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Synthetic Phenolic Antioxidants, Including Butylated Hydroxytoluene (BHT), in Resin-Based Dental Sealants

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Synthetic Phenolic Antioxidants, Including Butylated Hydroxytoluene (BHT), in Resin-Based Dental Sealants Environmental Research 151 (2016) 339–343 Contents lists available at ScienceDirect Environmental Research journal homepage: www.elsevier.com/locate/envres Synthetic phenolic antioxidants, including butylated hydroxytoluene (BHT), in resin-based dental sealants Wei Wang a, Pranav Kannan a, Jingchuan Xue a, Kurunthachalam Kannan a,b,n a Wadsworth Center, New York State Department of Health, and Department of Environmental Health Sciences, School of Public Health, State University of New York at Albany, Empire State Plaza, P.O. Box 509, Albany, NY 12201-0509, United States b Biochemistry Department, Faculty of Science, Experimental Biochemistry Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah, Saudi Arabia article info abstract Article history: Resin-based dental sealants (also referred to as pit-and-fissure sealants) have been studied for their Received 28 June 2016 contribution to bisphenol A (BPA) exposure in children. Nevertheless, little attention has been paid to the Received in revised form occurrence of other potentially toxic chemicals in dental sealants. In this study, the occurrence of six 29 July 2016 synthetic phenolic antioxidants (SPAs), including 2,6-di-tert-butyl-4-hydroxytoluene (BHT), 2,6-di-tert- Accepted 30 July 2016 butyl-4-(hydroxyethyl)phenol (BHT-OH), 3,5-di-tert-butyl-4-hydroxy-benzaldehyde (BHT-CHO), 2,6-di- tert-butylcyclohexa-2,5-diene-1,4-dione (BHT-Q), 3,5-di-tert-butyl-4-hydroxybenzoic acid (BHT-COOH) Keywords: and 2-tert-butyl-4-methoxyphenol (BHA), was examined in 63 dental sealant products purchased from Dental sealant the U.S. market. BHT was found in all dental sealants at median and maximum concentrations of 56.8 and Synthetic phenolic antioxidant 1020 mg/g, respectively. The metabolites of BHT and BHA were detected in 39–67% of samples, at con- BHT centration ranges of oLOQ to 242 mg/g. BHT is likely used in sealants to inhibit oxidative reactions, Human exposure Resin remove free radicals, and inhibit potential polymerization, which would eventually prolong the shelf-life of the products. The estimated daily intake (EDI) of BHT, following sealant placement, based on a worst- case scenario (application on eight teeth at 8 mg each tooth), was 930 and 6510 ng/kg bw/d for adults and children, respectively. The EDI of BHT from dental sealants was several orders of magnitude lower than the current acceptable daily intake (ADI) proposed by the European Food Safety Authority (EFSA). & 2016 Elsevier Inc. All rights reserved. 1. Introduction metabolites of BHT have been shown to elicit cellular DNA da- mage, genotoxicity, and carcinogenicity in animal models (Oikawa Synthetic phenolic antioxidants (SPAs) such as 2,6-di-tert-bu- et al., 1998). Some BHT metabolites, such as 3,5-di-tert-butyl-4- tyl-4-hydroxytoluene (BHT) are the most frequently used anti- hydroxy-benzaldehyde (BHT-CHO) and 2,6-di-tert-butylcyclohexa- oxidants in a wide range of consumer products worldwide, in- 2,5-diene-1,4-dione (BHT-Q), were reported to be more toxic than cluding foodstuffs, cosmetics, and plastics (Wang et al., 2016). Al- BHT itself (Nagai et al., 1993). Similarly, other related antioxidants, though considered safe for human health at authorized levels, such as 2-tert-butyl-4-methoxyphenol (BHA), were reported to be their widespread use, multiple sources of exposure, and con- tumor promoters, endocrine disruptors, or carcinogens (Grice, troversial toxicological data are a cause for concern (Nieva-Eche- 1988; Kahl and Kappus, 1993). Nevertheless, debate continues over varria et al., 2014). A number of animal studies have reported toxic the carcinogenic potentials of BHT and BHA (Hirose et al., 1981; effects of BHT, including carcinogenicity and reproductive toxicity Shirai et al., 1982; Williams et al., 1990; Bomhard et al., 1992; (Clapp et al., 1973; Grogan, 1986; Lindenschmidt et al., 1986; Olsen Iverson, 1995; Whysner et al., 1996; Williams et al., 1999; Botter- et al., 1986; Shlian and Goldstone, 1986; Inai et al., 1988; Takahashi, weck et al., 2000). Despite the widespread use of SPAs in various consumer products, little is known about human exposure doses. 1992; Rao et al., 2000; Al-Akid et al., 2001). Further, the Sources other than foodstuffs can contribute to BHT exposures, and, thus, such sources should be taken into account in the as- n Corresponding author at: Wadsworth Center, New York State Department of sessment of risks of BHT. Health, and Department of Environmental Health Sciences, School of Public Health, Dental sealants are thin plastic coatings that are painted on the State University of New York at Albany, Empire State Plaza, P.O. Box 509, Albany, NY 12201-0509, United States. chewing surfaces of teeth to provide a barrier for the protection E-mail address: [email protected] (K. Kannan). against bacterial decay (Truman et al., 2002; Ahovuo-Saloranta http://dx.doi.org/10.1016/j.envres.2016.07.042 0013-9351/& 2016 Elsevier Inc. All rights reserved. 