Influence of metabolism on endocrine activities of bisphenol S

Skledar, Darja Gramec; Schmidt, Jan; Fic, Anja; Klopčič, Ivana; Trontelj, Jurij; Dolenc, Marija Sollner; Finel, Moshe; Mašič, Lucíja Peterlin

doi:10.1016/j.chemosphere.2016.05.027

Chemosphere

2016

DOI: 10.1016/j.chemosphere.2016.05.027

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Influence of metabolism on endocrine activities of bisphenol S

Darja Gramec Skledar

Jan Schmidt

Anja Fic

et al.

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Cited by 80 publications

(35 citation statements)

References 33 publications

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“…16 It has high thermal stability and it is resistant to sunlight. 16,17 As a member of large and diverse group of bisphenols, BPS is commonly used in numerous consumer products as a replacement of BPA. As being the most commonly used alternative of BPA, BPS is frequently used in production of plastics and thermal papers.…”

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confidence: 99%

“…As being the most commonly used alternative of BPA, BPS is frequently used in production of plastics and thermal papers. 3,17 BPS is used as improver in thermal papers,stabilizer in canned soft drinks and canned food. 6,16 In addition BPS is used as fastening agent in cleaning products, electroplating solvent, a constituent of epoxy resins in various ındustrial applications.…”

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confidence: 99%

“…These products include personal care products, paper products and food such as hair products, toothpaste, currency, mailing envelopes, dairy products, canned food, cereals. 5 Skledar et al, 17 showed that glucuronidation is the most important pathway for metabolism and detoxicifation of BPS and UGT1A9 plays an important role in this process. 17 Cumulative evidences suggest that BPS is toxic to organisms because of it's similar chemical structure to BPA.…”

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“…5 Skledar et al, 17 showed that glucuronidation is the most important pathway for metabolism and detoxicifation of BPS and UGT1A9 plays an important role in this process. 17 Cumulative evidences suggest that BPS is toxic to organisms because of it's similar chemical structure to BPA. Recently it is reported that similar to BPA, BPS promotes eustrogenic activity, proarithmic effects and hypothalamic neurogenesis in cell lines in vitro and in animals in vivo.…”

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confidence: 99%

“…4 In a previous research it is reported that isopropilation of 4-hydroxy group decreases the eustrogenic activity. 17 BPS is also defined as a weak antiandrogenic compound. 16 BPS exposure in zebrafish larvae suggests that oxidative stress and interference of immune response is induced.…”

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Toxicological Evaluation of Bisphenol A and Its Analogs

İyigündoğdu¹,

Üstündağ²,

Duydu³

2019

tjps

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Bisphenol A(BPA) is known as one of the oldest sentetic compounds with endocrine activity. BPA is commonly used in production of epoxy resins, policarbonates, dental fillings, food storage containers, baby bottles and mineral water containers. BPA is associated with various health problems such as diabetes, obesity, cardiovascular diseases, chronic respiratory diseases, renal diseases, breast cancer, behaviour disorders, teeth development disorders and reproductive diorders. Increasing health concerns led the endustry to seek alternatives for BPA, as BPA has begun to be excluded from the products, the use of alternative bisphenols has been increased.However the chemicals used as a replacement of BPA are also bisphenols and may have similar physiological effects on organisms. According to the researches, it is demonstrated that BPA analogs may result in similar or higher toxic effects compared to BPA.

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confidence: 99%

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Toxicological Evaluation of Bisphenol A and Its Analogs

İyigündoğdu¹,

Üstündağ²,

Duydu³

2019

tjps

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Increased Endocrine Activity of Xenobiotic Chemicals as Mediated by Metabolic Activation

Kolanczyk,

Denny,

Sheedy

et al. 2023

Enviro Toxic and Chemistry

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The US EPA is faced with long lists of chemicals that require hazard assessment. This research is part of a larger effort to develop in vitro assays and QSARs applicable to untested chemicals on US EPA inventories through study of estrogen receptor (ER) binding and estrogen mediated gene expression in fish. The current effort investigates metabolic activation of chemicals resulting in increased estrogenicity. Phenolphthalin (PLIN) was shown not to bind rainbow trout (Oncorhynchus mykiss) ER (rtER) in a competitive binding assay but vitellogenin (Vtg) expression was induced in trout liver slices exposed to 10‐4 and 10‐3.7 M PLIN. Phenolphthalein (PLEIN), metabolite of PLIN, was subsequently determined to be formed when slices were exposed to PLIN. PLEIN binds rtER with a relative binding affinity (RBA) to 17β‐estradiol of 0.020%. Slices exposed to PLEIN expressed Vtg mRNA at 10‐4.3, 10‐4, and 10‐3.7 M, with no detectable PLIN present. Thus, Vtg expression noted in PLIN slice exposures was explained by metabolism to PLEIN in trout liver slices. A second model chemical, 4,4’‐methylenedianiline (MDA) was not shown to bind rtER but did induce Vtg mRNA production in tissue slices at 10‐4.3, 10‐4, and 10‐3.7 M in amounts nearly equal to reference estradiol induction, thus indicating metabolic activation of MDA. A series of experiments were performed to identify a potential metabolite responsible for the observed increase in activity. Potential metabolites hydroxylamine‐MDA, nitroso‐MDA, azo‐MDA, or azoxy‐MDA were not observed. However, acetylated‐MDA was observed and tested in both ER‐binding and tissue slice Vtg induction assays.

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The effects of different bisphenol derivatives on oxidative stress, DNA damage and DNA repair in RWPE‐1 cells: A comparative study

Köse

Rachidi

Béal

et al. 2019

J of Applied Toxicology

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Bisphenol A (BPA) is a well-known endocrine disruptor and it is widely used mainly in the plastics industry. Due to recent reports on its possible impact on health (particularly on the male reproductive system), bisphenol F (BPF) and bisphenol S (BPS) are now being used as alternatives. In this study, RWPE-1 cells were used as a model to compare cytotoxicity, oxidative stress-causing potential and genotoxicity of these chemicals. In addition, the effects of the bisphenol derivatives were assessed on DNA repair proteins. RWPE-1 cells were incubated with BPA, BPF, and BPS at concentrations of 0-600 μM for 24 h. The inhibitory concentration 20 (IC 20 , concentration that causes 20% of cell viability loss) values for BPA, BPF, and BPS were 45, 65, and 108 μM, respectively. These results indicated that cytotoxicity potentials were ranked as BPA > BPF > BPS. We also found alterations in superoxide dismutase, glutathione peroxidase and glutathione reductase activities, and glutathione and total antioxidant capacity in all bisphenol-exposed groups. In the standard and modified Comet assay, BPS produced significantly higher levels of DNA damage vs the control. DNA repair proteins (OGG1, Ape-1, and MyH) involved in the base excision repair pathway, as well as p53 protein levels were down-regulated in all of the bisphenol-exposed groups. We found that the BPA alternatives were also cytotoxic and genotoxic, and changed the expressions of DNA repair enzymes. Therefore, further studies are needed to assess whether they can be used safely as alternatives to BPA or not.

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Influence of metabolism on endocrine activities of bisphenol S

Cited by 80 publications

References 33 publications

Toxicological Evaluation of Bisphenol A and Its Analogs

Toxicological Evaluation of Bisphenol A and Its Analogs

Increased Endocrine Activity of Xenobiotic Chemicals as Mediated by Metabolic Activation

The effects of different bisphenol derivatives on oxidative stress, DNA damage and DNA repair in RWPE‐1 cells: A comparative study

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