Preparation and properties of Avermectin-loaded PDMDAAC modified Zein nanoparticles

doi:10.16085/j.issn.1000-6613.2021-0741

Abstract

Abstract:

In order to improve the leaf deposition rate of avermectin and its resistance to UV decomposition, a foliar affinity nanocarrier was designed. By free radical polymerization, dimethyldiallylammonium chloride (PDMDAAC) was used to modify Zein, and the modified Zein with positive charge on the surface was obtained, which was used to load avermectin. The drug-carrying nanoparticles with an average particle size of 64.92nm were prepared by anti-solvent precipitation method. The encapsulation efficiency of avermectin was (34.75±0.18)%. The electrostatic interaction with the plant surface improved the wettability of the suspension, and the contact angle decreased from 77.38° to 64.60° with the increase of the amount of PDMDAAC grafting. Leaf retention reached 33.69mg/cm². Avermectin coated with modified Zein improved the UV resistance, the half-life was extended from 15min to 40min, and the release rate of avermectin was regulated by the grafting rate of PDMDAAC.

Key words: polydimethyldiallyl ammonium chloride, zein, avermectin, sustained-release, UV resistance

摘要：

为提高阿维菌素叶面沉积率及其抗紫外分解性能，本文设计构建了叶面亲和的纳米载体。通过自由基聚合将聚二甲基二烯丙基氯化铵（PDMDAAC）改性玉米醇溶蛋白（Zein），得到表面携带正电荷的改性玉米醇溶蛋白，并将其用于负载阿维菌素。采用红外光谱（FTIR）、扫描电镜（SEM）等手段对改性产物结构和形貌进行表征。通过反溶剂沉淀法制备了平均粒径为64.92nm的载药纳米粒子，载体对阿维菌素的包封率为(34.75±0.18)%。与植物表面的静电作用提升了纳米粒子悬浮液在植物表面的润湿性能，接触角大小随PDMDAAC接枝量增大而降低，由77.38°减小到64.60°；叶面滞留量可达33.69mg/cm²。改性玉米醇溶蛋白对阿维菌素的包覆提升了其抗紫外性能，半衰期由15min延长至40min，且阿维菌素的释放速率可通过PDMDAAC接枝率进行调控。

关键词: 聚二甲基二烯丙基氯化铵, 玉米醇溶蛋白, 阿维菌素, 缓释, 抗紫外

CLC Number:

TQ450.6

LI Ziyong, CHEN Long, MA Wendan, ZHOU Hongjun, ZHOU Xinhua. Preparation and properties of Avermectin-loaded PDMDAAC modified Zein nanoparticles[J]. Chemical Industry and Engineering Progress, 2022, 41(4): 2068-2074.

李梓泳, 陈龙, 马文丹, 周红军, 周新华. PDMDAAC改性玉米醇溶蛋白负载阿维菌素纳米颗粒的制备与性能[J]. 化工进展, 2022, 41(4): 2068-2074.

