title: Design, synthesis and aphicidal activity of N-terminal modified insect kinin analogs.
abstract: The insect kinins are a class of multifunctional insect neuropeptides present in a diverse variety of insects. Insect kinin analogs showed multiple bioactivities, especially, the aphicidal activity. To find a biostable and bioactive insecticide candidate with simplified structure, a series of N-terminal modified insect kinin analogs was designed and synthesized based on the lead compound [Aib]-Phe-Phe-[Aib]-Trp-Gly-NH2. Their aphicidal activity against the soybean aphid Aphis glycines was evaluated. The results showed that all the analogs maintained the aphicidal activity. In particular, the aphicidal activity of the pentapeptide analog X Phe-Phe-[Aib]-Trp-Gly-NH2 (LC50=0.045mmol/L) was similar to the lead compound (LC50=0.048mmol/L). This indicated that the N-terminal protective group may not play an important role in the activity and the analogs structure could be simplified to pentapeptide analogs while retaining good aphicidal activity. The core pentapeptide analog X can be used as the lead compound for further chemical modifications to discover potential insecticides.
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, PR China.
authors.forename: Chuanliang
authors.initials: C
authors.lastname: Zhang
authors.affiliation: Department of Entomology, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, PR China.
authors.forename: Yanyan
authors.initials: Y
authors.lastname: Qu
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, PR China.
authors.forename: Xiaoqing
authors.initials: X
authors.lastname: Wu
authors.affiliation: Department of Entomology, College of Agronomy and Biotechnology, China Agricultural University, Beijing 100193, PR China.
authors.forename: Dunlun
authors.initials: D
authors.lastname: Song
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, PR China.
authors.forename: Yun
authors.initials: Y
authors.lastname: Ling
authors.affiliation: Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, PR China. Electronic address: yangxl@cau.edu.cn.
authors.forename: Xinling
authors.initials: X
authors.lastname: Yang
mesh_terms: D000818:Animals; D001042:Aphids / Q000187:drug effects; D015195:Drug Design; D019476:Insect Proteins / Q000138:chemical synthesis / Q000494:pharmacology*; D007306:Insecticides / Q000138:chemical synthesis / Q000494:pharmacology*; D007705:Kinins / Q000138:chemical synthesis / Q000494:pharmacology*; D057786:Peptidomimetics / Q000138:chemical synthesis / Q000494:pharmacology*
chemical_list: D019476:Insect Proteins; D007306:Insecticides; D007705:Kinins; D057786:Peptidomimetics
keywords: Aphicidal activity; Insect kinins; Insecticides; N-terminal modified; Peptidomimetics