endotoxemia is caused by abnormal metabolism of the intestinal flora or entry into the systemic circulation through an abnormal route.
细菌内毒素(Endotoxin，ET)其主要化学成分为脂多糖(lipopolysaccharide，LPS)是革兰氏阴性杆菌(Gram-negative bacteria，GNB)不仅在细胞死亡时，而且在细胞生长和分裂过程中或细胞壁崩解时释放出的毒性物质。脂多糖分子量大于10000，由三部分组成，与磷脂相似，有一亲水头和一疏水尾。其脂酰链嵌入细菌外膜，其糖链暴露于细菌的表面，其毒性成分主要为类脂质A。脂质A(Lipid A)为构成内毒素活性的糖脂，以共价键联结到杂多糖链，当细菌崩裂时释出。释放到血液中引起的一系列反应，最终导致全身性损害，不可逆休克而死亡。LPS通过与细胞膜上的蛋白质或特殊细胞膜上的受体，如内皮细胞、单核细胞、巨噬细胞等作用，导致他们大量释放介质如氧自由基、花生四烯酸的代谢产物，血小板激活因子，1L-1、1L-6、1L-8及TNF-α等，这些介质对内毒素引起器官受损和脓毒性休克的病理学十分重要。The main chemical component of endotoxin (ET) is lipopolysaccharide (LPS), which is a Gram-negative bacteria (GNB) not only in cell death, but also during cell growth and division or cell wall. Toxic substances released during disintegration. Lipopolysaccharide has a molecular weight of more than 10,000 and consists of three parts. Similar to phospholipids, it has a hydrophilic head and a hydrophobic tail. Its fatty acyl chain is embedded in the outer membrane of the bacteria, and its sugar chain is exposed to the surface of the bacteria, and its toxic component is mainly lipidoid A. Lipid A is a glycolipid that constitutes endotoxin activity and is covalently linked to the heteropolysaccharide chain and released when the bacteria break. A series of reactions caused by release into the blood, eventually leading to systemic damage, irreversible shock and death. LPS interacts with proteins on cell membranes or receptors on specific cell membranes, such as endothelial cells, monocytes, macrophages, etc., causing them to release large amounts of mediators such as oxygen free radicals, arachidonic acid metabolites, platelet activating factor. , 1L-1, 1L-6, 1L-8 and TNF-α, etc. These mediators are important for the pathology of endotoxin-induced organ damage and septic shock.
医学研究表明：血液中内毒素的元凶是LPS，LPS的水平与癌症、创伤、烧伤、急性炎症等疾病所引起的多脏器衰竭(MODS)及全身
性炎症反应(SIRS)等病症密切相关，是导致ETM的主要原因。为此众多专家和学者试图寻找一种安全、有效、快捷、廉价的治疗ETM的方法和手段具有重要而深远的意义。Medical research shows that the main cause of endotoxin in the blood is LPS, the level of LPS and multiple organ failure (MODS) caused by diseases such as cancer, trauma, burns, acute inflammation and whole body.
Conditions such as sexual inflammatory response (SIRS) are closely related and are the main cause of ETM. To this end, many experts and scholars have tried to find a safe, effective, fast and inexpensive method and means of treating ETM, which has important and far-reaching significance.
日本早在二十世纪九十年代就将多粘菌素B(Polymyxin-B，PMB)固载纤维柱(PMX-F)应用于临床上广泛使用血液灌流多脏器功能障碍综合征患者取得一定的疗效。然而PMB本身具有神经毒性和肾毒性，且在血液灌流治疗时会造成血液中大量血浆蛋白的损失。Japan used Polymyxin-B (PMB) immobilized fiber column (PMX-F) as a clinically widely used patient in the multi-organ dysfunction syndrome of blood perfusion in the 1990s. Efficacy. However, PMB itself is neurotoxic and nephrotoxic, and causes a large loss of plasma protein in the blood during blood perfusion therapy.
