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Estrogenic potential of halogenated derivatives of nonylphenol ethoxylates and carboxylates
Author(s) -
GarcíaReyero Natàlia,
Requena Vanessa,
Petrovic Mira,
Fischer Birgit,
Hansen PeterDiedrich,
Díaz Alfredo,
Ventura Francesc,
Barceló Damiá,
Piña Benjamin
Publication year - 2004
Publication title -
environmental toxicology and chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.1
H-Index - 171
eISSN - 1552-8618
pISSN - 0730-7268
DOI - 10.1897/03-141
Subject(s) - nonylphenol , estrogen receptor , chemistry , yeast , endocrine disruptor , in vitro , receptor , estrogen , cytotoxicity , in vitro toxicology , alkylphenol , biochemistry , biology , hormone , environmental chemistry , endocrinology , endocrine system , organic chemistry , cancer , alkyl , breast cancer , genetics
Hlogenated derivatives of nonylphenol and of its alkylates are generated during drinking water disinfection and treatment procedures. In this paper we analyze the potential of these compounds to interact with the estrogen receptor and to activate hormone‐regulated gene promoters. We used the recombinant yeast assay (RYA) and the human breast cancer cell MCF7 proliferation assay for both estrogenic and antiestrogenic activities and the enzyme‐linked receptor assay to examine in vitro binding to the receptor Many nonylphenol derivatives were very weak estrogens in our functional tests when compared to nonylphenol while retaining a substantial affinity for the estrogen receptor in vitro. Antiestrogenicity tests demonstrated that brominated nonylphenol and most of the carboxylated compounds studied here behaved as estrogenic antagonists in the RYA. We also detected an increased cytotoxicity for the carboxylated derivatives in both yeast and mammalian cells. We conclude that derivatization may mask the apparent estrogenicity of nonylphenol, but the resulting compounds still represent a potential hazard since they are still able to bind the estrogen receptor and to influence the physiological response to estrogens. Our results also illustrate the advantage of combining different methods to assay estrogenicity of unknown substances.