메뉴 건너뛰기




Volumn 16, Issue 4, 2003, Pages 541-550

K-ras gene sequence effects on the formation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-DNA adducts

Author keywords

[No Author keywords available]

Indexed keywords

4 (METHYLNITROSAMINO) 1 (3 PYRIDYL) 1 BUTANONE; 6 O [4 OXO 4 (3 PYRIDYL)BUTYL]GUANINE; 6 O METHYLGUANINE; 7 METHYLGUANINE; ADENINE; CARCINOGEN; GUANINE; THYMINE; UNCLASSIFIED DRUG;

EID: 0242417425     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx025619o     Document Type: Article
Times cited : (42)

References (48)
  • 1
    • 0018889232 scopus 로고
    • Comparative carcinogenicity in F344 rats of the tobacco-specific nitrosamines, N′-nitrosonornicotine and 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone
    • Hecht, S. S., Chen, C. B., Ohmori, T., and Hoffmann, D. (1980) Comparative carcinogenicity in F344 rats of the tobacco-specific nitrosamines, N′-nitrosonornicotine and 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res. 40, 298-302.
    • (1980) Cancer Res. , vol.40 , pp. 298-302
    • Hecht, S.S.1    Chen, C.B.2    Ohmori, T.3    Hoffmann, D.4
  • 2
    • 0033591845 scopus 로고    scopus 로고
    • Tobacco smoke carcinogens and lung cancer
    • Hecht, S. S. (1999) Tobacco smoke carcinogens and lung cancer. J. Natl. Cancer Inst. 91, 1194-1210.
    • (1999) J. Natl. Cancer Inst. , vol.91 , pp. 1194-1210
    • Hecht, S.S.1
  • 3
    • 0031831381 scopus 로고    scopus 로고
    • Biochemistry, biology, and carcinogenicity of tobacco-specific N-nitrosamines
    • Hecht, S. S. (1998) Biochemistry, biology, and carcinogenicity of tobacco-specific N-nitrosamines. Chem. Res. Toxicol. 11, 559-603.
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 559-603
    • Hecht, S.S.1
  • 4
    • 0033535375 scopus 로고    scopus 로고
    • DNA adduct formation from tobacco-specific N-nitrosamines
    • Hecht, S. S. (1999) DNA adduct formation from tobacco-specific N-nitrosamines. Mutat. Res. 424, 127-142.
    • (1999) Mutat. Res. , vol.424 , pp. 127-142
    • Hecht, S.S.1
  • 6
    • 0021505055 scopus 로고
    • In vivo mutagenesis by O6-methylguanine built into a unique site in a viral genome
    • Loechler, E. L., Green, C. L., and Essigmann, J. M. (1984) In vivo mutagenesis by O6-methylguanine built into a unique site in a viral genome. Proc. Natl. Acad. Sci. U.S.A. 81, 6271-6275.
    • (1984) Proc. Natl. Acad. Sci. U.S.A. , vol.81 , pp. 6271-6275
    • Loechler, E.L.1    Green, C.L.2    Essigmann, J.M.3
  • 7
    • 0021287519 scopus 로고
    • Mechanism of mutagenesis by O6-methylguanine
    • Eadie, J. S., Conrad, M., Toorchen, D., and Topal, M. D. (1984) Mechanism of mutagenesis by O6-methylguanine. Nature 308, 201-203.
    • (1984) Nature , vol.308 , pp. 201-203
    • Eadie, J.S.1    Conrad, M.2    Toorchen, D.3    Topal, M.D.4
  • 8
    • 0025831694 scopus 로고
    • Site-specific mutagenesis: Retrospective and prospective
    • Singer, B., and Essigmann, J. M. (1991) Site-specific mutagenesis: retrospective and prospective. Carcinogenesis 12, 949-955.
    • (1991) Carcinogenesis , vol.12 , pp. 949-955
    • Singer, B.1    Essigmann, J.M.2
  • 12
    • 0035422061 scopus 로고    scopus 로고
    • Interactions between methylating and pyridyloxobutylating agents in A/J mouse lungs: Implications for 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced lung tumorigenesis
    • Peterson, L. A., Thomson, N. M., Crankshaw, D. L., Donaldson, E. E., and Kenney, P. J. (2001) Interactions between methylating and pyridyloxobutylating agents in A/J mouse lungs: implications for 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced lung tumorigenesis. Cancer Res. 61, 5757-5763.
