US EPA

2160044 

Journal Article 

Natural and anthropogenic environmental oestrogens: the scientific basis for risk assessment. Structure/activity relationships 

Dodge, JA 

1998 

1 

Pure and Applied Chemistry
ISSN: 0033-4545
EISSN: 1365-3075 

70 

9 

1725-1733 

English 

10.1351/pac199870091725 

WOS:000078507500011 

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0000180135&doi=10.1351%2fpac199870091725&partnerID=40&md5=6147a463b234c191cbed4eb8d0ff24be
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Accumulated structure-activity data on environmental oestrogens has focused on several structural sub-categories within this general family of chemical agents. Of these compounds, the most extensively studied include phyto-oestrogens, macrolactones, alkylphenols and arylphenols. For phyto-oestrogens, binding to the oestrogen receptor (ER) is observed for the flavone and isoflavone nucleus particularly when the stilbene-like core is appropriately functionalized with hydroxylation at the 4' and/or 7 positions. Simple alkyl phenols behave as weak oestrogens when substituted at the para position with a branched aliphatic group such as found in p-octyl and p-nonyl phenol. In the case of polychlorinated biphenyls (PCBs), quantitative structure-activity studies (QSAR) indicate that the electron donating properties of the hydroxyl moiety and the aromatic component correlate highly with affinity to the ER. Further studies have shown that the phenolic ring of PCBs favour orientation over the oestradiol D-ring with the hydroxyl group of the PCB in close proximity to the 17-hydroxyl of oestradiol while maximizing the hydrophobic overlap in the central regions. Structure-activity studies on diphenylethanes, such as dichlorodiphenyltrichloroethane (DDT), demonstrate the significance of the substituents present on both the aryl rings and the side-chain. Other structural classifications include polyhalogenated carbocyles.