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Volumn 74, Issue 5, 2009, Pages 626-632

Mechanisms of cytotoxicity of 2- or 2,6-di-tert-butylphenols and 2-methoxyphenols in terms of inhibition rate constant and a theoretical parameter

Author keywords

Cytotoxicity; Inhibition rate constants; QSAR; tert Butyl or methoxy substituted complex phenols; Theoretical parameters

Indexed keywords

ANTI-OXIDANTS; AZOBISISOBUTYRONITRILE; BENZOYL PEROXIDES; BUTYLPHENOL; BUTYLPHENOLS; CARCINOMA CELLS; CURCUMIN; CYTOTOXIC; HOMOLYTIC BONDS; HUMAN GINGIVAL FIBROBLASTS; HUMAN PERIODONTAL LIGAMENT FIBROBLASTS; HUMAN PULP FIBROBLASTS; HUMAN SUBMANDIBULAR GLANDS; INDUCTION PERIODS; INHIBITION RATE CONSTANTS; LINEAR RELATIONSHIPS; METHOXYPHENOLS; ORAL TISSUES; POTENT ANTIOXIDANTS; PRIMARY CELLS; PROMYELOCYTIC LEUKEMIAS; QSAR; QUANTITATIVE STRUCTURES; RADICAL REACTIONS; RADICAL SCAVENGING; SCAVENGING ACTIVITIES; STERIC HINDRANCES; SUBSTITUTED PHENOLS; TERT-BUTYL OR METHOXY-SUBSTITUTED COMPLEX PHENOLS; THEORETICAL PARAMETERS; TUMOR CELLS;

EID: 58149488773     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2008.10.039     Document Type: Article
Times cited : (26)

