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Volumn 9, Issue 8, 1996, Pages 1298-1304

Kinetics of the reaction of a potential chemopreventive agent, 2,6- dithiopurine, and its major metabolite, 2,6-dithiouric acid, with multiple classes of electrophilic toxicants

Author keywords

[No Author keywords available]

Indexed keywords

2,6 DIMERCAPTOPURINE; 2,6 DITHIOURIC ACID; 6 MERCAPTOPURINE DERIVATIVE; ACROLEIN; CISPLATIN; DIHYDROXYBENZO[A]PYRENE OXIDE; DIMETHYL SULFATE; ETHYLNITROSOUREA; MELPHALAN; METHYLNITRONITROSOGUANIDINE; METHYLNITROSOUREA; SCAVENGER; UNCLASSIFIED DRUG;

EID: 0029852202     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx960088n     Document Type: Article
Times cited : (15)

References (41)
  • 1
    • 0014757218 scopus 로고
    • Carcinogenesis by chemicals: An overview
    • Miller, J. A. (1970) Carcinogenesis by chemicals: An overview. Cancer Res. 30, 559-576.
    • (1970) Cancer Res. , vol.30 , pp. 559-576
    • Miller, J.A.1
  • 2
    • 0019519171 scopus 로고
    • Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules
    • Miller, E. C., and Miller, J. A. (1981) Searches for ultimate chemical carcinogens and their reactions with cellular macromolecules. Cancer 47, 2327-2345.
    • (1981) Cancer , vol.47 , pp. 2327-2345
    • Miller, E.C.1    Miller, J.A.2
  • 3
    • 0022438130 scopus 로고
    • Glutathione transferase and carcinogenesis
    • Shankel, D. M., Hartman, P. E., Kada, T., and Hollaender, A., Eds. Plenum Press, New York
    • Ketterer, B., Meyer, D. J., Coles, B., Taylor, J. B., and Pemmble, S. (1986) Glutathione transferase and carcinogenesis. In Antimutagenesis and Anticarcinogenesis Mechanisms (Shankel, D. M., Hartman, P. E., Kada, T., and Hollaender, A., Eds.) pp 103-126, Plenum Press, New York.
    • (1986) Antimutagenesis and Anticarcinogenesis Mechanisms , pp. 103-126
    • Ketterer, B.1    Meyer, D.J.2    Coles, B.3    Taylor, J.B.4    Pemmble, S.5
  • 5
    • 0029048396 scopus 로고
    • Intermittent dosing with Oltipraz: Relationship between chemoprevention of aflatoxin-induced tumorigenesis and induction of glutathione S-transferases
    • Primiano, T., Egner, P. A., Sutter, T. R., Kelloff, G. J., Roebuck, B. D., and Kensler, T. W. (1995) Intermittent dosing with Oltipraz: relationship between chemoprevention of aflatoxin-induced tumorigenesis and induction of glutathione S-transferases. Cancer Res. 55, 4319-4324.
    • (1995) Cancer Res. , vol.55 , pp. 4319-4324
    • Primiano, T.1    Egner, P.A.2    Sutter, T.R.3    Kelloff, G.J.4    Roebuck, B.D.5    Kensler, T.W.6
  • 6
    • 0345680855 scopus 로고
    • Inhibition of the mutagenicity of bay-region diol epoxides of polycyclic aromatic hydrocarbons by naturally occurring plant phenols: Exceptional activity of ellagic acid
    • Wood, A. W., Huang, M.-T., Chang, R. L., Newmark, H. L., Lehr, R. E., Yagi, H., Sayer, J. M., Jerina, D. M., and Conney, A. H. (1982) Inhibition of the mutagenicity of bay-region diol epoxides of polycyclic aromatic hydrocarbons by naturally occurring plant phenols: exceptional activity of ellagic acid. Proc Natl. Acad. Sci. U.S.A. 79, 5513-5517.
