title: Radical modulating activity and cytotoxic activity of synthesized eugenol-related compounds.
abstract: The ability of nine synthetic eugenol-related compounds to scavenge O2- (generated by the hypoxanthine-xanthine oxidase reaction) was compared with their radical generation and cytotoxic activity. ESR spectroscopy showed that eugenol (4-allyl-2-methoxyphenol), 2-allyl-4-methoxyphenol, 2-allyl-4-t-butylphenol and 2,4-dimethoxyphenol efficiently scavenged O2- and produced radicals under alkaline conditions. 2-allyl-4-t-butylphenol showed the highest cytotoxic activity and DNA-synthesis inhibitory activity, possibly due to the hydrophobic radical reactivity. 2-allyl-4-methoxyphenol and 2,4-dimethoxyphenol showed higher antioxidant activity than 3-t-butyl-4-hydroxyanisol (BHA), but all these compounds showed comparable cytotoxic activity with each other. These findings suggest a possible link between the cytotoxic activity and radical generation/scavenging activity in eugenol-related compounds.
authors.affiliation: Department of Oral Diagnosis, Meikai University School of Dentistry, Saitama, Japan.
authors.forename: N
authors.initials: N
authors.lastname: Okada
authors.forename: K
authors.initials: K
authors.lastname: Satoh
authors.forename: T
authors.initials: T
authors.lastname: Atsumi
authors.forename: M
authors.initials: M
authors.lastname: Tajima
authors.forename: M
authors.initials: M
authors.lastname: Ishihara
authors.forename: Y
authors.initials: Y
authors.lastname: Sugita
authors.forename: I
authors.initials: I
authors.lastname: Yokoe
authors.forename: H
authors.initials: H
authors.lastname: Sakagami
authors.forename: S
authors.initials: S
authors.lastname: Fujisawa
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology*; D005054:Eugenol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology*; D005609:Free Radicals; D006801:Humans; D012468:Salivary Gland Neoplasms; D013481:Superoxides; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D000975:Antioxidants; D016166:Free Radical Scavengers; D005609:Free Radicals; D013481:Superoxides; D005054:Eugenol