References (28)
  • 1
    • 27944462172 scopus 로고    scopus 로고
    • Induction of cytotoxicity and apoptosis and inhibition of cyclooxygenase-2 gene expression, by curcumin and its analog, α-diisoeugenol
    • 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 (2005) 4029-4036
    • (2005) Anticancer Res. , vol.25 , pp. 4029-4036
    • Atsumi, T.1    Murakami, Y.2    Shibuya, K.3    Tonosaki, K.4    Fujisawa, S.5
  • 2
    • 0020074850 scopus 로고
    • Autoxidation of biological molecules. 1. The antioxidant activity of vitamin E and related chain-braking phenolic antioxidants in vitro
    • Burton G.W., and Ingold K.U. Autoxidation of biological molecules. 1. The antioxidant activity of vitamin E and related chain-braking phenolic antioxidants in vitro. J. Am. Chem. Soc. 103 (1981) 6472-6477
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 6472-6477
    • Burton, G.W.1    Ingold, K.U.2
  • 3
    • 0034802673 scopus 로고    scopus 로고
    • Development of quantitative structure-activity relationships for the toxicity of aromatic compounds to tetrahymena pyriformis: comparative assessment of the methodologies
    • Cronin M.T.D., and Schluz T.W. Development of quantitative structure-activity relationships for the toxicity of aromatic compounds to tetrahymena pyriformis: comparative assessment of the methodologies. Chem. Res. Toxicol. 14 (2001) 1284-1295
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 1284-1295
    • Cronin, M.T.D.1    Schluz, T.W.2
  • 5
    • 0036679683 scopus 로고    scopus 로고
    • Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity
    • Fujisawa S., Atsumi T., Kadoma K., and Sakagami H. Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity. Toxicology 177 (2002) 39-54
    • (2002) Toxicology , vol.177 , pp. 39-54
    • Fujisawa, S.1    Atsumi, T.2    Kadoma, K.3    Sakagami, H.4
  • 6
    • 0036783086 scopus 로고    scopus 로고
    • Kinetic evaluation of the reactivity of flavonoids as radical scavengers
    • Fujisawa S., Ishihara M., and Kadoma K. Kinetic evaluation of the reactivity of flavonoids as radical scavengers. SAR QSAR Environ. Res. 13 (2002) 617-627
    • (2002) SAR QSAR Environ. Res. , vol.13 , pp. 617-627
    • Fujisawa, S.1    Ishihara, M.2    Kadoma, K.3
  • 7
    • 2442571064 scopus 로고    scopus 로고
    • Cytotoxicity, ROS-generation activity and radical-scavenging activity of curcumin and related compounds
    • 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 (2004) 563-569
    • (2004) Anticancer Res. , vol.24 , pp. 563-569
    • Fujisawa, S.1    Atsumi, T.2    Ishihara, M.3    Kadoma, Y.4
  • 8
    • 2542435790 scopus 로고    scopus 로고
    • Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites
    • Fujisawa S., Kadoma Y., and Yokoe I. Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites. Chem. Phys. Lipids 130 (2004) 189-195
    • (2004) Chem. Phys. Lipids , vol.130 , pp. 189-195
    • Fujisawa, S.1    Kadoma, Y.2    Yokoe, I.3
  • 9
    • 28444440544 scopus 로고    scopus 로고
    • Comparative study of the alkyl and peroxy radical scavenging activities of polyphenols
    • Fujisawa S., and Kadoma K. Comparative study of the alkyl and peroxy radical scavenging activities of polyphenols. Chemosphere 62 (2006) 71-79
    • (2006) Chemosphere , vol.62 , pp. 71-79
    • Fujisawa, S.1    Kadoma, K.2
  • 10
    • 0034659106 scopus 로고    scopus 로고
    • Comparative QSAR evidence for a free-radical mechanism of phenol-induced toxicity
    • Hansch C., McKarns S.C., Smith C.J., and Doolittle D.J. Comparative QSAR evidence for a free-radical mechanism of phenol-induced toxicity. Chem. Biol. Interact. 127 (2000) 61-72
    • (2000) Chem. Biol. Interact. , vol.127 , pp. 61-72
    • Hansch, C.1    McKarns, S.C.2    Smith, C.J.3    Doolittle, D.J.4
  • 11
    • 0000398293 scopus 로고
    • Absolute rate constants for hydrocarbon autoxidation 1. Styrene
    • Howard J.A., and Ingold K.U. Absolute rate constants for hydrocarbon autoxidation 1. Styrene. Can. J. Chem. 43 (1965) 2729-2736
    • (1965) Can. J. Chem. , vol.43 , pp. 2729-2736
    • Howard, J.A.1    Ingold, K.U.2
  • 12
    • 0034333692 scopus 로고    scopus 로고
    • Kinetic evaluation of reactivity of bisphenol A derivatives as radical scavengers for methacrylate polymerization
    • Kadoma Y., and Fujisawa S. Kinetic evaluation of reactivity of bisphenol A derivatives as radical scavengers for methacrylate polymerization. Biomaterials 21 (2000) 2125-2130
    • (2000) Biomaterials , vol.21 , pp. 2125-2130
    • Kadoma, Y.1    Fujisawa, S.2
  • 13
    • 33845417289 scopus 로고    scopus 로고
    • Stereo structure-controlled and electro structure-controlled, estrogen-like chemicals to design and develop non-estrogenic bisphenol A analogs based on chemical hardness concept
    • Kobayashi S., Shinohara H., Tabata K., and Yamamoto N. Stereo structure-controlled and electro structure-controlled, estrogen-like chemicals to design and develop non-estrogenic bisphenol A analogs based on chemical hardness concept. Chem. Pharma. Bull. 54 (2006) 1633-1638
    • (2006) Chem. Pharma. Bull. , vol.54 , pp. 1633-1638
    • Kobayashi, S.1    Shinohara, H.2    Tabata, K.3    Yamamoto, N.4
  • 14
    • 14644394217 scopus 로고    scopus 로고
