Abstract
Incorporating the photoisomerizable azobenzene into imidacloprid produced a photoswitchable insecticidal molecule as the first neonicotinoid example of remote control insecticide performance with spatiotemporal resolution. The designed photoswitchable insecticides showed distinguishable activity against Musca both in vivo and in vitro upon irradiation. Molecular docking study further suggested the binding difference of the two photoisomers. The generation of these photomediated insecticides provides novel insight into the insecticidal activity facilitating further investigation on the functions of insect nicotinic acetylcholine receptors and opens a novel way to control and study insect behavior on insecticide poisoning using light.
Highlights
IntroductionThe spatiotemporal regulation of chemical[10] or biological events[11,12] using artificial molecular photoswitches has been successfully achieved in many systems such as catalyst[13,14,15], peptides[16,17], cells[18], receptors[19,20,21,22,23], ion channel[24,25,26,27,28], nucleic acid[29] and in living organism[30,31,32]
Three approaches, replacing the chloropyridinyl with AB, introducing AB into imidazolidine and combining two IMI molecules together, were adopted here for generating the azobenzene-modified imidacloprid (AMI) hoping that the mediation of insecticidal activity with light would be addressed by the introduction of photoswitchable AB
Using light as external physical stimuli to perturb insecticidal activity was realized by merging IMI with azobenzene
Summary
The spatiotemporal regulation of chemical[10] or biological events[11,12] using artificial molecular photoswitches has been successfully achieved in many systems such as catalyst[13,14,15], peptides[16,17], cells[18], receptors[19,20,21,22,23], ion channel[24,25,26,27,28], nucleic acid[29] and in living organism[30,31,32] This methodology was applied to the pharmaceutical chemistry generating the photo-controllable molecules which can be activated or deactivated upon irradiation[33,34,35,36,37,38]. As an entry to seeking photoswitchable insecticide, the present investigation describes the azobenzene-modified imidacloprid (AMI) analogues, which enable rapid regulation of activity by light and may lead to the development of novel insecticides driven by available physical stimuli
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