Biotransformation of genistein and bisphenol A in cell lines used for screening endocrine disruptors

Bursztyka, Julian; Perdu, Elisabeth; Pettersson, Katarina; Pongratz, Ingemar; Fernández-Cabrera, M.; Olea, Nicolás; Debrauwer, Laurent; Zalko, Daniel; Cravedi, Jean Pierre

doi:10.1016/j.tiv.2008.06.013

Cited by 31 publications

(22 citation statements)

References 56 publications

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“…MCF-7 cells have been shown to express the glucuronosyl and sulfo transferase enzymes involved in the biotransformation of compounds. Despite this, conjugation of compounds such as genistein and 2-methoxy-estradiol with glucuronic acid have been shown not to occur, whereas conjugation with sulphate was observed (Bursztyka et al, 2008;Spink et al, 2000). Contrary to this, bisphenol A glucuronide was formed by MCF-7 cells whereas sulphate conjugates were not.…”

Section: Discussionmentioning

confidence: 91%

Biotransformation of zearalenone and zearalenols to their major glucuronide metabolites reduces estrogenic activity

Frizzell

Uhlig

Miles

et al. 2015

Toxicology in Vitro

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Section: Discussionmentioning

confidence: 91%

Biotransformation of zearalenone and zearalenols to their major glucuronide metabolites reduces estrogenic activity

Frizzell

Uhlig

Miles

et al. 2015

Toxicology in Vitro

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“…However, structural differences alone cannot clearly explain the structure-activity relationship in this series of BPA analogues or why BPF, BPAF, BPZ, and DMBPA did not induce DNA damage, and why BPA and BPS did induce signifi cant DNA damage only after 24 h of exposure. It has recently been demonstrated that BPA and BPF are metabolised in HepG2 cells predominantly to conjugated sulphate metabolites (31,60). However, we still do not know to what extent BPA and its analogues are biotransformed into reactive quinone intermediates in HepG2 cells, and how stable these intermediates are.…”

Section: Bisphenol-induced Dna Strand Breaks In Hepg2 Cellsmentioning

confidence: 96%

Mutagenicity and DNA Damage of Bisphenol a and its Structural Analogues in Hepg2 Cells

Fic

Žegura

Dolenc

et al. 2013

Archives of Industrial Hygiene and Toxicology

105

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Environmental oestrogen bisphenol A (BPA) and its analogues are widespread in our living environment. Because their production and use are increasing, exposure of humans to bisphenols is becoming a signifi cant issue. We evaluated the mutagenic and genotoxic potential of eight BPA structural analogues (BPF, BPAF, BPZ, BPS, DMBPA, DMBPS, BP-1, and BP-2) using the Ames and comet assay, respectively. None of the tested bisphenols showed a mutagenic effect in Salmonella typhimurium strains TA98 and TA100 in either the presence or absence of external S9-mediated metabolic activation (Aroclor 1254-induced male rat liver). Potential genotoxicity of bisphenols was determined in the human hepatoma cell line (HepG2) at non-cytotoxic concentrations (0.1 μmol L -1 to 10 μmol L -1 ) after 4-hour and 24-hour exposure. In the comet assay, BPA and its analogue BPS induced signifi cant DNA damage only after the 24-hour exposure, while analogues DMBPS, BP-1, and BP-2 induced a transient increase in DNA strand breaks observed only after the 4-hour exposure. BPF, BPAF, BPZ, and DMBPA did not induce DNA damage.

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“…Radioactivity recovery and BPA and metabolite quantifications were performed with the analytic procedures previously described by Bursztyka et al (2008). The radioactivity in each incubation medium and tissue was measured from aliquots (10 ml) by liquid scintillation counting in a Packard Tricarb 4430 counter with Ultima Gold (Packard Instruments, Meriden, CT) as the scintillation cocktail.…”

Section: Bpa Conjugation/deconjugation Reactions In Target Tissuesmentioning

confidence: 99%

Conjugation and Deconjugation Reactions within the Fetoplacental Compartment in a Sheep Model: A Key Factor Determining Bisphenol A Fetal Exposure

et al. 2015

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The widespread human exposure to bisphenol A (BPA), an endocrine disruptor targeting developmental processes, underlines the need to better understand the mechanisms of fetal exposure. Animal studies have shown that at a late stage of pregnancy BPA is efficiently conjugated by the fetoplacental unit, mainly into BPAglucuronide (BPA-G), which remains trapped within the fetoplacental unit. Fetal exposure to BPA-G might in turn contribute to in situ exposure to bioactive BPA, following its deconjugation into parent BPA at the level of fetal sensitive tissues. The objectives of our study were 1) to characterize the BPA glucurono-and sulfoconjugation capabilities of the ovine fetal liver at different developmental stages, 2) to compare hepatic conjugation activities in human and sheep, and 3) to evaluate the extent of BPA conjugation and deconjugation processes in placenta and fetal gonads. At an early stage of pregnancy, and despite functional sulfoconjugation activity, ovine fetuses expressed low hepatic BPA conjugation capabilities, suggesting that this stage of development represents a critical window in terms of BPA exposure. Conversely, the late ovine fetus expressed an efficient detoxification system that metabolized BPA into BPA-G. Hepatic glucuronidation activities were quantitatively similar in adult sheep and humans. In placenta, BPA conjugation and BPA-G deconjugation activities were relatively balanced, whereas BPA-G hydrolysis was systematically higher than BPA conjugation in gonads. The possible reactivation of BPA-G into BPA could contribute to an increased exposure of fetal sensitive tissues to bioactive BPA in situ.

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Biotransformation of genistein and bisphenol A in cell lines used for screening endocrine disruptors

Cited by 31 publications

References 56 publications

Biotransformation of zearalenone and zearalenols to their major glucuronide metabolites reduces estrogenic activity

Biotransformation of zearalenone and zearalenols to their major glucuronide metabolites reduces estrogenic activity

Mutagenicity and DNA Damage of Bisphenol a and its Structural Analogues in Hepg2 Cells

Conjugation and Deconjugation Reactions within the Fetoplacental Compartment in a Sheep Model: A Key Factor Determining Bisphenol A Fetal Exposure

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