Interaction between 2-Ethoxybenzoic Acid (EBA) and Eugenol, and Related Changes in Cytotoxicity

Journal of Dental Research

Volumn 82, Issue 1, 2003, Pages 43-47

  Fujisawa, S ^a   Atsumi, T ^a   Satoh, K ^b   Sakagami, H ^c  

^a Departments of Oral Diagnosis   (Japan)

^b MEIKAI UNIVERSITY SCHOOL OF DENTISTRY   (Japan)

^c SHOWA UNIVERSITY   (Japan)

Author keywords

2 ethoxybenzoic acid; cytotoxicity; eugenol; eugenol radical; radical scavenging

Indexed keywords

2 ETHOXYBENZOIC ACID; 2-ETHOXYBENZOIC ACID; ACETYLSALICYLIC ACID; BICARBONATE; BIOMATERIAL; CALCIUM HYDROXIDE; DIMETHYL SULFOXIDE; EUGENOL; FREE RADICAL; HYDROXYBENZOIC ACID DERIVATIVE; SCAVENGER; TOOTH CEMENT;

ARTICLE; CELL CULTURE; CHEMISTRY; CULTURE TECHNIQUE; CYTOLOGY; DOSE RESPONSE; DRUG EFFECT; ELECTRON SPIN RESONANCE; FIBROBLAST; HUMAN; OXIDATION REDUCTION REACTION; PATHOLOGY; PATHOPHYSIOLOGY; PH; SALIVARY GLAND TUMOR; TOOTH PULP;

ASPIRIN; BIOCOMPATIBLE MATERIALS; CALCIUM HYDROXIDE; CELL CULTURE TECHNIQUES; DENTAL CEMENTS; DENTAL PULP; DIMETHYL SULFOXIDE; DOSE-RESPONSE RELATIONSHIP, DRUG; ELECTRON SPIN RESONANCE SPECTROSCOPY; EUGENOL; FIBROBLASTS; FREE RADICAL SCAVENGERS; FREE RADICALS; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROXYBENZOIC ACIDS; OXIDATION-REDUCTION; SODIUM BICARBONATE; SUBMANDIBULAR GLAND NEOPLASMS; TUMOR CELLS, CULTURED;

EID: 0037216602     PISSN: 00220345     EISSN: 15440591     Source Type: Journal    
DOI: 10.1177/154405910308200110     Document Type: Article

References (28)

