CN115581229A - 一种单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒制备方法及其抗菌应用 - Google Patents
一种单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒制备方法及其抗菌应用 Download PDFInfo
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
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- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
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Abstract
本发明公开了一种单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒制备方法及其抗菌应用。所述的制备方法具体是在乙基纤维素纳米颗粒上负载咪鲜胺，其后采用多酚类单宁酸界面修饰负载咪鲜胺乙基纤维素载药纳米体系。基于溶剂挥发法构建具备抗真菌效应的咪鲜胺乙基纤维素纳米颗粒，进而制备出单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒。所制备的单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒，可以有效提高咪鲜胺抗光解能力，增强咪鲜胺与菌体细胞相互作用，从而实现提质增效目标。本发明涉及的乙基纤维素和单宁酸生物相容性好、安全、低成本、可再生，且制备工艺简单，有利于提高药物稳定性及抗菌活性，具有广阔的应用前景。
Description
技术领域
本发明属于药物剂型制备技术领域，具体涉及一种单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒制备方法及其抗菌应用。
背景技术
咪鲜胺基于杂环氮原子与P450上14α脱甲基化酶的相结合，干扰脱甲氧基反应，进而抑制麦角甾醇的生物合成，使得细胞膜流动性和可塑性受损，导致细胞膜完整性和功能性丧失。此外，咪鲜胺作用于靶标菌体，使菌体内产生过量的活性氧，造成菌体代谢紊乱，导致作物病原体中的氧化损伤和细胞凋亡。咪鲜胺具有独特的抗菌机制，是一种广谱性杀菌剂，且有低毒、不易产生抗药性的优势，广泛应用于水果、蔬菜及草皮等农作物白粉菌、炭疽菌、稻瘟菌及禾谷镰刀菌等多种病害防控领域。然而，由于难溶特性，咪鲜胺在作物抵御真菌侵蚀的过程中面临生物利用度偏低的问题。咪鲜胺相对不稳定，易被阳光、碱和强酸降解，极大降低药物持效性，严重制约其在作物病害防控领域的高效利用。
由于咪鲜胺的大量不合理使用，耐药性将面临巨大挑战。因此，开发咪鲜胺药物新制剂是提高抗菌活性，解决耐药性的有效途径。将可生物降解的纳米颗粒与抗真菌药物相结合，行程一种新纳米药物递送体系，增强药物对光稳定性并延长持效期，从而提高抗菌剂的生物利用度。如今，多种天然高分子材料，尤其是纤维素、壳聚糖和淀粉，以其可再生、易获取、低成本和安全、无毒等特性备受关注。纤维素在自然界中分布最广、含量是最丰富的、可降解的多糖高分子聚合物，其主要来源于植物、微生物。乙基纤维素是由纤维素经碱化处理后，与氯乙烷反应制得的一种疏水性纤维素醚。乙基纤维素广泛应用于医药领域，主要作为缓控释载体材料，其优良的生物相容性、较高的机械强度、耐酸碱性、成膜性、疏水性和热稳定性，被世界卫生组织专家委员会批准为安全的食品添加剂。因此，乙基纤维素可以作为一种绿色纳米药物缓释递送载体材料。基于纳米颗粒的小尺寸效应和大比表面效应，乙基纤维素纳米颗粒为抗菌药物递送的提供全新药物剂型，有效改善药物稳定性、延长持效期，进而提高抗菌药物有效利用度。
单宁酸是一种分布广泛的天然水溶性多酚化合物，由没食子单元与葡萄糖核心上的羟基脱水酯化而形成，主要存在于柿子、石榴、核桃、葡萄和绿茶等植物中。单宁酸已被美国食品药品监督管理局认定具有较高生物安全性，具有清除自由基、抗氧化、抗炎、抗菌和抗癌等重要的生物学功效，在医疗输送生物材料、国内化工和食品工业等领域广为关注。单宁酸多酚羟基赋予其独特的化学特性，易于与蛋白质、生物碱、多糖、核酸发生静电吸附、氢键等非共价作用和共价作用，同时单宁酸与金属离子形成螯合反应。因此，单宁酸是一种安全、理想的生物改性材料，易与相应底物发生交联反应，增强对靶粘附性，进而提高药物递送系统的生物利用度。
发明内容
