메뉴 건너뛰기




Volumn 47, Issue 7, 2009, Pages 1075-1081

Depurinating naphthalene-DNA adducts in mouse skin related to cancer initiation

Author keywords

1,2 Naphthalene quinone ultimate carcinogenic metabolite; Depurinating naphthalene DNA adducts; Metabolic activation of naphthalene; Naphthalene; Stable naphthalene DNA adducts

Indexed keywords

1 NAPHTHOL; 1,2 DIHYDRODIOLNAPHTHALENE; 1,2 NAPHTHALENEDIOL; 1,2 NAPHTHOQUINONE; DEOXYRIBONUCLEOTIDE; NAPHTHALENE; PHOSPHORUS 32; UNCLASSIFIED DRUG;

EID: 69249210944     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2009.07.020     Document Type: Article
Times cited : (31)

References (41)
  • 6
    • 0003530301 scopus 로고
    • Toxicology and carcinogenesis studies of naphthalene (CAS No. 91-20-3) in B6C3F1 mice (inhalation studies)
    • National Toxicology Program NTP, NIH Publication No. 92-3141; Research Triangle Park, NC: U.S. Department of Health and Human Services, Public Health Service, National Institutes of Health;
    • National Toxicology Program (NTP). Toxicology and carcinogenesis studies of naphthalene (CAS No. 91-20-3) in B6C3F1 mice (inhalation studies). Technical Report Series No. 410, NIH Publication No. 92-3141; Research Triangle Park, NC: U.S. Department of Health and Human Services, Public Health Service, National Institutes of Health; 1992.
    • (1992) Technical Report Series No , vol.410
  • 8
    • 0034751637 scopus 로고    scopus 로고
    • Toxicity and carcinogenicity study in F344 rats following 2 years of whole-body exposure to naphthalene vapors
    • Abdo K.M., Grumbein S., Chou B.J., and Herbert R. Toxicity and carcinogenicity study in F344 rats following 2 years of whole-body exposure to naphthalene vapors. Inhal. Toxicol. 13 (2001) 931-950
    • (2001) Inhal. Toxicol. , vol.13 , pp. 931-950
    • Abdo, K.M.1    Grumbein, S.2    Chou, B.J.3    Herbert, R.4
  • 9
    • 0003433212 scopus 로고    scopus 로고
    • Toxicology and carcinogenesis studies of naphthalene (CAS No. 91-20-3) in F344/N rats (inhalation studies)
    • National Toxicology Program NTP, NIH publication No. 01-4434, Research Triangle Park, NC
    • National Toxicology Program (NTP). Toxicology and carcinogenesis studies of naphthalene (CAS No. 91-20-3) in F344/N rats (inhalation studies). CNTP Technical Report Series No. 500; NIH publication No. 01-4434, Research Triangle Park, NC. 2000
    • (2000) CNTP Technical Report Series No , vol.500
  • 11
    • 0023232528 scopus 로고
    • Stereoselectivity of naphthalene epoxidation by mouse, rat and hamster pulmonary, hepatic and renal microsomal enzymes
    • Buckpitt A.R., Castagnoli N., Nelson S.D., Jones A.D., and Bahnson L.S. Stereoselectivity of naphthalene epoxidation by mouse, rat and hamster pulmonary, hepatic and renal microsomal enzymes. Drug Metab. Dispos. 15 (1987) 491-498
    • (1987) Drug Metab. Dispos. , vol.15 , pp. 491-498
    • Buckpitt, A.R.1    Castagnoli, N.2    Nelson, S.D.3    Jones, A.D.4    Bahnson, L.S.5
  • 12
    • 0014934298 scopus 로고
    • 1,2-Naphthalene oxide as an intermediate in the microsomal hydroxylation of naphthalene