    • (1982) Proc Natl. Acad. Sci. U.S.A. , vol.79 , pp. 5513-5517
    • Wood, A.W.1    Huang, M.-T.2    Chang, R.L.3    Newmark, H.L.4    Lehr, R.E.5    Yagi, H.6    Sayer, J.M.7    Jerina, D.M.8    Conney, A.H.9
  • 7
    • 0022255969 scopus 로고
    • Effect of ellagic acid and hydroxylated flavonoids on the tumorigenicity of benzo[a]pyrene and (±)-7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10- tetrahydrobenzo[a]pyrene on mouse skin and in the newborn mouse
    • Chang, R. L., Huang, M.-T., Wood, A. W., Wong, C.-Q., Newmark, H. L., Yagi, H., Sayer, J. M., Jerina, D. M., and Conney, A. H. (1985) Effect of ellagic acid and hydroxylated flavonoids on the tumorigenicity of benzo[a]pyrene and (±)-7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10- tetrahydrobenzo[a]pyrene on mouse skin and in the newborn mouse. Carcinogenesis 6, 1127-1133.
    • (1985) Carcinogenesis , vol.6 , pp. 1127-1133
    • Chang, R.L.1    Huang, M.-T.2    Wood, A.W.3    Wong, C.-Q.4    Newmark, H.L.5    Yagi, H.6    Sayer, J.M.7    Jerina, D.M.8    Conney, A.H.9
  • 8
    • 0027450675 scopus 로고
    • Reaction of nontoxic, potentially chemopreventive purinethiols with a direct-acting, electrophilic carcinogen, benzo[a]pyrene-7,8-diol 9,10-epoxide
    • MacLeod, M. C., Qing, W.-G., Powell, K. L., Daylong, A., and Evans, F. E. (1993) Reaction of nontoxic, potentially chemopreventive purinethiols with a direct-acting, electrophilic carcinogen, benzo[a]pyrene-7,8-diol 9,10-epoxide. Chem. Res. Toxicol. 6, 159-167.
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 159-167
    • MacLeod, M.C.1    Qing, W.-G.2    Powell, K.L.3    Daylong, A.4    Evans, F.E.5
  • 9
    • 0026425668 scopus 로고
    • Inhibition by 2,6-dithiopurine and thiopurinol of binding of a benzo(a)pyrene diol epoxide to DNA in mouse epidermis and the initiation phase of two-stage tumorigenesis
    • MacLeod, M. C., Powell, L. K., Thai, G., Conti, C. J., and Reiner, J. J., Jr. (1991) Inhibition by 2,6-dithiopurine and thiopurinol of binding of a benzo(a)pyrene diol epoxide to DNA in mouse epidermis and the initiation phase of two-stage tumorigenesis. Cancer Res. 51, 4859-4864.
    • (1991) Cancer Res. , vol.51 , pp. 4859-4864
    • MacLeod, M.C.1    Powell, L.K.2    Thai, G.3    Conti, C.J.4    Reiner Jr., J.J.5
  • 10
    • 0025999122 scopus 로고
    • Reaction of a chemotherapeutic agent, 6-mercaptopurine, with a direct-acting, electrophilic carcinogen, benzo[a]pyrene-7,8-diol 9,10-epoxide
    • MacLeod, M. C., Stewart, E., Daylong, A., Lew, L. K., and Evans, F. E. (1991) Reaction of a chemotherapeutic agent, 6-mercaptopurine, with a direct-acting, electrophilic carcinogen, benzo[a]pyrene-7,8-diol 9,10-epoxide. Chem. Res. Toxicol. 4, 453-462.
    • (1991) Chem. Res. Toxicol. , vol.4 , pp. 453-462
    • MacLeod, M.C.1    Stewart, E.2    Daylong, A.3    Lew, L.K.4    Evans, F.E.5
  • 11
    • 0025288295 scopus 로고
    • Inhibition by 6-mercaptopurine of the binding of a benzo[a]pyrene diol epoxide to DNA in Chinese hamster ovary cells
    • MacLeod, M. C., Humphrey, R. M., Bickerstaff, T., and Daylong, A. (1990) Inhibition by 6-mercaptopurine of the binding of a benzo[a]pyrene diol epoxide to DNA in Chinese hamster ovary cells. Cancer Res. 50, 4355-4359.
    • (1990) Cancer Res. , vol.50 , pp. 4355-4359
    • MacLeod, M.C.1    Humphrey, R.M.2    Bickerstaff, T.3    Daylong, A.4
  • 13
    • 0023475510 scopus 로고
    • Murine epidermal xanthine oxidase activity: Correlation with degree of hyperplasia induced by tumor promoters
    • Pence, B. C., and Reiners, J. J., Jr. (1987) Murine epidermal xanthine oxidase activity: correlation with degree of hyperplasia induced by tumor promoters. Cancer Res. 47, 6388-6392.
