메뉴 건너뛰기




Volumn 10, Issue 3, 1997, Pages 296-301

Evidence for thiol-dependent production of oxygen radicals by 4-methyl- 5-pyrazinyl-3H-1,2-dithiole-3-thione (oltipraz) and 3H-1,2-dithiole-3- thione: Possible relevance to the anticarcinogenic properties of 1,2- dithiole-3-thiones

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DITHIOLE 3 THIONE DERIVATIVE; 3H 1,2 DITHIOLE 3 THIONE; ANTINEOPLASTIC AGENT; DIMETHYL SULFOXIDE; OLTIPRAZ; OXYGEN RADICAL; SCAVENGER; UNCLASSIFIED DRUG;

EID: 0030944162     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9601667     Document Type: Article
Times cited : (51)

References (58)
  • 1
    • 0000781521 scopus 로고
    • The inhibitory action of methylcholanthrene on rats fed the azo dye 3′-methyl-4-dimethylaminobenzene
    • Richardson, H. L. and Cunningham, L. (1951) The inhibitory action of methylcholanthrene on rats fed the azo dye 3′-methyl-4-dimethylaminobenzene. Cancer Res. 11, 274.
    • (1951) Cancer Res. , vol.11 , pp. 274
    • Richardson, H.L.1    Cunningham, L.2
  • 2
    • 0030038193 scopus 로고    scopus 로고
    • Chemopreventive efficacy of arylalkyl isothiocyanates and N-acetylcysteine for lung tumorigenesis in Fischer rats
    • Chung, F. L., Kelloff, G., Steele, V., Pittman, B., Zang, E., Jiao, D., Rigotty, J., Choi, C.-I., and Rivenson, A. (1996) Chemopreventive efficacy of arylalkyl isothiocyanates and N-acetylcysteine for lung tumorigenesis in Fischer rats. Cancer Res. 56, 772-778.
    • (1996) Cancer Res. , vol.56 , pp. 772-778
    • Chung, F.L.1    Kelloff, G.2    Steele, V.3    Pittman, B.4    Zang, E.5    Jiao, D.6    Rigotty, J.7    Choi, C.-I.8    Rivenson, A.9
  • 4
    • 0020587373 scopus 로고
    • Inhibition of neoplasia by minor dietary constituents
    • Wattenberg, L. W. (1983) Inhibition of neoplasia by minor dietary constituents. Cancer Res. 43, 2448s-2453s.
    • (1983) Cancer Res. , vol.43
    • Wattenberg, L.W.1
  • 5
    • 0027487416 scopus 로고
    • The electrophile counterattack response: Protection against neoplasia and toxicity
    • Prestera, T., Zhang, Y., Spencer, S. R., Wilczak, C. A., and Talalay, P. (1993) The electrophile counterattack response: protection against neoplasia and toxicity. Adv. Enzyme Regul. 33, 281-296.
    • (1993) Adv. Enzyme Regul. , vol.33 , pp. 281-296
    • Prestera, T.1    Zhang, Y.2    Spencer, S.R.3    Wilczak, C.A.4    Talalay, P.5
  • 9
    • 0000731884 scopus 로고
    • Chemoprotection by 1,2-dithiole-3-thiones
    • ( Huang, M.-T., Osawa, T., Ho, C.-T., and Rosen, R. T., Eds.) ACS Symposium Series 546, American Chemical Society, Washington, DC
    • Kensler, T. W., Groopman, J. D., Roebuck, B. D., and Curphey, T. J. (1994) Chemoprotection by 1,2-dithiole-3-thiones. In Food Phytochemicals for Cancer Prevention: Volume I ( Huang, M.-T., Osawa, T., Ho, C.-T., and Rosen, R. T., Eds.) pp 154-163, ACS Symposium Series 546, American Chemical Society, Washington, DC.
    • (1994) Food Phytochemicals for Cancer Prevention: Volume I , vol.1 , pp. 154-163
    • Kensler, T.W.1    Groopman, J.D.2    Roebuck, B.D.3    Curphey, T.J.4
  • 10
    • 0344915418 scopus 로고
    • Identification of a common signal regulating the induction of enzymes that protect against chemical carcinogenesis
    • Talalay, P., DeLong, M. J., and Prochaska, H. J. (1988) Identification of a common signal regulating the induction of enzymes that protect against chemical carcinogenesis. Proc. Natl. Acad. Sci. U.S.A. 85, 8261-8265.
