2,5-Dihydroxy-4-methoxybenzophenone: a novel major in vitro metabolite of benzophenone-3 formed by rat and human liver microsomes

References

• Brand RM, Spalding M, Mueller C. (2002). Sunscreens can increase dermal penetration of 2,4-dichlorophenoxyacetic acid. J Toxicol Clin Toxicol 40:827–832.
   PubMed Web of Science ®Google Scholar
• Brand RM, Pike J, Wilson RM, Charron AR. (2003). Sunscreens containing physical UV blockers can increase transdermal absorption of pesticides. Toxicol Ind Health 19:9–16.
   PubMed Web of Science ®Google Scholar
• Burdock GA, Pence DH, Ford RA. (1991). Safety evaluation of benzophenone. Food Chem Toxicol 29:741–750.
   Google Scholar
• Dutta K, Das M, Rahman T. (1993). Toxicological impacts of benzophenone on the liver of guinea pig (Cavia porcellus). Bull Environ Contam Toxicol 50:282–285.
   Google Scholar
• el Dareer SM, Kalin JR, Tillery KF, Hill DL. (1986). Disposition of 2-hydroxy-4-methoxybenzophenone in rats dosed orally, intravenously, or topically. J Toxicol Environ Health 19:491–502.
   PubMed Web of Science ®Google Scholar
• Felix T, Hall BJ, Brodbelt JS. (1998). Determination of benzophenone-3 and metabolites in water and human urine by solid-phase microextraction and quadrupole ion trap GC-MS. Anal Chim Acta 371:195–203.
   Web of Science ®Google Scholar
• Gustavsson Gonzalez H, Farbrot A, Larkö O. (2002). Percutaneous absorption of benzophenone-3, a common component of topical sunscreens. Clin Exp Dermatol 27:691–694.
   PubMed Web of Science ®Google Scholar
• Gonzalez H, Jacobson CE, Wennberg AM, Larkö O, Farbrot A. (2008). Solid-phase extraction and reverse-phase HPLC: Application to study the urinary excretion pattern of benzophenone-3 and its metabolite 2,4-dihydroxybenzophenone in human urine. Anal Chem Insights 3:1–7.
   PubMedGoogle Scholar
• Hagedorn-Leweke U, Lippold BC. (1995). Absorption of sunscreens and other compounds through human skin in vivo: Derivation of a method to predict maximum fluxes. Pharm Res 12:1354–1360.
   PubMed Web of Science ®Google Scholar
• Hany J, Nagel R. (1995). Detection of sunscreen agents in human breast milk. Deutsche Lebensmittel-Rundschau 91:341–345.
   Web of Science ®Google Scholar
• Hayden CG, Roberts MS, Benson HA. (1997). Systemic absorption of sunscreen after topical application. Lancet 350:863–864.
   PubMed Web of Science ®Google Scholar
• Heneweer M, Muusse M, van den Berg M, Sanderson JT. (2005). Additive estrogenic effects of mixtures of frequently used UV filters on pS2-gene transcription in MCF-7 cells. Toxicol Appl Pharmacol 208:170–177.
   PubMed Web of Science ®Google Scholar
• Jeon HK, Sarma SN, Kim YJ, Ryu JC. (2008). Toxicokinetics and metabolisms of benzophenone-type UV filters in rats. Toxicology 248:89–95.
   PubMed Web of Science ®Google Scholar
• Jiang R, Roberts MS, Collins DM, Benson HA. (1999). Absorption of sunscreens across human skin: An evaluation of commercial products for children and adults. Br J Clin Pharmacol 48:635–637.
   PubMed Web of Science ®Google Scholar
• Kawamura Y, Ogawa Y, Nishimura T, Kikuchi Y, Nishikawa J, Nishihara T. (2003). Estrogenic activities of UV stabilizers used in food contact plastics and benzophenone derivatives tested by the yeast two-hybrid assay. J Health Sci 49:205–212.
   Web of Science ®Google Scholar
• Klein K. (1992). Encyclopedia of UV absorbers for sunscreen products. Cosm Toiletriesl 107:45–64.
   Google Scholar
• Kuroyanagi M, Ueno A, Hirayama Y, Hakamata Y, Gokita T, Ishimaru T, Kameyama S, Yanagawa T, Satake M, Sekita S. (1996). Anti-androgen active constituents from Dalbergia cochinchinensis Pierre. Natural Med 50:408–412.
   Google Scholar
• Ma R, Cotton B, Lichtensteiger W, Schlumpf M. (2003). UV filters with antagonistic action at androgen receptors in the MDA-kb2 cell transcriptional-activation assay. Toxicol Sci 74:43–50.
   PubMed Web of Science ®Google Scholar
• Martini R, Ingelman-Sundberg M, Murray M. (1997). Pretranslational and posttranslational regulation of rat hepatic CYPs 3A2 and 2E1 by disulfiram. Biochem Pharmacol 54:1323–1329.