340 W. Wang et al. / Environmental Research 151 (2016) 339–343 et al., 2008; Beauchamp et al., 2008; Griffin et al., 2008; Momoi nitrogen stream, and the solvent was exchanged to 150 mL ethyl et al., 2012). Dental sealants are widely used in the U.S., with 50% acetate. The remaining eight SPAs were analyzed by high perfor- of children, aged 9–11 years, have had at least one dental sealant mance liquid chromatograph-tandem mass spectrometer (HPLC- on a permanent tooth as well as 31% of children, aged 6–8 years, MS/MS). and 43% of adolescents, aged 12–19 years, in 2011–2012 (Dye et al., 2015). Human exposure to synthetic and toxic chemicals such as bisphenol A (BPA) present in dental sealants has received con- 2.4. Instrumental analysis siderable attention (Rathee et al., 2012; Kloukos et al., 2013; Van Landuyt et al., 2011). Resin-based dental sealants may release BHT was analyzed using a GC (Agilent Technologies 6890) other chemical additives, including SPAs, in the oral environment. coupled to an MS (Agilent Technologies 5975) in the selected ion Nevertheless, limited information is available on the occurrence of monitoring (SIM) mode. A fused-silica capillary column (DB-5; SPAs and their metabolites in dental sealants. Given the growing 15 m  0.25 mm i.d.  0.25 mm film thickness) was used for se- public concern about the release of toxic components from resin- paration. Other SPAs were determined using an Agilent 1260 HPLC based dental materials (Rathee et al., 2012; McKinney et al., 2014), (Agilent Technologies Inc., Santa Clara, CA, USA) interfaced with an there is a need to investigate the occurrence of SPAs in dental Applied Biosystems QTRAP 4500 mass spectrometer (ESI-MS/MS; sealants. In this study, SPAs, including BHT and its metabolites, Applied Biosystems, Foster City, CA, USA). An analytical column were determined in 21 brands of dental sealants collected in the U. (Betasils C18, 100  2.1 mm column; Thermo Electron Corpora- S. market, for the first time, to elucidate the occurrence and hu- tion, Waltham, MA, USA) connected to a Javelin guard column man exposure through dental material restoration. s (Betasil C18, 20  2.1 mm) was used for chromatographic se- paration. The negative ion multiple reaction monitoring (MRM) mode was used. Nitrogen was used as both a curtain and collision 2. Chemicals and reagents gas. The MS/MS parameters were optimized by infusion of in- fl 2.1. Sample collection dividual compounds into the MS through a ow injection system (Table A2; Appendix. A). The MRM transitions of the target che- Dental sealants (n¼63; pit-and-fissure) were purchased from micals monitored are listed in Table A3 (Appendix. A). June to August 2015 from several vendors and distributors of the products. They were products of the U.S., Korea, Greece, and 2.5. Quality assurance and quality control (QA/QC) Liechtenstein and represented popular brands used in the U.S. The resin-based sealant samples represented 18 brands, featured in With every set of 20 samples analyzed, a procedural blank, a various shades (e.g., opaque, clear, natural, off-white). Approxi- pair of pre-extraction matrix spikes (standards fortified in samples mately 20% of the samples were labeled as containing fluoride, 86% were pit-and-fissure, and all were light-cure-type (100%) prior to extraction), a pair of post-extraction matrix spikes (stan- fi products. dards forti ed in sample extracts after extraction), and duplicate samples were analyzed. Trace levels of BHA (median: 0.67 ng/g) 2.2. Chemicals and reagents were found in procedural blanks, and a background subtraction was performed when reporting concentrations of this compound. The target chemicals and their structures are shown in Table A1 Recoveries of SPAs in spiked dental sealant matrices ranged from (Appendix. A; Supporting information). BHT, BHT-d21, 2,6-di-tert- 93.0712.2% for BHT-OH to 114712.4% for BHT (Table A3). Du- butyl-4-(hydroxyethyl)phenol (BHT-OH), BHT-Q, BHT-CHO, and plicate analysis of randomly selected samples (n¼3) yielded a 3,5-di-tert-butyl-4-hydroxybenzoic acid (BHT-COOH) were ob- coefficient of variation of o20%. Quantification of SPAs was per- tained from Sigma-Aldrich (St. Louis, MO, USA). Isotopically- formed by an isotope-dilution method, based on the responses of 13 13 13 labeled C12-methyl paraben ( C12-MeP; RING- C12, 99%) was 13 BHT-d21 (for BHT) and C12-MeP (for BHT-Q, BHA, BHT-OH, BHT- obtained from Cambridge Isotope Laboratories (Andover, MA, CHO, and BHT-COOH). The limits of quantification (LOQs) were USA). HPLC-grade methanol was supplied by J.T. Baker (Phillips- 1 ng/g for BHA and BHT-Q, 2 ng/g for BHT-CHO, 4 ng/g for BHT-OH, burg, NJ, USA).
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