纳米载体用于临床见于文献报道的都是以脂质体作为纳米载体。脂质体是一种膜材料，磷脂是其主要成分。其作用是将药物载入人体发挥治疗作用，脂质体在体内会被消融。没有吸附致病物质载出人体的功能。Nanocarriers for clinical use are reported in the literature as liposomes as nanocarriers. Liposomes are a membrane material and phospholipids are their main constituents. Its role is to load drugs into the body to play a therapeutic role, liposomes will be ablated in the body. There is no function of adsorbing pathogenic substances to carry the human body.
血液灌流器作为辅助性医疗器械已经在临床应用了数十年，期间使用的吸附剂经过了活性炭到大孔吸附树脂发展过程。目前广为应用的是大孔吸附树脂。其作用是通过血液净化途径，将血液中的致病物质载出体外。发明人已经研发出有待上市的产品中有专用于清除血液内毒素，治疗内毒素血症的血液灌流器。The blood perfusion device has been in clinical use for several decades as an auxiliary medical device, and the adsorbent used during the development of activated carbon to macroporous adsorption resin. Currently widely used is a macroporous adsorption resin. Its role is to carry out the pathogenic substances in the blood out of the body through the blood purification route. The inventors have developed a blood perfusion device that is designed to remove blood endotoxin and treat endotoxemia in products to be marketed.
目前没有用于治疗内毒素血症的吸附树脂纳米载体的文献报道。发明内容：There are currently no reports on the adsorption of resin nanocarriers for the treatment of endotoxemia. Summary of the invention:
本发明的目的是提出专用于内毒素血症的纳米吸附树脂载体技术方案，为快速治疗内毒素血症提供一种新的治疗途径。The object of the present invention is to propose a nano-adsorbing resin carrier technical solution dedicated to endotoxemia, which provides a new therapeutic route for rapid treatment of endotoxemia.
本发明专用于治疗内毒素血症的纳米载体是以聚醋酸乙烯酯为骨架的双亲性糖基化树脂的微纳米级粒径吸附树脂的粉料；或以聚醋酸乙烯酯为骨架的双亲性糖基化吸附树脂的微纳米级粒径的单质粉料和糖基化苯乙烯-二乙烯苯为骨架亲脂性吸附树脂微纳米级粒径粉料的混合粉料。
The nano carrier for treating endotoxemia according to the present invention is a powder of a micro-nano-sized particle size adsorption resin of an amphiphilic glycosylated resin having a polyvinyl acetate as a skeleton; or an amphiphilic structure based on polyvinyl acetate. The micro-nano-sized elemental powder of the glycosylated adsorption resin and the glycosylated styrene-divinylbenzene are mixed powders of the micro-nano-sized particle powder of the skeleton lipophilic adsorption resin.
本发明的实施例之一：单质或混和粉料的粒径范围是50-1000nm。One of the embodiments of the present invention: the elemental or mixed powder has a particle size ranging from 50 to 1000 nm.
本实施例可以用于制作口服或皮肤涂覆使用的粉剂，或者压制成栓剂。This embodiment can be used to prepare a powder for oral or skin application, or to be compressed into a suppository.
本发明的实施例之二：单质或混和粉料的粒径范围是100-200nm。Embodiment 2 of the present invention: the particle size of the elemental or mixed powder ranges from 100 to 200 nm.
本实施例可以用于制作注射剂或者输液剂直接用于病患部位或者直接血液给予用于抢救措施。This embodiment can be used for making an injection or an infusion agent for direct use in a patient's site or direct blood for rescue measures.
本发明的实施例之三：本发明粉料可以单质使用，在混合使用时，混合粉料的成分比为1∶1。The third embodiment of the present invention: the powder of the present invention can be used as a single substance, and when mixed, the composition ratio of the mixed powder is 1:1.
在临床使用时，本发明纳米载体可以直接口服，或者制成缓释胶囊口服，或制成注射剂、输液剂，或者制成栓剂。In clinical use, the nanocarrier of the present invention can be directly administered orally, or can be orally administered as a sustained release capsule, or as an injection, an infusion solution, or as a suppository.
