Predicting the biological activities of 2-methoxyphenol antioxidants: Effects of dimers

In Vivo

Volumn 21, Issue 2, 2007, Pages 181-188

  Fujisawa, Seiichiro ^a   Ishihara, Mariko ^a   Murakami, Yukio ^a   Atsumi, Toshiko ^a   Kadoma, Yoshinori ^b   Yokoe, Ichiro ^c  

^a MEIKAI UNIVERSITY SCHOOL OF DENTISTRY   (Japan)

^b TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

^c JOSAI UNIVERSITY   (Japan)

Author keywords

2 Methoxyphenols; COX 2 inhibition; Cytotoxicity; Electronic descriptors; QSAR; Radical scavenging activity

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 2 FERULIC ACID; 2 GUIAICOL; 2 METHOXYPHENOL 4 METHYLPHENOL; 2 VANILLIN; ANTIOXIDANT; BENZOYL PEROXIDE; CRESOL; CURCUMIN; CYCLOOXYGENASE 2 INHIBITOR; CYTOTOXIC AGENT; DI EUGENOL; DIMER; EUGENOL; FERULIC ACID; GUAIACOL; HESPERETIN; ISOEUGENOL; METHACRYLIC ACID METHYL ESTER; SCAVENGER; UNCLASSIFIED DRUG; VANILLIN DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CHEMICAL STRUCTURE; DRUG STRUCTURE; ELECTRIC ACTIVITY; GENE EXPRESSION; HUMAN; HUMAN CELL; NORTHERN BLOTTING; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RADICAL REACTION; SALIVARY GLAND TUMOR;

EID: 34047200041     PISSN: 0258851X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (31)

