Interaction between 2-Ethoxybenzoic Acid (EBA) and Eugenol, and Related Changes in Cytotoxicity
S. Fujisawa1,*,
T. Atsumi2,
K. Satoh3, and
H. Sakagami4
1 Departments of Oral Diagnosis,
2 Oral Physiology, and
3 Dental Pharmacology, Meikai University, School of Dentistry, 1-1 Keyakidai, Sakado, Saitama 350-0283, Japan; and
4 Medicinal Information, Center, School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa -Ku, Tokyo, 142-8555, Japan;
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Figure 1. ESR spectra of eugenol radical at pH 6.9–12.7. Eugenol, 100 mM: (a) 50% dimethylsulfoxide with NaHCO3/NaCO3; (b) 50% dimethylsulfoxide with potassium hydroxide (KOH); (c-f) 50% dimethylsulfoxide with calcium hydroxide [Ca(OH)2]; * = eugenol radical; arrow = amplified eugenol radical. Assay for the radical intensity of eugenol with or without potassium hydroxide or calcium hydroxide has been described in the text.
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Figure 2. Effects of 2-ethoxybenzoic acid (A) and acetylsalicylic acid (B) on the radical intensity of eugenol. The chemical structures of eugenol radical, 2-ethoxybenzoic acid, and a hydrolysis reaction of acetylsalicylic acid into salicylic acid sodium salt are shown in the inset.
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Figure 3. The cytotoxicity of 2-ethoxybenzoic acid (EBA), acetylsalicylic acid (ASA), and calcium hydroxide [Ca(OH)2] with or without the addition of eugenol (EUG) (0.1 or 0.3 mM) against human submandibular gland (HSG) cells (a) and human pulp fibroblast (HPF) cells (b). The bars indicate the means ± SD for 8 separate experiments. An asterisk denotes significance between controls and EUG by Student’s t test (*p < 0.05, **p < 0.01, ***p < 0.001). No significant differences between groups of EUG (0.1 and 0.3 mM) are observed in EBA, ASA, or Ca(OH)2-treated HSG cells (a). A significance in HSG cells (a) between blank and EUG is observed at 0.3 mM.
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