Degradation of 17α-ethinylestradiol by ozonation--identification of the by-products and assessment of their estrogenicity and toxicity.
The presence of the synthetic estrogen 17α-ethinylestradiol (EE2) in waters at low levels is a concern due to its ability to act as an endocrine disruptor. Ozone (O(3)) is commonly used in water treatment and reacts with EE2 to form by-products having characteristics that are mostly unknown. The aim of this study was to identify the by-products of E2 and EE2 ozonation and determine their estrogenicity and toxicity relative to the parent compound. Ozonation by-products were identified via LC-MS analysis. The estrogenicity was measured using the YES assay, and toxicity was determined by monitoring effects on histology of fetal rat testes and testosterone secretion by these tissues. Two EE2 by-products were identified with open phenolic ring structures (masses 302 and 344 u). The Yeast Estrogen Screening (YES) assay showed a decreased but incomplete removal of estrogenicity after ozonation of EE2. Histological analysis of fetal testes revealed that neither E2 nor EE2, with or without ozonation, had any effect on seminiferous cord formation; however, a remarkable negative effect on testosterone secretion was observed, with EE2 by-products after ozonation showing the most rapid and extensive inhibition. These results show that the removal of EE2 via reaction with O(3) resulted in the formation of by-products that are less estrogenic (as demonstrated by the YES assay), but have a greater negative impact on testosterone secretion. Thus, the disappearance of the parent compound is not a sufficient endpoint, as the by-products created may be more toxic. Care should be taken when implementing oxidation applications such as ozone during waste water treatment.
Department of Chemical Engineering, McGill University, Montréal, Québec, Canada.
Simone
S
Larcher
Geraldine
G
Delbès
Bernard
B
Robaire
Viviane
V
Yargeau
D000818:Animals; D001681:Biological Assay; D052244:Endocrine Disruptors / Q000032:analysis / Q000737:chemistry / Q000633:toxicity; D045166:Estradiol Congeners / Q000032:analysis / Q000737:chemistry / Q000633:toxicity; D004967:Estrogens / Q000032:analysis / Q000737:chemistry / Q000633:toxicity; D004970:Estrone / Q000737:chemistry / Q000633:toxicity; D004997:Ethinyl Estradiol / Q000032:analysis / Q000737:chemistry* / Q000633:toxicity; D010084:Oxidation-Reduction; D010126:Ozone / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry; D051381:Rats; D014865:Waste Disposal, Fluid / Q000379:methods; D014874:Water Pollutants, Chemical / Q000032:analysis / Q000737:chemistry* / Q000633:toxicity; D018508:Water Purification / Q000379:methods
D052244:Endocrine Disruptors; D045166:Estradiol Congeners; D004967:Estrogens; D010636:Phenols; D014874:Water Pollutants, Chemical; D004970:Estrone; D004997:Ethinyl Estradiol; D010126:Ozone