Pest management science · 2025
Structural optimization of SDH-targeting chalcone derivatives: piperazine-driven binding stability against Xanthomonas pathogens.
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Deng Tianyu, Meng Kaini, Fu Hong, Wang Yuhong, Zou Hongqian, Yang Ying, Sun Mingman, Xing Lang, Yu Xiujie, Liu Da, Xue Wei
Аннотация
BACKGROUND: Natural green pesticides have become a global research hotspot, and identifying chemical structural frameworks with excellent biological activity has become the research direction of numerous researchers.
RESULTS: Twenty chalcone derivatives incorporating 1,2,3,4-tetrahydroquinoline scaffolds were systematically evaluated for their antibacterial activity against six plant pathogenic bacteria. Among the tested compounds, H1-H10 exhibited superior in vitro inhibition against Xanthomonas citri pv. mangiferaeindicae (Xcm) compared to Y1-Y10. Notably, compound H6 demonstrated exceptional potency, with a median effective concentration (EC50) value of 3.25 μg mL-1 against Xcm, significantly surpassing the commercial agent (TC, EC50 = 75.34 μg mL-1). In vivo efficacy trials revealed that H6 achieved 65.24% curative activity at 100 μg mL-1, outperforming TC (42.81%). Scanning electron microscopy further confirmed H6's disruptive effects on bacterial membrane integrity. Mechanistic studies targeting succinate dehydrogenase (SDH), a key respiratory enzyme, revealed structural and energetic similarities between H6 and the commercial SDH inhibitor bixafen through molecular docking and dynamics simulations.
CONCLUSION: The 1,2,3,4-tetrahydroquinoline moiety enhanced SDH binding affinity, while the introduced piperazine substructure in H6 improved both complex stability (root mean square deviation <1.5 Å) and target engagement. These findings establish H6 as a promising lead compound for developing next-generation SDH inhibitors, providing critical insights into structure-activity relationships for agricultural antimicrobial design. © 2025 Society of Chemical Industry.
RESULTS: Twenty chalcone derivatives incorporating 1,2,3,4-tetrahydroquinoline scaffolds were systematically evaluated for their antibacterial activity against six plant pathogenic bacteria. Among the tested compounds, H1-H10 exhibited superior in vitro inhibition against Xanthomonas citri pv. mangiferaeindicae (Xcm) compared to Y1-Y10. Notably, compound H6 demonstrated exceptional potency, with a median effective concentration (EC50) value of 3.25 μg mL-1 against Xcm, significantly surpassing the commercial agent (TC, EC50 = 75.34 μg mL-1). In vivo efficacy trials revealed that H6 achieved 65.24% curative activity at 100 μg mL-1, outperforming TC (42.81%). Scanning electron microscopy further confirmed H6's disruptive effects on bacterial membrane integrity. Mechanistic studies targeting succinate dehydrogenase (SDH), a key respiratory enzyme, revealed structural and energetic similarities between H6 and the commercial SDH inhibitor bixafen through molecular docking and dynamics simulations.
CONCLUSION: The 1,2,3,4-tetrahydroquinoline moiety enhanced SDH binding affinity, while the introduced piperazine substructure in H6 improved both complex stability (root mean square deviation <1.5 Å) and target engagement. These findings establish H6 as a promising lead compound for developing next-generation SDH inhibitors, providing critical insights into structure-activity relationships for agricultural antimicrobial design. © 2025 Society of Chemical Industry.