    • (1988) Proc. Natl. Acad. Sci. U.S.A. , vol.85 , pp. 8261-8265
    • Talalay, P.1    DeLong, M.J.2    Prochaska, H.J.3
  • 12
    • 0028364075 scopus 로고
    • Transcriptional regulation of a rat liver glutathione S-transerase Ya subunit gene
    • Nguyen, T., Rushmore, T. H., and Pickett, C. B. (1994) Transcriptional regulation of a rat liver glutathione S-transerase Ya subunit gene. J. Biol. Chem. 269, 13656-13662.
    • (1994) J. Biol. Chem. , vol.269 , pp. 13656-13662
    • Nguyen, T.1    Rushmore, T.H.2    Pickett, C.B.3
  • 14
    • 0025852479 scopus 로고
    • Modulation of transcription factor NF-κB binding by oxidation-reduction in vitro
    • Toleando, M. B., and Leonard, W. J. (1991) Modulation of transcription factor NF-κB binding by oxidation-reduction in vitro. Proc. Natl. Acad. Sci. U.S.A. 88, 4328-4332.
    • (1991) Proc. Natl. Acad. Sci. U.S.A. , vol.88 , pp. 4328-4332
    • Toleando, M.B.1    Leonard, W.J.2
  • 15
    • 0025677250 scopus 로고
    • Intracellular thiols regulate activation of nuclear factor κB and transcription of human immunodeficiency virus
    • Staal, F. J. T., Roederer, M., and Herzenberg, L. A. (1990) Intracellular thiols regulate activation of nuclear factor κB and transcription of human immunodeficiency virus. Proc. Natl. Acad. Sci. U.S.A. 87, 9943-9947.
    • (1990) Proc. Natl. Acad. Sci. U.S.A. , vol.87 , pp. 9943-9947
    • Staal, F.J.T.1    Roederer, M.2    Herzenberg, L.A.3
  • 16
    • 0025739254 scopus 로고
    • Reactive oxygen intermediates as apparently widely used messengers in the activation of NF-κB transcription factor and HIV-1
    • Schreck, R., Rieber, P., and Baeuerle, P. A. (1991) Reactive oxygen intermediates as apparently widely used messengers in the activation of NF-κB transcription factor and HIV-1. EMBOJ. 10, 2247-2258.
    • (1991) EMBO J. , vol.10 , pp. 2247-2258
    • Schreck, R.1    Rieber, P.2    Baeuerle, P.A.3
  • 17
    • 0025721047 scopus 로고
    • Redox redux: The control of oxidative stress responses
    • Demple, B., and Amabile-Cuevas, C. F. (1991) Redox redux: the control of oxidative stress responses. Cell 67, 837-839.
    • (1991) Cell , vol.67 , pp. 837-839
    • Demple, B.1    Amabile-Cuevas, C.F.2
  • 18
    • 0025946152 scopus 로고
    • 6-methylguanine-DNA alkyltransferase protects against some of the biological effects of N-methyl-N′-nitro-N-nitrosoguanidine in in C3H/10T1/2 cells
    • 6-methylguanine-DNA alkyltransferase protects against some of the biological effects of N-methyl-N′-nitro-N-nitrosoguanidine in in C3H/10T1/2 cells. Radiat. Res. 127, 220-225.
    • (1991) Radiat. Res. , vol.127 , pp. 220-225
    • Von Hofe, E.1    Kennedy, A.R.2
  • 19
    • 0025214474 scopus 로고
    • Transcriptional regulator of oxidative stress-induced genes: Direct activation by oxidation
    • Storz, G., Tartaglia, L. A., and Ames, B. N. (1990) Transcriptional regulator of oxidative stress-induced genes: direct activation by oxidation. Science 248, 189-194.
