Design, synthesis, insecticidal evaluation and molecular docking studies of cis-nitenpyram analogues bearing diglycine esters

详细信息    查看全文

• 作者：YanXia Chen (1)
  ChuanWen Sun (1) (2)
  XiaXia Wen (1)
  WangGeng Zhang (2)
  
• 关键词：cis ; nitenpyram analogues ; hydrogen bonds ; diglycine ester ; synthesis ; insecticidal activity ; molecular docking ; nAChRs ; peptide bond
• 刊名：SCIENCE CHINA Chemistry
• 出版年：2013
• 出版时间：February 2013
• 年：2013
• 卷：56
• 期：2
• 页码：159-168
• 全文大小：708KB
• 参考文献：1. Denholm I, Devine G, Foster S, Gorman K, Nauen R. Incidence and management of insecticide resistance to neonicotinoids. / Proc Brighton Crop Prot Conf-Pests and Diseases. BCPC: Farnham, Surrey, U.K., 2002. 161鈥?68
  2. Nauen R, Denholm I. Resistance of insect pests to neonicotinoid insecticides: Current status and future prospects. / Arch Ins Biochem Physiol, 2005, 58: 200鈥?15 CrossRef
  3. Jeschke P, Nauen R. Neonicotinoids鈥擣rom zero to hero in insecticide chemistry. / Pest Manag Sci, 2008, 64: 1084鈥?098 CrossRef
  4. Elbert A, Becker B, Hartwig J, Erdelen C. Imidacloprid: A new systemic insecticide. / Pflanzenschutz-Nachrichten Baye, 1990, 44: 113鈥?36
  5. Matsuda K, Buckingham SD, Kleier D, Rauh JJ, Grauso M, Sattelle DB. Neonicotinoids: Insecticides acting on insect nicotinic acetylcholine receptors. / Trends Pharmacol Sci, 2001, 22: 573鈥?80 CrossRef
  6. Tomizawa M, Casida JE. Neonicotinoid insecticide toxicology: Mechanisms of selective action. / Annu Rev Pharmacol Toxicol, 2005, 45: 247鈥?68 CrossRef
  7. Elbert A, Nauen R. Resistance of Bemisia tabaci (Homoptera: Aleyrodidae) to insecticides in southern Spain with special reference to neonicotinoids. / Pest Manag Sci, 2000, 56: 60鈥?4 CrossRef
  8. Zhao JZ, Bishop BA, Grafius EJ. Inheritance and synergism of resistance to imidacloprid in the Colorado potato beetle (Coleoptera: Chrysomelidae). / J Econ Entomol, 2000, 93: 1508鈥?514 CrossRef
  9. Liu ZW, Han ZJ, Wang YC, Zhang LC, Zhang HW, Liu CJ. Selection for imidacloprid resistance in Nilaparvata lugens: Cross-resistance patterns and possible mechanisms. / Pest Manag Sci, 2003, 59: 1355鈥?359 CrossRef
  10. Ninsin KD. Acetamiprid resistance and cross-resistance in the diamondback moth, Plutella xylostella. / Pest Manag Sci, 2004, 60: 839鈥?41 CrossRef
  11. Sanchez DM, Hollingworth RM, Grafius EJ, Moyer DD. Resistance and cross-resistance to neonicotinoid insecticides and spinosad in the Colorado potato beetle, / Leptinotarsa decemlineata (Say) (Coleoptera: Chrysomelidae). / Pest Manag Sci, 2006, 62: 30鈥?7 CrossRef
  12. Gorman, KG, Devine G, Bennison J, Coussons P, Punchard N, Denholm I. Report of resistance to the neonicotinoid insecticide imidacloprid in / Trialeurodes vaporariorum (Hemiptera: Aleyrodidae). / Pest Manag Sci, 2007, 63: 555鈥?58 CrossRef
  13. Kristensen M, Jespersen JB. Susceptibility to thiamethoxam of Musca domestica from Danish livestock farms. / Pest Manag Sci, 2008, 64: 126鈥?32 CrossRef
  14. Liu ZW, Williamson MS, Lansdell SJ, Denholm I, Han ZJ, Millar NS. A nicotinic acetylcholine receptor mutation conferring target-site resistance to imidacloprid in / Nilaparvata lugens (brown planthopper). / Proc Natl Acad Sci USA, 2005, 102: 8420鈥?425 CrossRef
  15. Shao XS, Zhang WW, Peng YQ, Li Z, Tian ZZ, Qian XH. / cis-Nitromethylene neonicotinoids as new nicotinic family: Synthesis, structural diversity, and insecticidal evaluation of hexahydroimidazo-[1,2- / R]pyridine. / Bioorg Med Chem Lett, 2008, 18: 6513鈥?516 CrossRef
  16. Shao XS, Li Z, Qian XH, Xu XY. Design, synthesis, and insecticidal activities of novel analogues of neonicotinoids: Replacement of nitromethylene with nitroconjugated system. / J Agric Food Chem, 2009, 57: 951鈥?57 CrossRef
  17. Shao XS, Fu H, Xu XY, Xu XL, Liu ZW, Li Z, Qian XH. Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: Design, synthesis, crystal structure, and insecticidal activities. / J Agric Food Chem, 2010, 58: 2696鈥?702 CrossRef
  18. Sun CW, Xu X, Xu JH, Yan DR, Fang T, Liu TY. Synthesis, insecticidal activity, and molecular docking studies of nitenpyram analogues with a fexible ester arm anchored on tetrahydropyrimidine ring. / J Agric Food Chem, 2011, 59: 4828鈥?835 CrossRef
  19. Sewald N, Jakubke HD. / Peptides: Chemistry and Biology. Wiley-VCH, Wienheim. 2002 CrossRef
  20. Wagner I, Musso H. New naturally occurring amino acids. / Angew Chem Int Ed Engl, 1983, 95: 827鈥?30
  21. Pastor IM, V盲stil盲 P, Adolfsson H. Employing the structural diversity of nature: Development of modular dipeptide-analogue ligands for ruthenium-catalyzed enantioselective transfer hydrogenation of ketones. / Chem Eur J, 2003, 9: 4031鈥?045 CrossRef
  22. Lu XQ, Zhao GQ, Song X, Xie JM. A novel method of synthesis of polar amino acid methyl ester hydrochlorides. / Chem World, 2007, 48: 357鈥?59
  23. Wang DS. Synthesis of nitenpyram. / Nongyao, 2002, 41: 43鈥?4
  24. Dallinger D, Kappe CO. Microwave-assisted synthesis in water as solvent. / Chem Rev, 2007, 107: 2563鈥?591 CrossRef
  25. Zhao PL, Wang F, Zhang ZM. Synthesis, fungicidal, and insecticidal activities of 渭-methoxyacrylate-containing N-acetyl pyrazoline derivatives. / J Agric Food Chem, 2008, 56: 10767鈥?0773 CrossRef
  26. Abbott WS. A method of computing the effectiveness of an insecticide. / J Econ Entomol, 1995, 18: 265鈥?67
  27. Huey R, Morris GM, Olson AJ. A semiempirical free energy force field with charge-based desolvation. / J Comput Chem, 2007, 28: 1145鈥?152 CrossRef
  28. Ihara M, Okajima T, Yamashita A. Crystal structures of Lymnaea stagnalis AChBP in complex with neonicotinoid insecticides imidacloprid and clothianidin. / Invert Neurosci, 2008, 8: 71鈥?1 CrossRef
  
