CN115005219A - 一种双向传导的荧光纳米杀菌剂及其制备方法 - Google Patents
一种双向传导的荧光纳米杀菌剂及其制备方法 Download PDFInfo
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- CN115005219A CN115005219A CN202210564583.5A CN202210564583A CN115005219A CN 115005219 A CN115005219 A CN 115005219A CN 202210564583 A CN202210564583 A CN 202210564583A CN 115005219 A CN115005219 A CN 115005219A
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- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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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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- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明公开了一种双向传导的荧光纳米杀菌剂及其制备方法。利用荧光分子制备荧光介孔二氧化硅纳米颗粒，并在其表面修饰上氨基酸、氨基葡萄糖功能分子，再负载杀菌剂分子得到双向传导的荧光纳米杀菌剂。本发明的制备的双向传导的荧光纳米杀菌剂可经植物叶面喷施后在植株体内双向传导，避免了土壤施药，进而减少了土壤施药导致药用成本高、药效低和严重的环境问题。并且，能够通过活体荧光成像技术，实时监测到所制备的纳米杀菌剂在植株内的运动情况，不必破坏植株完整性取样观察，更能反映纳米杀菌剂在植物活体内的真实运动情况。
Description
技术领域：
本发明属于植物保护应用领域，具体涉及一种双向传导的荧光纳米杀菌剂及其制备方法。
背景技术：
内吸治疗性杀菌剂是指病菌侵入作物后或作物发病后，施用的杀菌剂能渗入到作物体内或被作物吸收并在体内传导，对病菌直接产生作用或影响植物代谢，杀灭或抑制病菌的致病过程，清除病害或减轻病害。内吸性杀菌剂在植物维管束病害和根部病害防治中发挥了巨大作用。但杀菌剂的使用在实际生产中也存在一些问题。比如，很多杀菌剂性质不稳定，易挥发、见光易分解或反应，导致其活性大大降低，给储存和使用带来严峻考验；杀菌剂没有缓释功能，需要多次用药才能达到使用效果，造成农作物成本增加和浪费；大多数杀菌剂在作物体内只能顶向传导，常用作土壤施药，而土壤施药导致药用成本高、药效低和严重的环境问题，是影响未来智能、精准农业可持续发展的关键。
将先进的纳米技术引入到农药研究领域，有望巧妙地解决上述问题，但目前国内外在这方面的研究均处于起步阶段。利用纳米颗粒比表面积大和结构可控的独特优势，可以高效负载杀菌剂，并将杀菌剂活性成分保护起来，也可以有效提高杀菌剂的生物利用度，减少浪费和过度使用。同时，纳米杀菌剂还可以实现杀菌剂的缓释，进一步提高药效。更重要的，由于纳米颗粒表面有很多活性基团，还可以在颗粒表面修饰上特定的靶向基团等功能分子，赋予杀菌剂纳米体系导向性等功能，进而可以通过叶面喷施等方式实现杀菌剂的减量提效化使用。
研究杀菌剂在植物体内的运动及分布情况，之前都是通过在不同部位采样，然后进行成分分析进行鉴定的。这种监测杀菌剂运动行为的方式具有一定的滞后性，不能实时对杀菌剂的传导行为进行判断。利用荧光标记成像技术可以实现对杀菌剂的示踪，但目前已报道的工作都是对植物细胞或组织的成像，不能反映植物活体的整体真实情况。或者采用植物切片等方式进行电镜等方法成像，需要对植物进行破坏性取样，也无法实时监测活体成像效果。
纳米材料在动物体内的运动及分布可以通过活体荧光成像技术实现，已有很多报道，但由于动物与植物的细胞、组织有很大不同，不能理所当然的将可用于动物成像的纳米体系直接应用在植物上。而且2022年最新发表在权威期刊《Nature Nanotechnology》上的一篇文章明确指出，对于动物细胞膜与纳米材料相互作用的相关研究成果并不适用于有细胞壁的植物系统。
