Abstract
Bisphenols represent a large group of structurally similar compounds. In contrast to bisphenol A (BPA) and bisphenol S (BPS), however, toxicological data are usually scarce, thus making bisphenols an ideal candidate for read-across assessments. BPA, bisphenol C (BPC) and a newly synthesized bisphenol A/C (BPA/C) differ only by one methyl group attached to the phenolic ring. Their EC50 values for cytotoxicity and logPOW values are comparable. However, the estrogenic activities of these bisphenols are not comparable and among this group only BPC leads to a decrease of the mitochondrial membrane potential and ATP concentration in HepG2 cells. Conversely, the cell division rate was decreased by BPS, BPA, BPC and BPA/C at 10% toxicity (EC10). At lower concentrations, only BPC significantly affected proliferation. The pro-inflammatory cytokines TGFB1 and TNF were significantly upregulated by BPC only, while SPP1 was upregulated by BPA, BPA/C and BPS. BPC led to the release of cytochrome c from mitochondria, indicating that this compound is capable of inducing apoptosis. In conclusion, the read-across approach revealed non-applicable in the case of the various structurally and physicochemically comparable bisphenols tested in this study, as the presence of one or two additional methyl group(s) attached at the phenol ring profoundly affected cellular physiology.
Highlights
Bisphenol A (BPA, see Table 1) is used in different consumer products
bisphenol A (BPA)/C, bisphenol C (BPC) and bisphenol S (BPS) are of comparable molecular weights (MW), that is, between 242.31 g/mol and 256.34 g/mol (Table 1)
BPA and bisphenol F (BPF) are of lower MW, being 228.29 g/mol and 200.23 g/mol, respectively
Summary
Bisphenol A (BPA, see Table 1) is used in different consumer products. At high nanomolar concentrations it exhibits estrogenic activity, as well as liver and kidney toxicity (EFSA 2017). BPA is often replaced by bisphenol S (BPS) in its manufacture (Rochester and Bolden 2015). The presence of BPS has been reported in thermal paper, advertised as “BPA-free” (Liao et al 2012). The presence of bisphenol C (BPC) has been detected in bottled carbonated beverages (Mandrah et al 2017) as well as in waste water (Cesen et al 2018). In MCF7 cells BPS and BPA showed a lower estrogenic activity compared to BPC (Kitamura et al 2005). In the urine of cashiers a twofold increase of BPA (up to 2.76 μg/g creatinine) and a slight increase of BPS (up to 0.54 μg/g creatinine) compared to non-cashiers has been determined, dependent upon the use of thermal paper (Thayer et al 2016).
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