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Bisphenol A and Orthodontic Materials

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Plastics in Dentistry and Estrogenicity

Abstract

Orthodontic polymers, and their applications, have been instrumental in introducing aesthetics, innovation, and practicality into the orthodontic specialty. Such materials constitute a large class of components including plastic elements and auxiliaries such as adhesives, polycarbonate brackets, and aligners.

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References

  1. Artham T, Doble M (2008) Biodegradation of aliphatic and aromatic polycarbonates. Macromol Biosci 8:14–24

    Article  PubMed  Google Scholar 

  2. Fleisch AF, Sheffield PE, Chinn C, Edelstein BL, Landrigan PJ (2010) Bisphenol A and related compounds in dental materials. Pediatrics 126:760–768

    Article  PubMed  Google Scholar 

  3. Van Landuyt KL, Nawrot T, Geebelen B, De Munck J, Snauwaert J, Yoshihara K et al (2011) How much do resin- based dental materials release? A meta-analytical approach. Dent Mater 27:723–747

    Article  PubMed  Google Scholar 

  4. Ranks CT, Craig RG, Diehi ML, Pashley DH (1988) Cytotoxicity in dental composites and other materials in a new in vitro device. J Oral Pathol 17:396–403

    Article  Google Scholar 

  5. Hensten-Pettersen A, Helgeland K (1981) Sensitivity of different human cell lines in the biologic evaluation of dental resin-based restorative materials. Scand J Dent Res 89:102–107

    PubMed  Google Scholar 

  6. Terakado M, Yamazaki M, Tsujimoto Y, Kawashima T, Nagashima K, Ogawa J, Fujita Y, Sugiya H, Sakai T, Furuyama S (1984) Lipid peroxidation as a possible cause of benzoyl peroxide toxicity in rabbit dental pulp a microsomal lipid peroxidation in vitro. J Dent Res 63:901–905

    Article  PubMed  Google Scholar 

  7. Hanks CT, Strawn SE, Wataha JC, Craig RG (1991) Cytotoxic effects of resin components on cultured mammalian fibroblasts. J Dent Res 70:1450–1455

    Article  PubMed  Google Scholar 

  8. Bourne LB, Milner FJM, Alberman KB (1959) Health problems of epoxy resins and amine curing agents. Br J Ind Med 16:81–97

    PubMed  Google Scholar 

  9. Morrissey RE, George JD, Price CJ, Tyl RW, Marr MC, Kimmel CA (1987) The developmental toxicity of bisphenol A in rats and in mice. Fundam Appl Toxicol 8:571–582

    Article  PubMed  Google Scholar 

  10. Mohsen NM, Craig RG, Hanks CT (1998) Cytotoxicity of urethane dimethacrylate composites before and after aging and leaching. J Biomed Mater Res 39:252–260

    Article  PubMed  Google Scholar 

  11. Vandenberg LN, Hauser R, Marcus M, Olea N, Welshons WV (2007) Human exposure to bisphenol A (BPA). Reprod Toxicol 24:139–177

    Article  PubMed  Google Scholar 

  12. Chapin RE, Adams J, Boekelheide K, Gray LE Jr, Hayward SW, Lees PS et al (2008) NTP-CERHR Expert Panel report on the reproductive and developmental toxicity of bisphenol A. Birth Defects Res B 83:157–395

    Article  Google Scholar 

  13. Roy JR, Chakraborty S, Chakraborty TR (2009) Estrogen-like endocrine disrupting chemicals affecting puberty in humans – a review. Med Sci Monit 15:137–145

    Google Scholar 

  14. Diamanti-Kandarakis E, Bourguignon JP, Giudice LC, Hauser R, Prins GS, Soto AM et al (2009) Endocrine-disrupting chemicals: an endocrine society scientific statement. Endocr Rev 30:293–342

    Article  PubMed  Google Scholar 

  15. Institute of National Health and Medical Research (INSERM) (2010) Bisphenol A: effects on reproduction. Preliminary report. INSERM, Paris

    Google Scholar 

  16. Maserejian NN, Trachtenberg FL, Hauser R, McKinlay S, Shrader P, Tavares M, Bellinger DC (2012) Dental composite restorations and psychosocial function in children. Pediatrics 130:328–338