• 作者单位：YanXia Chen (1)
  ChuanWen Sun (1) (2)
  XiaXia Wen (1)
  WangGeng Zhang (2)
  
  1. College of Life and Environment Sciences, Shanghai Normal University, Shanghai, 200234, China
  2. Jiangsu Institute of Ecomones Co., Ltd., Jintan, 213200, China
  
• ISSN：1869-1870

文摘

Based on the strategies of receptor structure-guided neonicotinoid design, a series of novel cis-nitenpyram analogues bearing diglycine esters were designed and synthesized. Preliminary bioassays indicated that the insecticidal spectra of the target compounds were expanded compared with our previous work, while all the target compounds presented excellent insecticidal activities against Nilaparvata lugens and Aphis medicagini at 100 mg/L. Among these analogues, 6b showed 100% mortality against Nilaparvata lugens (LC50 = 0.163 mg/L) and 90% against Aphis medicagini at 4 mg/L. SARs suggested that the insecticidal potency of our designed cis-nitenpyram analogues was dual-controlled by the size and species of the ester groups. The molecular docking simulations revealed that the structural uniqueness of these analogues may lead to a unique molecular recognition and binding mode compared with the previously designed compounds. Introduction of the peptide bond gave rise to more significant hydrogen bonds between the nitenpyram analogues bonding with the amino acid residues of insect nAChRs. The docking results explained the SARs observed in vitro, and shed light on the novel insecticidal mechanism of these cis-nitenpyram analogues.