本发明针对咪鲜胺存在水溶性和稳定性差等不足之处，提供一种单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒制备方法，可以改善药物抗光解能力和跨膜转运效率，从而提高药物纳米制剂对Fusarium graminearum禾谷镰刀菌抗菌活性。
因此，本发明的第一个目的是提供一种单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒的制备方法，是在乙基纤维素纳米颗粒负载咪鲜胺，然后用单宁酸界面修饰负载咪鲜胺的乙基纤维素纳米颗粒，得到单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒。
具体的，所述的制备方法，包括以下步骤：
(1)将咪鲜胺和乙基纤维素溶于有机溶剂，制得有机相溶液；将聚乙烯醇溶于水，制得水相溶液；
(2)将有机相溶液滴加至水相溶液中，搅拌制备初乳，随后超声乳化，乳液搅拌固化，将固化后的乳液离心，取沉淀，水洗，得到咪鲜胺乙基纤维素纳米颗粒；
(3)将咪鲜胺乙基纤维素纳米颗粒分散于单宁酸Tris盐酸缓冲液中，经搅拌聚合反应后，单宁酸界面修饰于咪鲜胺乙基纤维素纳米颗粒，离心收集沉淀，水洗，去除未结合的单宁酸，制得单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒。
优选的，步骤(1)中，所述的咪鲜胺与乙基纤维素的质量比为1:(2～10)。
优选的，步骤(1)中，所述的水相溶液中聚乙烯醇的质量百分浓度为0.5～4％。
优选的，步骤(2)中，所述的有机相溶液和水相溶液的体积比为1:(4～20)。
优选的，步骤(2)中，所述的超声乳化的功率为250～600w，时间为2～6min；所述的搅拌固化是在300～800rpm搅拌固化4～12h；所述的离心是在7000～10000rpm，离心15～30min。
优选的，步骤(3)中，所述的单宁酸Tris盐酸缓冲液中单宁酸的质量百分浓度为0.1～1％。
本发明的第二目的是提供一种按照上述的制备方法制备得到的单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒。
优选，所述的单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒水合平均粒径为167～219nm，相应zeta电位为-18～-24mV。
本发明的第三目的是提供上述的单宁酸界面修饰的咪鲜胺乙基纤维素纳米复合物在抗真菌中的应用。所述的真菌包括禾谷镰孢菌Fusarium graminearum。
本发明基于溶剂挥发法构建负载咪鲜胺乙基纤维素纳米颗粒药物制剂，将多酚类单宁酸修饰在纳米颗粒表面，得到单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒。所制备的单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒具有良好的抗光解性，增强纳米颗粒与靶标菌体粘附力，进而有效提高纳米颗粒跨膜转运效率以其抗菌活性，本发明药物制备体系所涉及流程工艺简单，生产成本低，可规模化量产，具有广阔的应用前景。
附图说明
图1是乙基纤维素纳米颗粒水合粒径；(A)咪鲜胺乙基纤维素纳米颗粒；(B)单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒。
图2是乙基纤维素纳米颗粒zeta电位；(A)咪鲜胺乙基纤维素纳米颗粒；(B)单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒。
图3是单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒的抗光解性能分析。
图4是罗丹明6G荧光标记的乙基纤维素纳米颗粒跨膜转运分析；(A)荧光光谱；(B)荧光值。
图5是乙基纤维素纳米颗粒对膜电位的影响；(A)荧光光谱；(B)荧光值。
具体实施方式
以下实施例是对本发明的进一步说明，而不是对本发明的限制。
下述实施例中乙基纤维素的粘度为6-9，聚乙烯醇的醇解度为87％-89％，粘度为3.2-3.6。
实施例1：咪鲜胺乙基纤维素纳米颗粒制备
具体步骤如下所示：
(1)有机相配制
称取60mg咪鲜胺和240mg的乙基纤维素溶解到12mL二氯甲烷中，得到有机相；
(2)水相配制
将288mg聚乙烯醇溶于48mL水中，得到水相；
(3)制备咪鲜胺乙基纤维素纳米颗粒
将有机相与水相按体积比为1:4混合，磁力搅拌，得到初乳，冰浴条件下，对初乳采用探头式超声乳化，功率400w，超声时间5min，然后常温下500rpm搅拌固化4h，至有机溶剂完全挥发，固化后的乳液于25℃，9000rpm，离心25min，取沉淀，水洗3～5次，得到咪鲜胺乙基纤维素纳米颗粒，所制备的咪鲜胺乙基纤维素纳米颗粒水合平均粒径为167nm(图1A)，相应zeta电位为-18mV(图2A)。
