文献类型：期刊文献

英文题名：A Terminal ModificationStrategy for Enhancing theDifference in Photoregulated Activity of Azobenzene-TolfenpyradHybrids

作者：Zhang, Yongchao[1];Qiao, Zhi[2];Zhou, Cuncun[1];Yin, Qi[1];Shi, Lei[4];Li, Zhong[1,3];Fu, Wen[1];Shao, Xusheng[1,3,5,6]

机构：[1]East China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China;[2]Yantai Lannacheng Biotechnol Co Ltd, Yantai 264100, Shandong, Peoples R China;[3]East China Univ Sci & Technol, State Key Lab Bioreactor Engn, Shanghai 200237, Peoples R China;[4]Hangzhou Sinotek Qual & Technol Serv Co Ltd, Hangzhou 310052, Zhejiang, Peoples R China;[5]East China Univ Sci & Technol, Sch Pharm, Shanghai Frontier Sci Res Base Optogenet Tech Cell, Shanghai 200237, Peoples R China;[6]East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Sch Pharm, Minist Educ, Shanghai 200237, Peoples R China

年份：2026

卷号：74

期号：27

起止页码：21109

外文期刊名：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

收录：;EI(收录号：20262921137215);Scopus(收录号：2-s2.0-105044764022);WOS:【SCI-EXPANDED(收录号:WOS:001810483900001)】；

基金：This work was financially supported by the National Natural Science Foundation of China (32472610 and 32402439) and the Shanghai Frontiers Science Center of Optogenetic Techniques for Cell Metabolism (Shanghai Municipal Education Commission).

语种：英文

外文关键词：photopharmacology; tolfenpyrad; photochromicligand; azobenzene; photoinduced activity enhancement; photoinduced activity reduction

摘要：Photopharmacology provides a strategy for green pesticide design. Starting from tolfenpyrad, azobenzene-modified photochromic ligands ABT1-6 were synthesized. ABT6 showed high bioactivity and photoisomerization efficiency but limited trans/cis activity difference. To enhance this, terminal phenyl modifications yielded ABT7-15, which displayed amplified photoregulatory activity differences across pests. Notably, ABT14 exhibited a 4.8-fold photoinduced activity enhancement against Culex pipiens pallens larvae and a 6.6-fold photoinduced activity reduction against , while ABT11 achieved a 35-fold reduction against . Molecular docking and binding free energy calculations indicated stronger cis-isomer binding to the target via multiple hydrogen bonds. Molecular orbital analysis revealed a minimal HOMO-LUMO gap difference (0.05 eV) between isomers, suggesting activity differences arise from conformational changes in charge distribution rather than energy variations. This work demonstrates a rational design approach for high-performance photoresponsive pesticides.