Products of Aqueous Chlorination of 17-Estradiol and Their Estrogenic Activities
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- 作者：Jianying Hu ; Shuijie Cheng ; Takako Aizawa ; Yoshiyasu Terao ; and Shoichi Kunikane
- 刊名：Environmental Science & Technology
- 出版年：2003
- 出版时间：December 15, 2003
- 年：2003
- 卷：37
- 期：24
- 页码：5665 - 5670
- 全文大小：187K
- 年卷期：v.37,no.24(December 15, 2003)
- ISSN：1520-5851
文摘
To assess the estrogenic activity potentially stemmingfrom 17
-estradiol (E2) in drinking water, ESI-LC-MS wasused to identify the products of its aqueous chlorination underthe following conditions: 50 
g/L E2, 1.46 mg/L sodiumhypochlorite, pH 7.5, 25 
C. Seven products, including 2,4-dichloro-17-estradiol, monochloroestrone, 2,4-dichloroestrone, and the four byproducts such as 4-[2-(2,6-dichloro-3-hydroxyphenyl)ethyl]-7
-methyloctahydroinden-5-one(product C in the text) were identified in chlorinated E2solution. The estrogenic activities of the aqueous chlorinatedE2 solution at 10, 30, 60, 120, and 180 min contact timewere assessed by a yeast two-hybrid system based on theligand-dependent interaction of two proteins, a humanestrogen receptor (ER) and a coactivator. All five solutionselicited transcriptional activation induction. The maximal-galactosidase activities induced by the chlorinated solutionat 10, 30, and 60 min were similar and slightly lowerthan those before chlorination, while the activities of thechlorinated solution at 120 and 180 min were about 40% ofthose before chlorination. Finally, 4-chloro-17-estradiol (4-chloro-E2) (we failed to synthesize the 2-chloroestrone (2-chloro-E1)), 2,4-dichloro-17-estradiol (2,4-dichloro-E2), and2,4-dichloroestrone (2,4-dichloro-E1) were synthesized,and product C was fractionated by HPLC. It was found that4-chloro-E2 elicited strong estrogenic activity, at almostthe same level as that of estrone (EC50 = 102 nM), while 2,4-dichloro-E2 elicited weaker -galactosidase activitycompared with that of 4-chloro-E2. The EC50 was ca. 103nM. The maximal -galactosidase activity for 2,4-dichloro-E1 was lower than that of 2,4-dichloro-E2, while its EC50was similar to that of 2,4-dichloro-E2. In addition, product C,4-[2-(2,6-dichloro-3-hydroxyphenyl)ethyl]-7-methyloctahydroinden-5-one, induced high -galactosidaseactivity at the relatively higher concentration of 3.5 × 105nM. On the basis of the dose-response curve of asingle byproduct of chlorinated E2, the estrogenic activityat 120 and 180 min appears to be induced mainly by 2,4-dichloro-E2 and 2,4-dichloro-E1.
-estradiol (E2) in drinking water, ESI-LC-MS wasused to identify the products of its aqueous chlorination underthe following conditions: 50 g/L E2, 1.46 mg/L sodiumhypochlorite, pH 7.5, 25 C. Seven products, including 2,4-dichloro-17-estradiol, monochloroestrone, 2,4-dichloroestrone, and the four byproducts such as 4-[2-(2,6-dichloro-3-hydroxyphenyl)ethyl]-7-methyloctahydroinden-5-one(product C in the text) were identified in chlorinated E2solution. The estrogenic activities of the aqueous chlorinatedE2 solution at 10, 30, 60, 120, and 180 min contact timewere assessed by a yeast two-hybrid system based on theligand-dependent interaction of two proteins, a humanestrogen receptor (ER) and a coactivator. All five solutionselicited transcriptional activation induction. The maximal-galactosidase activities induced by the chlorinated solutionat 10, 30, and 60 min were similar and slightly lowerthan those before chlorination, while the activities of thechlorinated solution at 120 and 180 min were about 40% ofthose before chlorination. Finally, 4-chloro-17-estradiol (4-chloro-E2) (we failed to synthesize the 2-chloroestrone (2-chloro-E1)), 2,4-dichloro-17-estradiol (2,4-dichloro-E2), and2,4-dichloroestrone (2,4-dichloro-E1) were synthesized,and product C was fractionated by HPLC. It was found that4-chloro-E2 elicited strong estrogenic activity, at almostthe same level as that of estrone (EC50 = 102 nM), while 2,4-dichloro-E2 elicited weaker -galactosidase activitycompared with that of 4-chloro-E2. The EC50 was ca. 103nM. The maximal -galactosidase activity for 2,4-dichloro-E1 was lower than that of 2,4-dichloro-E2, while its EC50was similar to that of 2,4-dichloro-E2. In addition, product C,4-[2-(2,6-dichloro-3-hydroxyphenyl)ethyl]-7-methyloctahydroinden-5-one, induced high -galactosidaseactivity at the relatively higher concentration of 3.5 × 105nM. On the basis of the dose-response curve of asingle byproduct of chlorinated E2, the estrogenic activityat 120 and 180 min appears to be induced mainly by 2,4-dichloro-E2 and 2,4-dichloro-E1.