    • (2001) Cancer Res. , vol.61 , pp. 5757-5763
    • Peterson, L.A.1    Thomson, N.M.2    Crankshaw, D.L.3    Donaldson, E.E.4    Kenney, P.J.5
  • 15
    • 0028292587 scopus 로고
    • Mechanism of mutation on DNA templates containing synthetic abasic sites: Study with a double strand vector
    • Takeshita, M., and Eisenberg, W. (1994) Mechanism of mutation on DNA templates containing synthetic abasic sites: study with a double strand vector. Nucleic Acids Res. 22, 1897-1902.
    • (1994) Nucleic Acids Res. , vol.22 , pp. 1897-1902
    • Takeshita, M.1    Eisenberg, W.2
  • 16
    • 0037133706 scopus 로고    scopus 로고
    • Quantitative measurement of translesion replication in human cells: Evidence for bypass of abasic sites by a replicative DNA polymerase
    • Avkin, S., Adar, S., Blander, G., and Livneh, Z. (2002) Quantitative measurement of translesion replication in human cells: evidence for bypass of abasic sites by a replicative DNA polymerase. Proc. Natl. Acad. Sci. U.S.A. 99, 3764-3769.
    • (2002) Proc. Natl. Acad. Sci. U.S.A. , vol.99 , pp. 3764-3769
    • Avkin, S.1    Adar, S.2    Blander, G.3    Livneh, Z.4
  • 17
    • 0025297169 scopus 로고
    • 6-methylguanine formation in Clara cells and induction of pulmonary neoplasia in the rat by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone
    • 6-methylguanine formation in Clara cells and induction of pulmonary neoplasia in the rat by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res. 50, 3772-3780.
    • (1990) Cancer Res. , vol.50 , pp. 3772-3780
    • Belinsky, S.A.1    Foley, J.F.2    White, C.M.3    Anderson, M.W.4    Maronpot, R.R.5
  • 18
    • 0025925258 scopus 로고
    • 6-methylguanine is a critical determinant of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone tumorigenesis in A/J mouse lung
    • 6-methylguanine is a critical determinant of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone tumorigenesis in A/J mouse lung. Cancer Res. 51, 5557-5564.
    • (1991) Cancer Res. , vol.51 , pp. 5557-5564
    • Peterson, L.A.1    Hecht, S.S.2
  • 19
    • 0023707058 scopus 로고
    • Incidence and possible clinical significance of K-ras oncogene activation in adenocarcinoma of the human lung
    • Rodenhuis, S., Slebos, R. J., Boot, A. J., Evers, S. G., Mooi, W. J., Wagenaar, S. S., van Bodegom, P. C., and Bos, J. L. (1988) Incidence and possible clinical significance of K-ras oncogene activation in adenocarcinoma of the human lung. Cancer Res. 48, 5738-5741.
    • (1988) Cancer Res. , vol.48 , pp. 5738-5741
    • Rodenhuis, S.1    Slebos, R.J.2    Boot, A.J.3    Evers, S.G.4    Mooi, W.J.5    Wagenaar, S.S.6    Van Bodegom, P.C.7    Bos, J.L.8
  • 20
    • 0026680448 scopus 로고
    • Clinical significance of ras oncogene activation in human lung cancer
    • Rodenhuis, S., and Slebos, R. J. (1992) Clinical significance of ras oncogene activation in human lung cancer. Cancer Res. 52, 2665s-2669s.
    • (1992) Cancer Res. , vol.52
    • Rodenhuis, S.1    Slebos, R.J.2
  • 22
    • 0027166695 scopus 로고
    • K-ras oncogene activation in lung adenocarcinomas from former smokers. Evidence that K-ras mutations are an early and irreversible event in the development of adenocarcinoma of the lung
    • Westra, W. H., Slebos, R. J., Offerhaus, G. J., Goodman, S. N., Evers, S. G., Kensler, T. W., Askin, F. B., Rodenhuis, S., and Hruban, R. H. (1993) K-ras oncogene activation in lung adenocarcinomas from former smokers. Evidence that K-ras mutations are an early and irreversible event in the development of adenocarcinoma of the lung. Cancer 72, 432-438.
    • (1993) Cancer , vol.72 , pp. 432-438
    • Westra, W.H.1    Slebos, R.J.2    Offerhaus, G.J.3    Goodman, S.N.4    Evers, S.G.5    Kensler, T.W.6    Askin, F.B.7    Rodenhuis, S.8    Hruban, R.H.9
  • 23
    • 0028958222 scopus 로고
    • Increased prevalence of K-ras oncogene mutations in lung adenocarcinoma
    • Mills, N. E., Fishman, C. L., Rom, W. N., Dubin, N., and Jacobson, D. R. (1995) Increased prevalence of K-ras oncogene mutations in lung adenocarcinoma. Cancer Res. 55, 1444-1447.
