The synthesis and photoactivated cytotoxicity of 2-methyl-4-oxo-3-prop-2-yn-1-ylcyclopent-2-en-1-yl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate conjugated with alpha-terthienyl derivatives.
The synthesis of one pyrethroid insecticide [2-methyl-4-oxo-3-prop-2-yn-1-ylcyclopent-2-en-1-yl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (Abbrev. JZ) (Fig. 1)] conjugated with a series of alpha-terthienyl derivatives (2-8) (Fig. 1) by palladium/copper-catalyzed cross-coupling reaction is presented here for evaluating the photoactivated cytotoxicity. The photoactivated cytotoxicity on Spodoptera litura (SL) cell line was detected by MTT assay. The inhibitory activity of all the conjugates was enhanced in the irradiation condition, compared with that of JZ. The IC(50) values of the most effective compound 9 (Fig. 1) treated with irradiation were 11.60 microg mL(-1) at 24h and 8.93 microg mL(-1) at 48 h, respectively. Generation of intracellular reactive oxygen species (ROS) and change of mitochondrial transmembrane potential (MMP) on SL cells treated with compound 9 were used for the further photoactivated study. A summary of these experiments on compound 9 demonstrated the notable ROS generation and dramatic MMP decrease when irradiated with UVA light. The results also represented statistically significant difference between dark and irradiation treatment of compound 9. However, in control and JZ groups, the effects were not statistically different. It was proved that our prepared compounds were ideal candidates for new photoactivated pyrethroid insecticides.
Li
Na
N
Laboratory of Insect Toxicology and Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education, South China Agricultural University, Guangzhou, China.
Xu
Han-Hong
HH
Liu
Zheng-Yong
ZY
Yang
Zhuo-Hong
ZH
D000818:Animals; D002384:Catalysis; D002460:Cell Line; D003300:Copper / Q000737:chemistry; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000633:toxicity; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D053078:Membrane Potential, Mitochondrial / Q000528:radiation effects; D010165:Palladium / Q000737:chemistry; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D017382:Reactive Oxygen Species / Q000378:metabolism / Q000528:radiation effects; D018411:Spodoptera / Q000528:radiation effects; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000633:toxicity; D014466:Ultraviolet Rays
C545951:2-methyl-4-oxo-3-(3-(5'-bromo-2,2'-5',2'-terthien-5-yl)prop-2-yn-1-yl)cyclopent-2-en-1-yl-3-(2,2-dichlorovinyl)-2,2-dimethycyclopropanecarboxylate; D003521:Cyclopropanes; D007306:Insecticides; D017319:Photosensitizing Agents; D017382:Reactive Oxygen Species; D013876:Thiophenes; C015766:cyclopropanecarboxylic acid; C019101:alpha-terthienyl; D010165:Palladium; D003300:Copper