    • Jerina D.M., Daly J.W., Witkop B., Zaltzman-Nirenberg Z., and Udenfriend S. 1,2-Naphthalene oxide as an intermediate in the microsomal hydroxylation of naphthalene. Biochemistry 9 (1970) 147-156
    • (1970) Biochemistry , vol.9 , pp. 147-156
    • Jerina, D.M.1    Daly, J.W.2    Witkop, B.3    Zaltzman-Nirenberg, Z.4    Udenfriend, S.5
  • 14
    • 0026057999 scopus 로고
    • Metabolism and cytotoxicity of naphthalene oxide in the isolated perfused mouse lung
    • Kanekal S., Plopper C., Morin D., and Buckpitt A. Metabolism and cytotoxicity of naphthalene oxide in the isolated perfused mouse lung. J. Pharmacol. Exp. Ther. 256 (1991) 391-401
    • (1991) J. Pharmacol. Exp. Ther. , vol.256 , pp. 391-401
    • Kanekal, S.1    Plopper, C.2    Morin, D.3    Buckpitt, A.4
  • 15
    • 0022922042 scopus 로고
    • Naphthalene metabolism by human lung microsomal enzymes
    • Buckpitt A.R., and Bahnson L.S. Naphthalene metabolism by human lung microsomal enzymes. Toxicology 41 (1986) 333-341
    • (1986) Toxicology , vol.41 , pp. 333-341
    • Buckpitt, A.R.1    Bahnson, L.S.2
  • 16
    • 0027375818 scopus 로고
    • An investigation of the formation of cytotoxic, genotoxic, protein-reactive and stable metabolites from naphthalene by human liver microsomes
    • Tingle M.D., Pirmohamed M., Templeton E., Wilson A.S., Madden S., Kitteringham N.R., and Park B.K. An investigation of the formation of cytotoxic, genotoxic, protein-reactive and stable metabolites from naphthalene by human liver microsomes. Biochem. Pharmacol. 46 (1993) 1529-1538
    • (1993) Biochem. Pharmacol. , vol.46 , pp. 1529-1538
    • Tingle, M.D.1    Pirmohamed, M.2    Templeton, E.3    Wilson, A.S.4    Madden, S.5    Kitteringham, N.R.6    Park, B.K.7
  • 17
    • 0023907050 scopus 로고
    • Spectroscopic identification of ortho-quinones as the products of polycyclic aromatic trans-dihydrodiol oxidation catalyzed by dihydrodiol dehydrogenase
    • Smithgall T.E., Harvey R.G., and Penning T.M. Spectroscopic identification of ortho-quinones as the products of polycyclic aromatic trans-dihydrodiol oxidation catalyzed by dihydrodiol dehydrogenase. J. Biol. Chem. 263 (1988) 1814-1820
    • (1988) J. Biol. Chem. , vol.263 , pp. 1814-1820
    • Smithgall, T.E.1    Harvey, R.G.2    Penning, T.M.3
  • 18
    • 0028361550 scopus 로고
    • A comparative study of the kinetics and bioavailability of pure and soil-absorbed naphthalene in dermally exposed male rats
    • Turkall R.M., Skowronski G.A., Kadry A.M., and Abdel-Rahman M.S. A comparative study of the kinetics and bioavailability of pure and soil-absorbed naphthalene in dermally exposed male rats. Arch. Environ. Toxicol. 26 (1994) 504-509
    • (1994) Arch. Environ. Toxicol. , vol.26 , pp. 504-509
    • Turkall, R.M.1    Skowronski, G.A.2    Kadry, A.M.3    Abdel-Rahman, M.S.4
  • 19
    • 0021987813 scopus 로고
    • Catabolism of premercapturic acid pathway metabolites of naphthalene to naphthols and methylthio-containing metabolites in rats
    • Bakke J., Struble C., Gustafsson J.-Å., and Gustafsson B. Catabolism of premercapturic acid pathway metabolites of naphthalene to naphthols and methylthio-containing metabolites in rats. Biochemistry 82 (1985) 668-671
    • (1985) Biochemistry , vol.82 , pp. 668-671