近年来，利用荧光技术研究农药纳米体系在细胞内的成像分布方面也有一些基础工作。研究人员首先在实验室培养植物细胞，然后将荧光分子标记的农药纳米体系与植物细胞共孵育从而观察这些农药纳米制剂在植物细胞内的分布。这些研究分析了特定条件下农药纳米体系在植物细胞的运动，然而，体外培养的植物细胞与实际生产环境中的植物本身仍有很大差别。如何在更接近实际应用的实验条件下，高分辨、长时间、实时、三维监测纳米杀菌剂在植物活体内的传导情况，仍是一项非常艰巨的挑战。目前，这方面的系统研究在国内外仍未见报道。
发明内容：
本发明的目的是提供一种双向传导的荧光纳米杀菌剂及其制备方法。
本发明利用荧光性能稳定、量子产率高的荧光分子制备荧光介孔二氧化硅纳米颗粒，并在其表面修饰上氨基酸、氨基葡萄糖等功能分子，用来负载杀菌剂分子得到小粒径的双向传导的荧光纳米杀菌剂；然后将上述双向传导的荧光纳米杀菌剂喷洒到植株叶片上，并将其置于活体成像仪器中，可实现对双向传导的荧光纳米杀菌剂在植物体内运动行为的实时荧光成像观察，从而实现了本发明的目的。
本发明的双向传导的荧光纳米杀菌剂是通过以下方法制备的：
利用荧光性能稳定、量子产率高的荧光分子制备荧光介孔二氧化硅纳米颗粒并在其表面修饰上氨基酸、氨基葡萄糖功能分子，再负载杀菌剂分子得到双向传导的荧光纳米杀菌剂。所得双向传导的荧光纳米杀菌剂可进入植物体内。
优选，所述的杀菌剂分子为内吸性杀菌剂，包括噻菌灵、多菌灵或甲基托布津。
优选，所述的氨基酸包括谷氨酸、丝氨酸、甘氨酸、组氨酸、赖氨酸、色氨酸、蛋氨酸、苯丙氨酸、脯氨酸、苏氨酸、酪氨酸中的一种或几种。
优选，所述的双向传导的荧光纳米杀菌剂粒径范围在10-70nm之间。
优选，所述的利用荧光分子制备荧光介孔二氧化硅纳米颗粒是称取十六烷基三甲基溴化铵、泊洛沙姆F127和三乙醇胺溶于乙醇水溶液中，再加入AIE溶液，避光充分搅拌；然后加入正硅酸乙酯，剧烈搅拌后静置反应；反应后加入乙醇水溶液摇匀，离心倒出清液后再次加入乙醇溶液超声分散，离心，固体烘干，将干燥后固体溶于盐酸甲醇溶液中，水浴回流，离心去除清液，加入甲醇超声分散洗涤，分散液烘干得到荧光介孔二氧化硅纳米颗粒。
优选，所述的表面修饰上氨基酸、氨基葡萄糖功能分子是取荧光介孔二氧化硅纳米颗粒分散在甲醇中，加入(3-巯基丙基)三甲氧基硅烷，搅拌反应，得到巯基修饰的荧光介孔二氧化硅纳米颗粒；再取4-(N-马来酰亚胺甲基)环己烷-1-羧酸磺酸基琥珀酰亚胺酯钠盐溶于磷酸缓冲溶液中，加入氨基酸或氨基葡萄糖，搅拌反应，得到活化的氨基酸或氨基葡萄糖溶液；将巯基修饰的荧光介孔二氧化硅纳米颗粒与活化的氨基酸或氨基葡萄糖溶液混合，搅拌反应，离心清洗得到氨基酸或氨基葡萄糖修饰的荧光介孔二氧化硅纳米颗粒。
优选，所述的负载杀菌剂分子是将氨基酸或氨基葡萄糖修饰的荧光介孔二氧化硅纳米颗粒分散于甲醇中，加入杀菌剂分子混合搅拌反应，离心清洗，冷冻干燥得到双向传导的荧光纳米杀菌剂。
所述的荧光分子，激发波长和发射波长应避开植物体叶绿素的激发波长(450nm)和发射波长(676nm)，并具有很好的抗淬灭性能和较强的量子产率，可用于长时间的荧光成像观察。
优选，所述的荧光介孔二氧化硅纳米颗粒，可高效负载杀菌剂分子，包括但不限于荧光介孔二氧化硅纳米颗粒。
将上述双向传导的荧光纳米杀菌剂喷洒到植株叶片上，并将其置于活体成像仪器中观察，根据荧光分子选定激发和发射波长，观察整株植株的荧光成像结果，实现实时监测纳米杀菌剂在植物体内的运动情况。
本发明的制备的双向传导的荧光纳米杀菌剂可经植物叶面喷施后在植株体内双向传导，避免了土壤施药，进而减少了土壤施药导致药用成本高、药效低和严重的环境问题。并且，能够通过活体荧光成像技术，实时监测到所制备的纳米杀菌剂在植株内的运动情况，不必破坏植株完整性取样观察，更能反映纳米杀菌剂在植物活体内的真实运动情况。
附图说明
图1是双向传导的荧光纳米杀菌剂喷洒在黄瓜幼苗上第一天和第八天的活体荧光成像图。(A)纳米杀菌剂喷洒在黄瓜幼苗上第一天的荧光成像图，白色箭头所指为喷洒叶片；(B)纳米杀菌剂喷洒在黄瓜幼苗上第八天的荧光成像图；(C)纳米杀菌剂喷洒在黄瓜幼苗上第一天的荧光成像图与白光图片的叠加效果图，白色箭头所指为喷洒叶片；(D)纳米杀菌剂喷洒在黄瓜幼苗上第八天的荧光成像图与白光图片的叠加效果图。
