Estrogenic Potential of Certain Pyrethroid Compounds in the MCF-7 Human Breast Carcinoma Cell Line

Go, Vera S; Garey, Joan D; Wolff, Mary S.; Pogo, Beatríz G. T.

doi:10.2307/3434505

Cited by 24 publications

(33 citation statements)

References 9 publications

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“…In addition to the acute lethality afforded by SPs, the U.S. Environmental Protection Agency has listed this insecticide class as a likely endocrine disrupter in humans and wildlife (26). Estrogenic and antiestrogenic effects from SP insecticides have been observed in terrestrial invertebrates and mammalian cell lines (27)(28)(29). Potential enantioselectivity in these chronic effects should be explored.…”

Section: Enantioselectivity In Degradationmentioning

confidence: 99%

Enantioselectivity in environmental safety of current chiral insecticides

Liu

Gan

Schlenk

et al. 2005

Proc. Natl. Acad. Sci. U.S.A.

452

395

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Chiral pesticides currently constitute about 25% of all pesticides used, and this ratio is increasing as more complex structures are introduced. Chirality occurs widely in synthetic pyrethroids and organophosphates, which are the mainstay of modern insecticides. Despite the great public concerns associated with the use of insecticides, the environmental significance of chirality in currently used insecticides is poorly understood. In this study, we resolved enantiomers of a number of synthetic pyrethroid and organophosphate insecticides on chiral selective columns and evaluated the occurrence of enantioselectivity in aquatic toxicity and biodegradation. Dramatic differences between enantiomers were observed in their acute toxicity to the freshwater invertebrates Ceriodaphnia dubia and Daphnia magna, suggesting that the aquatic toxicity is primarily attributable to a specific enantiomer in the racemate. In field sediments, the (؊) enantiomer of cis-bifenthrin or cispermethrin was preferentially degraded, resulting in relative enrichment of the (؉) enantiomer. Enantioselective degradation was also observed during incubation of sediments under laboratory conditions. Enantioselectivity in these processes is expected to result in ecotoxicological effects that cannot be predicted from our existing knowledge and must be considered in future risk assessment and regulatory decisions. chiral contaminants ͉ chirality ͉ enantiomers ͉ chiral pesticides ͉ chiral selectivity T he significance of molecular chirality is widely recognized in life sciences (1, 2). A lesser-known fact is that many modern pesticides also contain chiral structures and thus consist of enantiomers (3, 4). About 25% of currently used pesticides are chiral, and this ratio is increasing as compounds with more complex structures are introduced into use (3). Enantiomers of the same compound have identical physical-chemical properties and thus appear as a single compound in standard analysis. For economic reasons, chiral pesticides are primarily used as mixtures of enantiomers, or racemates. However, enantiomers are known to selectively interact with biological systems that are usually enantioselective and may behave as drastically different compounds. The role of enantioselectivity in environmental safety is poorly understood for pesticides, and the knowledge gap is reflected in that the great majority of chiral pesticides are used and regulated as if they were achiral, that is, single compounds.Studies on chiral pesticides started to appear in the early 1990s (4,(5)(6)(7)(8)(9)(10)(11)(12). Studies so far show that microbial degradation of chiral pesticides is commonly enantioselective. As one enantiomer is preferentially degraded, the enantiomer ratio (ER), defined as the ratio of (ϩ) enantiomers to (Ϫ) enantiomers, increasingly deviates from the original value (typically 1.0) (8, 9). Enantioselectivity was found to result in changes of ER in ␣-HCH along the polar bear food chain, causing ER to increase from Ϸ1.0 in cod to 2.3 in liver samples of polar be...

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Section: Enantioselectivity In Degradationmentioning

confidence: 99%

Enantioselectivity in environmental safety of current chiral insecticides

Liu

Gan

Schlenk

et al. 2005

Proc. Natl. Acad. Sci. U.S.A.

