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In Vitro Metabolism of Cis- And Trans-Permethrin by Rat Liver Microsomes, and Its Effect on Estrogenic and Anti-Androgenic Activities

In Vitro Metabolism of Cis- And Trans-Permethrin by Rat Liver Microsomes, and Its Effect on Estrogenic and Anti-Androgenic Activities

Satoko Tange, Nariaki Fujimoto, Naoto Uramaru, Kazumi Sugihara, Shigeru Ohta, Shigeyuki Kitamura

Environ Toxicol Pharmacol. 2014 May;37(3):996-1005.

PMID: 24731973

Abstract:

Permethrin is a widely applied broad-spectrum pyrethroid insecticide that consists of a mixture of cis- and trans-isomers. We examined the changes of estrogenic and anti-androgenic activities resulting from metabolism of the isomers. Both cis- and trans-permethrin were hydrolyzed to 3-phenoxybenzyl alcohol (PBAlc) by rat liver microsomes, but the extent of hydrolysis of trans-permethrin was much greater than that of the cis-isomer. In the presence of NADPH, PBAlc was further transformed to 4'-hydroxylated PBAlc (4'-OH PBAlc), 3-phenoxybenzaldehyde (PBAld) and 3-phenoxybenzoic acid (PBAcid). cis-Permethrin, but not trans-permethrin, also afforded its 4'-hydroxylated derivative (4'-OH cis-permethrin). trans-Permethrin was an anti-androgen, but also showed weak estrogenic activity, while cis-permethrin was a weak estrogen and a weak anti-androgen. After incubation with rat liver microsomes in the presence of NADPH, cis-permethrin but not trans-permethrin was metabolically activated for estrogenic activity. On the other hand, estrogenic activity of trans-permethrin was not changed, but its anti-androgenic activity was enhanced after incubation. 4'-OH PBAlc and PBAlc showed estrogenic activity, while PBAld and PBAlc showed anti-androgenic activity. PBAcid showed neither activity. 4'-OH cis-permethrin showed both estrogenic and anti-androgenic activities. Overall, our results indicate that permethrin is metabolically activated for estrogenic and anti-androgen activities, and the microsomal transformation of permethrin to 4'-OH cis-permethrin, 4'-OH PBAlc and PBAlc contributes to the both metabolic activations.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
CS353685	trans-Permethrin-(phenoxy-d5)			Price

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