   PubMed Web of Science ®Google Scholar
• Meinerling M, Daniels M. (2006). A validated method for the determination of traces of UV filters in fish using LC-MS/MS. Anal Bioanal Chem 386:1465–1473.
   PubMed Web of Science ®Google Scholar
• Morohoshi K, Yamamoto H, Kamata R, Shiraishi F, Koda T, Morita M. (2005). Estrogenic activity of 37 components of commercial sunscreen lotions evaluated by in vitro assays. Toxicol In Vitro 19:457–469.
   PubMed Web of Science ®Google Scholar
• Nagtegaal M, Ternes TA, Baumann W, Nagel R. (1997). UV-filtersubstanzen in wasser und fishen. Umweltwissenschaften und Schadstoff-Forschung 9:79–86.
   Google Scholar
• Nakagawa Y, Tayama K. (2001). Estrogenic potency of benzophenone and its metabolites in juvenile female rats. Arch Toxicol 75:74–79.
   PubMed Web of Science ®Google Scholar
• Nakagawa Y, Suzuki T. (2002). Metabolism of 2-hydroxy-4-methoxybenzophenone in isolated rat hepatocytes and xenoestrogenic effects of its metabolites on MCF-7 human breast cancer cells. Chem Biol Interact 139:115–128.
   PubMed Web of Science ®Google Scholar
• Okereke CS, Kadry AM, Abdel-Rahman MS, Davis RA, Friedman MA. (1993). Metabolism of benzophenone-3 in rats. Drug Metab Dispos 21:788–791.
   PubMed Web of Science ®Google Scholar
• Okereke CS, Abdel-Rhaman MS, Friedman MA. (1994). Disposition of benzophenone-3 after dermal administration in male rats. Toxicol Lett 73:113–122.
   PubMed Web of Science ®Google Scholar
• Okereke CS, Barat SA, Abdel-Rahman MS. (1995). Safety evaluation of benzophenone-3 after dermal administration in rats. Toxicol Lett 80:61–67.
   PubMed Web of Science ®Google Scholar
• Poiger T, Buser HR, Balmer ME, Bergqvist PA, Müller MD. (2004). Occurrence of UV filter compounds from sunscreens in surface waters: Regional mass balance in two Swiss lakes. Chemosphere 55:951–963.
   PubMed Web of Science ®Google Scholar
• Sarveiya V, Risk S, Benson HA. (2004). Liquid chromatographic assay for common sunscreen agents: Application to in vivo assessment of skin penetration and systemic absorption in human volunteers. J Chromatogr B Analyt Technol Biomed Life Sci 803:225–231.
   PubMed Web of Science ®Google Scholar
• Schauder S, Ippen H. (1997). Contact and photocontact sensitivity to sunscreens. Review of a 15-year experience and of the literature. Contact Derm 37:221–232.
   PubMed Web of Science ®Google Scholar
• Schlecht C, Klammer H, Jarry H, Wuttke W. (2004). Effects of estradiol, benzophenone-2 and benzophenone-3 on the expression pattern of the estrogen receptors (ER) α and β, the estrogen receptor-related receptor 1 (ERR1) and the aryl hydrocarbon receptor (AhR) in adult ovariectomized rats. Toxicology 205:123–130.
   PubMed Web of Science ®Google Scholar
• Schlumpf M, Cotton B, Conscience M, Haller V, Steinmann B, Lichtensteiger W. (2001). In vitro and in vivo estrogenicity of UV screens. Environ Health Perspect 109:239–244.
   PubMed Web of Science ®Google Scholar
• Suzuki T, Kitamura S, Khota R, Sugihara K, Fujimoto N, Ohta S. (2005). Estrogenic and antiandrogenic activities of 17 benzophenone derivatives used as UV stabilizers and sunscreens. Toxicol Appl Pharmacol 203:9–17.
   PubMed Web of Science ®Google Scholar
• Van Liempd SM, Kool J, Meerman JH, Irth H, Vermeulen NP. (2007). Metabolic profiling of endocrine-disrupting compounds by on-line cytochrome p450 bioreaction coupled to on-line receptor affinity screening. Chem Res Toxicol 20:1825–1832.
   PubMed Web of Science ®Google Scholar
• Yamasaki K, Takeyoshi M, Sawaki M, Imatanaka N, Shinoda K, Takatsuki M. (2003). Immature rat uterotrophic assay of 18 chemicals and Hershberger assay of 30 chemicals. Toxicology 183:93–115.
   PubMed Web of Science ®Google Scholar
• Zhang Z, Ren N, Li YF, Kunisue T, Gao D, Kannan K. (2011). Determination of benzotriazole and benzophenone UV filters in sediment and sewage sludge. Environ Sci Technol 45:3909–3916.
   PubMed Web of Science ®Google Scholar