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。
实施例1：
1、荧光纳米杀菌剂的制备：
荧光介孔二氧化硅纳米颗粒的制备：称取221.1mg十六烷基三甲基溴化铵，0.89g泊洛沙姆F127，5.21g三乙醇胺，在250mL烧瓶中溶于19mL乙醇与41.6mL水中，再加入5mL密度为0.5mg/mL的四苯乙烯甲醇溶液，放入磁转子，以500rpm转速搅拌过夜，烧瓶包裹锡纸避光；待充分搅拌均匀后，于室温下用移液枪快速加入0.85mL正硅酸乙酯，调转速至1200rpm剧烈搅拌一分钟后静置24h；加入66.7ml 95％乙醇溶液摇匀，转入50ml离心管中以10000rpm离心5min，倒出清液后再次加入乙醇溶液超声分散，离心。置于65℃烘箱中烘干备用。将干燥后固体移入烧瓶，加入3mL浓盐酸与50mL甲醇，于80℃水浴回流2h，移入离心管中离心去除清液。加入甲醇超声分散洗涤两次并离心，得分散液，烘干得到荧光介孔二氧化硅纳米颗粒。
表面功能修饰：取100mg上述荧光介孔二氧化硅纳米颗粒分散在20mL甲醇溶液中，加入3mL(3-巯基丙基)三甲氧基硅烷(MPTMS)，室温下搅拌反应24h，得到巯基修饰的荧光介孔二氧化硅纳米颗粒；再取5mg 4-(N-马来酰亚胺甲基)环己烷-1-羧酸磺酸基琥珀酰亚胺酯钠盐(Sulfo-SMCC)溶于磷酸缓冲溶液中，加入10mg氨基葡萄糖，4℃冰箱中搅拌24h，得到活化的氨基葡萄糖溶液；将上述巯基修饰的荧光介孔二氧化硅纳米颗粒与活化的氨基葡萄糖溶液混合，室温下搅拌反应过夜，然后离心清洗得到氨基葡萄糖修饰的荧光介孔二氧化硅纳米颗粒。
负载杀菌剂：将10mg上述氨基葡萄糖修饰的荧光介孔二氧化硅纳米颗粒分散于50mL甲醇中，加入20mg内吸性杀菌剂噻菌灵溶液混合搅拌24h，离心清洗，冷冻干燥，得到双向传导的荧光纳米杀菌剂。
2.实时荧光监测：然后将上述双向传导的荧光纳米杀菌剂喷洒到黄瓜幼苗叶片上，并将植株整体置于活体成像仪器中，调节激发波长为365nm，荧光采集中心波长为450nm，进行成像效果观察，在不同时间点观察成像结果，调节成像参数，可实现实时监测双向传导的荧光纳米杀菌剂在植物体内的运动情况(如图1所示)。
以上所述仅为本发明的优选实例而已，并不用于限制本发明，本发明的保护范围不仅如此，凡在本发明的技术原则之内，有明显地修改、同等替换，改进等，均应包含在本发明的保护范围之内。
Claims (10)
1.一种双向传导的荧光纳米杀菌剂的制备方法，其特征在于，利用荧光性能稳定、量子产率高的荧光分子制备荧光介孔二氧化硅纳米颗粒，并在其表面修饰上氨基酸、氨基葡萄糖功能分子，再负载杀菌剂分子得到双向传导的荧光纳米杀菌剂。
2.根据权利要求1所述的制备方法，其特征在于，所述的荧光分子为聚集诱导发光(AIE)分子。
3.根据权利要求1所述的制备方法，其特征在于，所述的杀菌剂分子为内吸性杀菌剂。
4.根据权利要求3所述的制备方法，其特征在于，所述的内吸性杀菌剂为噻菌灵、多菌灵或甲基托布津。
5.根据权利要求1所述的制备方法，其特征在于，所述的氨基酸为谷氨酸、丝氨酸、甘氨酸、组氨酸、赖氨酸、色氨酸、蛋氨酸、苯丙氨酸、脯氨酸、苏氨酸、酪氨酸中的一种或几种。
6.根据权利要求1所述的制备方法，其特征在于，所述的利用荧光分子制备荧光介孔二氧化硅纳米颗粒是称取十六烷基三甲基溴化铵、泊洛沙姆F127和三乙醇胺溶于乙醇水溶液中，再加入荧光分子的溶液，避光充分搅拌；然后加入正硅酸乙酯，剧烈搅拌后静置反应；反应后加入乙醇水溶液摇匀，离心倒出清液后再次加入乙醇溶液超声分散，离心，固体烘干，将干燥后固体溶于盐酸甲醇溶液中，水浴回流，离心去除清液，加入甲醇超声分散洗涤，分散液烘干得到荧光介孔二氧化硅纳米颗粒。
7.根据权利要求1所述的制备方法，其特征在于，所述的表面修饰上氨基酸、氨基葡萄糖功能分子是取荧光介孔二氧化硅纳米颗粒分散在甲醇中，加入(3-巯基丙基)三甲氧基硅烷，搅拌反应，得到巯基修饰的荧光介孔二氧化硅纳米颗粒；再取4-(N-马来酰亚胺甲基)环己烷-1-羧酸磺酸基琥珀酰亚胺酯钠盐溶于磷酸缓冲溶液中，加入氨基酸或氨基葡萄糖，搅拌反应，得到活化的氨基酸或氨基葡萄糖溶液；将巯基修饰的荧光介孔二氧化硅纳米颗粒与活化的氨基酸或氨基葡萄糖溶液混合，搅拌反应，离心清洗得到氨基酸或氨基葡萄糖修饰的荧光介孔二氧化硅纳米颗粒。