452

395

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“…These substances have been associated with degenerative effects such as reduced fecundity, changes in the sex ratio, developmental degeneration in both animal and human embryos (Knçrr and Braunbeck 2002), as well as an increase in breast and testis cancer in humans (Toppari et al, 1996). Numerous specific testing systems have been developed for the detection of the estrogenic effects (Routledge and Sumpter 1996;Sohoni and Soto 1998;Go et al 1999). Among them, recently developed recombinant yeast screen (Routledge and Sumpter, 1996) can serve as a very useful tool to rapidly and inexpensively determine the total potency of estrogenic chemicals in the mixtures of chemicals.…”

mentioning

confidence: 99%

Assessing the Detoxication Efficiencies of Wastewater Treatment Processes Using a Battery of Bioassays/Biomarkers

Wang

2005

Arch Environ Contam Toxicol

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Abstract. A battery of in vitro bioassays, including a Neutral Red (NR) assay using MCF-7 cells for predicting cytotoxic chemicals, an ethoxy resorufin-O-deethylase (EROD) activity assay using H4IIE cells to check for dioxin-like chemicals, and a recombinant gene yeast assay for screening estrogenic chemicals, was conducted to assess the removal efficiencies of trace toxic chemicals by different treatment processes in the waste water treatment plant (WWTP). The effluents were extracted by solid phase extraction (SPE) and were fractionated into three fractions based on polarities. The battery of bioassays was performed for each fraction. In the battery, the toxicities of the effluents were described according to their modes of actions (MOA) or biomarkers and the properties of the toxic chemicals were categorized by their polarities and MOAs. The proposed procedure could be used as a tool to diagnose the toxic characteristics of the complicate mixture. The results showed that cytotoxic, dioxin-like and estrogenic chemicals could be detected in all samples. In the influent, cytotoxic and dioxin-like chemicals were mainly in polar fraction and estrogenic chemicals were in non-polar and moderate-polar fractions. The secondary treatment (active sludge) could remove a small amount of these toxicants. Among different types of advanced treatments, flocculation was good enough to remove most of the cytotoxic chemicals and a combination of flocculation, ozone oxidation, and post-biological treatment could eliminate most of the dioxin-like and estrogenic chemicals.

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“…Also, for (1a), (1b), and (1c) the abundance-ratio of the Eform to Z-form was confirmed to be 6:4 from the 1 H-NMR analysis. 164.67 (C (1) ), 162.44 (C (1') ), 158.79 (C (2') ), 153.53 (C (3) ), 138.13 (C (7) ), 132.42 (C (3') ), 122.46 (C (6) ), 116.51 (C (2) ), 113.01 (C (5') ), 41.13 (C (4) ), 25.90 (C (5) ), 25.61 (C (9) ), 19.34 (C (8) ), 17.68 (C (10) ), 15.01 (C (7') ) Z -form 171.96 (C (4') ), 165.10 (C (1) ), 162.44 (C (1') ), 158.79 (C (2') ), 153.53 (C (3) ), 138.13 (C (7) ), 131.97 (C (3') ), 123.09 (C (6) ), 116.51 (C (2) ), 113.75 (C (5') ), 41.13 (C (4) ), 26.62 (C (5) ), 25.68 (C (9) ), 19.34 (C (8) ), 17.59 (C (10) ), 15.01 (C (7') ). (1) ), 163.59 (C (4') ), 162.47 (C (2') ), 161.40 (C (3) ), 137.84 (C (6') ), 132.71 (C (7) ), 122.10 (C (6) ), 113.11 (C (2) ), 106.44 (C (5') ), 101.35 (C (3') ), 41.22 (C (4) ), 25.86 (C (9) ) 25.62 (C (5) ), 20.06 (C (7') ), 19.48 (C (8) ), 17.69 (C (10) ) Z -form 166.78 (C (1) ), 163.06 (C (4') ), 162.47 (C (2') ), 160.95 (C (3) ), 137.84 (C (6') ), 132.71 (C (7) ), 122.66 (C (6) ), 113.67 (C (2) ), 106.42 (C (5') ), 101.33 (C (3') ), 41.22 (C (4) ), 25.86 (C …”

Section: Synthesismentioning

confidence: 99%

“…among others (5,6,7). The organophosphorus compound type insecticide can have a late-onset neurotoxic effect on a person (8,9).…”

mentioning

confidence: 99%

Synthesis and Physiological Activities of Monoterpene Carboxylic Acid Esters with Pyrones

Tachibana¹,

Ohno

Fujihara

et al. 2006

J. Oleo Sci.

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Estrogenic Potential of Certain Pyrethroid Compounds in the MCF-7 Human Breast Carcinoma Cell Line

Cited by 24 publications

References 9 publications

Enantioselectivity in environmental safety of current chiral insecticides

Enantioselectivity in environmental safety of current chiral insecticides

Assessing the Detoxication Efficiencies of Wastewater Treatment Processes Using a Battery of Bioassays/Biomarkers

Synthesis and Physiological Activities of Monoterpene Carboxylic Acid Esters with Pyrones

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