    • (1987) Cancer Res. , vol.47 , pp. 6388-6392
    • Pence, B.C.1    Reiners Jr., J.J.2
  • 14
    • 0003683686 scopus 로고
    • The influence of the reagent on organic reactivity
    • Chapman, N. B., and Shorter, J., Eds. Plenum, London
    • Pearson, R. G. (1972) The influence of the reagent on organic reactivity. In Advances in Linear Free Energy Relationships (Chapman, N. B., and Shorter, J., Eds.) pp 281-319, Plenum, London.
    • (1972) Advances in Linear Free Energy Relationships , pp. 281-319
    • Pearson, R.G.1
  • 15
    • 0021610533 scopus 로고
    • Effects of modifying structure on electrophilic reactions with biological nucleophiles
    • Coles, B. (1985) Effects of modifying structure on electrophilic reactions with biological nucleophiles. Drug Metab. Rev. 15, 1307-1334.
    • (1985) Drug Metab. Rev. , vol.15 , pp. 1307-1334
    • Coles, B.1
  • 16
    • 0018882074 scopus 로고
    • Genetic effects of dimethyl sulfate, diethyl sulfate, and related compounds
    • Hoffmann, G. R. (1980) Genetic effects of dimethyl sulfate, diethyl sulfate, and related compounds. Mutat. Res. 75, 63-129.
    • (1980) Mutat. Res. , vol.75 , pp. 63-129
    • Hoffmann, G.R.1
  • 17
    • 10544250920 scopus 로고
    • Comparison of alkylating agent and radiation carcinogenesis: Some aspects of the possible involvement of effects on DNA
    • Yuhas, J. M., Tennant, R., and Regan, J. D., Eds. Raven Press, New York
    • Lawley, P. D. (1976) Comparison of alkylating agent and radiation carcinogenesis: some aspects of the possible involvement of effects on DNA. In Biology of Radiation Carcinogenesis (Yuhas, J. M., Tennant, R., and Regan, J. D., Eds.) pp 165-174, Raven Press, New York.
    • (1976) Biology of Radiation Carcinogenesis , pp. 165-174
    • Lawley, P.D.1
  • 18
    • 0029000066 scopus 로고
    • High-dose intravenous melphalan: A review
    • Samuels, B. L., and Bitran, J. D. (1995) High-dose intravenous melphalan: a review. J. Clin. Oncol. 13, 1786-1799.
    • (1995) J. Clin. Oncol. , vol.13 , pp. 1786-1799
    • Samuels, B.L.1    Bitran, J.D.2
  • 19
    • 0021319465 scopus 로고
    • 2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde
    • 2-propanodeoxyguanosine adducts in DNA upon reaction with acrolein or crotonaldehyde. Cancer Res. 44, 990-995.
    • (1984) Cancer Res. , vol.44 , pp. 990-995
    • Chung, F.-L.1    Young, R.2    Hecht, S.S.3
  • 20
    • 0027514969 scopus 로고
    • Alkylation of DNA by melphalan with special reference to adenine derivatives and adenine-guanine cross-linking
    • Osborne, M. R., and Lawley, P. D. (1993) Alkylation of DNA by melphalan with special reference to adenine derivatives and adenine-guanine cross-linking. Chem.-Biol. Interact. 89, 49-60.
    • (1993) Chem.-Biol. Interact. , vol.89 , pp. 49-60
    • Osborne, M.R.1    Lawley, P.D.2
  • 21
    • 0029664516 scopus 로고    scopus 로고
    • Detection of 1,N2-propanodeoxyguanosine adducts as potential endogenous DNA lesions in rodent and human tissues
    • Nath, R. G., Ocando, J. E., and Chung, F.-L. (1996) Detection of 1,N2-propanodeoxyguanosine adducts as potential endogenous DNA lesions in rodent and human tissues. Cancer Res. 56, 452-456.
    • (1996) Cancer Res. , vol.56 , pp. 452-456
    • Nath, R.G.1    Ocando, J.E.2    Chung, F.-L.3
  • 22
    • 0024366151 scopus 로고
    • Cisplatin dose intensity
    • Ozols, R. F. (1989) Cisplatin dose intensity. Semin. Oncol. 16, 22-30.