Figures/Tables 11

References 24

1	GHORMADE V, DESHPANDE M V, PAKNIKAR K M. Perspectives for nano-biotechnology enabled protection and nutrition of plants[J]. Biotechnology Advances, 2011, 29(6): 792-803.
2	KAH M, TUFENKJI N, WHITE J C. Nano-enabled strategies to enhance crop nutrition and protection[J]. Nature Nanotechnology, 2019, 14(6): 532-540.
3	GAO Y H, ZHANG Y H, HE S, et al. Fabrication of a hollow mesoporous silica hybrid to improve the targeting of a pesticide[J]. Chemical Engineering Journal, 2019, 364: 361-369.
4	HAO L, GONG L H, CHEN L, et al. Composite pesticide nanocarriers involving functionalized boron nitride nanoplatelets for pH-responsive release and enhanced UV stability[J]. Chemical Engineering Journal, 2020, 396: 125233.
5	CHEN H Y, CHEN L S, SHEN Z C, et al. Synthesis of mesoporous silica post-loaded by methyl eugenol as an environment-friendly slow-release bio pesticide[J]. Scientific Reports, 2020, 10: 6108.
6	ZHAO M, ZHOU H J, CHEN L, et al. Carboxymethyl chitosan grafted trisiloxane surfactant nanoparticles with pH sensitivity for sustained release of pesticide[J]. Carbohydrate Polymers, 2020, 243: 116433.
7	LIN M H, FANG S, ZHAO X J, et al. Natamycin-loaded zein nanoparticles stabilized by carboxymethyl chitosan: evaluation of colloidal/chemical performance and application in postharvest treatments[J]. Food Hydrocolloids, 2020, 106: 105871.
8	PALIWAL R, PALAKURTHI S. Zein in controlled drug delivery and tissue engineering[J]. Journal of Controlled Release, 2014, 189: 108-122.
9	PEÑALVA R, ESPARZA I, GONZÁLEZ-NAVARRO C J, et al. Zein nanoparticles for oral folic acid delivery[J]. Journal of Drug Delivery Science and Technology, 2015, 30: 450-457.
10	SOLTANI S, MADADLOU A. Gelation characteristics of the sugar beet pectin solution charged with fish oil-loaded zein nanoparticles[J]. Food Hydrocolloids, 2015, 43: 664-669.
11	HAO L, LIN G, WANG H, et al. Preparation and characterization of zein-based nanoparticles via ring-opening reaction and self-assembly as aqueous nanocarriers for pesticides[J]. Journal of Agricultural and Food Chemistry, 2020, 68(36): 9624-9635.
12	ZHAO X L, WANG X J, SONG G J, et al. Microwave assisted copolymerization of sodium alginate and dimethyl diallyl ammonium chloride as flocculant for dye removal[J]. International Journal of Biological Macromolecules, 2020, 156: 585-590.
13	LIU G H, LIN G Q, LIN X D, et al. Enzyme and pH dual-responsive avermectin nano-microcapsules for improving its efficacy[J]. Environmental Science and Pollution Research, 2019, 26(24): 25107-25116.
14	邱松发, 许斌华, 林冠权, 等. 2,4-D/CMC接枝物纳米粒子的制备与缓释性能研究[J]. 化工学报, 2019, 70(5): 2007-2015.
	QIU Songfa, XU Binhua, LIN Guanquan, et al. Preparation and sustained release performance of 2,4-D/grafted CMC nanoparticles[J]. CIESC Journal, 2019, 70(5): 2007-2015.
15	王春鑫. 功夫菊酯和吡唑醚菌酯纳米载药系统构建与表征[D]. 北京: 中国农业科学院, 2019.
	WANG Chunxin. Construction and characterization of lambda-cyhalothrin and pyraclostrobin nanopesticide delivery system[D]. Beijing: Chinese Academy of Agricultural Sciences, 2019.
16	DENG L L, LI Y, FENG F Q, et al. Study on wettability, mechanical property and biocompatibility of electrospun gelatin/zein nanofibers cross-linked by glucose[J]. Food Hydrocolloids, 2019, 87: 1-10.
17	田立颖, 杜杨, 吉法祥, 等. 二甲基二烯丙基氯化铵-丙烯酰胺共聚物的合成与结构表征[J]. 精细化工, 2000, 17(10): 567-569.
	TIAN Liying, DU Yang, JI Faxiang, et al. Synthesis and structural characterization of copolymer of dimethyldiallylammonium chloride and acrylamide[J]. Fine Chemicals, 2000, 17(10): 567-569.
18	CHEN L, ZHOU H J, HAO L, et al. Dialdehyde carboxymethyl cellulose-zein conjugate as water-based nanocarrier for improving the efficacy of pesticides[J]. Industrial Crops and Products, 2020, 150: 112358.
19	HOLLOWAY P J. Surface factors affecting the wetting of leaves[J]. Pesticide Science, 1970, 1(4): 156-163.
20	HAO L, LIN G Q, LIAN J J, et al. Carboxymethyl cellulose capsulated zein as pesticide nano-delivery system for improving adhesion and anti-UV properties[J]. Carbohydrate Polymers, 2020, 231: 115725.
21	林冠权. 改性玉米醇溶蛋白负载阿维菌素纳米农药的制备及性能[D]. 广州: 仲恺农业工程学院, 2019.
	LIN Guanquan. Preparation and properties of modified zein loaded avermectin nano-pesticide[D]. Guangzhou: Zhongkai University of Agriculture and Engineering, 2019.
22	陈龙, 周红军, 江海科, 等. 叶面亲和型阿维菌素微胶囊的制备及pH响应性释放性能[J]. 化工进展, 2020, 39(1): 348-355.
	CHEN Long, ZHOU Hongjun, JIANG Haike, et al. Preparation and pH responsive release properties of foliar affinity avermectin microcapsules[J]. Chemical Industry and Engineering Progress, 2020, 39(1): 348-355.
23	KHAN M A, YUE C, FANG Z, et al. Alginate/chitosan-coated zein nanoparticles for the delivery of resveratrol[J]. Journal of Food Engineering, 2019, 258: 45-53.
24	SHEN Z C, WEN H J, ZHOU H J, et al. Coordination bonding-based polydopamine-modified mesoporous silica for sustained avermectin release[J]. Materials Science and Engineering: C, 2019, 105: 110073.