为快速取得治疗效果，本发明粉料可以与以血液灌流器配合使用，灌流器中填充常规颗粒的同类材质的大孔吸附树脂。In order to achieve a rapid therapeutic effect, the powder of the present invention can be used in combination with a blood perfusion device filled with a macroporous adsorption resin of the same type of conventional particles.
与现有技术中以磷脂为主要成分的的纳米载体膜材料具有实质性的区别是：本发明的纳米载体是粉料，不会在体内降解或消融；纳米级粉料具有高比表面积和强表面吸附力；可以穿透人体组织包括血管壁和细胞膜，对细菌细胞壁上和血液中的粘多糖分子的疏水头及亲水尾具有强亲和吸附性；吸附细菌细胞壁上的脂多糖可以促使细菌细胞灭活，有杀菌作用；本发明纳米载体可以快速从血液中吸附并携带粘多糖分子排出体外，从而避免其与体内受体结合；进而达到治疗内毒素血症的目的。The nanocarrier film material with phospholipid as a main component in the prior art has substantial difference: the nanocarrier of the invention is a powder and does not degrade or ablate in vivo; the nanometer powder has high specific surface area and strong Surface adsorption; can penetrate human tissues including blood vessel walls and cell membranes, and has strong affinity adsorption on hydrophobic heads and hydrophilic tails of mucopolysaccharide molecules on bacterial cell walls and blood; adsorption of lipopolysaccharide on bacterial cell walls can promote bacteria The cells are inactivated and have a bactericidal effect; the nanocarrier of the invention can be quickly adsorbed from the blood and carried to carry out the mucopolysaccharide molecules, thereby avoiding binding to the receptors in the body; thereby achieving the purpose of treating endotoxemia.
本发明采用的双亲性或与亲脂性糖基化大孔医用树脂纳米级粒径粉料具有优良的血液相容性，且无神经毒性和肾毒性，在治疗中
也不会造成血液中大量血浆蛋白的损失；克服了现有技术中日本使用的多粘菌素B固载纤维柱存在的缺点。The amphiphilic or lipophilic glycosylated macroporous medical resin nano-sized particle powder used in the invention has excellent blood compatibility, and has no neurotoxicity and nephrotoxicity, and is in treatment.
It also does not cause a loss of a large amount of plasma protein in the blood; it overcomes the disadvantages of the polymyxin B-supported fiber column used in the prior art in Japan.
本发明纳米级载体粉料是一种人工合成的化工产品，在人体环境中具有化学稳定性，其载体功能是物质表面微环境中的爱德华力物理吸附作用，并不参与体内任何生物化学反应。为治疗内毒素血症提供了一种安全、有效、快捷和廉价的临床治疗方法。The nano-scale carrier powder of the invention is a synthetic chemical product, which has chemical stability in the human environment, and the carrier function is the physical adsorption of Edwardian force in the surface micro-environment of the substance, and does not participate in any biochemical reaction in the body. It provides a safe, effective, fast and inexpensive clinical treatment for endotoxemia.
本发明的纳米材料清除体内致病的靶向物质是脂多糖，对其它具有类似脂多糖分子一头疏水，而另一头亲水的致病物质具有相似的吸附清除作用；对由其引发的其它疾患具有同样的治疗效果。
The nano-materials of the present invention are capable of removing pathogenic target substances in vivo, which are lipopolysaccharides, and have similar adsorption and scavenging effects on other pathogenic substances having similar lipopolysaccharide molecules and hydrophilic substances on the other side; and other diseases caused by them Have the same therapeutic effect.