    Article  Google Scholar 

  17. European Food Safety Authority (EFSA) (2006) Opinion of the scientific panel on food additives, flavourings, processing aids and materials in contact with food on a request from the commission related to 2,2-bis(4-hydroxyphenyl) propane (Bisphenol A). Question number EFSA-Q-2005-100. Eur Food Saf Auth J 428:1–75

    Google Scholar 

  18. French Agency for Food, Environmental and Occupational Health & Safety (ANSES) (2010) Opinion of 29 January 2010 of the French Agency for Food Safety on the critical analysis of the results of a toxicity study on the development of the nervous system as well as other recently published data on the toxic effects of bisphenol A. ANSES, Paris

    Google Scholar 

  19. Olea N, Pulgar R, Olea-Serrano F, Rivas A, Novillo-Fertrell A, Pedraza V et al (1996) Estrogenicity of resin-based composites and sealant used in dentistry. Environ Health Perspect 104:298–305

    Article  PubMed  Google Scholar 

  20. Eliades T (2007) Orthodontic materials research and applications: Part 2. Current status and projected future developments in materials and biocompatibility. Am J Orthod Dentofacial Orthop 131:253–262

    Article  PubMed  Google Scholar 

  21. Kloukos D, Pandis N, Eliades T (2013) Bisphenol-A and residual monomer leaching from orthodontic adhesive resins and polycarbonate brackets: a systematic review. Am J Orthod Dentofacial Orthop 143(4):S104-12.e1-2

    Article  PubMed  Google Scholar 

  22. Brantley WA, Eliades T (2001) Orthodontic materials: scientific and clinical aspects, 1st edn. Thieme, Stuttgart

    Google Scholar 

  23. Eliades T, Viazis AD, Eliades G (1991) Bonding of ceramic brackets to enamel: morphologic and structural considerations. Am J Orthod Dentofacial Orthop 99:369–375

    Article  PubMed  Google Scholar 

  24. Renkema AM, Al-Assad S, Bronkhorst EM, Weindel S, Katsaros C, Lisson JA (2008) Effectiveness of lingual retainers bonded to the canines in preventing mandibular incisor relapse. Am J Orthod Dentofacial Orthop 134:1–8

    Article  Google Scholar 

  25. Eliades T, Voutsa D, Sifakakis I, Makou M, Katsaros C (2011) Release of bisphenol-A from a light-cured adhesive bonded to lingual fixed retainers. Am J Orthod Dentofacial Orthop 139:192–195

    Article  PubMed  Google Scholar 

  26. Gioka C, Eliades T, Zinelis S, Pratsinis H, Athanasiou AE, Eliades G et al (2009) Characterization and in vitro estrogenicity of orthodontic adhesive particulates produced by simulated debonding. Dent Mater 25:376–382

    Article  PubMed  Google Scholar 

  27. Almeida MA (2006) Analysis of aerodynamically respirable dust generated from quartz containing orthodontic and dental composites utilizing air rotary abrasion. MS thesis, Oregon Health & Science University, Portland

    Google Scholar 

  28. Ireland AJ, Moreno T, Price R (2003) Airborne particles produced during enamel cleanup after removal of orthodontic appliances. Am J Orthod Dentofacial Orthop 124:683–686

    Article  PubMed  Google Scholar 

  29. Day CJ, Price R, Sandy JR, Ireland AJ (2008) Inhalation of aerosols produced during the removal of fixed orthodontic appliances: a comparison of 4 enamel cleanup methods. Am J Orthod Dentofacial Orthop 133:11–17

    Article  PubMed  Google Scholar 

  30. Tarumi H, Imazato S, Narimatsu M, Matsuo M, Ebisu S (2000) Estrogenicity of fissure sealants and adhesive resins determined by reporter gene assay. J Dent Res 79:1838–1843

    Article  PubMed  Google Scholar 

  31. Schmalz G, Preiss A, Arenholt-Bindslev D (1999) Bisphenol-A content of resin monomers and related degradation products. Clin Oral Investig 3:114–119

    Article  PubMed  Google Scholar 

  32. Pulgar R, Olea-Serrano MF, Novillo-Fertrell A, Rivas A, Pazos P, Pedraza V et al (2000) Determination of bisphenol A and related aromatic compounds released from bis-GMA-based composites and sealants by high performance liquid chromatography. Environ Health Perspect 108:21–27

