De Novo Design of Potent, Insecticidal Synthetic Mimics of the Spinosyn Macrolide Natural Products

Sci Rep. 2018 Mar 20;8(1):4861. doi: 10.1038/s41598-018-22894-6.

Abstract

New insect pest control agents are needed to meet the demands to feed an expanding global population, to address the desire for more environmentally-friendly insecticide tools, and to fill the loss of control options in some crop-pest complexes due to development of insecticide resistance. The spinosyns are a highly effective class of naturally occurring, fermentation derived insecticides, possessing a very favorable environmental profile. Chemically, the spinosyns are composed of a large complex macrolide tetracycle coupled to two sugars. As a means to further exploit this novel class of natural product-based insecticides, molecular modeling studies coupled with bioactivity-directed chemical modifications were used to define a less complex, synthetically accessible replacement for the spinosyn tetracycle. These studies lead to the discovery of highly insecticidal analogs, possessing a simple tri-aryl ring system as a replacement for the complex macrolide tetracycle.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / pharmacology
  • Biological Products / pharmacology
  • Insect Control / methods*
  • Insecta / drug effects
  • Insecticide Resistance / drug effects
  • Insecticides / chemical synthesis
  • Insecticides / pharmacology
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Macrolides / pharmacology*
  • Models, Molecular
  • Protein Synthesis Inhibitors / pharmacology

Substances

  • Anti-Bacterial Agents
  • Biological Products
  • Insecticides
  • Macrolides
  • Protein Synthesis Inhibitors