Prediction of the reduced glutathione (GSH) reactivity of dental methacrylate monomers using NMR spectra - Relationship between toxicity and GSH reactivity

Dental Materials Journal

Volumn 28, Issue 6, 2009, Pages 722-729

  Fujisawa, Seiichiro ^a   Kadoma, Yoshinori ^b  

^a MEIKAI UNIVERSITY SCHOOL OF DENTISTRY   (Japan)

^b TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

Author keywords

Dental methacrylates; NMR spectra; Structure activity relationships

Indexed keywords

2 HYDROXYETHYL METHACRYLATE; 2-ETHYLHEXYL ACRYLATE; ACRYLIC ACID 2 ETHYLHEXYL ESTER; ACRYLIC ACID BUTYL ESTER; ACRYLIC ACID DERIVATIVE; ACRYLIC ACID ETHYL ESTER; ACRYLIC ACID HEXYL ESTER; ALLYL METHACRYLATE; BENZYL METHACRYLATE; BIOMEDICAL AND DENTAL MATERIALS; BISPHENOL A BIS(2 HYDROXYPROPYL) ETHER DIMETHACRYLATE; ETHYLENE GLYCOL DIMETHACRYLATE; GLUTATHIONE; MACROGOL DERIVATIVE; METHACRYLIC ACID DERIVATIVE; METHACRYLIC ACID METHYL ESTER; N-BUTYL ACRYLATE; POLY(ETHYLMETHACRYLATE); POLYMETHACRYLIC ACID DERIVATIVE; TETRAETHYLENE GLYCOL DIMETHACRYLATE; TRIETHYLENE GLYCOL DIMETHACRYLATE;

ANIMAL; ARTICLE; CHEMISTRY; COMPARATIVE STUDY; DRUG EFFECT; FORECASTING; INSTITUTE FOR CANCER RESEARCH MOUSE; INTRAPERITONEAL DRUG ADMINISTRATION; LD 50; MALE; MATERIALS TESTING; MOUSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORAL DRUG ADMINISTRATION; STRUCTURE ACTIVITY RELATION;

ACRYLATES; ADMINISTRATION, ORAL; ANIMALS; BISPHENOL A-GLYCIDYL METHACRYLATE; DENTAL MATERIALS; FORECASTING; GLUTATHIONE; INJECTIONS, INTRAPERITONEAL; LETHAL DOSE 50; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MATERIALS TESTING; METHACRYLATES; METHYLMETHACRYLATE; METHYLMETHACRYLATES; MICE; MICE, INBRED ICR; POLYETHYLENE GLYCOLS; POLYMETHACRYLIC ACIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 70649099977     PISSN: 02874547     EISSN: None     Source Type: Journal    
DOI: 10.4012/dmj.28.722     Document Type: Article

References (31)

