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| Hauptseite > Publikationsdatenbank > Isomer-specific degradation and endocrine disrupting activity of nonylphenols > print |
| Hauptseite > Publikationsdatenbank > Isomer-specific degradation and endocrine disrupting activity of nonylphenols > print |
| 001 | 432 | ||
| 005 | 20201217122713.0 | ||
| 024 | 7 | _ | |a 10.1021/es800577a |2 DOI |
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| 084 | _ | _ | |2 WoS |a Engineering, Environmental |
| 084 | _ | _ | |2 WoS |a Environmental Sciences |
| 100 | 1 | _ | |a Gabriel, F. L. P. |b 0 |0 P:(DE-HGF)0 |
| 245 | _ | _ | |a Isomer-specific degradation and endocrine disrupting activity of nonylphenols |
| 260 | _ | _ | |c 2008 |a Columbus, Ohio |b American Chemical Society |
| 300 | _ | _ | |a 6399 - 6408 |
| 336 | 7 | _ | |a Journal Article |0 PUB:(DE-HGF)16 |2 PUB:(DE-HGF) |
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| 440 | _ | 0 | |a Environmental Science and Technology |x 0013-936X |0 1865 |y 17 |v 42 |
| 500 | _ | _ | |a This 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. |
| 520 | _ | _ | |a Degradation 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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| 700 | 1 | _ | |a Routledge, E.J. |b 1 |0 P:(DE-HGF)0 |
| 700 | 1 | _ | |a Heidlberger, A. |b 2 |0 P:(DE-HGF)0 |
| 700 | 1 | _ | |a Rentsch, D. |b 3 |0 P:(DE-HGF)0 |
| 700 | 1 | _ | |a Günther, K. |b 4 |u FZJ |0 P:(DE-Juel1)129325 |
| 700 | 1 | _ | |a Giger, W. |b 5 |0 P:(DE-HGF)0 |
| 700 | 1 | _ | |a Sumpter, J.P. |b 6 |0 P:(DE-HGF)0 |
| 700 | 1 | _ | |a Kohler, H.-P.E. |b 7 |0 P:(DE-HGF)0 |
| 773 | _ | _ | |0 PERI:(DE-600)1465132-4 |a 10.1021/es800577a |g Vol. 42, p. 6399 - 6408 |p 6399 - 6408 |q 42<6399 - 6408 |t Environmental Science & Technology |v 42 |x 0013-936X |y 2008 |
| 856 | 4 | _ | |u https://juser.fz-juelich.de/record/432/files/Gabriel-2008-Isomer-specific_degradation_and_endocrine_disrupting-%28accepted_version%29.pdf |y Published on 2008-07-23. Available in OpenAccess from 2009-07-23. |
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