    • Theoretical elucidation on mechanism and reactivity of bisphenol A derivatives as inhibitors and radical scavengers in methacrylate polymerization
    • Kong L., Wang L.-F., and Zhang H.-Y. Theoretical elucidation on mechanism and reactivity of bisphenol A derivatives as inhibitors and radical scavengers in methacrylate polymerization. J. Mol. Struct. (Theochem) 716 (2005) 27-31
    • (2005) J. Mol. Struct. (Theochem) , vol.716 , pp. 27-31
    • Kong, L.1    Wang, L.-F.2    Zhang, H.-Y.3
  • 15
    • 0000641673 scopus 로고
    • The distribution of wave function and characteristic value among the individual electrons of an atom
    • Koopmans T. The distribution of wave function and characteristic value among the individual electrons of an atom. Physica 1 (1933) 104-113
    • (1933) Physica , vol.1 , pp. 104-113
    • Koopmans, T.1
  • 16
    • 0000034589 scopus 로고
    • Allyl polymerization
    • Laible R.C. Allyl polymerization. Chem. Rev. 58 (1958) 807-843
    • (1958) Chem. Rev. , vol.58 , pp. 807-843
    • Laible, R.C.1
  • 17
    • 31344440910 scopus 로고    scopus 로고
    • The cytotoxicity of ortho alkyl substituted 4-X-phenols: a QSAR based on theoretical bond length and electron densities
    • Loader R.J., Singh N., O'malley P.J., and Popelier P.L. The cytotoxicity of ortho alkyl substituted 4-X-phenols: a QSAR based on theoretical bond length and electron densities. Bioorg. Med. Chem. Lett. 16 (2006) 1249-1254
    • (2006) Bioorg. Med. Chem. Lett. , vol.16 , pp. 1249-1254
    • Loader, R.J.1    Singh, N.2    O'malley, P.J.3    Popelier, P.L.4
  • 18
    • 0037422460 scopus 로고    scopus 로고
    • Quantitative structure toxicity relationships for phenols in isolated rat hepatocytes
    • Moridani M.Y., Siraki A., and O'Brien P.J. Quantitative structure toxicity relationships for phenols in isolated rat hepatocytes. Chem. Biol. Interact. 145 (2003) 213-223
    • (2003) Chem. Biol. Interact. , vol.145 , pp. 213-223
    • Moridani, M.Y.1    Siraki, A.2    O'Brien, P.J.3
  • 19
    • 0242500948 scopus 로고    scopus 로고
    • Structure-antioxidant activity relationships of ferulic acid effectiveness: effect of carbon side chain characteristic groups
    • Nenadis N., Zahng H.Y., and Tsimidou M.Z. Structure-antioxidant activity relationships of ferulic acid effectiveness: effect of carbon side chain characteristic groups. J. Agric. Food Chem. 51 (2003) 1874-1879
    • (2003) J. Agric. Food Chem. , vol.51 , pp. 1874-1879
    • Nenadis, N.1    Zahng, H.Y.2    Tsimidou, M.Z.3
  • 20
    • 0000716034 scopus 로고
    • Kinetic evaluation of reactivity of phenolic derivatives as antioxidants for polypropylenesays
    • Ohkatsu Y., Haruna T., and Osa T. Kinetic evaluation of reactivity of phenolic derivatives as antioxidants for polypropylenesays. J. Macromol. Sci. Chem. A11 (1977) 1975-1988
    • (1977) J. Macromol. Sci. Chem. , vol.A11 , pp. 1975-1988
    • Ohkatsu, Y.1    Haruna, T.2    Osa, T.3
  • 21
    • 20844445334 scopus 로고    scopus 로고
    • Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements
    • Prior R.L., Wu X., and Schaich K. Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements. J. Agric. Food Chem. 53 (2005) 4290-4302
    • (2005) J. Agric. Food Chem. , vol.53 , pp. 4290-4302
    • Prior, R.L.1    Wu, X.2    Schaich, K.3
  • 24
    • 0035999951 scopus 로고    scopus 로고
    • QRSA for the cytotoxicity of 2-alkyl or 2, 6-dialkyl, 4-X-phenols: the nature of the radical reaction
    • Selassie C.D., Verma R.P., Kapur S., Shusterman A.J., and Hansch C. QRSA for the cytotoxicity of 2-alkyl or 2, 6-dialkyl, 4-X-phenols: the nature of the radical reaction. J. Chem. Soc., Perkin Trans. 2 (2002) 1112-1117
    • (2002) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 1112-1117
    • Selassie, C.D.1    Verma, R.P.2    Kapur, S.3    Shusterman, A.J.4    Hansch, C.5
  • 26
    • 0019283383 scopus 로고
    • The living state and cancer
    • Szent-Gyorgy A. The living state and cancer. Physico. Chem. Phys. 12 (1980) 99-110
    • (1980) Physico. Chem. Phys. , vol.12 , pp. 99-110
    • Szent-Gyorgy, A.1
  • 27
    • 0024369622 scopus 로고
    • Generation of reactive intermediates from the tumor promoter butylated hydroxytoluene hydroperoxide in isolated murine keratinocytes or by hematin
    • Taffe B.G., Zweier J.L., Pannell L.K., and Kensler T.W. Generation of reactive intermediates from the tumor promoter butylated hydroxytoluene hydroperoxide in isolated murine keratinocytes or by hematin. Carcinogenesis 10 (1989) 1264-1268
    • (1989) Carcinogenesis , vol.10 , pp. 1264-1268
    • Taffe, B.G.1    Zweier, J.L.2    Pannell, L.K.3    Kensler, T.W.4
  • 28
    • 0000163478 scopus 로고    scopus 로고
    • Molecular orbital parameters and comparative QSAR in the analysis of phenol toxicity to leukemia cells
    • Zhang L., Gao H., Hansch C., and Selassie C.D. Molecular orbital parameters and comparative QSAR in the analysis of phenol toxicity to leukemia cells. J. Chem. Soc., Perkin Trans. 2 (1998) 2553-2556
    • (1998) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 2553-2556
    • Zhang, L.1    Gao, H.2    Hansch, C.3    Selassie, C.D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.