1. Vankerckhoven H, Lambrechts P, van Beylen M, Davidson CL, Vanherle G. Unreacted methacrylate groups on the surfaces of composite resins. J Dent Res 1982; 60: 791-795.
2. Schweikl H, Spagnuolo G, Schmalz G. Genetic and cellular toxicology of dental resin monomers. J Dent Res 2006; 85: 870-877.
3. Aalto-Korte K, Alanko K, Kuuliala O, Jolanki R. Methacrylate and acrylate allergy in dental personnel. Contact Dermatitis 2007; 57: 324-330.
4. Geurtsen W, Leyhausen G. Chemical-biological interactions of the resin monomer triethyleneglycol dimethacrylate (TEGDMA). J Dent Res 2001; 80: 2046-2050.
5. McCarthy TJ, Hayes EP, Schwartz CS, Witz G. The reactivity of selected acrylate esters toward glutathione and deoxyribonucleosides in vitro: Structure-activity relationships. Fundam Appl Toxicol 1994; 22: 543-548.
6. Freidig AP, Verhaar HJM, Hermens JLM. Quantitative structure-property relationships for the chemical reactivity of acrylates and methacrylates. Environ Toxicol Chem 1999; 18: 1133-1139.
7. Yarbrough JW, Schultz TW. Abiotic sulfhydryl reactivity: a predictor of aquatic toxicity for carbonyl-containing alpha, beta-unsaturated compounds. Chem Res Toxicol 2007; 20: 558-562.
8. Ahlfors SR, Sterner O, Hansson C. Reactivity of contact allergenic haptens to amino acid residues in a model carrier peptide, and characterization of formed peptide-hapten adducts. Skin Pharmacol Appl Skin Physiol 2003; 16: 59-68.
9. Volk J, Engelmann J, Leyhausen G, Geurtsen W. Effects of three resin monomers on the cellular glutathione concentration of cultured human gingival fibroblasts. Dent Mater 2006; 22: 499-505.
10. Hatada K, Kitayama T, Nishiura T, Shibuya W. Relation between reactivities of vinyl monomers and their NMR spectra. Current Org Chem 2002; 6: 121-153.
11. Ishihara M, Fujisawa S. A structure-activity relationship study on the mechanisms of methacrylate-induced toxicity using NMR chemical shift of β-carbon, RP-HPLC log P and semiempirical molecular descriptor. Dent Mater J 2009; 28: 113-120.
12. Fujisawa S. Nuclear magnetic resonance spectra of bis-GMA and iso-bis-GMA. Dent Mater J 1994; 13: 251-255.
13. Vankerckhoven H, Lambrechts P, van Beylen M, Vanherle G. Characterization of composite resins by NMR and TEM. J Dent Res 1981; 60: 1957-1965.
14. Tanii H, Hashimoto K. Structure-toxicity relationship of acrylates and methacrylates. Toxicol Lett 1982; 1: 125-129.
15. Lawrence WH, Bass GE, Purcell WP, Autian J. Use of mathematical models in the study of structure-toxicity relationships of dental compounds. I. Esters of acrylic and methacrylic acids. J Dent Res 1972; 51: 526-535.
16. Weil CS. Tables for convenient calculation of median effective dose (LD50 or ED50) and instructions in their use. Biometrics 1952; 8: 249-263.
17. Material Safety Data Sheet. Ethyl acrylate, allyl methacrylate MSDS, ARKEMA Canada Inc., Canada, 2007
18. Material Safety Data Sheet. Methyl methacrylate MSDS, Catalog No.18800, Electron Microscopy Science (EMS), PA, USA, 2006.
19. Material Safety Data Sheet. Benzyl methacrylate MSDS, Physical and Theoretical Chemistry Laboratory, Oxford University, England, 2005.
20. Material Safety Data Sheet. n-Butyl methacrylate MSDS, ScienceLab.com, Texas, USA, 2008.
21. Material Safety Data Sheet. Triethylene glycol dimethacrylate MSDS, Sigma-Aldrich, Germany, 1995.
22. Schmalz G. The biocompatibility of non-amalgam dental filling materials. Eur J Oral Sci 1998;106: 696-706.
23. Karabunarliev S, Mekenyan OG, Karcher W, Russom CL, Bradbury SP. Quantum-chemical descriptors for estimating the acute toxicity of electrophiles to the fathead minnow (pimephales promelas): An analysis based on molecular mechanisms. Quant Struct-Act Relat 1996; 15: 302-310.
24. Ohno Y, Jones TW, Ormstad K. Allyl alcohol toxicity in isolated renal epithelial cells: protective effects of low molecular weight thiols. Chem Biol Interact 1985; 52: 289-299.
25. Jacobsen D, McMartin KE. Methanol and ethylene glycol poisonings: mechanism of toxicity, clinical course, diagnosis and treatment. Med Toxicol 1986; 1: 309-334.
26. Freidig A, Hofhuis M, van Holstijn I, Hermens J. Glutathione depletion in rat hepatocytes: a mixture toxicity study with α, β-unsaturated esters. Xenobiotica 2001; 31: 295-307.
27. Kapur S, Shusterman A, Verma RP, Hansch C, Selassi CD. Toxicology of benzyl alcohols: a QSAR analysis. Chemosphere 2000; 41: 1643-1649.
28. Engelmann J, Leyhausen G, Leibfritz D, Geurtsen W. Metabolic effects of dental resin components in vitro detected by NMR spectroscopy. J Dent Res 2001; 80: 869-875.
29. Kostoryz EL, Eick JD, Glaros AG, Judy BM, Welshons WV, Burmaster S, Yourtee DM. Biocompatibility of hydroxylated metabolites of BISGMA and BFDGE. J Dent Res 2003; 82: 367-371.
30. Kadoma Y, Tanaka M. Acid and base-catalyzed hydrolysis of bisphenol A-related compounds. Dent Mater J 2000; 19: 139-152.
31. Elovaara E, Kivistö H, Vainio H. Effects of methyl methacrylate on non-protein thiols and drug metabolizing enzymes in rat liver and kidneys. Arch Toxicol 1983; 52: 109-121.