实施例2：单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒的制备
具体步骤如下所示：
(1)有机相配制
称取60mg咪鲜胺和240mg的乙基纤维素溶解到12mL二氯甲烷中，得到有机相；
(2)水相配制
将288mg聚乙烯醇溶于48mL水中，得到水相；
(3)制备咪鲜胺乙基纤维素纳米颗粒
将有机相与水相按体积比为1:4混合，磁力搅拌，得到初乳，冰浴条件下，对初乳采用探头式超声乳化，功率400w，超声时间5min，然后常温下500rpm搅拌固化4h，至有机溶剂完全挥发，固化后的乳液于25℃，9000rpm，离心25min，取沉淀，水洗3～5次，得到咪鲜胺乙基纤维素纳米颗粒。
(4)制备单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒
称取20mg的单宁酸溶于20mL Tris盐酸缓冲液(100mM,pH 8.5)中，随后加入所述的咪鲜胺乙基纤维素纳米颗粒，常温避光下500rpm搅拌12h，然后于25℃，9000rpm，离心25min，沉淀水洗3～5次，即得到所述的单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒，所制备的单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒水合平均粒径为219nm(图1B)，相应zeta电位为-24mV(图2B)。
实施例3：罗丹明6G荧光标记乙基纤维素纳米颗粒制备
具体步骤如下所示：
(1)有机相配制
称取3mg罗丹明6G和240mg的乙基纤维素溶解到12mL二氯甲烷中，得到有机相；
(2)水相配制
将288mg聚乙烯醇溶于48mL水中，得到水相；
(3)制备罗丹明6G荧光标记乙基纤维素纳米颗粒
将有机相与水相按体积比为1:4混合，磁力搅拌，得到初乳，冰浴条件下，对初乳采用探头式超声乳化，功率400w，超声时间5min，然后常温下500rpm搅拌固化4h，至有机溶剂完全挥发，固化后的乳液于25℃，9000rpm，离心25min，取沉淀，水洗3～5次，得到罗丹明6G荧光标记乙基纤维素纳米颗粒。
实施例4：罗丹明6G荧光标记单宁酸界面修饰乙基纤维素纳米颗粒制备
具体步骤如下所示：
(1)有机相配制
称取3mg罗丹明6G和240mg的乙基纤维素溶解到12mL二氯甲烷中，得到有机相；
(2)水相配制
将288mg聚乙烯醇溶于48mL水中，得到水相；
(3)制备罗丹明6G荧光标记乙基纤维素纳米颗粒
将有机相与水相按体积比为1:4混合，磁力搅拌，得到初乳，冰浴条件下，对初乳采用探头式超声乳化，功率400w，超声时间5min，然后常温下500rpm搅拌固化4h，至有机溶剂完全挥发，固化后的乳液于25℃，9000rpm，离心25min，取沉淀，水洗3～5次，得到罗丹明6G荧光标记乙基纤维素纳米颗粒。
(4)制备罗丹明6G荧光标记单宁酸界面修饰乙基纤维素纳米颗粒
称取20mg的单宁酸溶于20mL Tris盐酸缓冲液(100mM,pH 8.5)中，随后加入所述的罗丹明6G荧光标记乙基纤维素纳米颗粒，常温避光下500rpm搅拌12h，然后于25℃，9000rpm，离心25min，沉淀水洗3～5次，即得到所述的罗丹明6G荧光标记单宁酸界面修饰乙基纤维素纳米颗粒。
下面将描述本发明单宁酸界面修饰乙基纤维素纳米颗粒的性能测评实验。
实验例1：抗光解性能分析
分别称取有效成分咪鲜胺为5mg的咪鲜胺原药、咪鲜胺乙基纤维素纳米颗粒或单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒分散于2mL水中，并转移到石英管。随后，将样品在置于氙弧灯光照箱，进行光解实验，在25℃，300W，10cm距离连续光照。分别于4h、8h、12h和36h取出样品，将所取样品冷冻干燥，经过乙醇稀释后，采用UV-Vis光谱仪进行定量分析，并计算光解率。经过36h连续光照处理，咪鲜胺原药(Pro)、咪鲜胺乙基纤维素纳米颗粒(Pro-EC)和单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒(Pro-EC-TA)分别光解率为80.75％、20.93％和5.22％(图3)。该结果表明本发明所制备的乙基纤维素纳米颗粒上负载咪鲜胺，可以降低咪鲜胺光解率，当单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒时，进一步提高咪鲜胺药物对光稳定性。