    Article  PubMed  Google Scholar 

  33. Atkinson JC, Diamond F, Eichmiller F, Selwitz R, Jones G (2002) Stability of bisphenol A, triethylene-glycol dimethacrylate, and bisphenol A dimethacrylate in whole saliva. Dent Mater 18:128–135

    Article  PubMed  Google Scholar 

  34. Eliades T, Hiskia A, Eliades G, Athanasiou AE (2007) Assessment of bisphenol-A release from orthodontic adhesives. Am J Orthod Dentofacial Orthop 131:72–75

    Article  PubMed  Google Scholar 

  35. Timms BG, Howdeshell KL, Barton L, Bradley S, Richter CA, vom Saal FS (2005) Estrogenic chemicals in plastic and oral contraceptives disrupt development of the fetal mouse prostate and urethra. Proc Natl Acad Sci U S A 102:7014–7019

    Article  PubMed  Google Scholar 

  36. Lee YK, Lim BS, Powers JM (2004) Color changes of dental resin composites by a salivary enzyme. J Biomed Mater Res B Appl Biomater 70:66–72

    Article  PubMed  Google Scholar 

  37. Sunitha C, Kailasam V, Padmanabhan S, Chitharanjan AB (2011) Bisphenol A release from an orthodontic adhesive and its correlation with the degree of conversion on varying light-curing tip distances. Am J Orthod Dentofacial Orthop 140:239–244

    Article  PubMed  Google Scholar 

  38. Eliades GC, Vougiouklakis GJ, Caputo AA (1987) Degree of double bond conversion in light-cured composites. Dent Mater 3:19–25

    Article  PubMed  Google Scholar 

  39. Ferracane JL, Greener EH (1986) The effect of resin formulation on the degree of conversion and mechanical properties of dental restorative resins. J Biomed Mater Res 20:121–131

    Article  PubMed  Google Scholar 

  40. Ruyter IE (1985) Monomer systems and polymerization. In: Vanherle G, Smith DC (eds) Posterior composite resin dental restorative materials. Szulc Publishing, Amsterdam, pp 109–135

    Google Scholar 

  41. Ferracane JL, Moser JB, Greener EH (1985) Ultraviolet light- induced yellowing of dental restorative resins. J Prosthet Dent 54:483–487

    Article  PubMed  Google Scholar 

  42. Söderholm K-J, Zigan M, Ragan M, Fischlschweiger W, Bergman M (1984) Hydrolytic degradation of dental composites. J Dent Res 63:1248–1254

    Article  PubMed  Google Scholar 

  43. Rathbun MA, Craig RG, Hanks CT, Filisko FE (1991) Cytotoxicity of a Bis-GMA dental composite before and after leaching in organic solvents. J Biomed Mater Res 25:443–457

    Article  PubMed  Google Scholar 

  44. Miyamoto K, Kotake M (2006) Estimation of daily bisphenol A intake of Japanese individuals with emphasis on uncertainty and variability. Environ Sci 13:15–29

    PubMed  Google Scholar 

  45. Christian M, Gillies G (1999) Developing hypothalamic dopaminergic neurones as potential targets for environmental estrogens. J Endocrinol 160:R1–R6

    Article  PubMed  Google Scholar 

  46. Eliades T, Gioni V, Kletsas D, Athanasiou A, Eliades G (2007) Oestrogenicity of orthodontic adhesive resins. Eur J Orthod 29:404–407

    Article  PubMed  Google Scholar 

  47. Al-Hiyasat AS, Darmani H, Elbetieha AM (2004) Leached components from dental composites and their effects on fertility of female mice. Eur J Oral Sci 112:267–272

    Article  PubMed  Google Scholar 

  48. Elsby R, Maggs JL, Ashby J, Park BK (2001) Comparison of the modulatory effects of human and rat liver microsomal metabolism on the estrogenicity of bisphenol A: implications for extrapolation to humans. J Pharmacol Exp Ther 297:103–113

    PubMed  Google Scholar 

  49. Vittek J, Hernandez MR, Wenk EJ, Rappaport SC, Southren AL (1982) Specific estrogen receptors in human gingiva. J Clin Endocrinol Metab 54:608–612

    Article  PubMed  Google Scholar 

  50. Herlofson BB, Barkvoll P (1996) Oral mucosal desquamation of pre- and post-menopausal women. A comparison of response to sodium lauryl sulphate in toothpastes. J Clin Periodontol 23:567–571

