Excretion of dental resin monomers and metabolic intermediates via urine in guinea pigs

Dental Materials

Volumn 25, Issue 4, 2009, Pages 481-485

  Seiss, Mario ^a   Marquardt, Wolfgang ^a   Hickel, Reinhard ^a   Reichl, Franz Xaver ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

BisGMA; Metabolites; TEGDMA; Urine

Indexed keywords

ANIMAL CELL CULTURE; ANIMALS; BIOCHEMISTRY; BIOMOLECULES; BODY FLUIDS; DENTAL MATERIALS; DENTAL PROSTHESES; DIMETHYL SULFOXIDE; DISSOLUTION; ETHERS; METABOLITES; MONOMERS; PHENOLS; PHYSIOLOGY; RESINS; SODIUM CHLORIDE; THREE DIMENSIONAL;

BIS PHENOLS; BISGMA; BISPHENOL-A; BODY WEIGHTS; CO-MONOMERS; DENTAL RESINS; DENTAL RESTORATIVE MATERIALS; FILLING MATERIALS; GUINEA PIGS; METABOLIC INTERMEDIATES; NACL SOLUTIONS; REACTION PRODUCTS; RELATIVE CONCENTRATIONS; TEGDMA; THREE-DIMENSIONAL NETWORKS; TRIETHYLENEGLYCOLDIMETHACRYLATE; URINE;

METABOLISM;

2,3 EPOXYMETHACRYLIC ACID; 2,3-EPOXYMETHACRYLIC ACID; 4,4' ISOPROPYLIDENEDIPHENOL; BISPHENOL A BIS(2 HYDROXYPROPYL) ETHER DIMETHACRYLATE; MACROGOL DERIVATIVE; METHACRYLIC ACID DERIVATIVE; PHENOL DERIVATIVE; POLYMETHACRYLIC ACID DERIVATIVE; RESIN; TRIETHYLENE GLYCOL DIMETHACRYLATE;

ANIMAL; ARTICLE; GUINEA PIG; MALE; METABOLISM; URINE;

ANIMALS; BISPHENOL A-GLYCIDYL METHACRYLATE; COMPOSITE RESINS; GUINEA PIGS; MALE; METHACRYLATES; PHENOLS; POLYETHYLENE GLYCOLS; POLYMETHACRYLIC ACIDS; URINE;

EID: 60449087633     PISSN: 01095641     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dental.2008.08.013     Document Type: Article

References (38)