1. Atsumi T, Iwakura I, Fujisawa S, Ueha T -2001-. Reactive oxygen species generation and photo-cytotoxicity of eugenol in solution of various pH. Biomaterials 122:1459–1466.
2. Diez L, Livertoux NM, Stark AA, Wellman-Rousseau M, Leroy P -2001-. High-performance liquid chromatographic assay of hydroxy free radical using salicylic acid hydroxylation during in vitro experiments involving thiols. J Chromatogr B Biomed Sci Appl 5:185–193.
3. Fujisawa S, Kadoma Y -1988-. Effect of dental metallic salts on the DSC phase transition properties of phospholipid-cholesterol liposomes. J Jpn Soc Dent Mater 7:748–755 -in Japanese-.
4. Fujisawa S, Kadoma Y, Masuhara E -1982-. Action of drugs, detergents, and monomers on liposomes. J Dent Res 61:1206–1210.
5. Fujisawa S, Kadoma Y, Masuhara E -1983-. Action of drugs on liposomes with varying charges. J Dent Res 62:65–68.
6. Fujisawa S, Kadoma Y, Masuhara E -1987-. A calorimetric study of the interaction of synthetic phospholipid liposomes with lipid-soluble small molecules used as dental materials and devices. J Biomed Mater Res 21:89–98.
7. 13C NMR studies of interaction of eugenol, phenol, and triethyleneglycol dimethacrylate with phospholipid liposomes as a model system for odontoblast membranes. J Dent Res 67:1438–1441.
8. Fujisawa S, Komada Y, Kadoma Y -1993-. DSC and NMR spectroscopic studies of the interaction of eugenol and its related compounds with phospholipid liposomes. J Jpn Soc Dent Mater 12:406–411 -in Japanese-.
9. Fujisawa S, Kadoma Y, Komoda Y -1994-. NMR, DSC studies of the interaction of o-ethoxybenzoic acid -EBA- and p-vinyl benzoic acid -VBA- with phospholipid liposomes. J Jpn Soc Dent Mater 13:206–212 -in Japanese-.
10. Fujisawa S, Kashiwagi Y, Atsumi T, Iwakura I, Ueha T, Hibino Y, et al. -1999-. Application of bis-eugenol to a zinc oxide eugenol cement. J Dent 27:291–295.
11. Fujisawa S, Atsumi T, Kadoma Y, Sakagami H -2002-. Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity. Toxicology 177:39–54.
12. Fulkerson MS, Czerw RJ, Donnelly JC -1996-. An in vitro evaluation of the sealing ability of Super-EBA cement used as a root canal sealer. J Endod 22:13–18.
13. Gerosa R, Borin M, Menegazzi G, Puttini M, Cavalleri G -1996-. In vitro evaluation of the cytotoxicity of pure eugenol. J Endod 22:532–534.
14. Hume WR -1984-. Effect of eugenol on respiration and division in human pulp, mouse fibroblasts, and liver cells in vitro. J Dent Res 63:1262–1265.
15. Jeng JH, Hahn LJ, Lu FJ, Wang YJ, Kuo MY -1994-. Eugenol triggers different pathobiological effects on human oral mucosal fibroblasts. J Dent Res 73:1050–1055.
16. Kawano T, Muto S -2000-. Mechanism of peroxidase actions for salicylic acid-induced generation of active oxygen species and an increase in cytosolic calcium in tobacco cell suspension culture. J Exp Bot 51:685–693.
17. Lindqvist L, Otteskog P -1980-. Eugenol: liberation from dental materials and effect on human diploid fibroblast cells. Scand J Dent Res 88:552–556.
18. O’Neil MJ, Smith A, Heckelman PE, editors - 2001-. The Merck Index. Whitehouse Station, NJ: Merck & Co. Inc.
19. Pantschev A, Carlsson AP, Andersson L -1994-. Retrograde root filling with EBA cement or amalgam. A comparative clinical study. Oral Surg Oral Med Oral Pathol 78:101–104.
20. Sagone AL Jr, Decker MA, Wells RM, Democko C -1980-. A new method for the detection of hydroxyl radical production by phagocytic cells. Biochim Biophys Acta 628:90–97.
21. Satoh K, Sakagami H, Yokoe I, Kochi M, Fujisawa S -1998a-. Interaction between eugenol-related compounds and radicals. Anticancer Res 18:425–428.
22. Satoh K, Ida Y, Sakagami H, Tanaka T, Fujisawa S -1998b-. Effect of antioxidants on radical intensity and cytotoxic activity of eugenol. Anticancer Res 18:1549–1552.
23. Shirasuna K, Sato M, Miyazaki T -1981-. A neoplastic epithelial duct cell line established from an irradiated human salivary gland. Cancer 48:745–752.
24. Tassery H, Remusat M, Koubi G, Pertot WJ -1997-. Comparison of the intraosseous biocompatibility of Vitremer and super EBA by implantation into the mandible of rabbits. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 83:602–608.
25. Thompson D, Norbeck K, Olsson LI, Constantin-Teodosiu D, Van der Zee J, Moldeus P -1989-. Peroxidase-catalyzed oxidation of eugenol: formation of a cytotoxic metabolite-s-. J Biol Chem 264:1016–1021.
26. Thompson DC, Barhoumi R, Burghardt RC -1998-. Comparative toxicity of eugenol and its quinone methide metabolite in cultured liver cells using kinetic fluorescence bioassays. Toxicol Appl Pharmacol 149:56–63.
27. von Fraunhofer JA - 1975-. Scientific aspects of dental materials. London: Butterworth’s, pp. 178–180.
28. Yokoyama A -1975-. The effect of the alkaline earth salts on the NMR spectrum of phenols. Chem Pharm Bull 23:1169–1170.