Understanding the endocrine disruption of chiral pesticides: The enantioselectivity in estrogenic activity of synthetic pyrethroids
作者： Cui Wang , Quan Zhang , XiaoFeng Zhang , Jing Liu , WeiPing Liu
DOI: 10.1007/S11426-010-0143-7
关键词:
摘要: Synthetic pyrethroids (SPs), a family of chiral insecticides consisting multiple stereoismers, have been regarded as estrogenic endocrine-disrupting chemicals (EDCs). In this study, we applied the yeast two-hybrid and molecular docking (MD) assay to assess enantioselective activities three commonly used SPs, bifenthrin (cis-BF), permethrin (PM) fenvalerate (Fen). The β-galactosidase analyses indicated that all testing displayed significant (p<0.05) enantioselectivity. results showed potential cis-BF was mainly attributed 1S-cis-BF. Neither PM nor Fen effects. However, two stereoisomers possessed activities. αR-2R-Fen αS-2S-Fen also induced activity. inability initiate reporter gene expression by racemic may be due low ratios these isomers or antagonism among them. strong hydrophobic interaction hydrogen bond between positive ERα support our biological results. This research demonstrated activity SPs selective binding their receptor. data suggests enantioselectivity pesticides is
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J. Miyamoto, N. Kurihara, Chirality in agrochemicals. John Wiley & Sons. ,(1998)
Synthetic Pyrethroids: Occurrence and Behavior in Aquatic Environments American Chemical Society. ,(2008) , 10.1021/BK-2008-0991
Lumei Wang, Weiping Liu, Caixia Yang, Zhiyan Pan, Jianying Gan, Chao Xu, Meirong Zhao, Daniel Schlenk, None, Enantioselectivity in estrogenic potential and uptake of bifenthrin. Environmental Science & Technology. ,vol. 41, pp. 6124- 6128 ,(2007) , 10.1021/ES070220D
L. A. Greene, A. S. Tischler, Establishment of a noradrenergic clonal line of rat adrenal pheochromocytoma cells which respond to nerve growth factor. Proceedings of the National Academy of Sciences of the United States of America. ,vol. 73, pp. 2424- 2428 ,(1976) , 10.1073/PNAS.73.7.2424
Shanshan Zhou, Kunde Lin, Huayun Yang, Ling Li, Weiping Liu, Jian Li, Stereoisomeric separation and toxicity of a new organophosphorus insecticide chloramidophos. Chemical Research in Toxicology. ,vol. 20, pp. 400- 405 ,(2007) , 10.1021/TX600281N
J Payne, N Rajapakse, M Wilkins, A Kortenkamp, Prediction and assessment of the effects of mixtures of four xenoestrogens. Environmental Health Perspectives. ,vol. 108, pp. 983- 987 ,(2000) , 10.1289/EHP.00108983
Chao Xu, Meirong Zhao, Weiping Liu, Shengwen Chen, Jiangying Gan, Enantioselectivity in zebrafish embryo toxicity of the insecticide acetofenate. Chemical Research in Toxicology. ,vol. 21, pp. 1050- 1055 ,(2008) , 10.1021/TX8000016
Meirong Zhao, Weiping Liu, ENANTIOSELECTIVITY IN THE IMMUNOTOXICITY OF THE INSECTICIDE ACETOFENATE IN AN IN VITRO MODEL Environmental Toxicology and Chemistry. ,vol. 28, pp. 578- 585 ,(2009) , 10.1897/08-246.1
Joern Faller, Heinrich Huehnerfuss, Wilfried A. Koenig, Ralph Krebber, Peter Ludwig, Do marine bacteria degrade .alpha.-hexachlorocyclohexane stereoselectively? Environmental Science & Technology. ,vol. 25, pp. 676- 678 ,(1991) , 10.1021/ES00016A011
Willem Dhooge, Katrien Arijs, Isabel D’Haese, Sabrina Stuyvaert, Bram Versonnen, Colin Janssen, Willy Verstraete, Frank Comhaire, Experimental parameters affecting sensitivity and specificity of a yeast assay for estrogenic compounds: results of an interlaboratory validation exercise Analytical and Bioanalytical Chemistry. ,vol. 386, pp. 1419- 1428 ,(2006) , 10.1007/S00216-006-0669-X