메뉴 건너뛰기




Volumn 23, Issue 6, 2010, Pages 1089-1096

Detection of 7-(2′-Carboxyethyl)guanine but not 7- carboxymethylguanine in human liver DNA

Author keywords

[No Author keywords available]

Indexed keywords

3 (METHYLNITROSAMINO)PROPIONIC ACID; 7 (2' CARBOXYETHYL)GUANINE; 7 GUANINEACETIC ACID; ACETIC ACID DERIVATIVE; ACETYL CHLORIDE; ACRYLIC ACID; DNA; ESTER DERIVATIVE; GUANINE DERIVATIVE; METHANOL; N NITROSOSARCOSINE; NITROGEN 15; PROPIONIC ACID DERIVATIVE; PROTEIN HYDROLYSATE; SARCOSINE; UNCLASSIFIED DRUG; 7-CARBOXYMETHYLGUANINE; DNA ADDUCT; GUANINE;

EID: 77953748361     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx100062v     Document Type: Article
Times cited : (20)

References (55)
  • 1
    • 38949209776 scopus 로고    scopus 로고
    • Biological properties of single chemical-DNA adducts: A twenty year perspective
    • Delaney, J. C. and Essigmann, J. M. (2008) Biological properties of single chemical-DNA adducts: a twenty year perspective Chem. Res. Toxicol. 21, 232-252
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 232-252
    • Delaney, J.C.1    Essigmann, J.M.2
  • 2
    • 0037152628 scopus 로고    scopus 로고
    • Tobacco smoke carcinogens, DNA damage and p53 mutations in smoking-associated cancers
    • Pfeifer, G. P., Denissenko, M. F., Olivier, M., Tretyakova, N., Hecht, S. S., and Hainaut, P. (2002) Tobacco smoke carcinogens, DNA damage and p53 mutations in smoking-associated cancers Oncogene 21, 7435-7451
    • (2002) Oncogene , vol.21 , pp. 7435-7451
    • Pfeifer, G.P.1    Denissenko, M.F.2    Olivier, M.3    Tretyakova, N.4    Hecht, S.S.5    Hainaut, P.6
  • 5
    • 33746530663 scopus 로고
    • Some N -nitroso Compounds
    • International Agency for Research on Cancer. IARC, Lyon, France
    • International Agency for Research on Cancer. ((1978) Some N -nitroso Compounds, in IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans, Vol. 17, pp 83 - 124, IARC, Lyon, France.
    • (1978) IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans , vol.17 , pp. 83-124
  • 6
    • 0030783061 scopus 로고    scopus 로고
    • N-nitroso compounds and man: Sources of exposure, endogenous formation and occurrence in body fluids
    • Tricker, A. R. (1997) N-nitroso compounds and man: sources of exposure, endogenous formation and occurrence in body fluids Eur. J. Cancer Prev. 6, 226-268
    • (1997) Eur. J. Cancer Prev. , vol.6 , pp. 226-268
    • Tricker, A.R.1
  • 7
    • 0038522158 scopus 로고    scopus 로고
    • U.S. Department of Health and Human Services
    • U.S. Department of Health and Human Services. ((2002) 10th Report on Carcinogens.
    • (2002) 10th Report on Carcinogens
  • 8
    • 0020055282 scopus 로고
    • Monitoring N-nitrosamino acids excreted in the urine and feces of rats as an index for endogenous nitrosation
    • Ohshima, H., Bereziat, J. C., and Bartsch, H. (1982) Monitoring N-nitrosamino acids excreted in the urine and feces of rats as an index for endogenous nitrosation Carcinogenesis 3, 115-120
    • (1982) Carcinogenesis , vol.3 , pp. 115-120
    • Ohshima, H.1    Bereziat, J.C.2    Bartsch, H.3
  • 9
    • 0002624810 scopus 로고
    • N -Nitroso Carcinogens
    • 2nd ed. (Searle, C. E., Ed.), ACS Monograph 182, American Chemical Society, Washington, DC
    • Preussmann, R. and Stewart, B. W. (1984) N -Nitroso Carcinogens, in Chemical Carcinogens, 2nd ed. (Searle, C. E., Ed.), ACS Monograph 182, Vol. 2, pp 643 - 828, American Chemical Society, Washington, DC.
    • (1984) Chemical Carcinogens , vol.2 , pp. 643-828
    • Preussmann, R.1    Stewart, B.W.2
  • 10
    • 0020048127 scopus 로고
    • Identification of 7-carboxymethylguanine in DNA from pancreatic acinar cells exposed to azaserine