Claims (5)
- 专用于治疗内毒素血症的纳米载体，其特征在于：是以聚醋酸乙烯酯为骨架的双亲性糖基化树脂的微纳米级粒径吸附树脂的粉料；或以聚醋酸乙烯酯为骨架的双亲性糖基化吸附树脂的微纳米级粒径的单质粉料和糖基化苯乙烯-二乙烯苯为骨架亲脂性吸附树脂微纳米级粒径粉料的混合粉料。A nanocarrier specially designed for treating endotoxemia, characterized in that: a powder of a micro-nano-sized particle size adsorption resin of an amphiphilic glycosylated resin having a polyvinyl acetate as a skeleton; or a polyvinyl acetate as a skeleton The micro-nano-sized elemental powder of the amphiphilic glycosylation adsorption resin and the glycosylated styrene-divinylbenzene are mixed powders of the micro-nano-sized particle powder of the skeleton lipophilic adsorption resin.
- 如权利要求1所述的本发明的实施专用于治疗内毒素血症的纳米载体，其特征在于：单质或混和粉料的粒径范围是50-1000nm。The nanocarrier according to the invention as claimed in claim 1 for treating endotoxemia, characterized in that the elemental or mixed powder has a particle size ranging from 50 to 1000 nm.
- 如权利要求1所述的本发明的实施专用于治疗内毒素血症的纳米载体，其特征在于：单质或混和粉料的粒径范围是100-200nm。The nanocarrier according to the invention of claim 1 for treating endotoxemia is characterized in that the elemental or mixed powder has a particle size ranging from 100 to 200 nm.
- 如权利要求1所述的本发明的实施专用于治疗内毒素血症的纳米载体，其特征在于：混合粉料的成分比为1:1。The nanocarrier according to the invention of claim 1 for treating endotoxemia, characterized in that the composition ratio of the mixed powder is 1:1.
- 如权利要求1所述的本发明的实施专用于治疗内毒素血症的纳米载体的使用方法，其特征在于：纳米载体可以直接口服，或者制成缓释胶囊口服，或者制成注射剂，或者制成栓剂。 The method for using the nanocarrier according to the invention for treating endotoxemia according to claim 1, wherein the nanocarrier can be directly administered orally, or can be made into a sustained release capsule orally, or made into an injection, or made. A suppository.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002263486A (en) * | 2001-03-14 | 2002-09-17 | Chisso Corp | Endotoxin adsorbent and method of removing endotoxin by using the same |
| WO2005049653A1 (en) * | 2003-07-14 | 2005-06-02 | Genway Biotech, Inc. | Affinity separation composition and method |
| CN102361689A (en) * | 2009-01-22 | 2012-02-22 | 弗雷森纽斯医疗护理德国有限责任公司 | Sorbent for endotoxins |
| CN103980403A (en) * | 2014-05-16 | 2014-08-13 | 李涛 | Styrene system ion exchange resin as well as preparation method and application thereof |
| CN104497193A (en) * | 2014-10-01 | 2015-04-08 | 于杰 | Active vector for removing in vivo toxic substance including endotoxin in intestinal tracts |
| CN104693332A (en) * | 2014-10-01 | 2015-06-10 | 于杰 | Glycosylated medical macroporous adsorption resin |
-
2016
- 2016-09-21 WO PCT/CN2016/099518 patent/WO2018053696A1/en active Application Filing
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002263486A (en) * | 2001-03-14 | 2002-09-17 | Chisso Corp | Endotoxin adsorbent and method of removing endotoxin by using the same |
| WO2005049653A1 (en) * | 2003-07-14 | 2005-06-02 | Genway Biotech, Inc. | Affinity separation composition and method |
| CN102361689A (en) * | 2009-01-22 | 2012-02-22 | 弗雷森纽斯医疗护理德国有限责任公司 | Sorbent for endotoxins |
| CN103980403A (en) * | 2014-05-16 | 2014-08-13 | 李涛 | Styrene system ion exchange resin as well as preparation method and application thereof |
| CN104497193A (en) * | 2014-10-01 | 2015-04-08 | 于杰 | Active vector for removing in vivo toxic substance including endotoxin in intestinal tracts |
| CN104693332A (en) * | 2014-10-01 | 2015-06-10 | 于杰 | Glycosylated medical macroporous adsorption resin |
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