    • (1989) Semin. Oncol. , vol.16 , pp. 22-30
    • Ozols, R.F.1
  • 23
    • 0021894582 scopus 로고
    • Adducts of the antitumor drug cis-diamminedichloroplatinum(II) with DNA: Formation, identification and quantitation
    • Fichtinger-Schepman, A. M. J., Van der Veer, J. L., DenHartog, J. H. J., Lohman, P. H. M., and Reedijk, J. (1985) Adducts of the antitumor drug cis-diamminedichloroplatinum(II) with DNA: Formation, identification and quantitation. Biochemistry 24, 707-713.
    • (1985) Biochemistry , vol.24 , pp. 707-713
    • Fichtinger-Schepman, A.M.J.1    Van der Veer, J.L.2    DenHartog, J.H.J.3    Lohman, P.H.M.4    Reedijk, J.5
  • 24
    • 0344370784 scopus 로고
    • Thionation of purine and pyrimidine oxoderivatives in sulfones
    • Ozola, I., and Mikstais, U. (1978) Thionation of purine and pyrimidine oxoderivatives in sulfones. Khim.-Farm. Zh. 12, 85-87.
    • (1978) Khim.-Farm. Zh. , vol.12 , pp. 85-87
    • Ozola, I.1    Mikstais, U.2
  • 25
    • 0008005503 scopus 로고
    • Synthesis of 6-thiopuric acid and its derivatives
    • Levin, G., Kalmus, A., and Bergmann, A. (1960) Synthesis of 6-thiopuric acid and its derivatives. J. Org. Chem. 25, 1752-1754.
    • (1960) J. Org. Chem. , vol.25 , pp. 1752-1754
    • Levin, G.1    Kalmus, A.2    Bergmann, A.3
  • 26
    • 0023757445 scopus 로고
    • A rapid spectrophotometric assay for the integrity of diol epoxides
    • MacLeod, M. C., and Lew, L. (1988) A rapid spectrophotometric assay for the integrity of diol epoxides. Carcinogenesis 9, 2133-2135.
    • (1988) Carcinogenesis , vol.9 , pp. 2133-2135
    • MacLeod, M.C.1    Lew, L.2
  • 27
    • 0019797879 scopus 로고
    • Quantitative analysis of melphalan and its major hydrolyzate in patients and animals by reversed-phase high-performance liquid chromatography
    • Ahmed, A. E., and Hsu, T. F. (1981) Quantitative analysis of melphalan and its major hydrolyzate in patients and animals by reversed-phase high-performance liquid chromatography. J. Chromatogr. 222, 453-460.
    • (1981) J. Chromatogr. , vol.222 , pp. 453-460
    • Ahmed, A.E.1    Hsu, T.F.2
  • 28
    • 0342296201 scopus 로고
    • Experiments on determination of melphalan by fluorescence. Interaction with protein and various solutions
    • Chirigos, M. A., and Mead, J. A. R. (1964) Experiments on determination of melphalan by fluorescence. Interaction with protein and various solutions. Anal. Biochem. 7, 259-268.
    • (1964) Anal. Biochem. , vol.7 , pp. 259-268
    • Chirigos, M.A.1    Mead, J.A.R.2
  • 29
    • 0345275404 scopus 로고
    • Potential purine antagonists. XX. the preparation and reactions of some methylthiopurines
    • Noell, C. W., and Robins, R. K. (1959) Potential purine antagonists. XX. The preparation and reactions of some methylthiopurines. J. Am. Chem. Soc. 81, 5997-6007.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 5997-6007
    • Noell, C.W.1    Robins, R.K.2
  • 30
    • 10544226451 scopus 로고
    • Influence of pH and concentration of phosphate buffer on the degradation of alkyl alkane sulfonates
    • Wickham, I. M., Narayanan, K. R., and Konozk, C. F. (1969) Influence of pH and concentration of phosphate buffer on the degradation of alkyl alkane sulfonates. Chem. Abstr. 74, 29, 1971.
    • (1969) Chem. Abstr. , vol.74 , Issue.29 , pp. 1971
    • Wickham, I.M.1    Narayanan, K.R.2    Konozk, C.F.3
  • 31
    • 8344279944 scopus 로고
    • Kinetics of solvolysis of various N-alkyl-N-nitrosoureas in neutral and alkaline solutions
    • Garrett, E. R., Goto, S., and Stubbing, J. F. (1964) Kinetics of solvolysis of various N-alkyl-N-nitrosoureas in neutral and alkaline solutions. J. Pharm. Sci. 54, 119-123.