    • (1990) Science , vol.248 , pp. 189-194
    • Storz, G.1    Tartaglia, L.A.2    Ames, B.N.3
  • 20
    • 0026714672 scopus 로고
    • Redox activation of Fos-Jun DNA-binding activity is mediated by a DNA-repair enzyme
    • Xanthoudakis, S., Miao, G., Wang, F., E., Pan, Y.-C., and Curran, T. (1992) Redox activation of Fos-Jun DNA-binding activity is mediated by a DNA-repair enzyme. EMBO J. 11, 3323-3335.
    • (1992) EMBO J. , vol.11 , pp. 3323-3335
    • Xanthoudakis, S.1    Miao, G.2    Wang, F.E.3    Pan, Y.-C.4    Curran, T.5
  • 21
    • 0029990552 scopus 로고    scopus 로고
    • Role of oxidants and antioxidants in the induction of AP-1, NF-κB, and glutathione S-transferase gene expression
    • Pinkus, R., Weiner, L. M., and Daniel, V. (1996) Role of oxidants and antioxidants in the induction of AP-1, NF-κB, and glutathione S-transferase gene expression. J. Biol. Chem. 271, 13422-13429.
    • (1996) J. Biol. Chem. , vol.271 , pp. 13422-13429
    • Pinkus, R.1    Weiner, L.M.2    Daniel, V.3
  • 23
    • 0022763396 scopus 로고
    • Inhibitory effects of 4-methyl-5-(2-pyrazinyl)-1,2-dithiole-3-thione (oltipraz) on carcinogenesis induced by benzo[a]pyrene, diethylnitrosamine and uracil mustard
    • Wattenberg, L. W., and Bueding, E. (1986) Inhibitory effects of 4-methyl-5-(2-pyrazinyl)-1,2-dithiole-3-thione (oltipraz) on carcinogenesis induced by benzo[a]pyrene, diethylnitrosamine and uracil mustard. Carcinogenesis 7, 1379-1381.
    • (1986) Carcinogenesis , vol.7 , pp. 1379-1381
    • Wattenberg, L.W.1    Bueding, E.2
  • 24
    • 0029095529 scopus 로고
    • Oltipraz: Clinical opportunities for cancer chemoprevention
    • Kensler, T. W., and Helzsouer, K. J. (1995) Oltipraz: clinical opportunities for cancer chemoprevention. J. Cell. Biochem. Suppl. 22, 101-107.
    • (1995) J. Cell. Biochem. Suppl. , vol.22 , pp. 101-107
    • Kensler, T.W.1    Helzsouer, K.J.2
  • 25
    • 0006755281 scopus 로고
    • Chemoprevention of colon cancer by thiol and other organosulfur compounds
    • (Huang, M.-T., Osawa, T., Ho. C.-T., and Rosen, R. T., Eds.) ACS Symposium Series 546, American Chemical Society, Washington, DC
    • Reddy, B. S., and Rao, C. V., (1994) Chemoprevention of colon cancer by thiol and other organosulfur compounds. In Food Phytochemicals for Cancer Prevention: Volume I (Huang, M.-T., Osawa, T., Ho. C.-T., and Rosen, R. T., Eds.) pp 164-172, ACS Symposium Series 546, American Chemical Society, Washington, DC .
    • (1994) Food Phytochemicals for Cancer Prevention: Volume I , vol.1 , pp. 164-172
    • Reddy, B.S.1    Rao, C.V.2
  • 27
    • 85067346111 scopus 로고
    • Eine einfache und ergiebige herstellung von 3-thioxo-1,2-dithiol ( 1,2-trithion)
    • Meinetsberger, E., Schoffer, A., and Behringer, H. (1977) Eine einfache und ergiebige herstellung von 3-thioxo-1,2-dithiol ( 1,2-trithion). Synthesis, 802-803.
    • (1977) Synthesis , pp. 802-803
    • Meinetsberger, E.1    Schoffer, A.2    Behringer, H.3
  • 29
    • 0014413509 scopus 로고
    • The interaction of closed circular DNA with intercalative dyes. I. the superhelix density of SV40 DNA in the presence and absence of dye
    • Bauer, W., and Vinograd, J. (1968) The interaction of closed circular DNA with intercalative dyes. I. The superhelix density of SV40 DNA in the presence and absence of dye. J. Mol. Biol. 33, 141-171.
