Design, synthesis, insecticidal activity and molecular docking of doramectin derivatives

doi:10.1016/j.bmc.2018.12.040

CORC > 成都生物研究所 > 中国科学院成都生物研究所 > 国家天然药物工程技术研究中心 > 天然产物研究

	Design, synthesis, insecticidal activity and molecular docking of doramectin derivatives
	Zhang, Qi 1,3; Bai, Ping 1,3; Zheng, Cheng 1,3; Cheng, Yao 1,3; Wang, Tao 1,3; Lu, Xiaoxia 2,3
刊名	BIOORGANIC & MEDICINAL CHEMISTRY
	2019
卷号	27 期号:12(SI)页码:2387-2396
关键词	Doramectin derivatives Insecticidal activities Molecular docking Oriental armyworm Diamondback moth Corn borer
ISSN号	0968-0896
DOI	10.1016/j.bmc.2018.12.040
产权排序	1
文献子类	Article
英文摘要	A series of new doramectin derivatives containing carbamate, ester and sulfonate were synthesized, and their structures were characterized by H-1 and C-13 nuclear magnetic resonance (NMR) and high-resolution mass spectrum (HRMS). Their insecticidal activities against oriental armyworm, diamondback moth, and corn borer were evaluated and compared with the parent doramectin and commercial avermectins, metolcarb, fenpropathrin. Among all compounds, three compounds (3a, 3g and 3h) showed excellent insecticidal effect. In particular, compound 3g containing cyclopropyl carbamate against oriental armyworm, diamondback moth, and corn borer, exhibited the most promising insecticidal activity with the final mortality rate of 66.67%, 36.67%, 40.00% at the concentration of 12.5 mg/L, respectively. The LC50 values of 3g were 5.8859, 22.3214, and 22.0205 mg/L, showing 6.74, 2.23, 2.21-fold higher potency than parent doramectin (LC50 values of 39.6907, 49.7736, and 48.6129 mg/L) and 6.83, 1.93, 3.36-fold higher potency than commercial avermectins (LC50 values of 40.2489, 42.9922, and 73.9508 mg/L). Additionally, molecular docking simulations revealed that 3g displayed stronger hydrogen-bonding action in binding with the GABA receptor than parent doramectin, which were crucial for keeping high insecticidal activity. The present work demonstrated that these compounds containing alkyl carbamate group could be considered as potential candidates for the development of novel pesticides in the future.
学科主题	Chemistry & Analysis
URL标识	查看原文
WOS关键词	BIOLOGICAL-ACTIVITIES ; AVERMECTIN ; TOXICITY ; ANALOGS
WOS研究方向	Biochemistry & Molecular Biology ; Pharmacology & Pharmacy ; Chemistry
语种	英语
出版者	PERGAMON-ELSEVIER SCIENCE LTD
WOS记录号	WOS:000468879400013
内容类型	期刊论文
源URL	[http://210.75.237.14/handle/351003/30932]
专题	国家天然药物工程技术研究中心_天然产物研究
通讯作者	Lu, Xiaoxia
作者单位	1.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 2.Hainan Normal Univ, Minist Educ, Key Lab Trop Med Plant Chem, Haikou 571127, Hainan, Peoples R China; 3.Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610041, Sichuan, Peoples R China;
推荐引用方式 GB/T 7714	Zhang, Qi,Bai, Ping,Zheng, Cheng,et al. Design, synthesis, insecticidal activity and molecular docking of doramectin derivatives[J]. BIOORGANIC & MEDICINAL CHEMISTRY,2019,27(12(SI)):2387-2396.
APA	Zhang, Qi,Bai, Ping,Zheng, Cheng,Cheng, Yao,Wang, Tao,&Lu, Xiaoxia.(2019).Design, synthesis, insecticidal activity and molecular docking of doramectin derivatives.BIOORGANIC & MEDICINAL CHEMISTRY,27(12(SI)),2387-2396.
MLA	Zhang, Qi,et al."Design, synthesis, insecticidal activity and molecular docking of doramectin derivatives".BIOORGANIC & MEDICINAL CHEMISTRY 27.12(SI)(2019):2387-2396.