    • (1964) J. Pharm. Sci. , vol.54 , pp. 119-123
    • Garrett, E.R.1    Goto, S.2    Stubbing, J.F.3
  • 32
    • 0014321087 scopus 로고
    • Inactivation of biologically active N-methyl-N-nitroso compounds in aqueous solution: Effect of various conditions of pH and illumination
    • McCIla, D. R., Reuvers, A., and Kitai, R. (1968) Inactivation of biologically active N-methyl-N-nitroso compounds in aqueous solution: effect of various conditions of pH and illumination. Can. J. Biochem. 46, 807-811.
    • (1968) Can. J. Biochem. , vol.46 , pp. 807-811
    • McCila, D.R.1    Reuvers, A.2    Kitai, R.3
  • 33
    • 0001549302 scopus 로고
    • The hydrolysis of some cyclic esters of sulfuric acid
    • Kaiser, E. T., Panar, M., and Wetheimer, F. H. (1963) The hydrolysis of some cyclic esters of sulfuric acid. J. Am. Chem. Soc. 85, 602-607.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 602-607
    • Kaiser, E.T.1    Panar, M.2    Wetheimer, F.H.3
  • 35
    • 0017765845 scopus 로고
    • Changes of mechanisms and product distributions in the hydrolysis of benzolalpyrene-7,8-diol 9,10-epoxide metabolites induced by changes in pH
    • Whalen, D. L., Montemarano, J. A., Thakker, D. R., Yagi, H., and Jerina, D. M. (1977) Changes of mechanisms and product distributions in the hydrolysis of benzolalpyrene-7,8-diol 9,10-epoxide metabolites induced by changes in pH. J. Am. Chem. Soc. 99, 5522-5524.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 5522-5524
    • Whalen, D.L.1    Montemarano, J.A.2    Thakker, D.R.3    Yagi, H.4    Jerina, D.M.5
  • 37
    • 0028301897 scopus 로고
    • N2 reaction mechanisms, explains why carcinogenic alkylating agents can form different proportion of adducts at oxygen versus nitrogen in DNA
    • N2 reaction mechanisms, explains why carcinogenic alkylating agents can form different proportion of adducts at oxygen versus nitrogen in DNA. Chem. Res. Toxicol. 7, 277-280.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 277-280
    • Loechler, E.L.1
  • 38
    • 0002782332 scopus 로고
    • DNA adducts and carcinogenesis
    • Sirica, A., Ed. Plenum Press, New York
    • Beland, F. A., and Poirier, M. C. (1989) DNA adducts and carcinogenesis. In The Pathobiology of Neoplasia (Sirica, A., Ed.) pp 55-80, Plenum Press, New York.
    • (1989) The Pathobiology of Neoplasia , pp. 55-80
    • Beland, F.A.1    Poirier, M.C.2
  • 40
    • 0019780445 scopus 로고
    • Facilitated transport of 6-mercaptopurine and 6-thioguanine and non-mediated permeation of 8-azaguanine in Novikoff rat hepatoma cells and relationship to intracellular phophoribosylation
    • Plagemann, P. G. W., Marz, R., Wohlhueter, R. M., Graff, J. C., and Zylka, J. M. (1981) Facilitated transport of 6-mercaptopurine and 6-thioguanine and non-mediated permeation of 8-azaguanine in Novikoff rat hepatoma cells and relationship to intracellular phophoribosylation. Biochim. Biophys. Acta 647, 49-62.
    • (1981) Biochim. Biophys. Acta , vol.647 , pp. 49-62
    • Plagemann, P.G.W.1    Marz, R.2    Wohlhueter, R.M.3    Graff, J.C.4    Zylka, J.M.5
  • 41
    • 0019087871 scopus 로고
    • Specificity in interaction of benzolalpyrene with nuclear macromolecules: Implication of derivatives of two dihydrodiols in protein binding
    • MacLeod, M. C., Kootstra, A., Mansfield, B. K., Slaga, T. J., and Selkirk, J. K. (1980) Specificity in interaction of benzolalpyrene with nuclear macromolecules: Implication of derivatives of two dihydrodiols in protein binding. Proc. Natl. Acad Sci. U.S.A. 77, 6396-6400.
    • (1980) Proc. Natl. Acad Sci. U.S.A. , vol.77 , pp. 6396-6400
    • MacLeod, M.C.1    Kootstra, A.2    Mansfield, B.K.3    Slaga, T.J.4    Selkirk, J.K.5


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