    • (1968) J. Mol. Biol. , vol.33 , pp. 141-171
    • Bauer, W.1    Vinograd, J.2
  • 30
    • 0021762388 scopus 로고
    • Cleavage of DNA with methidiumpropyl-EDTA-iron(II): Reaction conditions and product analysis
    • Hertzberg, R. P., and Dervan, P. B. (1984) Cleavage of DNA with methidiumpropyl-EDTA-iron(II): Reaction conditions and product analysis. Biochemistry 23, 3934-3945.
    • (1984) Biochemistry , vol.23 , pp. 3934-3945
    • Hertzberg, R.P.1    Dervan, P.B.2
  • 31
    • 0029670818 scopus 로고    scopus 로고
    • DNA cleavage by 1,2-dithiolan-3-one 1-oxides: A class of thiol-activated DNA cleaving agents structurally related to the anti-tumor antibiotic leinamycin
    • Behroozi, S. J., Kim, W., Dannaldson, J., and Gates, K. S. (1996) DNA cleavage by 1,2-dithiolan-3-one 1-oxides: A class of thiol-activated DNA cleaving agents structurally related to the anti-tumor antibiotic leinamycin. Biochemistry 35, 1768-1774.
    • (1996) Biochemistry , vol.35 , pp. 1768-1774
    • Behroozi, S.J.1    Kim, W.2    Dannaldson, J.3    Gates, K.S.4
  • 32
    • 0029037105 scopus 로고
    • The reaction of n-propanethiol with 3H-1,2-benzodithiol-3-one 1-oxide and 5,5-dimethyl-1,2-dithiolan-3-one 1-oxide: Studies related to the reaction of antitumor antibiotic leinamycin with DNA
    • Behroozi, S. B., Kim, W., and Gates, K. S. (1995) The reaction of n-propanethiol with 3H-1,2-benzodithiol-3-one 1-oxide and 5,5-dimethyl-1,2-dithiolan-3-one 1-oxide: studies related to the reaction of antitumor antibiotic leinamycin with DNA. J. Org. Chem. 60, 3964-3966.
    • (1995) J. Org. Chem. , vol.60 , pp. 3964-3966
    • Behroozi, S.B.1    Kim, W.2    Gates, K.S.3
  • 33
    • 0017672745 scopus 로고
    • Electrophoresis of DNA in agarose gels. Optimizing separations of conformational isomers of double- and single-stranded DNAs
    • Jonson, P. H., and Grossman, L. I. (1977) Electrophoresis of DNA in agarose gels. Optimizing separations of conformational isomers of double- and single-stranded DNAs. Biochemistry 16, 4217-4224.
    • (1977) Biochemistry , vol.16 , pp. 4217-4224
    • Jonson, P.H.1    Grossman, L.I.2
  • 34
    • 0028909094 scopus 로고
    • Evaluation of chemopreventive agents in different mechanistic classes using a rat tracheal epithelial cell culture transformation assay
    • Arnold, J. T., Wilkinson, B. P., Sharma, S., and Steele, V. E. (1995) Evaluation of chemopreventive agents in different mechanistic classes using a rat tracheal epithelial cell culture transformation assay. Cancer Res. 55, 537-543.
    • (1995) Cancer Res. , vol.55 , pp. 537-543
    • Arnold, J.T.1    Wilkinson, B.P.2    Sharma, S.3    Steele, V.E.4
  • 36
    • 0029103994 scopus 로고
    • Carbon-hydrogen bonds of DNA sugar units as targets for chemical nucleases and drugs
    • Oxygen radicals are known to damage DNA; see: Pratviel, G., Bernadou, J., and Meunier, B. (1995) Carbon-hydrogen bonds of DNA sugar units as targets for chemical nucleases and drugs. Angew. Chem., Int. Ed. Engl. 34, 746-769.
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 746-769
    • Pratviel, G.1    Bernadou, J.2    Meunier, B.3
  • 37
    • 0028927261 scopus 로고
    • Reactions of oxyl radicals with DNA
    • Breen A. P., and Murphy, J. A. (1995) Reactions of oxyl radicals with DNA. Free Radical Biol. Med. 18, 1033-1077.