    • Bakke, J.1    Struble, C.2    Gustafsson, J.-Å.3    Gustafsson, B.4
  • 20
    • 0021839442 scopus 로고
    • Cytochrome P-450 dependent metabolic activation of 1-naphthol to naphthoquinones and covalent binding species
    • d'Arcy Doherty M., Makowski R., Gibson G.G., and Cohen G.M. Cytochrome P-450 dependent metabolic activation of 1-naphthol to naphthoquinones and covalent binding species. Biochem. Pharmacol. 34 (1985) 2261-2267
    • (1985) Biochem. Pharmacol. , vol.34 , pp. 2261-2267
    • d'Arcy Doherty, M.1    Makowski, R.2    Gibson, G.G.3    Cohen, G.M.4
  • 22
    • 33846868665 scopus 로고    scopus 로고
    • Formation of depurinating N3adenine and N7guanine adducts after reaction of 1,2-naphthoquinone or enzyme-activated 1,2-dihydroxynaphthalene with DNA. Implications for the mechanism of tumor initiation by naphthalene
    • Saeed M., Higginbotham S., Rogan E., and Cavalieri E. Formation of depurinating N3adenine and N7guanine adducts after reaction of 1,2-naphthoquinone or enzyme-activated 1,2-dihydroxynaphthalene with DNA. Implications for the mechanism of tumor initiation by naphthalene. Chem.-Biol. Interact. 165 (2007) 175-188
    • (2007) Chem.-Biol. Interact. , vol.165 , pp. 175-188
    • Saeed, M.1    Higginbotham, S.2    Rogan, E.3    Cavalieri, E.4
  • 23
    • 33845551079 scopus 로고
    • Efficient synthesis of non-K-region trans-dihydro diols of polycyclic aromatic hydrocarbons from o-quinones and catechols
    • Platt K.L., and Oesch F. Efficient synthesis of non-K-region trans-dihydro diols of polycyclic aromatic hydrocarbons from o-quinones and catechols. J. Org. Chem. 48 (1983) 265-268
    • (1983) J. Org. Chem. , vol.48 , pp. 265-268
    • Platt, K.L.1    Oesch, F.2
  • 25
    • 0036006440 scopus 로고    scopus 로고
    • 32P-Postlabeling/polyacrylamide gel electrophoresis analysis: application to the detection of DNA adducts
    • 32P-Postlabeling/polyacrylamide gel electrophoresis analysis: application to the detection of DNA adducts. Chem. Res. Toxicol. 15 (2002) 305-311
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 305-311
    • Terashima, I.1    Suzuki, N.2
  • 27
    • 26844489382 scopus 로고    scopus 로고
    • Determination of dihydroxynaphthalenes in human urine by gas chromatography-mass spectrometry
    • Wu R., Waidyanatha S., Henderson A.P., Serdar B., Zheng Y., and Rappaport S.M. Determination of dihydroxynaphthalenes in human urine by gas chromatography-mass spectrometry. J. Chromatogr. B 826 (2005) 206-213
    • (2005) J. Chromatogr. B , vol.826 , pp. 206-213
    • Wu, R.1    Waidyanatha, S.2    Henderson, A.P.3    Serdar, B.4    Zheng, Y.5    Rappaport, S.M.6
  • 28
    • 0002492927 scopus 로고    scopus 로고
    • Mechanisms of tumor initiation by polycyclic aromatic hydrocarbons in mammals
    • Neilson A.H. (Ed), Springer-Verlag, Heidelberg
    • Cavalieri E., and Rogan E. Mechanisms of tumor initiation by polycyclic aromatic hydrocarbons in mammals. In: Neilson A.H. (Ed). The handbook of environmental chemistry. PAHs and related compounds vol. 3J (1998), Springer-Verlag, Heidelberg 81-117
    • (1998) The handbook of environmental chemistry. PAHs and related compounds , vol.3 J , pp. 81-117
