Changes in the Mutagenic and Estrogenic Activities of 17β-Estradiol after Treatment with Nitrite

Masuda, S.; Terashima, Yumeko; Sano, Ayako; Okada, Masaki; Deguchi, Yuya; Toyoizumi, Tomoyasu; Sugiyama, Chitose; Kumazawa, Shigenori; Kamihira, Miya; Yoshioka, Hisashi; Terao, Yoshiyasu; Kinae, Naohide

doi:10.1271/bbb.70.890

Cited by 6 publications

(9 citation statements)

References 25 publications

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“…The potential of applying estrogen nitration in wastewater treatment depends on whether estrogenic activity is reduced after nitration. Reduced estrogenic activity following E2 nitration has been reported for 2-nitro-E2, but not for 4-nitro-E2 (Masuda et al, 2006;Palomino et al, 1996;Pezzella et al, 2004). However, Wang et al (2007) also reported that estrogenic activity of nitro-E2 was reduced when compared with E2, when evaluating a mixture of 2-nitro-and 4-nitro-E2.…”

Section: Resultsmentioning

confidence: 99%

Estrogen Nitration Kinetics and Implications for Wastewater Treatment

Gaulke

Strand

Kalhorn

et al. 2009

Water Environment Research

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Understanding estrogen‐removal mechanisms in wastewater treatment is imperative, as estrogens have environmental effects at trace concentrations. Previous research investigating co‐metabolic degradation of 17α‐ethinylestradiol (EE2) by ammonia‐oxidizing bacteria (AOB) revealed that, in batch tests where high nitrite‐nitrogen (NO2‐N) concentrations occurred as a result of ammonia‐nitrogen (NH4‐N) oxidation by AOB, an abiotic estrogen nitration reaction actually was occurring—not co‐metabolic degradation. This paper addresses nitration kinetics. A first‐order abiotic nitration model was developed that predicts nitration of EE2, 17β‐estradiol (E2), and estrone (E1) as a function of temperature, pH, estrogen (EE2, E2, and E1), and NO2‐N concentration. A contact time of 3.6 to 4.1 days is required for 90% estrogen nitration at 500 mg/L NO2‐N and pH 6.4. At 20°C and pH 6.4, the threshold NO2‐N concentration for nitration to occur is 9 mg/L; therefore, estrogen nitration is not likely in activated sludge treatment of domestic wastewater, but has potential for high‐NH4‐N‐strength wastewaters.

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Section: Resultsmentioning

confidence: 99%

Estrogen Nitration Kinetics and Implications for Wastewater Treatment

Gaulke

Strand

Kalhorn

et al. 2009

Water Environment Research

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“…The reaction mixture of bisphenol A or 17-estradiol and nitrite, which showed mutagenic activities, has previously been demonstrated to generate radicals by ESR. 13,14) We therefore tested the radical generation from the reaction mixture of nitrite and genistein by ESR in this study. Figure 3 shows that the radical intensity of nitrite-treated genistein increased with time after adding DMPO.…”

Section: Resultsmentioning

confidence: 99%

“…12) An earlier study has also demonstrated that bisphenol A and 17-estradiol showed mutagenic activities after a nitrite treatment under acidic conditions. 13,14) Isoflavones, which are known as plant polyphenols, might therefore show mutagenicity after the reaction with nitrite under acidic conditions. The present study examines the mutagenic activities of genistein with the Ames test and micronucleus test after a nitrite treatment under acidic conditions by using ICR male mice.…”

mentioning

confidence: 99%

Change in Mutagenic Activity of Genistein after a Nitrite Treatment

Masuda

Shimamura

Kato

et al. 2012

Bioscience, Biotechnology, and Biochemistry

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“…Reduced estrogenic activity following E2 nitration has been reported for 2-nitro-E2, but not for 4-nitro-E2 (Palomino et al 1996;Pezzella et al 2004;Masuda et al 2006). However, Wang et al(2007) also reported that estrogenic activity of nitro-E2 was reduced when compared to E2, when evaluating a mixture of 2-nitro-and 4-nitro-E2.…”

Section: Potential Applications Of Estrogen Nitration In Wastewater Tmentioning

confidence: 97%

“…The estrogenic activity of nitro-EE2 has not been reported. The possibility of increased mutagenic or carcinogenic properties of nitrated estrogen compounds also should be considered (Masuda et al 2006), although the relevance at ng/L concentrations is questionable.…”

Section: Potential Applications Of Estrogen Nitration In Wastewater Tmentioning

confidence: 99%

Transformation of Estrogen with Ammonia Oxidizing Bacteria

Gaulke¹,

Strand²,

Kalhorn³

et al. 2008

proc water environ fed

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Understanding estrogen removal mechanisms in wastewater treatment is imperative, as estrogens have environmental impacts at trace concentrations. Research has focused on cometabolic degradation by ammonia oxidizing bacteria (AOB), because greater estrogen removal occurs in treatment plants with nitrification. In this study, no cometabolic degradation was observed in batch tests with Nitrosomonas europaea; LC-MS-MS was employed to measure 17α-ethinylestradiol (EE2) and transformation products. Instead, EE2 was transformed abiotically to nitro-EE2 by reaction with high NO 2 -N (200-500 mg/L) produced by the AOB. A nitration rate model and first order rate constants for EE2, 17β-estradiol (E2), and estrone (E1) nitration was developed as a function of estrogen, NO 2 -N, temperature and pH. 90% nitration of the estrogens is achieved at 500 mg/L NO 2 -N and pH 6.4 over 3.6-4.1 days. Estrogen removal by nitration is not likely in activated sludge of domestic wastewater, but has potential for treatment of high NH 4 -N strength wastewaters, such as centrate, feedlot wastes and urine.

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Changes in the Mutagenic and Estrogenic Activities of 17β-Estradiol after Treatment with Nitrite

Cited by 6 publications

References 25 publications

Estrogen Nitration Kinetics and Implications for Wastewater Treatment

Estrogen Nitration Kinetics and Implications for Wastewater Treatment

Change in Mutagenic Activity of Genistein after a Nitrite Treatment

Transformation of Estrogen with Ammonia Oxidizing Bacteria

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