实验例2：室内抗菌活性评价
本实验通过马铃薯葡萄糖琼脂培养基中培养，十字交叉法测量菌丝体生长直径，来评定咪鲜胺原药、咪鲜胺乙基纤维素纳米颗粒和单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒对Fusarium graminearum抗菌活性。以未含咪鲜胺的马铃薯葡萄糖琼脂培养基作为对照组，将咪鲜胺原药、咪鲜胺乙基纤维素纳米颗粒和单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒有效成分-咪鲜胺稀释制备成终浓度为2.5ng/mL、5ng/mL、10ng/mL、50ng/mL和100ng/mL的马铃薯葡萄糖琼脂培养基，用灭菌打孔器(直径10mm)在Fusarium graminearum菌落边缘打孔，获得10mm菌饼，随后菌饼反向接种于含有咪鲜胺及对照组马铃薯葡萄糖琼脂培养基中心，28℃培养4天后，对Fusarium graminearum抗菌活性进行分析，其结果如表1所示。结果表明，咪鲜胺原药、咪鲜胺乙基纤维素纳米颗粒和单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒对Fusarium graminearum的EC50值分别为59.71ng/mL、20.35ng/mL和12.04ng/mL。以咪鲜胺原药作为标准药剂，咪鲜胺乙基纤维素纳米颗粒和单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒对Fusarium graminearum相对毒力是咪鲜胺原药的2.93倍和4.96倍。单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒对Fusarium graminearum的EC50最小，其抗菌活性最高，因此，单宁酸界面修饰可以有效提高生物活性，增强咪鲜胺药物抗菌效果。
表1.咪鲜胺、咪鲜胺乙基纤维素纳米颗粒和单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒对Fusarium graminearum毒力分析
实验例3：跨膜转运分析
采用罗丹明6G荧光标记乙基纤维素纳米颗粒(EC)和罗丹明6G荧光标记单宁酸界面修饰乙基纤维素纳米颗粒(EC-TA)对Fusarium graminearum跨膜转运能力分析。将Fusarium graminearum接种于5mL PDB培养基中，28℃培养180r/min震荡培养2d，分别加入一定量的罗丹明6G荧光标记法乙基纤维素纳米颗粒和罗丹明6G荧光标记单宁酸界面修饰乙基纤维素纳米颗粒，使乙基纤维素浓度为500ng/mL，分别振荡培养1h、3h和5h，取样，在5000rpm和25℃下离心5分钟收集菌丝，采用无菌PBS(10mM,pH 7.4)洗3次，将洗涤过的菌丝过滤并称鲜重，菌丝超声分散于1mL无菌PBS中，采用荧光分光光度计，在507nm的激发波长，发射波长扫描范围为527nm～700nm，测定菌体内罗丹明6G荧光值(图4)。起初共孵育1h，菌体内罗丹明6G标记的乙基纤维素纳米颗粒和单宁酸界面修饰乙基纤维素纳米颗粒的荧光强度分别为每毫克菌丝体鲜重143.68和180.50。与罗丹明6G标记的乙基纤维素纳米颗粒共孵育的Fusarium graminearum的荧光强度相比，罗丹明6G荧光标记单宁酸界面修饰乙基纤维素纳米颗粒处理组荧光值显著增加，且呈现时间效应关系。基于单宁酸与细胞膜蛋白静电吸附、氢键等作用，本发明所制备多酚类单宁酸界面修饰乙基纤维素纳米颗粒具备更优越的跨膜渗透性和细胞粘附性。
实验例4：膜电位分析
采用罗丹明123阳离子亲脂性绿色荧光染料评价咪鲜胺乙基纤维素纳米颗粒和单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒对Fusarium graminearum膜电位的影响。将Fusarium graminearum接种于5mL PDB培养基中，28℃培养180r/min震荡培养2d，分别加入一定量的咪鲜胺乙基纤维素纳米颗粒(Pro-EC)和单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒(Pro-EC-TA)，使活性有效成分咪鲜胺浓度为20ng/mL，并用等量的无菌去离子水代替咪鲜胺乙基纤维素纳米颗粒作为对照组(CK)，共孵育5h，然后，每个样品中加入适量的罗丹明123荧光探针，使其终浓度为5μg/mL，避光共培养30min，在5000rpm和25℃下离心5分钟收集菌丝，采用无菌PBS(10mM,pH 7.4)洗3次，将洗涤过的菌丝过滤并称鲜重，菌丝分散于1mL无菌PBS中，采用荧光分光光度计，在488nm的激发波长，发射波长扫描范围为500nm～700nm，测定菌体内罗丹明123荧光值(图5)。