    • (1995) Cancer Res. , vol.55 , pp. 1444-1447
    • Mills, N.E.1    Fishman, C.L.2    Rom, W.N.3    Dubin, N.4    Jacobson, D.R.5
  • 24
  • 25
    • 0027333129 scopus 로고
    • G to A transitions and G to T transversions in codon 12 of the Ki-ras oncogene isolated from mouse lung tumors induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and related DNA methylating and pyridyloxobutylating agents
    • Ronai, Z. A., Gradia, S., Peterson, L. A., and Hecht, S. S. (1993) G to A transitions and G to T transversions in codon 12 of the Ki-ras oncogene isolated from mouse lung tumors induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and related DNA methylating and pyridyloxobutylating agents. Carcinogenesis 14, 2419-2422.
    • (1993) Carcinogenesis , vol.14 , pp. 2419-2422
    • Ronai, Z.A.1    Gradia, S.2    Peterson, L.A.3    Hecht, S.S.4
  • 26
    • 0023757136 scopus 로고
    • Sequence specificity of guanine alkylation and repair
    • Dolan, M. E., Oplinger, M., and Pegg, A. E. (1988) Sequence specificity of guanine alkylation and repair. Carcinogenesis 9, 2139-2143.
    • (1988) Carcinogenesis , vol.9 , pp. 2139-2143
    • Dolan, M.E.1    Oplinger, M.2    Pegg, A.E.3
  • 27
    • 0025743532 scopus 로고
    • DNA sequence dependence of guanine-O6 alkylation by the N-nitroso carcinogens N-methyl- and N-ethyl-N-nitrosourea
    • Sendowski, K., and Rajewsky, M. F. (1991) DNA sequence dependence of guanine-O6 alkylation by the N-nitroso carcinogens N-methyl- and N-ethyl-N-nitrosourea. Mutat. Res. 250, 153-160.
    • (1991) Mutat. Res. , vol.250 , pp. 153-160
    • Sendowski, K.1    Rajewsky, M.F.2
  • 29
    • 0032845760 scopus 로고    scopus 로고
    • Treatment of human cells with N-Nitroso(acetoxymethyl)methylamine: Distribution patterns of piperidine-sensitive DNA damage at the nucleotide level of resolution are related to the sequence context
    • Cloutier, J. F., Drouin, R., and Castonguay, A. (1999) Treatment of human cells with N-Nitroso(acetoxymethyl)methylamine: distribution patterns of piperidine-sensitive DNA damage at the nucleotide level of resolution are related to the sequence context. Chem. Res. Toxicol. 12, 840-849.
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 840-849
    • Cloutier, J.F.1    Drouin, R.2    Castonguay, A.3
  • 30
    • 0035955554 scopus 로고    scopus 로고
    • Characterization and mapping of DNA damage induced by reactive metabolites of 4 (methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) at nucleotide resolution in human genomic DNA
    • Cloutier, J. F., Drouin, R., Weinfeld, M., O'Connor, T. R., and Castonguay, A. (2001) Characterization and mapping of DNA damage induced by reactive metabolites of 4 (methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) at nucleotide resolution in human genomic DNA. J. Mol. Biol. 313, 539-557.
    • (2001) J. Mol. Biol. , vol.313 , pp. 539-557
    • Cloutier, J.F.1    Drouin, R.2    Weinfeld, M.3    O'Connor, T.R.4    Castonguay, A.5
  • 31
    • 0024476862 scopus 로고
    • 6-methyldeoxyguanosine at specific sites in a synthetic oligonucleotide designed to resemble a known mutagenic hotspot
    • 6-methyldeoxyguanosine at specific sites in a synthetic oligonucleotide designed to resemble a known mutagenic hotspot. J. Biol. Chem. 264, 838-841.
    • (1989) J. Biol. Chem. , vol.264 , pp. 838-841
    • Richardson, F.C.1    Boucheron, J.A.2    Skopek, T.R.3    Swenberg, J.A.4
  • 32
    • 0023944958 scopus 로고
    • The effect of DNA sequence, ionic strength, and cationic DNA affinity binders on the methylation of DNA by N-methyl-N-nitrosourea
    • Wurdeman, R. L., and Gold, B. (1988) The effect of DNA sequence, ionic strength, and cationic DNA affinity binders on the methylation of DNA by N-methyl-N-nitrosourea. Chem. Res. Toxicol. 1, 146-147.