    • Cavalieri, E.1    Rogan, E.2
  • 31
    • 31844450313 scopus 로고    scopus 로고
    • The greater reactivity of estradiol-3,4-quinone vs estradiol-2,3-quinone with DNA in the formation of depurinating adducts: implications for tumor-initiating activity
    • Zahid M., Kohli E., Saeed M., Rogan E., and Cavalieri E. The greater reactivity of estradiol-3,4-quinone vs estradiol-2,3-quinone with DNA in the formation of depurinating adducts: implications for tumor-initiating activity. Chem. Res. Toxicol. 19 (2006) 164-172
    • (2006) Chem. Res. Toxicol. , vol.19 , pp. 164-172
    • Zahid, M.1    Kohli, E.2    Saeed, M.3    Rogan, E.4    Cavalieri, E.5
  • 32
    • 11144333530 scopus 로고    scopus 로고
    • Slow loss of deoxyribose from the N7deoxyguanosine adducts of estradiol-3,4-quinone and hexestrol-3′,4′-quinone. Implications for mutagenic activity
    • Saeed M., Zahid M., Gunselman S.J., Rogan E., and Cavalieri E. Slow loss of deoxyribose from the N7deoxyguanosine adducts of estradiol-3,4-quinone and hexestrol-3′,4′-quinone. Implications for mutagenic activity. Steroids 70 (2005) 29-35
    • (2005) Steroids , vol.70 , pp. 29-35
    • Saeed, M.1    Zahid, M.2    Gunselman, S.J.3    Rogan, E.4    Cavalieri, E.5
  • 33
    • 11144304046 scopus 로고    scopus 로고
    • Formation of the depurinating N3Adenine and N7Guanine adducts by reaction of DNA with hexestrol-3′,4′-quinone or enzyme activated 3′-hydroxyhexestrol. Implications for a unifying mechanism of tumor initiation by natural and synthetic estrogens
    • Saeed M., Gunselman S.J., Higginbotham S., Rogan E., and Cavalieri E. Formation of the depurinating N3Adenine and N7Guanine adducts by reaction of DNA with hexestrol-3′,4′-quinone or enzyme activated 3′-hydroxyhexestrol. Implications for a unifying mechanism of tumor initiation by natural and synthetic estrogens. Steroids 70 (2005) 37-45
    • (2005) Steroids , vol.70 , pp. 37-45
    • Saeed, M.1    Gunselman, S.J.2    Higginbotham, S.3    Rogan, E.4    Cavalieri, E.5
  • 34
    • 60549105044 scopus 로고    scopus 로고
    • Mechanism of metabolic activation and DNA adduct formation by the human carcinogen diethylstilbestrol: the defining link to natural estrogens
    • Saeed M., Rogan E., and Cavalieri E. Mechanism of metabolic activation and DNA adduct formation by the human carcinogen diethylstilbestrol: the defining link to natural estrogens. Int. J. Cancer 124 (2009) 1276-1284
    • (2009) Int. J. Cancer , vol.124 , pp. 1276-1284
    • Saeed, M.1    Rogan, E.2    Cavalieri, E.3
  • 35
    • 0036309549 scopus 로고    scopus 로고
    • Catechol ortho-quinones: the electrophilic compounds that form depurinating DNA adducts and could initiate cancer and other diseases
    • Cavalieri E.L., Li K.-M., Balu N., Saeed M., Devanesan P., Higginbotham S., Zhao J., Gross M.L., and Rogan E. Catechol ortho-quinones: the electrophilic compounds that form depurinating DNA adducts and could initiate cancer and other diseases. Carcinogenesis 23 (2002) 1071-1077
    • (2002) Carcinogenesis , vol.23 , pp. 1071-1077
    • Cavalieri, E.L.1    Li, K.-M.2    Balu, N.3    Saeed, M.4    Devanesan, P.5    Higginbotham, S.6    Zhao, J.7    Gross, M.L.8    Rogan, E.9
