title: Antiestrogenic activity and related disinfection by-product formation induced by bromide during chlorine disinfection of sewage secondary effluent.
abstract: Chlorine disinfection, widely used in wastewater reclamation, can form toxic and harmful disinfection by-products (DBPs), some of which are associated with endocrine disruption. In this study, the presence of bromide was found to promote an increase in antiestrogenic activity using a yeast two-hybrid assay in the sewage secondary effluent during chlorine disinfection. Among the dissolved organic matters in the secondary effluent, hydrophobic acids and hydrophilic substance fractions were determined as potential precursors associated with increase in antiestrogenic activity in the secondary effluent induced by bromide. Further antiestrogenic activity evaluation and mass spectrum characterization following the semipreparative liquid chromatography fractionation of a natural organic matter precursor, tyrosine, after chlorination under the presence of bromide revealed, for the first time, that 2-(bromo-4-hydroxyphenyl) acetonitrile (Br-HPAN) and 2-(dibromo-4-hydroxyphenyl) acetonitrile (DBr-HPAN) exhibited antiestrogenic activity. Br-HPAN and DBr-HPAN were the DBPs involved in the increase in antiestrogenic activity in the tyrosine solution. Bromide was shown to induce the formation of Br-HPAN and DBr-HPAN in the secondary effluent during chlorine disinfection.
authors.affiliation: Shenzhen Laboratory of Microorganism Application and Risk Control, Graduate School at Shenzhen, Tsinghua University, Shenzhen 518055, PR China.
authors.forename: Qian-Yuan
authors.initials: QY
authors.lastname: Wu
authors.affiliation: Environmental Simulation and Pollution Control State Key Joint Laboratory, and State Environmental Protection Key Laboratory of Microorganism Application and Risk Control (SMARC), School of Environment, Tsinghua University, Beijing 100084, PR China.
authors.forename: Xin
authors.initials: X
authors.lastname: Tang
authors.affiliation: Environmental Simulation and Pollution Control State Key Joint Laboratory, and State Environmental Protection Key Laboratory of Microorganism Application and Risk Control (SMARC), School of Environment, Tsinghua University, Beijing 100084, PR China.
authors.forename: Huang
authors.initials: H
authors.lastname: Huang
authors.affiliation: Key Laboratory of Integrated Regulation and Resource Development on Shallow Lakes, Ministry of Education, College of Environment, Hohai University, Nanjing 210098, PR China.
authors.forename: Yi
authors.initials: Y
authors.lastname: Li
authors.affiliation: Shenzhen Laboratory of Microorganism Application and Risk Control, Graduate School at Shenzhen, Tsinghua University, Shenzhen 518055, PR China; Environmental Simulation and Pollution Control State Key Joint Laboratory, and State Environmental Protection Key Laboratory of Microorganism Application and Risk Control (SMARC), School of Environment, Tsinghua University, Beijing 100084, PR China. Electronic address: hyhu@tsinghua.edu.cn.
authors.forename: Hong-Ying
authors.initials: HY
authors.lastname: Hu
authors.affiliation: Key Laboratory of Integrated Regulation and Resource Development on Shallow Lakes, Ministry of Education, College of Environment, Hohai University, Nanjing 210098, PR China; Nanjing Institute of Environmental Sciences, Ministry of Environmental Protection, Nanjing 210042, PR China.
authors.forename: Ya-Nan
authors.initials: YN
authors.lastname: Ding
authors.affiliation: Shenzhen Laboratory of Microorganism Application and Risk Control, Graduate School at Shenzhen, Tsinghua University, Shenzhen 518055, PR China.
authors.forename: Yi-Ru
authors.initials: YR
authors.lastname: Shao
mesh_terms: D000097:Acetonitriles / Q000737:chemistry* / Q000494:pharmacology; D000818:Animals; D001965:Bromides / Q000737:chemistry*; D002713:Chlorine / Q000737:chemistry*; D004203:Disinfection; D004958:Estradiol / Q000494:pharmacology; D020847:Estrogen Receptor Modulators / Q000737:chemistry* / Q000494:pharmacology; D047628:Estrogen Receptor alpha / Q000235:genetics / Q000378:metabolism; D004967:Estrogens / Q000494:pharmacology; D051381:Rats; D012441:Saccharomyces cerevisiae / Q000235:genetics / Q000378:metabolism; D012722:Sewage / Q000737:chemistry*; D014443:Tyrosine / Q000737:chemistry / Q000494:pharmacology; D014873:Water Pollutants / Q000737:chemistry* / Q000494:pharmacology; D018508:Water Purification; D001616:beta-Galactosidase / Q000378:metabolism
chemical_list: D000097:Acetonitriles; D001965:Bromides; D020847:Estrogen Receptor Modulators; D047628:Estrogen Receptor alpha; D004967:Estrogens; D012722:Sewage; D014873:Water Pollutants; D014443:Tyrosine; D002713:Chlorine; D004958:Estradiol; D001616:beta-Galactosidase
keywords: Antiestrogenic activity; Bromide; Chlorine disinfection; Toxicity; Wastewater reclamation