    Article  PubMed  Google Scholar 

  51. Kang YG, Kim JY, Kim J, Won PJ, Nam JH (2011) Release of bisphenol A from resin composite used to bond orthodontic lingual retainers. Am J Orthod Dentofacial Orthop 140:779–789

    Article  PubMed  Google Scholar 

  52. Environment Protection Agency (EPA) (1988) Oral RfD assessment: bisphenol A. Integrated Risk Information System

    Google Scholar 

  53. vom Saal FS, Hughes C (2005) An extensive new literature concerning low-dose effects of bisphenol A shows the need for a new risk assessment. Environ Health Perspect 113:926–933

    Article  Google Scholar 

  54. Kanerva L, Estlander T, Jolanki R (1989) Allergic contact dermatitis from dental composite resins due to aromatic epoxy acrylates and aliphatic acrylates. Contact Dermatitis 20:201–211

    Article  PubMed  Google Scholar 

  55. Kanerva L, Turjanmaa K, Estlander T, Jolanki R (1991) Occupational allergic contact dermatitis caused by 2- hydroxyethyl methacrylate (2-HEMA) in a new dentin adhesive. Am J Cont Dermatol 2:24–30

    Google Scholar 

  56. Kanerva L, Henriks-Eckerman M-L, Estlander T, Jolanki R, Tarvainen K (1994) Occupational allergic contact dermatitis and composition of acrylates in dental bonding systems. J Eur Acad Dermatol Venereol 3:157–169

    Article  Google Scholar 

  57. Munksgaard EC (1999) Toxicology versus allergy in restorative dentistry. Adv Dent Res 6:17–21

    Google Scholar 

  58. Slavin RG, Ducomb DF (1999) Allergic contact dermatitis. Hosp Pract 30:39–51

    Google Scholar 

  59. Connolly M, Shaw L, Hutchinson I, Ireland AJ, Dunnill M, Sansom J (2006) Allergic contact dermatitis from bisphenol-A- glycidyldimethacrylate during application of orthodontic fixed appliance. Contact Dermatitis 55:367–368

    Article  PubMed  Google Scholar 

  60. Suzuki K, Ishikawa K, Sugiyama K, Furuta H, Nishimura F (2000) Content and release of bisphenol A from polycarbonate dental products. Dent Mater J 19:389–395

    Article  PubMed  Google Scholar 

  61. Watanabe M, Hase T, Imai Y (2001) Change in the bisphenol A content in a polycarbonate orthodontic bracket and its leaching characteristics in water. Dent Mater J 20:353–358

    Article  PubMed  Google Scholar 

  62. Watanabe M (2004) Degradation and formation of bisphenol A in polycarbonate used in dentistry. J Med Dent Sci 51:1–6

    PubMed  Google Scholar 

  63. Align Technology, Inc. (2002) The Invisalign reference guide. Santa Clara, p 8

    Google Scholar 

  64. Align Technology, Inc. (2003) Material safety data sheet. MSDS Aligner EX203040. Customer support, 11 Aug 2003

    Google Scholar 

  65. Eliades T, Eliades G, Watts DC (1999) Structural conformation of in vitro and in vivo aged orthodontic elastomeric modules. Eur J Orthod 21:649–658

    Article  PubMed  Google Scholar 

  66. Huget EF, Patrick KS, Nunez LJ (1990) Observations on the elastic behavior of a synthetic orthodontic elastomer. J Dent Res 69:496–501

    Article  PubMed  Google Scholar 

  67. Eliades T, Pratsinis H, Athanasiou AE, Eliades G, Kletsas D (2009) Cytotoxicity and estrogenicity of Invisalign appliances. Am J Orthod Dentofacial Orthop 136:100–103

    Article  PubMed  Google Scholar 

  68. Eliades T, Eliades G, Silikas N, Watts DC (2005) In vitro degradation of polyurethane orthodontic elastomeric chains. J Oral Rehabil 32:72–77

    Article  PubMed  Google Scholar 

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Kloukos, D., Eliades, T. (2014). Bisphenol A and Orthodontic Materials. In: Eliades, T., Eliades, G. (eds) Plastics in Dentistry and Estrogenicity. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-29687-1_6

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  • DOI: https://doi.org/10.1007/978-3-642-29687-1_6

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