与对照组相比，咪鲜胺乙基纤维素纳米颗粒和单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒处理的Fusarium graminearum菌体内罗丹明123荧光值分别显着降低了66.92％和74.91％，菌丝细胞膜的完整性遭受严重破坏，增加细胞膜的通透性，进而导致细胞代谢异常，甚至菌丝细胞死亡。多酚类单宁酸可以协同提高抗菌、抗真菌、抗病毒和抗炎的作用，单宁酸与多糖、蛋白质和金属离子相关的丰富的疏水、氢键和静电相互作用，经过单宁酸界面修饰咪鲜胺乙基纤维素纳米颗粒可以有效提高抗菌活性。
以上仅是本发明的优选实施方式，应当指出的是，上述优选实施方式不应视为对本发明的限制，本发明的保护范围应当以权利要求所限定的范围为准。对于本技术领域的普通技术人员来说，在不脱离本发明的精神和范围内，还可以做出若干改进和润饰，这些改进和润饰也应视为本发明的保护范围。
Claims (10)
1.一种单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒的制备方法，其特征在于，是在乙基纤维素纳米颗粒负载咪鲜胺，然后用单宁酸界面修饰负载咪鲜胺的乙基纤维素纳米颗粒，得到单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒。
2.根据权利要求1所述的制备方法，其特征在于，包括以下步骤：
(1)将咪鲜胺和乙基纤维素溶于有机溶剂，制得有机相溶液；将聚乙烯醇溶于水，制得水相溶液；
(2)将有机相溶液滴加至水相溶液中，搅拌制备初乳，随后超声乳化，乳液搅拌固化，将固化后的乳液离心，取沉淀，水洗，得到咪鲜胺乙基纤维素纳米颗粒；
(3)将咪鲜胺乙基纤维素纳米颗粒分散于单宁酸Tris盐酸缓冲液中，经搅拌聚合反应后，单宁酸界面修饰于咪鲜胺乙基纤维素纳米颗粒，离心收集沉淀，水洗，去除未结合的单宁酸，制得单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒。
3.根据权利要求2所述的制备方法，其特征在于，步骤(1)中，所述的咪鲜胺与乙基纤维素的质量比为1:(2～10)。
4.根据权利要求2所述的制备方法，其特征在于，步骤(1)中，所述的水相溶液中聚乙烯醇的质量百分浓度为0.5～4％。
5.根据权利要求2所述的制备方法，其特征在于，步骤(2)中，所述的有机相溶液和水相溶液的体积比为1:(4～20)。
6.根据权利要求2所述的制备方法，其特征在于，步骤(2)中，所述的超声乳化的功率为250～600w，时间为2～6min；所述的搅拌固化是在300～800rpm搅拌固化4～12h；所述的离心是在7000～10000rpm，离心15～30min。
7.据权利要求2所述的制备方法，其特征在于，步骤(3)中，所述的单宁酸Tris盐酸缓冲液中单宁酸的质量百分浓度为0.1～1％。
8.一种按照权利要求1-7任一项所述的制备方法制备得到的单宁酸界面修饰的咪鲜胺乙基纤维素纳米颗粒。
9.权利要求8所述的单宁酸界面修饰的咪鲜胺乙基纤维素纳米复合物在抗真菌中的应用。
10.根据权利要求9所述的应用，其特征在于，所述的真菌包括禾谷镰孢菌Fusariumgraminearum。
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110059162A1 (en) * | 2009-09-04 | 2011-03-10 | Jess Dreher Reed | Tannin-chitosan composites |
| CN103622840A (zh) * | 2013-11-15 | 2014-03-12 | 上海应用技术学院 | 一种负载驱蚊剂伊默宁的乙基纤维素微粒及其制备方法 |
| CN105557741A (zh) * | 2016-03-04 | 2016-05-11 | 扬州大学 | 一种高效氯氰菊酯微胶囊及其制备方法 |
| CN105746509A (zh) * | 2016-02-01 | 2016-07-13 | 扬州大学 | 一种杀线虫剂微胶囊及其制备方法 |
| US20170006870A1 (en) * | 2014-02-28 | 2017-01-12 | Kumiai Chemical Industry Co., Ltd. | Agrochemical composition for foliage treatment |
