Prooxidant actions of bisphenol A (BPA) phenoxyl radicals: implications to BPA-related oxidative stress and toxicity

References

• Atkinson A, Roy D. (1995). In vitro conversion of environmental estrogenic chemical bisphenol A to DNA binding metabolite(s). Biochem Biophys Res Commun 210:424–33
   PubMed Web of Science ®Google Scholar
• Babu S. (2012). An integrated approach to understand molecular targets and cellular oxidative stress responses to bisphenol A, a xenoestrogen and semi-persistent organic pollutant in urban environments. Southern University and Agricultural and Mechanical College. ProQuest Dissertations and Theses [Dissertation/thesis number 3521604; ProQuest document ID 1038943331] 160. Available from: http://137.198.76.25/docview/1038943331?accountid=11272 [last accessed 27 December 2012]
   Google Scholar
• Bailin PS, Byrne M, Lewis S, Liroff R. (2008). Public awareness drives market for safer alternatives: bisphenol A market analysis report. Investor Environmental Health Network Reports. Available from: http://www.iehn.org/publications.reports.bpa.php [last accessed 27 December 2012]
   Google Scholar
• Batista TM, Alonso-Magdalena P, Vieira E, et al. (2012). Short-term treatment with bisphenol-A leads to metabolic abnormalities in adult male mice. PLoS One 7:e33814 [Epub 28 Mar 2012]
   PubMed Web of Science ®Google Scholar
• Biedermann S, Tschudin P, Grob K. (2010). Transfer of bisphenol A from thermal printer paper to the skin. Anal Bioanal Chem 398:571–6
   PubMed Web of Science ®Google Scholar
• Bindhumol V, Chitra KC, Mathur PP. (2003). Bisphenol A induces reactive oxygen species generation in the liver of male rats. Toxicology 188:117–24
   PubMed Web of Science ®Google Scholar
• Castor LR, Locatelli KA, Ximenes VF. (2010). Prooxidant activity of apocynin radical. Free Radic Biol Med 48:1636–43
   PubMed Web of Science ®Google Scholar
• Chitra KC, Latchoumycandane C, Mathur PP. (2003). Induction of oxidative stress by bisphenol A in the epididymal sperm of rats. Toxicology 185:119–27
   PubMed Web of Science ®Google Scholar
• Clement MV, Long LH, Ramalingam J, Halliwell B. (2002). The cytotoxicity of dopamine may be an artefact of cell culture. J Neurochem 81:414–21
   Google Scholar
• Doerge DR, Fisher JW. (2010). Metabolism and toxicokinetics of bisphenol A. Joint FAO/WHO Expert Meeting to Review Toxicological and Health Aspects of Bisphenol A; 2010 November 1–5, Ottawa, Canada. Available from: http://www.who.int/foodsafety/chem/chemicals/BPA_Summary2010.pdf [last accessed 27 December 2012]
   Google Scholar
• Ehlert KA, Beumer CW, Groot MC. (2008). Migration of bisphenol A into water from polycarbonate baby bottles during microwave heating. Food Addit Contam Part A Chem Anal Control Expo Risk Assess 25:904–10
   PubMed Web of Science ®Google Scholar
• Gallard H, Leclercq A, Croué JP. (2004). Chlorination of bisphenol A: kinetics and by-products formation. Chemosphere 56:465–73
   PubMed Web of Science ®Google Scholar
• Goldstein S, Czapski G. (2000). Reactivity of peroxynitrite versus simultaneous generation of •NO and toward NADH. Chem Res Toxicol 13:736–41
   PubMed Web of Science ®Google Scholar
• Hausladen A, Fridovich I. (1994). Superoxide and peroxynitrite inactivate aconitases, but nitric oxide does not. J Biol Chem 269:29405–8
   PubMed Web of Science ®Google Scholar
• Kabuto H, Amakawa M, Shishibori T. (2004). Exposure bisphenol A during embryonic/fetal life and infancy increases oxidative injury and causes underdevelopment of the brain and testis in mice. Life Sci 74:2931–40
   PubMed Web of Science ®Google Scholar
• Krishnan AV, Stathis P, Permuth SF, et al. (1993). Bisphenol-A: an estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrinology 132:2279–86
   PubMed Web of Science ®Google Scholar
• Lang IA, Galloway TS, Scarlett A, et al. (2008). Association of urinary bisphenol A concentration with medical disorders and laboratory abnormalities in adults. JAMA 300:1303–10
   PubMed Web of Science ®Google Scholar
• Le HH, Carlson EM, Chua JP, Belcher SM. (2008). Bisphenol A is released from polycarbonate drinking bottles and mimics the neurotoxic actions of estrogen in developing cerebellar neurons. Toxicol Lett 176:149–56
   PubMed Web of Science ®Google Scholar
• Lee S, Suk K, Kim IK, et al. (2008). Signaling pathways of bisphenol A-induced apoptosis in hippocampal neuronal cells: role of calcium-induced reactive oxygen species, mitogen-activated protein kinases, and nuclear factor-kappaB. J Neurosci Res 86:2932–42
   PubMed Web of Science ®Google Scholar