样品	m_zein/g	m_DMDAAC/g	接枝率/%
Zein-g-PDMDAAC-1	2.00	2.00	27.35
Zein-g-PDMDAAC-2	2.00	4.00	65.00
Zein-g-PDMDAAC-3	2.00	6.00	150.05

样品	m_zein/g	m_DMDAAC/g	接枝率/%
Zein-g-PDMDAAC-1	2.00	2.00	27.35
Zein-g-PDMDAAC-2	2.00	4.00	65.00
Zein-g-PDMDAAC-3	2.00	6.00	150.05

样品	粒径/nm	电位/mV	EE/%
Zein-g-PDMDAAC-1@AVM	1524.83±89.74	18.01±0.86	92.25±0.18
Zein-g-PDMDAAC-2@AVM	315.73±15.23	22.18±1.34	80.20±0.47
Zein-g-PDMDAAC-3@AVM	64.92±1.85	27.71±1.30	34.75±0.18

样品	粒径/nm	电位/mV	EE/%
Zein-g-PDMDAAC-1@AVM	1524.83±89.74	18.01±0.86	92.25±0.18
Zein-g-PDMDAAC-2@AVM	315.73±15.23	22.18±1.34	80.20±0.47
Zein-g-PDMDAAC-3@AVM	64.92±1.85	27.71±1.30	34.75±0.18

[1]	LI Ziyong, MA Jingxi, ZHAO Ming, CHEN Long, ZHOU Hongjun, ZHOU Xinhua. Preparation and performance of carboxymethyl cellulose-soybean protein isolate pesticides sustained-release particles [J]. Chemical Industry and Engineering Progress, 2021, 40(5): 2739-2746.
[2]	Long CHEN,Hongjun ZHOU,Haike JIANG,Li HAO,Huayao CHEN,Xinhua ZHOU. Preparation and pH responsive release properties of foliar affinity avermectin microcapsules [J]. Chemical Industry and Engineering Progress, 2020, 39(1): 348-355.
[3]	SUN Qing, LUO Wei, ZHANG Jian, SHENG Jiawei. Preparation of calcium alginate/halloysite drug-loaded microspheres and its sustained-release properties for metformin hydrochloride [J]. Chemical Industry and Engineering Progress, 2018, 37(08): 3138-3145.
[4]	ZHU Lihui1，CHEN Aizheng1，2，WANG Shibin1，2. Research progress in preparation and modification of porous polymeric microspheres for pulmonary drug delivery [J]. Chemical Industry and Engineering Progree, 2014, 33(07): 1832-1838.
[5]	SUN Xuezhan1，LIU Yuangang1，2，WANG Shibin1，2，LAN Qi1. Properties of calcium alginate/chitosan microcapsules with high [J]. Chemical Industry and Engineering Progree, 2010, 29(9): 1725-.