    • (1988) Chem. Res. Toxicol. , vol.1 , pp. 146-147
    • Wurdeman, R.L.1    Gold, B.2
  • 33
    • 0027300960 scopus 로고
    • Use of fluorescently tagged DNA and an automated DNA sequencer for the comparison of the sequence selectivity of SN1 and SN2 alkylating agents
    • Shoukry, S., Anderson, M. W., and Glickman, B. W. (1993) Use of fluorescently tagged DNA and an automated DNA sequencer for the comparison of the sequence selectivity of SN1 and SN2 alkylating agents. Carcinogenesis 14, 155-157.
    • (1993) Carcinogenesis , vol.14 , pp. 155-157
    • Shoukry, S.1    Anderson, M.W.2    Glickman, B.W.3
  • 34
    • 0035846522 scopus 로고    scopus 로고
    • Effect of sequence context on O(6)-methylguanine repair and replication in vivo
    • Delaney, J. C., and Essigmann, J. M. (2001) Effect of sequence context on O(6)-methylguanine repair and replication in vivo. Biochemistry 40, 14968-14975.
    • (2001) Biochemistry , vol.40 , pp. 14968-14975
    • Delaney, J.C.1    Essigmann, J.M.2
  • 35
    • 0022930076 scopus 로고
    • O6-methylguanine mutation and repair is nonuniform. Selection for DNA most interactive with O6-methylguanine
    • Topal, M. D., Eadie, J. S., and Conrad, M. (1986) O6-methylguanine mutation and repair is nonuniform. Selection for DNA most interactive with O6-methylguanine. J. Biol. Chem. 261, 9879-9885.
    • (1986) J. Biol. Chem. , vol.261 , pp. 9879-9885
    • Topal, M.D.1    Eadie, J.S.2    Conrad, M.3
  • 36
    • 0026341034 scopus 로고
    • 6-methylguanine residues in different positions in and around codon 12 of rat H-ras
    • 6-methylguanine residues in different positions in and around codon 12 of rat H-ras. Cancer Res. 51, 5843-5850.
    • (1991) Cancer Res. , vol.51 , pp. 5843-5850
    • Georgiadis, P.1    Smith, C.A.2    Swann, P.F.3
  • 37
    • 0037199429 scopus 로고    scopus 로고
    • Formation of benzo[α]pyrene diol epoxide-DNA adducts at specific guanines within K-ras and p53 gene sequences: Stable isotope-labeling mass spectrometry approach
    • Tretyakova, N., Matter, B., Jones, R., and Shallop, A. (2002) Formation of Benzo[α]pyrene Diol Epoxide-DNA Adducts at Specific Guanines within K-ras and p53 Gene Sequences: Stable Isotope-Labeling Mass Spectrometry Approach. Biochemistry 41, 9535-9544.
    • (2002) Biochemistry , vol.41 , pp. 9535-9544
    • Tretyakova, N.1    Matter, B.2    Jones, R.3    Shallop, A.4
  • 39
    • 0030667517 scopus 로고    scopus 로고
    • Use of a 13C atom to differentiate two 15N-labeled nucleosides. Syntheses of [15NH2]-adenosine, [1,NH2-15N2]-, and [2-13C-1,NH2-15N2]guanosine, and [1,7,NH2-15N3]-and [2-13C-1,7,NH2-15N3]-2′-deoxyguanosine
    • Zhao, H., Pagano, A. R., Wang, W., Shallop, A., Gaffney, B., and Jones, R. A. (1997) Use of a 13C Atom to Differentiate Two 15N-labeled Nucleosides. Syntheses of [15NH2]-Adenosine, [1,NH2-15N2]-, and [2-13C-1,NH2-15N2]Guanosine, and [1,7,NH2-15N3]-and [2-13C-1,7,NH2-15N3]-2′-Deoxyguanosine. J. Org. Chem. 62, 7832-7835.
    • (1997) J. Org. Chem. , vol.62 , pp. 7832-7835
    • Zhao, H.1    Pagano, A.R.2    Wang, W.3    Shallop, A.4    Gaffney, B.5    Jones, R.A.6
  • 40
    • 0034732883 scopus 로고    scopus 로고
    • p53 mutational spectra and the role of methylated CpG sequences
    • Pfeifer, G. P. (2000) p53 mutational spectra and the role of methylated CpG sequences. Mutat. Res 450, 155-166.
