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Electrophysiological Measurements from a Moth Olfactory System
Published on: March 29, 2011
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Perfluorinated moth pheromones : Synthesis and electrophysiological activity
G D Prestwich1, W C Sun, M S Mayer
1Department of Chemistry, State University of New York, 11794-3400, Stony Brook, New York.
Journal of Chemical Ecology
|November 23, 2013
Summary
Synthesizing perfluoroalkyl analogs of moth pheromones created more volatile compounds. These fluorinated pheromone analogs showed reduced sensitivity in moth olfactory receptor neurons, suggesting altered binding interactions.
Area of Science:
- Chemical Ecology
- Insect Behavior
- Organic Synthesis
Background:
- Moth sex pheromones are crucial for mating and communication.
- Understanding pheromone structure-activity relationships aids in pest control strategies.
- Perfluoroalkylation offers a method to modify molecular properties.
Purpose of the Study:
- To synthesize perfluoroalkyl analogs of pheromone constituents.
- To investigate the electrophysiological responses of moth olfactory neurons to these analogs.
- To determine how perfluoroalkylation affects pheromone volatility and receptor binding.
Main Methods:
- Synthesis of perfluoroalkyl analogs by replacing terminal alkyl groups with perfluorobutyl (Pfb) or perfluorohexyl (Pfh) moieties.
- Gas chromatography to assess volatility changes (Kovàts retention indices).
- Electrophysiological recordings from male antennal olfactory receptor neurons of three moth species (Heliothis zea, Trichoplusia ni, Diatraea grandiosella).
Main Results:
- Perfluoroalkyl analogs exhibited increased volatility compared to hydrocarbon counterparts.
- Specialist olfactory neurons showed similar spike discharge rates for native pheromones and their perfluoroalkyl analogs, but at different doses.
- Diatraea grandiosella sensilla displayed 100- to 1000-fold greater sensitivity to native pheromones than to Pfh- and Pfb-analogs.
- Electrophysiological response profiles were displaced, indicating altered sensitivity.
Conclusions:
- Replacement of terminal alkyl groups with perfluoroalkyl groups yields biologically active compounds with enhanced volatility.
- Reduced sensitivity to fluorinated analogs suggests diminished binding affinity to olfactory receptors.
- The more rigid and polar perfluoroalkyl moiety may interact less favorably with hydrophobic protein binding sites.
