Estro-Androgenic Disrupting Effects of Halogenated Disinfection Byproducts: A Comprehensive Evaluation and Comparison
Xueyao Chen1, Yaoming Ge1, Wei Shi1
1State Key Laboratory of Pollution Control and Resource Reuse, School of Environment, Nanjing University, Nanjing 210023, Jiangsu, China.
Abstract:
Drinking water halogenated disinfection byproducts (DBPs) have become an increasing health concern. However, the endocrine-disrupting effects of DBPs have not been well evaluated, and the limited available data have inhibited a comprehensive understanding of their health risks. In this study, a total of 43 DBPs were evaluated for their estro-androgenic effects using two types of human breast cancer cells. Among the tested DBPs, 16 exhibited estrogenic/antiestrogenic/androgenic/antiandrogenic effects, and the effects could be observed even at concentrations typically detected in drinking water. Iodinated and polyhalogenated DBPs generally showed higher effects than other species. For a broader comparison, DBP endocrine-disrupting effect data from this study and previous studies were summarized. It was found that the endocrine disruption efficacy of DBPs followed the rank order of iodinated > brominated > chlorinated species, and halophenolic DBPs were potential endocrine-disrupting compounds. Moreover, molecular docking results demonstrated that the binding of DBPs to estro-androgenic receptors was dominated by hydrophobic bonding, hydrogen bonding, halogen bonding, and van der Waals forces. The force strength and molecular volume were related to the magnitude of the estro-androgenic effects. Iodinated DBPs and polyhalogenated DBPs tended to have larger binding forces than other analogues and thus exhibited stronger effects.
Related Concept Videos
Chemical Agents for Microbial Control
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
ortho–para-Directing Deactivators: Halogens
Reactions at the Benzylic Position: Halogenation
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
Methods of Sterilization II: Chemical Methods
Using chemical sterilization rather than heat to clean out equipment is recommended. It eradicates and removes all bacteria,...


