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000000432 084__ $$2WoS$$aEngineering, Environmental
000000432 084__ $$2WoS$$aEnvironmental Sciences
000000432 1001_ $$0P:(DE-HGF)0$$aGabriel, F. L. P.$$b0
000000432 245__ $$aIsomer-specific degradation and endocrine disrupting activity of nonylphenols
000000432 260__ $$aColumbus, Ohio$$bAmerican Chemical Society$$c2008
000000432 300__ $$a6399 - 6408
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000000432 440_0 $$01865$$aEnvironmental Science and Technology$$v42$$x0013-936X$$y17
000000432 500__ $$aThis research was supported by the Swiss National Science Foundation within the framework of the National Research Programme NFP50 "Endocrine Disruptors: Relevance to Humans, Animals, and Ecosystems". We thank Dr. Ian Purvis and others at GlaxoSmithKline for kindly supplying the genetically modified yeast strain.
000000432 520__ $$aDegradation of technical nonylphenol by Sphingobium xenophagum Bayram led to a significant shift in the isomers composition of the mixture. By means of gas chromatography-mass spectrometry, we could observe a strong correlation between transformation of individual isomers and their a-substitution pattern, as expressed by their assignment to one of six mass spectrometric groups. As a rule, isomers with less bulkiness at the a-carbon and those with an optimally sized main alkyl chain (4-6 carbon atoms) were degraded more efficiently. By mass spectrometric analysis, we identified the two most recalcitrant main isomers of the technical mixture (Group4) as 4-(1,2-dimethyl-1-propylbutyl) phenols (NP193a and NP193b, which are diastereomers with a bulky alpha-CH3, alpha-CH(CH3)C2H5 substitution. Our experiments with strain Bayram show that the selective enrichment of isomers with bulky a-substitutions observed in nonylphenol fingerprints of natural systems can be caused by microbial ipso-hydroxylation. Based on the yeast estrogen assay (YES), we established an estrogenicity ranking with a variety of single isomers and compared it to rankings obtained with different reporter cell systems. Structure-activity relationships derived from these data suggest that Group 4 isomers have a high estrogenic potency. This indicates a substantial risk that enrichment of highly estrogenic isomers during microbial degradation by ipso-substitution will increase the specific estrogenicity of aging material.
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000000432 7001_ $$0P:(DE-HGF)0$$aRoutledge, E.J.$$b1
000000432 7001_ $$0P:(DE-HGF)0$$aHeidlberger, A.$$b2
000000432 7001_ $$0P:(DE-HGF)0$$aRentsch, D.$$b3
000000432 7001_ $$0P:(DE-Juel1)129325$$aGünther, K.$$b4$$uFZJ
000000432 7001_ $$0P:(DE-HGF)0$$aGiger, W.$$b5
000000432 7001_ $$0P:(DE-HGF)0$$aSumpter, J.P.$$b6
000000432 7001_ $$0P:(DE-HGF)0$$aKohler, H.-P.E.$$b7
000000432 773__ $$0PERI:(DE-600)1465132-4$$a10.1021/es800577a$$gVol. 42, p. 6399 - 6408$$p6399 - 6408$$q42<6399 - 6408$$tEnvironmental Science & Technology$$v42$$x0013-936X$$y2008
000000432 8564_ $$uhttps://juser.fz-juelich.de/record/432/files/Gabriel-2008-Isomer-specific_degradation_and_endocrine_disrupting-%28accepted_version%29.pdf$$yPublished on 2008-07-23. Available in OpenAccess from 2009-07-23.
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