8.根据权利要求1所述的制备方法，其特征在于，所述的负载杀菌剂分子是将氨基酸或氨基葡萄糖修饰的荧光介孔二氧化硅纳米颗粒分散于甲醇中，加入杀菌剂分子混合搅拌反应，离心清洗，冷冻干燥得到双向传导的荧光纳米杀菌剂。
9.一种按照权利要求1-8任意制备方法制备得到的双向传导的荧光纳米杀菌剂。
10.根据权利要求9所述的双向传导的荧光纳米杀菌剂，其特征在于，所述的双向传导的荧光纳米杀菌剂粒径范围在10-70nm之间。
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| US20120244205A1 (en) * | 2009-08-25 | 2012-09-27 | The Regents Of The University Of California | Nanotechnological Delivery of Microbicides and Other Substances |
| EP2712868A1 (en) * | 2012-09-28 | 2014-04-02 | B. Braun Melsungen AG | 5-Fluoruoracil Derivatives |
| CN103842472A (zh) * | 2011-09-01 | 2014-06-04 | 香港科技大学 | 用作荧光生物探针的具有聚集诱导发光性质的生物相容纳米粒子及其在体外／体内成像中的应用方法 |
| CN108310388A (zh) * | 2017-12-27 | 2018-07-24 | 湖北工业大学 | 二硫键功能化的荧光介孔二氧化硅纳米颗粒的制备方法及其用途 |
| WO2022048470A1 (zh) * | 2020-09-03 | 2022-03-10 | 华东理工大学 | 介孔氧化硅纳米粒子控释系统、其制备方法及其应用 |
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2022
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|---|---|---|---|---|
| JPH0848605A (ja) * | 1994-08-08 | 1996-02-20 | Matsushita Electric Ind Co Ltd | 抗菌性複合体およびその製造方法 |
| KR20010017952A (ko) * | 1999-08-16 | 2001-03-05 | 김상근 | 사이드로포어 생산 길항균주 슈도모나스 플루오레센스 ｇｌ7과 그 유전육종 및 형광단백 유전자 도입에 의한 모니터링 방법 |
| US20120244205A1 (en) * | 2009-08-25 | 2012-09-27 | The Regents Of The University Of California | Nanotechnological Delivery of Microbicides and Other Substances |
| CN102323424A (zh) * | 2011-06-02 | 2012-01-18 | 浙江大学 | 环境颗粒物表面外源生物分子的原位检测试剂及方法 |
| CN103842472A (zh) * | 2011-09-01 | 2014-06-04 | 香港科技大学 | 用作荧光生物探针的具有聚集诱导发光性质的生物相容纳米粒子及其在体外／体内成像中的应用方法 |
| EP2712868A1 (en) * | 2012-09-28 | 2014-04-02 | B. Braun Melsungen AG | 5-Fluoruoracil Derivatives |
| CN108310388A (zh) * | 2017-12-27 | 2018-07-24 | 湖北工业大学 | 二硫键功能化的荧光介孔二氧化硅纳米颗粒的制备方法及其用途 |
| WO2022048470A1 (zh) * | 2020-09-03 | 2022-03-10 | 华东理工大学 | 介孔氧化硅纳米粒子控释系统、其制备方法及其应用 |
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