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Related Experiment Videos

Mapping the elusive neonicotinoid binding site.

Motohiro Tomizawa1, Todd T Talley, David Maltby

  • 1Environmental Chemistry and Toxicology Laboratory, Department of Environmental Science, Policy, and Management, University of California, Berkeley, CA 94720-3112, USA.

Proceedings of the National Academy of Sciences of the United States of America
|May 9, 2007
PubMed
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This study reveals distinct binding interactions of neonicotinoid and nicotinoid insecticides with insect nicotinic acetylcholine receptors (nAChRs) using photoaffinity probes. Understanding these differences clarifies insecticide selectivity and aids in developing safer pest control strategies.

Area of Science:

  • Biochemistry
  • Pharmacology
  • Insecticide Development

Background:

  • Neonicotinoids and nicotinoids are structurally similar agonists with differing biological properties and target selectivities.
  • Neonicotinoids are nonprotonated insecticides targeting insect nicotinic receptors, while nicotinoids are cationic and target mammalian systems.
  • A mollusk acetylcholine binding protein (AChBP) serves as a structural surrogate for the extracellular ligand-binding domain of nicotinic receptors.

Purpose of the Study:

  • To investigate the distinct molecular interactions of neonicotinoids and nicotinoids with nicotinic receptors.
  • To elucidate the binding site of neonicotinoids using photoaffinity probes and AChBP as a model system.
  • To map the molecular determinants governing agonist selectivity on nicotinic receptors.

Main Methods:

Related Experiment Videos

  • Utilized optimized azidochloropyridinyl photoaffinity probes to examine neonicotinoid and nicotinoid interactions with AChBP.
  • Compared two azidoneonicotinoids (nitro or cyano substituted) with their desnitro/descyano counterparts.
  • Analyzed protein modification sites using intact derivatized protein analysis and collision-induced dissociation.

Main Results:

  • Four photoactivated nitrene probes modified AChBP, with identical modification sites observed for both neonicotinoids and nicotinoids.
  • Key modification sites included Tyr-195 (loop C) and Met-116 (loop E) at the subunit interface.
  • Neonicotinoids interact with loop C Tyr-188 via their guanidine/amidine planes, while nicotinoids form hydrogen bonds and cation-pi interactions with Trp-147 and Tyr-93.

Conclusions:

  • Structural models based on AChBP successfully map the neonicotinoid binding site.
  • Distinct electronic and structural features dictate the differential interactions of neonicotinoids and nicotinoids with nicotinic receptors.
  • This research provides molecular insights into insecticide selectivity and the design of novel nicotinic receptor modulators.