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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 α-terthienyl derivatives

Paper ID Volume ID Publish Year Pages File Format Full-Text
30249 44466 2009 8 PDF Available
Title
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 α-terthienyl derivatives
Abstract

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 α-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 IC50 values of the most effective compound 9 (Fig. 1) treated with irradiation were 11.60 μg mL−1 at 24 h and 8.93 μg 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.

Keywords
Pyrethroid insecticide; α-terthienyl; Photoactivated cytotoxicity; Spodoptera litura cell; ROS; MMP
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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 α-terthienyl derivatives
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology B: Biology - Volume 96, Issue 3, 4 September 2009, Pages 170–177
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us