• Lemercier JN, Padmaja S, Cueto R, et al. (2007). Carbon dioxide modulation of hydroxylation and nitration of phenol by peroxynitrite. Arch Biochem Biophys 345:160–70
   Google Scholar
• Loikkanen J, Naarala J, Vähäkangas KH, Savolainen KM. (2003). Glutamate increases toxicity of inorganic lead in GT1-7 neurons: partial protection induced by flunarizine. Arch Toxicol 77:663–71
   PubMed Web of Science ®Google Scholar
• Lymar SV, Jiang Q, Hurst JK. (1996). Mechanism of carbon dioxide-catalyzed oxidation of tyrosine by peroxynitrite. Biochemistry 35:7855–61
   PubMed Web of Science ®Google Scholar
• Meeker JD, Calafat AM, Hauser R. (2010). Urinary bisphenol A concentrations in relation to serum thyroid and reproductive hormone levels in men from an infertility clinic. Environ Sci Technol 44:1458–63
   PubMed Web of Science ®Google Scholar
• Melzer D, Rice NE, Lewis C, et al. (2010). Association of urinary bisphenol a concentration with heart disease: evidence from NHANES 2003/06. PLoS One 5:e8673
   PubMed Web of Science ®Google Scholar
• Mendum T, Stoler E, VanBenschoten H, Warner JC. (2011). Concentration of bisphenol A in thermal paper. Green Chem Lett Rev 4:81–6
   Web of Science ®Google Scholar
• Moors S, Diel P, Degen GH. (2006). Toxicokinetics of bisphenol A in pregnant DA/Han rats after single i.v. application. Arch Toxicol 80:647–55
   PubMedGoogle Scholar
• Nakamura S, Tezuka Y, Ushiyama A, et al. (2011). Ipso substitution of bisphenol A catalyzed by microsomal cytochrome P450 and enhancement of estrogenic activity. Toxicol Lett 203:92–5
   PubMed Web of Science ®Google Scholar
• Pritchett JJ, Kuester RK, Sipes IG. (2002). Metabolism of bisphenol A in primary cultured hepatocytes from mice, rats, and humans. Drug Metab Dispos 30:1180–5
   PubMed Web of Science ®Google Scholar
• Raghavamenon AC, Babu S, Uppu S, et al. (2011). Unusually high levels of bisphenol A in cash receipts (Abstract ID: 2256). Toxicologist 120:484
   Google Scholar
• Richter CA, Birnbaum LS, Farabollini F, et al. (2007). In vivo effects of bisphenol A in laboratory rodent studies. Reprod Toxicol 24:199–224
   PubMed Web of Science ®Google Scholar
• Rubin BS. (2011). Bisphenol A: an endocrine disruptor with widespread exposure and multiple effects. J Steroid Biochem Mol Biol 27:27–34
   Google Scholar
• Sathiskumar K, Raghavamenon AC, Ganeshkumar K, et al. (2010). Simultaneous analysis of expression of multiple redox-sensitive and apoptotic genes in hypothalamic neurons exposed to cholesterol secoaldehyde. Methods Mol Biol 610:263–84
   Google Scholar
• Sathishkumar K, Rangan V, Gao X, Uppu RM. (2007a). Methyl vinyl ketone induces apoptosis in murine GT1-7 hypothalamic neurons through glutathione depletion and the generation of reactive oxygwen species. Free Radic Res 41:469–77
   PubMed Web of Science ®Google Scholar
• Sathishkumar K, Xi X, Marin R, Uppu RM. (2007b). Chloesterol secoaldehyde, an ozonation product of chloesterol, induces amyloid aggregation and apoptosis in murine GT1-7 hypothalamic neurons. J Alzheimer’s Dis 11:261–74
   PubMed Web of Science ®Google Scholar
• Schneider B, Mutel V, Pietri M, et al. (2003). NADPH oxidase and extracellular regulated kinases 1/2 are targets of prion protein signaling in neuronal and nonneuronal cells. Proc Natl Acad Sci USA 100:13326–31
   PubMed Web of Science ®Google Scholar
• Shankar A, Teppala S. (2012). Urinary bisphenol A and hypertension in a multiethnic sample of US adults. J Environ Public Health 2012:481641, 5 pages; doi:10.1155/2012/481641
   PubMedGoogle Scholar
• Sortino MA, Battaglia A, Pamparana F, et al. (1999). Neuroprotective effects of nicergoline in immortalized neurons. Eur J Pharmacol 368:285–90
   PubMed Web of Science ®Google Scholar
• Uppu RM, Squadrito GL, Bolzan RM, Pryor WA. (2000). Nitration and nitrosation by peroxynitrite: role of CO2 and evidence for common intermediates. J Am Chem Soc 122:6911–16
   Web of Science ®Google Scholar
• vom Saal FS, Nagel SC, Coe BL, et al. (2012). The estrogenic endocrine disrupting chemical bisphenol A (BPA) and obesity. Mol Cell Endocrinol 354:74–84
   PubMed Web of Science ®Google Scholar
• Winterbourn CC. (1993). Superoxide as an intracellular radical sink. Free Radic Biol Med 14:85–90
   PubMed Web of Science ®Google Scholar
• Yang YJ, Hong YC, Oh SY, et al. (2009). Bisphenol A exposure is associated with oxidative stress and inflammation in postmenopausal women. Environ Res 109:797–801
   PubMed Web of Science ®Google Scholar
• Yoshihara S, Makishima M, Suzuki N, Ohta S. (2001). Metabolic activation of bisphenol A by rat liver S9 fraction. Toxicol Sci 62:221–7
   PubMed Web of Science ®Google Scholar