  • 36
    • 33847795224 scopus 로고    scopus 로고
    • Catechol quinones of estrogen in the initiation of breast, prostate, and other human cancers
    • Cavalieri E., and Rogan E. Catechol quinones of estrogen in the initiation of breast, prostate, and other human cancers. Ann. N. Y. Acad. Sci. 1089 (2006) 286-301
    • (2006) Ann. N. Y. Acad. Sci. , vol.1089 , pp. 286-301
    • Cavalieri, E.1    Rogan, E.2
  • 37
    • 85047695735 scopus 로고    scopus 로고
    • Evidence that a burst of DNA depurination in SENCAR mouse skin induces error-prone repair and forms mutations in the H-ras gene
    • Chakravarti D., Mailander P., Li K.-M., Higginbotham S., Zhang H., Gross M.L., Cavalieri E., and Rogan E. Evidence that a burst of DNA depurination in SENCAR mouse skin induces error-prone repair and forms mutations in the H-ras gene. Oncogene 20 (2001) 7945-7953
    • (2001) Oncogene , vol.20 , pp. 7945-7953
    • Chakravarti, D.1    Mailander, P.2    Li, K.-M.3    Higginbotham, S.4    Zhang, H.5    Gross, M.L.6    Cavalieri, E.7    Rogan, E.8
  • 38
    • 33750009769 scopus 로고    scopus 로고
    • Induction of A.T to G.C mutations by erroneous repair of depurinated DNA following estrogen treatment of the mammary gland of ACI rats
    • Mailander P.C., Meza J.L., Higginbotham S., and Chakravarti D. Induction of A.T to G.C mutations by erroneous repair of depurinated DNA following estrogen treatment of the mammary gland of ACI rats. J. Steroid Biochem. Mol. Biol. 101 (2006) 204-215
    • (2006) J. Steroid Biochem. Mol. Biol. , vol.101 , pp. 204-215
    • Mailander, P.C.1    Meza, J.L.2    Higginbotham, S.3    Chakravarti, D.4
  • 39
    • 33645462297 scopus 로고    scopus 로고
    • Mutagenic activity of 4-hydroxyestradiol, but not 2-hydroxyestradiol, in BB2 rat embryonic cells, and the mutational spectrum of 4-hydoxyestradiol
    • Zhao Z., Kosinska W., Khmelnitsky M., Cavalieri E.L., Rogan E.G., Chakravarti D., Sacks P., and Guttenplan J.B. Mutagenic activity of 4-hydroxyestradiol, but not 2-hydroxyestradiol, in BB2 rat embryonic cells, and the mutational spectrum of 4-hydoxyestradiol. Chem. Res. Toxicol. 19 (2006) 475-479
    • (2006) Chem. Res. Toxicol. , vol.19 , pp. 475-479
    • Zhao, Z.1    Kosinska, W.2    Khmelnitsky, M.3    Cavalieri, E.L.4    Rogan, E.G.5    Chakravarti, D.6    Sacks, P.7    Guttenplan, J.B.8
  • 41
    • 0034736284 scopus 로고    scopus 로고
    • Evidence that error-prone DNA repair converts dibenzo[a,l]pyrene-induced depurinating lesions into mutations: formation, clonal proliferation and regression of initiated cells carrying H-ras oncogene mutations in early preneoplasia
    • Chakravarti D., Mailander P.C., Cavalieri E.L., and Rogan E.G. Evidence that error-prone DNA repair converts dibenzo[a,l]pyrene-induced depurinating lesions into mutations: formation, clonal proliferation and regression of initiated cells carrying H-ras oncogene mutations in early preneoplasia. Mutat. Res. 456 (2000) 17-32
    • (2000) Mutat. Res. , vol.456 , pp. 17-32
    • Chakravarti, D.1    Mailander, P.C.2    Cavalieri, E.L.3    Rogan, E.G.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.