| CN107853299A (zh) * | 2017-12-03 | 2018-03-30 | 中国农业科学院农业环境与可持续发展研究所 | 一种叶面亲和型农药纳米载药系统制备方法 |
| CN110622965A (zh) * | 2019-08-14 | 2019-12-31 | 中国农业科学院农业环境与可持续发展研究所 | 一种基于单宁酸修饰的叶面亲和型农药纳米微胶囊制备方法 |
| US20200060277A1 (en) * | 2018-08-24 | 2020-02-27 | Química Agronómica de México S. de R.L. de C.V. | Tannin formulations for agricultural use in plants |
| CN112266486A (zh) * | 2020-10-21 | 2021-01-26 | 华南农业大学 | 一种单宁酸包覆纳米纤维素/聚丙烯酸粘附性水凝胶及其制备方法 |
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110059162A1 (en) * | 2009-09-04 | 2011-03-10 | Jess Dreher Reed | Tannin-chitosan composites |
| CN103622840A (zh) * | 2013-11-15 | 2014-03-12 | 上海应用技术学院 | 一种负载驱蚊剂伊默宁的乙基纤维素微粒及其制备方法 |
| US20170006870A1 (en) * | 2014-02-28 | 2017-01-12 | Kumiai Chemical Industry Co., Ltd. | Agrochemical composition for foliage treatment |
| CN105746509A (zh) * | 2016-02-01 | 2016-07-13 | 扬州大学 | 一种杀线虫剂微胶囊及其制备方法 |
| CN105557741A (zh) * | 2016-03-04 | 2016-05-11 | 扬州大学 | 一种高效氯氰菊酯微胶囊及其制备方法 |
| CN107853299A (zh) * | 2017-12-03 | 2018-03-30 | 中国农业科学院农业环境与可持续发展研究所 | 一种叶面亲和型农药纳米载药系统制备方法 |
| US20200060277A1 (en) * | 2018-08-24 | 2020-02-27 | Química Agronómica de México S. de R.L. de C.V. | Tannin formulations for agricultural use in plants |
| CN110622965A (zh) * | 2019-08-14 | 2019-12-31 | 中国农业科学院农业环境与可持续发展研究所 | 一种基于单宁酸修饰的叶面亲和型农药纳米微胶囊制备方法 |
| CN112266486A (zh) * | 2020-10-21 | 2021-01-26 | 华南农业大学 | 一种单宁酸包覆纳米纤维素/聚丙烯酸粘附性水凝胶及其制备方法 |
Non-Patent Citations (5)
| Title |
|---|
| CHANGYOU SHAO等: "Mussel-Inspired Cellulose Nanocomposite Tough Hydrogels with Synergistic Self-Healing, Adhesive, and Strain-Sensitive Properties", CHEMISTRY OF MATERIALS, no. 30, pages 3110 * |
| 徐华;林粤顺;周红军;周艺宇;陈喜;周新华;: "毒死蜱/乙基纤维素微胶囊的制备及其缓释性能", 化工进展, no. 12, pages 4622 - 4627 * |
| 谢凯桓;丁鹏;张云露;宋泽和;贺喜;范志勇;: "单宁及其组分的生物活性及在畜禽生产中的应用", 饲料研究, no. 04, pages 130 - 133 * |
| 陈龙;周红军;江海科;郝丽;陈铧耀;周新华;: "叶面亲和型阿维菌素微胶囊的制备及pH响应性释放性能", 化工进展, vol. 39, no. 01, pages 348 - 355 * |
| 高静等: "避蚊胺乙基纤维素微球的制备及其性质考察", 第二军医大学学报, vol. 25, no. 11, pages 1235 - 1237 * |
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