    • Zurlo, J., Curphey, T. J., Hiley, R., and Longnecker, D. S. (1982) Identification of 7-carboxymethylguanine in DNA from pancreatic acinar cells exposed to azaserine Cancer Res. 42, 1286-1288
    • (1982) Cancer Res. , vol.42 , pp. 1286-1288
    • Zurlo, J.1    Curphey, T.J.2    Hiley, R.3    Longnecker, D.S.4
  • 12
    • 0032936961 scopus 로고    scopus 로고
    • 6-methyl-2′-deoxyguanosine in DNA exposed to nitrosated glycine derivatives using a combined immunoaffinity/HPLC method
    • 6-methyl-2′-deoxyguanosine in DNA exposed to nitrosated glycine derivatives using a combined immunoaffinity/HPLC method Chem. Res. Toxicol. 12, 106-111
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 106-111
    • Harrison, K.L.1    Jukes, R.2    Cooper, D.P.3    Shuker, D.E.G.4
  • 13
    • 1642412759 scopus 로고    scopus 로고
    • 6-carboxymethyl-2′-deoxyguanosine in DNA following reaction of nitric oxide with glycine and in human blood DNA using a quantitative immunoslot blot assay
    • 6-carboxymethyl-2′-deoxyguanosine in DNA following reaction of nitric oxide with glycine and in human blood DNA using a quantitative immunoslot blot assay Chem. Res. Toxicol. 17, 294-300
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 294-300
    • Cupid, B.C.1    Zeng, Z.2    Singh, R.3    Shuker, D.E.4
  • 17
    • 39749097169 scopus 로고    scopus 로고
    • Smokeless Tobacco and Tobacco-Specific Nitrosamines
    • International Agency for Research on Cancer. IARC, Lyon, France
    • International Agency for Research on Cancer. ((2007) Smokeless Tobacco and Tobacco-Specific Nitrosamines, in IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol. 89, pp 41 - 417, IARC, Lyon, France.
    • (2007) IARC Monographs on the Evaluation of Carcinogenic Risks to Humans , vol.89 , pp. 41-417
  • 20
    • 0021844402 scopus 로고
    • In vitro and in vivo formation of 7-(2′-carboxyethyl)guanine from the liver carcinogen 1-nitroso-5,6-dihydrouracil and its reactions with water and methanol
    • Mirvish, S. S., Ross, A. E., Gold, B., and Drake, N. (1985) In vitro and in vivo formation of 7-(2′-carboxyethyl)guanine from the liver carcinogen 1-nitroso-5,6-dihydrouracil and its reactions with water and methanol J. Natl. Cancer Inst. 74, 1105-1110
    • (1985) J. Natl. Cancer Inst. , vol.74 , pp. 1105-1110
    • Mirvish, S.S.1    Ross, A.E.2    Gold, B.3    Drake, N.4
  • 21
    • 0028721094 scopus 로고
    • DNA Adducts of Lactones, Sultones, Acylating Agents and Acrylic Compounds
    • (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H., Eds.) International Agency for Research on Cancer, Lyon, France
    • Solomon, J. J. (1994) DNA Adducts of Lactones, Sultones, Acylating Agents and Acrylic Compounds, in DNA Adducts: Identification and Biological Significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H., Eds.) pp 179 - 198, International Agency for Research on Cancer, Lyon, France.
    • (1994) DNA Adducts: Identification and Biological Significance , pp. 179-198
    • Solomon, J.J.1
  • 23
    • 21144433997 scopus 로고    scopus 로고
    • Mass spectrometric analysis of relative levels of pyridyloxobutylation adducts formed in the reaction of DNA with a chemically activated form of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone
    • Sturla, S. J., Scott, J., Lao, Y., Hecht, S. S., and Villalta, P. W. (2005) Mass spectrometric analysis of relative levels of pyridyloxobutylation adducts formed in the reaction of DNA with a chemically activated form of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone Chem. Res. Toxicol. 18, 1048-1055
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 1048-1055
    • Sturla, S.J.1    Scott, J.2    Lao, Y.3    Hecht, S.S.4    Villalta, P.W.5
  • 24
    • 35848970068 scopus 로고    scopus 로고
    • Liquid chromatography-electrospray ionization tandem mass spectrometry analysis of 7-ethylguanine in human liver DNA
