Identification and steroid receptor activity of products formed from the bromination of technical nonylphenol

Hill, Elizabeth M and Smith, Michael D (2006) Identification and steroid receptor activity of products formed from the bromination of technical nonylphenol. Chemosphere, 64 (10). pp. 1761-1768. ISSN 0045-6535

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Alkylphenols are commonly present in wastewater effluents and may contribute to the total hormonal loading of receiving waters due to their weakly estrogenic properties. However the presence of reactive bromine species in some treated wastewaters can result in the formation of brominated alkylphenols which may also possess steroid receptor activity. In this study, the products of bromination of technical nonylphenol (NP) were identified, purified and tested in vitro in recombinant yeast steroid receptor transcription assays. Bromination of NP in the presence of acetic acid resulted in the formation of one major product which was identified as 2-bromo-4-nonylphenol (NPBr). In the presence of methanol/water, bromination of NP resulted in the formation 2,6-dibromo-4-nonylphenol (NPBr2) as well as a number of other minor polybrominated products. The EC50 of NPBr in the yeast estrogen receptor transcription (YES) assay was 6.7 × 10-6 M, which was 48 fold less active than NP and 86 000 fold less active than the estrogen agonist 17ß-estradiol NPBr2 was not active in the YES assay. NP, NPBr and NPBr2 were all weakly androgenic in the yeast androgen receptor transcription assay but at concentrations which were 100 000 fold less active than the androgen receptor agonist dihydrotestosterone. Neither NP, NPBr or NPBr2 exhibited appreciable anti-estrogenic or anti-androgenic activity in the yeast receptor transcription assays. This study suggests that bromination of NP markedly reduces its estrogen receptor transcription activity but has no effect on the weak androgen receptor transcription activity of the alkylphenol.

Item Type: Article
Schools and Departments: School of Life Sciences > Evolution, Behaviour and Environment
Depositing User: Elizabeth Hill
Date Deposited: 06 Feb 2012 21:17
Last Modified: 22 Mar 2012 15:12
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