    • (1995) Free Radical Biol. Med. , vol.18 , pp. 1033-1077
    • Breen, A.P.1    Murphy, J.A.2
  • 38
    • 0025126555 scopus 로고
    • Role of free radicals and catalytic metal ions in human disease: An overview
    • Halliwell, B., and Gutteridge, J. M. C. (1990) Role of free radicals and catalytic metal ions in human disease: an overview. Methods Enzymol. 186, 1-85.
    • (1990) Methods Enzymol. , vol.186 , pp. 1-85
    • Halliwell, B.1    Gutteridge, J.M.C.2
  • 39
    • 0029959898 scopus 로고    scopus 로고
    • DNA cleavage by the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (SR4233): Evidence for the involvement of hydroxyl radical
    • Daniels, J. S., and Gates, K. S. (1996) DNA cleavage by the antitumor agent 3-amino-1,2,4-benzotriazine 1,4-dioxide (SR4233): Evidence for the involvement of hydroxyl radical. J. Am. Chem. Soc. 118, 3380-3385.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 3380-3385
    • Daniels, J.S.1    Gates, K.S.2
  • 41
    • 1842412099 scopus 로고
    • Class 1.5-1.12: Oxidoreductases, Springer-Verlag, Berlin
    • Schomburg, D., Salzmann, M., and Stephan, D. (1994) Enzyme Handbook, Vol. 7: Class 1.5-1.12: Oxidoreductases, p 1.11.1.6, Springer-Verlag, Berlin. Walsh, C. T. (1979) Enzymatic Reaction Mechanisms, p 443, W. H. Freeman and Co., New York.
    • (1994) Enzyme Handbook , vol.7 , pp. 11116
    • Schomburg, D.1    Salzmann, M.2    Stephan, D.3
  • 42
    • 0004135644 scopus 로고
    • W. H. Freeman and Co., New York
    • Schomburg, D., Salzmann, M., and Stephan, D. (1994) Enzyme Handbook, Vol. 7: Class 1.5-1.12: Oxidoreductases, p 1.11.1.6, Springer-Verlag, Berlin. Walsh, C. T. (1979) Enzymatic Reaction Mechanisms, p 443, W. H. Freeman and Co., New York.
    • (1979) Enzymatic Reaction Mechanisms , pp. 443
    • Walsh, C.T.1
  • 43
    • 0000933501 scopus 로고
    • Superoxide radical and superoxide dismutase
    • Fridovich, I. (1972) Superoxide radical and superoxide dismutase. Acc. Chem. Res. 5, 321-326.
    • (1972) Acc. Chem. Res. , vol.5 , pp. 321-326
    • Fridovich, I.1
  • 45
    • 0018582229 scopus 로고
    • Inhibition of the iron-catalysed formation of hydroxyl radicals from superoxide and of lipid peroxidation by desferrioxamine
    • Gutteridge, J. M. C., Richmond, R., and Halliwell, B. (1979) Inhibition of the iron-catalysed formation of hydroxyl radicals from superoxide and of lipid peroxidation by desferrioxamine. Biochem. J. 184, 469-472.
    • (1979) Biochem. J. , vol.184 , pp. 469-472
    • Gutteridge, J.M.C.1    Richmond, R.2    Halliwell, B.3
  • 48
    • 0023595278 scopus 로고
    • Peroxyl free radicals: Potential mediators of tumor initiation and promotion
    • Marnett, L. J. (1987) Peroxyl free radicals: potential mediators of tumor initiation and promotion. Carcinogenesis 8, 1365-1373.
    • (1987) Carcinogenesis , vol.8 , pp. 1365-1373
    • Marnett, L.J.1
  • 49
    • 0001107906 scopus 로고
    • Reactivity of substituted 1,2-dithiole-3-thiones with sodium ethanethiolate: A convenient route to a novel heterocycle
    • Largeron, M., Martens, T., and Fleury, M. B. (1987) Reactivity of substituted 1,2-dithiole-3-thiones with sodium ethanethiolate: a convenient route to a novel heterocycle. Tetrahedron 43, 3421-3428.
