Odorant-Binding Protein 3-Oriented Rational Design and Discovery of Novel Jasmonate Derivatives as Potential Aphid-Repellent Agents.

Odorant-binding protein (OBP) is a potential target for developing insect behavior control agents due to its properties in transporting semiochemicals. In this study, 12 novel jasmonic acid (JA) derivatives were rationally designed and synthesized based on the binding features between OBP3 (ApisOBP3) and compound [()-3,7-dimethylocta-2,6-dien-1-yl 2-(3-oxo-2-pentylcyclopentyl)acetate] with a binding affinity () of 26.79 μM. Most novel JA derivatives displayed better binding affinities than ( = 1-26 μM). Among them, compound [()-3,7-dimethylocta-2,6-dien-1-yl-2-(()-3-((acryloyloxy)imino)-2-pentylcyclopentyl)acetate] is the most promising compound with an excellent of 1.33 μM and a significant repellent activity with repellent rates of 50-60% against and . Both hydrophobic and electrostatic interactions were found to contribute significantly to the binding of to ApisOBP3. This study provides significant guidance for the rational design and efficient identification of novel aphid repellents based on aphid OBPs.