Pure Appl. Chem.,
Vol. 70, No. 9, pp. 1725-1733,
anthropogenic environmental oestrogens:
the scientific basis for risk assessment
J. A. Dodge
Lilly Research Laboratories, Indianapolis,
Indiana 46285, USA.
E-mail: [email protected]
structure-activity data on environmental estrogens has focused
on several structural sub-categories within this general family of
chemical agents. Of these compounds, the most extensively studied
include phytoestrogens, macrolactones, alkylphenols and arylphenols.
For phytoestrogens, binding to the estrogen 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 estrogens
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 favor orientation
over the estradiol D-ring with the hydroxyl group of the PCB in close
proximity to the 17-hydroxyl of estradiol 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.
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