Radical modulating activity and cytotoxic activity of synthesized eugenol-related compounds.
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.
Okada
N
N
Department of Oral Diagnosis, Meikai University School of Dentistry, Saitama, Japan.
Satoh
K
K
Atsumi
T
T
Tajima
M
M
Ishihara
M
M
Sugita
Y
Y
Yokoe
I
I
Sakagami
H
H
Fujisawa
S
S
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
D000970:Antineoplastic Agents; D000975:Antioxidants; D016166:Free Radical Scavengers; D005609:Free Radicals; D013481:Superoxides; D005054:Eugenol