    • (2000) Mutat. Res. , vol.450 , pp. 155-166
    • Pfeifer, G.P.1
  • 41
    • 0030929794 scopus 로고    scopus 로고
    • Cytosine methylation determines hot spots of DNA damage in the human P53 gene
    • Denissenko, M. F., Chen, J. X., Tang, M. S., and Pfeifer, G. P. (1997) Cytosine methylation determines hot spots of DNA damage in the human P53 gene. Proc. Natl. Acad. Sci U.S.A. 94, 3893-3898.
    • (1997) Proc. Natl. Acad. Sci U.S.A. , vol.94 , pp. 3893-3898
    • Denissenko, M.F.1    Chen, J.X.2    Tang, M.S.3    Pfeifer, G.P.4
  • 42
    • 0027181011 scopus 로고
    • Detection of DNA adducts at the DNA sequence level by ligation-mediated PCR
    • Pfeifer, G. P., Drouin, R., and Holmquist, G. P. (1993) Detection of DNA adducts at the DNA sequence level by ligation-mediated PCR. Mutat. Res. 288, 39-46.
    • (1993) Mutat. Res. , vol.288 , pp. 39-46
    • Pfeifer, G.P.1    Drouin, R.2    Holmquist, G.P.3
  • 43
    • 0034860461 scopus 로고    scopus 로고
    • Locating nucleobase lesions within DNA sequences by MALDI-TOF mass spectral analysis of exonuclease ladders
    • Tretyakova, N., Matter, B., Ogdie, A., Wishnok, J. S., and Tannenbaum, S. R. (2001) Locating Nucleobase Lesions within DNA Sequences by MALDI-TOF Mass Spectral Analysis of Exonuclease Ladders. Chem. Res. Toxicol. 14, 1058-1070.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 1058-1070
    • Tretyakova, N.1    Matter, B.2    Ogdie, A.3    Wishnok, J.S.4    Tannenbaum, S.R.5
  • 44
    • 0028784536 scopus 로고
    • Role of electrostatics in the sequenc-selective reaction of charged alkylating agents with DNA
    • Liang, G., Encell, L., Nelson, M. G., Switzer, C., Shuker, D. E. G., and Gold, B. (1995) Role of Electrostatics in the Sequenc-Selective Reaction of Charged Alkylating Agents with DNA. J Am. Chem Soc. 117, 10135-10136.
    • (1995) J. Am. Chem Soc. , vol.117 , pp. 10135-10136
    • Liang, G.1    Encell, L.2    Nelson, M.G.3    Switzer, C.4    Shuker, D.E.G.5    Gold, B.6
  • 45
    • 0030999513 scopus 로고    scopus 로고
    • Regioselective effect of zwitterionic DNA substitutions on DNA alkylation: Evidence for a strong side chain orientational preference
    • Dande, P., Liang, G., Chen, F. X., Roberts, C., Nelson, M. G., Hashimoto, H., Switzer, C., and Gold, B. (1997) Regioselective effect of zwitterionic DNA substitutions on DNA alkylation: evidence for a strong side chain orientational preference. Biochemistry 36, 6024-6032.
    • (1997) Biochemistry , vol.36 , pp. 6024-6032
    • Dande, P.1    Liang, G.2    Chen, F.X.3    Roberts, C.4    Nelson, M.G.5    Hashimoto, H.6    Switzer, C.7    Gold, B.8
  • 46
    • 0023472241 scopus 로고
    • A regioselective mechanism for mutagenesis and oncogenesis caused by alkylnitrosourea sequence-specific DNA alkylation
    • Buckley, N. (1987) A regioselective mechanism for mutagenesis and oncogenesis caused by alkylnitrosourea sequence-specific DNA alkylation. J. Am. Chem. Soc. 109, 7918-7920.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 7918-7920
    • Buckley, N.1
  • 48
    • 0033601114 scopus 로고    scopus 로고
    • Chemistry of sequence-dependent remote guanine oxidation: Photoreaction of duplex DNA containing cyanobenzophenone-substituted uridine
    • Nakatani, K., Dohno, C., and Saito, I. (1999) Chemistry of sequence-dependent remote guanine oxidation: photoreaction of duplex DNA containing cyanobenzophenone-substituted uridine. J. Am. Chem. Soc. 121, 10854-10855.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 10854-10855
    • Nakatani, K.1    Dohno, C.2    Saito, I.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.