1. Hensten-Pettersen A., and Helgeland K. Sensitivity of different human cell-lines in the biologic evaluation of dental resin-based restorative materials. Scand J Dent Res 89 (1981) 102-107
2. Schedle A., Franz A., Rausch-Fan X., Spittler A., Lucas T., Samorapoompichit P., et al. Cytotoxic effects of dental composites, adhesive substances, copolymers and cements. Dent Mater 14 (1998) 429-440
3. Wennberg A., Mjor I.A., and Henstenpettersen A. Biological evaluation of dental restorative materials-a comparison of different test methods. J Biomed Mater Res 17 (1983) 23-36
4. Schmalz G. The biocompatibility of non-amalgam dental filling materials. Eur J Oral Sci 106 (1998) 696-706
5. Kleinsasser N., Wallner B., Harreus U., Kleinjung T., Folwaczny M., Hickel R., et al. Genotoxicity and cytotoxicity of dental materials in human lymphocytes as assessed by the single cell microgel electrophoresis (comet) assay. J Dent 32 (2004) 229-234
6. Darmani H., and Al-Hiyasat A.S. The resin monomer triethylene glycol dimethacrylate exhibits reproductive toxicity in male mice. Reprod Fertil Dev 17 (2005) 401-406
7. Darmani H., and Al-Hiyasat A.S. The effects of Bis-GMA and TEGDMA on female mouse fertility. Dent Mater 22 (2006) 353-358
8. Kostoryz E.L., Eick J.D., Glaros A.G., Burmaster S., and Yourtee D.M. Biocompatibility of hydroxylated metabolites of BISGMA and BFDGE. J Dent Res 82 (2003) 367-371
9. Munksgaard E., and Freund M. Enzymatic hydrolysis of (di)methacrylates and their polymers. Scand J Dent Res 98 (1990) 261-267
10. Seiss M., Nitz S., Kleinsasser N., Buters J., Behrendt H., Hickel R., et al. Identification of 2,3-epoxymethacrylic acid as an intermediate in the metabolism of dental materials in human liver microsomes. Dent Mater 23 (2007) 9-16
11. Spahl W., Budzikiewicz H., and Geurtsen W. Determination of leachable components from four commercial dental composites by gas and liquid chromatography mass spectrometry. J Dent 26 (1998) 137-145
12. Al-Hiyasat A.S., Darmani H., and Milhem M.M. Cytotoxicity evaluation of dental resin composites and their flowable derivatives. Clin Oral Invest 9 (2005) 21-25
13. Reichl F.X., Durner J., Kunzelmann K., Hickel R., Spahl W., Hume W., et al. Biological clearance of TEGDMA in guinea pigs. Arch Toxicol 75 (2001) 22-27
14. Reichl F.X., Durner J., Kehe K., Manhart J., Folwaczny M., Kleinsasser N., et al. Toxicokinetic of HEMA in guinea pigs. J Dent 30 (2002) 353-358
15. Reichl F.X., Durner J., Hickel R., Spahl W., Kehe K., Walther U., et al. Uptake, clearance and metabolism of TEGDMA in guinea pigs. Dent Mater 18 (2002) 581-589
16. Yao H.R., and Richardson D.E. Epoxidation of alkenes with bicarbonate-activated hydrogen peroxide. J Am Chem Soc 122 (2000) 3220-3221
17. Reichl F., Durner J., Hickel R., Kunzelmann K., Jewett A., Wang M., et al. Distribution and excretion of TEGDMA in guinea pigs and mice. J Dent Res 80 (2001) 1412-1415
18. Crout D., Lloyd E., and Singh J. Metabolism of methyl-methacrylate-evidence for metabolism by the valine pathway of catabolism in rat and in man. Xenobiotica 12 (1992) 821-829
19. Zolman B., Monroe-Augustus M., Thompson B., Hawes J., Krukenberg K., and Matsuda S. chy1, an Arabidopsis mutant with impaired β-oxidation, is defective in a peroxisomal β-hydroxyisobutyryl-CoA hydrolase. J Biol Chem 276 (2001) 31037-31046
20. Santerre J.P., Shajii L., and Tsang H. Biodegradation of commercial dental composites by cholesterol esterase. J Dent Res 78 (1999) 1459-1468
21. Yourtee D.M., Smith R.E., Russo K.A., Burmaster S., Cannon J.M., Eick J.D., et al. The stability of methacrylate biomaterials when enzyme challenged: kinetic and systematic evaluations. J Biomed Mater Res 57 (2001) 522-531
22. Freund N., and Munksgaard E.C. Enzymatic degradation of BisGMA/TEGDMA polymers causing decreased microhardness and greater wear in vitro. Scand J Dent Res 98 (1990) 351-355
23. Finer Y., and Santerre J.P. Salivary esterase activity and its association with the biodegradation of dental composites. J Dent Res 83 (2004) 22-26
24. Yamarik T., Escobar A., and Andersen F. Final report of the safety assessment of methacrylic acid. Int J Toxicol 24 (2005) 33-51
25. Kubinski H., Gutzke G.E., and Kubinski Z.O. DNA-cell-binding (Dcb) assay for suspected carcinogens and mutagens. Mutat Res 89 (1981) 95-136
26. Rogers J., Greenaway J., Mirkes P., and Shepard T. Methacrylic acid as a teratogen in rat embryo culture. Teratology 33 (1986) 113-117
27. Schwengberg S., Bohlen H., Kleinsasser N., Kehe K., Seiss M., Walther U., et al. In vitro embryotoxicity assessment with dental restorative materials. J Dent 33 (2005) 49-55
28. Burmaster S., Smith R., Eick D., Kostoryz E., and Yourtee D. In vitro stability, metabolism, and transport of dental monomers made from Bisphenol A and Bisphenol F. Macromol Biosci 2 (2002) 365-379
29. Filser J.G., Faller T.H., Bhowmik S., Schuster A., Kessler W., Putz C., et al. First-pass metabolism of 1,3-butadiene in once-through perfused livers of rats and mice. Chem Biol Interact 135 (2001) 249-265
30. Warwel S., and Klaas M.R.G. Chemo-enzymatic epoxidation of unsaturated carboxylic acids. J Mol Catal B 1 (1995) 29-35
31. Jackson T., Lilly P., Recio L., Schlosser P., and Medinsky M. Inhibition of cytochrome P4502E1 decreases, but does not eliminate, genotoxicity mediated by 1,3-butadiene. Toxicol Sci 55 (2000) 266-273
32. Himmelstein M.W., Carpenter S.C., Hinderliter P.M., Snow T.A., and Valentine R. The metabolism of β-chloroprene: preliminary in vitro studies using liver microsomes. Chem Biol Interact 135 (2001) 267-284
33. Shimomura Y., Honda T., Goto H., Nonami T., Kurokawa T., Nagasaki M., et al. Effects of liver failure on the enzymes in the branched-chain amino acid catabolic pathway. Biochem Biophys Res Commun 313 (2004) 381-385
34. Shimada T., Mimura M., Inoue K., Nakamura S., Oda H., Ohmori S., et al. Cytochrome P450-dependent drug oxidation activities in liver microsomes of various animal species including rats, guinea pigs, dogs, monkeys, and humans. Arch Toxicol 71 (1997) 401-408
35. Seiss M., Nitz S., Kleinsasser N., Kehe K., Buters J., Behrendt H., et al. Identification of 2,3-epoxymethacrylic acid as a product of methacrylic acid metabolism by human liver microsomes. Naunyn Schmiedebergs Arch Pharmacol 371 (2005) R97-R98
36. Guengerich F.P. Cytochrome P450 oxidations in the generation of reactive electrophiles: epoxidation and related reactions. Arch Biochem Biophys 409 (2003) 59-71
37. 13C nuclear magnetic resonance spectroscopy. Drug Metabol Dispos 20 (1992) 665-672
38. Sanders J., Burka L., and Matthews H. Metabolism and disposition of n-butyl acrylate in male Fischer rats. Drug Metab Dispos 16 (1988) 429-434