1. Murakami Y, Ito S, Atsumi T and Fujisawa S: Theoretical prediction of the relationship between phenol function and COX-2/AP-1 inhibition for ferulic acid-related compounds. In Vivo 19: 1039-1044, 2005.
2. Hirata Y, Murakami M, Shoji Y, Kadoma Y and Fujisawa S: Kinetics of radical-scavenging activity of hesperetin and hesperedin and their inhibitory activity on COX-2 expression. Anticancer Res 25: 3367-3374, 2005.
3. Okada N, Hirata A, Murakami Y, Shoji M, Sakagami H and Fujisawa S: Induction of cytotoxicity and apoptosis and inhibition of cyclooxygenase-2 gene expression by eugenol-related compounds. Anticancer Res 25: 3236-3270, 2005.
4. Atsumi T, Murakami Y, Shibuya K, Tonosaki K and Fujisawa S: Induction of cytotoxicity and apoptosis and inhibition of cyclooxygenase-2 gene expression, by curcumin and its analog, α-diisoeugenol. Anticancer Res 25: 4029-4036, 2005.
5. Murakami Y, Shoji M, Hirata A, Tanaka S, Yokoe I and Fujisawa S: Dehydrodiisoeugenol, an isoeugenol dimer, inhibits lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages. Arch Biochem Biophys 434: 326-332, 2005.
6. Murakami Y, Shoji M, Hirata A, Tanaka S, Hanazawa S, Yokoe I and Fujisawa S: An ortho dimer of butylated hydroxyanisole inhibits nuclear factor kappa B activation and gene expression of inflammatory cytokines in macrophages stimulated by Porphyromonas gingivalis fimbriae. Arch Biochem Biophys 449: 171-177, 2006.
7. Fujisawa S, Atsumi T, Murakami Y and Kadoma Y: Dimerization, ROS formation, and biological activity of o-methoxyphenols. Arch Immunol Ther Exp (Warsz) 53: 28-38, 2005.
8. Atsumi T, Fujisawa S and Tonosaki K: A comparative study of the antioxidant/prooxidant activities of eugenol and isoeugenol with various concentrations and oxidation conditions. Toxicol In Vitro 19: 1025-1033, 2005.
9. Fujisawa S, Atsumi T, Ishihara M and Kadoma Y: Cytotoxicity, ROS-generation activity and radical-scavenging activity of curcumin and related compounds. Anticancer Res 24: 563-569, 2004.
10. Murakami Y, Shoji M, Hanazawa S, Tanaka S and Fujisawa S: Preventive effect of bis-eugenol, a eugenol ortho dimer, on lipopolysaccharide-stimulated nuclear factor kappa B activation and inflammatory cytokine expression in macrophages. Biochem Pharmacol 66: 1061-1066, 2003.
11. Ogiwara T, Satoh K, Negoro T, Okayasu H, Sakagami H and Fujisawa S: Inhibition of NO production by activated macrophages by phenolcarboxylic acid monomers and polymers with radical scavenging activity. Anticancer Res 23: 1317-1323, 2003.
12. Ogiwara T, Satoh K, Kadoma Y, Murakami Y, Unten S, Atsumi T, Sakagami H and Fujisawa S: Radical scavenging activity and cytotoxicity of ferulic acid. Anticancer Res 22: 11-17, 2002.
13. Fujisawa S, Atsumi T, Satoh K and Sakagami H: Interaction between 2-ethoxybenzoic acid (EBA) and eugenol, and related changes in cytotoxicity. J Dent Res 82: 43-47, 2003.
14. Fujisawa S, Atsumi T, Kadoma Y and Sakagami H:Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity. Toxicology 177: 39-54, 2002.
15. Fujisawa S, Atsumi T, Satoh K, Kadoma Y, Ishihara M, Okada N, Nagasaki M, Yokoe I and Sakagami H: Radical generation, radical-scavenging activity, and cytotoxicity of eugenol-related compounds. In Vitr Mol Toxicol 13: 269-280, 2000.
16. Holder AH: Rational design of dental materials using computational chemistry. Transactions of the Forth International Congress of Dental Materials, Academy of Dental Materials and Japanese Society for Dental Materials and Devices Transaction 16: 55-71, 2002.
17. Hansh C and Gao H: Comparative QSAR, radical reactions of benzene derivatives in chemistry and biology. Chem Rev 75: 2929-3059, 1997.
18. Garg R, Kapur S and Hansch C: Radical toxicity of phenols: A reference point for obtaining perspective in the formulation of QRSA. Med Res Rev 21: 73-82, 2001.
19. Dudek AZ, Arodz T and Galvez J:Computational methods in developing quantitative structure-activity relationships (QSAR): a review. Comb Chem High Throughput Screen 9: 213-228, 2006.
20. Yap CW, Xue Y, Li H, Li ZR, Ung CY, Han LY, Zheng CJ, Cao ZW and Chen YZ: Prediction of compounds with specific pharmacodynamic, pharmacokinetic or toxicological property by statistical learning methods. Min Rev Med Chem 6: 449-459, 2006.
21. Karelson M, Lobanov VS and Katritzky AR: Quantum-chemical descriptors in QSAR/QSPR studies. Chem Rev 96: 1027-1043, 1996.
22. Kobayashi S, Hamashima H, Kurihara M, Miyata N and Tanaka A: Hardness controlled enzymes and electronegativity controlled enzymes: role of an absolute hardness-electronegativity (eta-chi) activity diagram as a coordinate for biological activities. Chem Pharm Bull (Tokyo) 46 :1108-1115, 1998.
23. Pasha FA, Srivastava HK and Singh PP: Comparative QSAR study of phenol derivatives with the help of density function theory. Bioorg Med Chem 13: 6823-6829, 2005.
24. Atsumi T, Fujisawa S, Satoh K, Sakagami H, Iwakura I, Ueha T, Sugita Y and Yokoe I: Cytotoxicity and radical intensity of eugenol, isoeugenol or related dimmers. Anticancer Res 20: 2519-2524, 2000.
25. Fujisawa S, Atsumi T, Kadoma Y, Ishihara M, Ito S and Yokoe I: Kinetic radical scavenging activity and cytotoxicity of 2-methoxy-and 2-t-butyl-substituted phenols and their dimmers. Anticancer Res 24: 3019-3026, 2004.
26. Koppel IA, Burk P, Koppel I, Leito I, Sonoda T and Mishima M: Gas-phase acidities of some Neutral Bonsted Superacid. A DEFT and ab initio study. J Am Chem Soc 122: 5114-5124, 2000.
27. Tribble MT and Traynham JG: Nuclear magnetic resonance studies of ortho-substituted phenols in dimethylsulfoxide solutions. J Am Chem Soc 91: 379-388, 1969.
28. Fujisawa S, Ishihara M and Kadoma Y: Kinetic evaluation of the reactivity of flavonoids as radical scavengers. SAR and QSAR in Environ Res 13: 617-627, 2002.
29. Atsumi T, Fujisawa S and Tonosaki K: A comparative study of the antioxidant/prooxidant activities of eugenol and isoeugenol with various concentrations and oxidation conditions. Toxicol In Vitro 19: 1025-1033, 2005.
30. Masuda T, Hidaka K, Shinohara A, Maekawa T, Takeda Y and Yamaguchi H: Chemical studies on antioxidant mechanism of curcuminoid: analysis of radical reaction products from curcumin. J Agric Food Chem 47: 71-77, 1999.
31. Ishihara M, Yokote Y and Sakagami H: Quantitative structure-cytotoxicity relationship analysis of coumarin and its derivatives by semiempirical molecular orbital method. Anticancer Res 26: 2883-2886, 2006.