    • (1987) Tetrahedron , vol.43 , pp. 3421-3428
    • Largeron, M.1    Martens, T.2    Fleury, M.B.3
  • 50
    • 0026022662 scopus 로고
    • Toward an understanding of the schistosomicidal effect of 4-methyl-5-(2-pyrazinyl)-1,2-dithiole-3-thione (oltipraz)
    • Fluery, M.-B., Largeron, M., and Martens, T. (1991) Toward an understanding of the schistosomicidal effect of 4-methyl-5-(2-pyrazinyl)-1,2-dithiole-3-thione (oltipraz). Biochem. Pharmacol. 41, 361-367.
    • (1991) Biochem. Pharmacol. , vol.41 , pp. 361-367
    • Fluery, M.-B.1    Largeron, M.2    Martens, T.3
  • 51
    • 0024389748 scopus 로고
    • Glutathione redox state, lipid peroxide levels, and activities of glutathione enzymes in oltipraz-treated adult Schistosoma mansoni
    • Mkoji, G. M., Smith, J. M., and Prichard, R. K. (1989) Glutathione redox state, lipid peroxide levels, and activities of glutathione enzymes in oltipraz-treated adult Schistosoma mansoni. Biochem. Pharmacol. 38, 4307-4313.
    • (1989) Biochem. Pharmacol. , vol.38 , pp. 4307-4313
    • Mkoji, G.M.1    Smith, J.M.2    Prichard, R.K.3
  • 52
    • 0028978712 scopus 로고
    • Involvement of NF-κB in the induction of NAD(P)H: Quinone oxidoreductase (DT-diapho-rase) by hypoxia, oltipraz and mitomycin C
    • O'Dwyer, P. J., and Yao, K.-S. (1995) Involvement of NF-κB in the induction of NAD(P)H: quinone oxidoreductase (DT-diapho-rase) by hypoxia, oltipraz and mitomycin C. Biochem. Pharmacol. 49, 275-282.
    • (1995) Biochem. Pharmacol. , vol.49 , pp. 275-282
    • O'Dwyer, P.J.1    Yao, K.-S.2
  • 53
    • 0027440878 scopus 로고
    • Repair of DNA methylpho-photriesters through a metalloactivated cysteine nucleophile
    • See, for example: Myers, L. C., Terranova, M. P., Ferentz, A. E., Wagner, G., and Verdine, G. L. (1993 ) Repair of DNA methylpho-photriesters through a metalloactivated cysteine nucleophile. Science 261, 1164-1167.
    • (1993) Science , vol.261 , pp. 1164-1167
    • See, F.E.1    Myers, L.C.2    Terranova, M.P.3    Ferentz, A.E.4    Wagner, G.5    Verdine, G.L.6
  • 54
    • 0002048709 scopus 로고
    • Adaptive response: Induced synthesis of DNA repair enzymes by alkylating agents
    • Sekiguchi, M., and Nakabeppu, Y. (1987) Adaptive response: induced synthesis of DNA repair enzymes by alkylating agents. Trends Genet. 3, 51-54.
    • (1987) Trends Genet. , vol.3 , pp. 51-54
    • Sekiguchi, M.1    Nakabeppu, Y.2
  • 55
    • 0027490279 scopus 로고
    • DNA damage and the DNA-activated protein kinase
    • Anderson, C. W. (1993) DNA damage and the DNA-activated protein kinase. Trends Biochem. Sci. 18, 433-437.
    • (1993) Trends Biochem. Sci. , vol.18 , pp. 433-437
    • Anderson, C.W.1
  • 56
    • 0023655407 scopus 로고
    • Protein damage and degradation by oxygen radicals
    • Davies, K. J. A., Delsignore, M. E., and Lin, S. W. (1987) Protein damage and degradation by oxygen radicals. J. Biol. Chem. 262, 9902-9907.
    • (1987) J. Biol. Chem. , vol.262 , pp. 9902-9907
    • Davies, K.J.A.1    Delsignore, M.E.2    Lin, S.W.3
  • 57
    • 84985570313 scopus 로고
    • Biochemistry of oxidative stress
    • Sies, H. (1986) Biochemistry of oxidative stress. Angew. Chem., Int. Ed. Engl. 25, 1058-1071.
    • (1986) Angew. Chem., Int. Ed. Engl. , vol.25 , pp. 1058-1071
    • Sies, H.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.