    • Chen, L., Wang, M., Villalta, P. W., and Hecht, S. S. (2007) Liquid chromatography-electrospray ionization tandem mass spectrometry analysis of 7-ethylguanine in human liver DNA Chem. Res. Toxicol. 20, 1498-1502
    • (2007) Chem. Res. Toxicol. , vol.20 , pp. 1498-1502
    • Chen, L.1    Wang, M.2    Villalta, P.W.3    Hecht, S.S.4
  • 25
    • 0024549718 scopus 로고
    • Detection of exocyclic guanine adducts in hydrolysates of hepatic DNA of rats treated with N -nitrosopyrrolidine and in calf thymus DNA reacted with α-acetoxy- N -nitrosopyrrolidine
    • Chung, F. L., Wang, M., and Hecht, S. S. (1989) Detection of exocyclic guanine adducts in hydrolysates of hepatic DNA of rats treated with N -nitrosopyrrolidine and in calf thymus DNA reacted with α-acetoxy- N -nitrosopyrrolidine Cancer Res. 49, 2034-2041
    • (1989) Cancer Res. , vol.49 , pp. 2034-2041
    • Chung, F.L.1    Wang, M.2    Hecht, S.S.3
  • 26
    • 0018911059 scopus 로고
    • The biotransformation of allyl alcohol and acrolein in rat liver and lung preparation
    • Patel, J. M., Wood, J. C., and Leibman, K. C. (1980) The biotransformation of allyl alcohol and acrolein in rat liver and lung preparation Drug Metab. Dispos. 8, 305-308
    • (1980) Drug Metab. Dispos. , vol.8 , pp. 305-308
    • Patel, J.M.1    Wood, J.C.2    Leibman, K.C.3
  • 27
    • 0030065406 scopus 로고    scopus 로고
    • Biotransformation of acrolein in rat: Excretion of mercapturic acids after inhalation and intraperitoneal injection
    • Linhart, I., Frantik, E., Vodickova, L., Vosmanska, M., Smejkal, J., and Mitera, J. (1996) Biotransformation of acrolein in rat: excretion of mercapturic acids after inhalation and intraperitoneal injection Toxicol. Appl. Pharmacol. 136, 155-160
    • (1996) Toxicol. Appl. Pharmacol. , vol.136 , pp. 155-160
    • Linhart, I.1    Frantik, E.2    Vodickova, L.3    Vosmanska, M.4    Smejkal, J.5    Mitera, J.6
  • 30
    • 0033257464 scopus 로고    scopus 로고
    • 2-Propanodeoxyguanosine Adducts As Endogenous DNA Lesions in Rodents and Humans
    • (Singer, B. and Bartsch, H., Eds.) International Agency for Research on Cancer, Lyon, France
    • 2-Propanodeoxyguanosine Adducts As Endogenous DNA Lesions in Rodents and Humans, in Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis (Singer, B. and Bartsch, H., Eds.), pp 45 - 54, International Agency for Research on Cancer, Lyon, France.
    • (1999) Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis , pp. 45-54
    • Chung, F.L.1    Zhang, L.2    Ocando, J.E.3    Nath, R.G.4
  • 31
    • 0029420650 scopus 로고
    • Acrolein
    • International Agency for Research on Cancer. IARC, Lyon, France
    • International Agency for Research on Cancer. ((1995) Acrolein, in IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol. 63, pp 337 - 372, IARC, Lyon, France.
    • (1995) IARC Monographs on the Evaluation of Carcinogenic Risks to Humans , vol.63 , pp. 337-372
  • 32
    • 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
  • 34
    • 0029664516 scopus 로고    scopus 로고
    • 2-propanodeoxyguanosine adducts as potential endogenous DNA lesions in rodent and human tissues
    • 2-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
  • 35
    • 0032518993 scopus 로고    scopus 로고
    • 2-Propanodeoxyguanosine adducts: Potential new biomarkers of smoking-induced DNA damage in human oral tissue
    • 2-Propanodeoxyguanosine adducts: Potential new biomarkers of smoking-induced DNA damage in human oral tissue Cancer Res. 58, 581-584
    • (1998) Cancer Res. , vol.58 , pp. 581-584
    • Nath, R.G.1    Ocando, J.E.2    Guttenplan, J.B.3    Chung, F.L.4
  • 38
    • 24944565214 scopus 로고    scopus 로고
    • Development of a method for quantification of acrolein-deoxyguanosine adducts in DNA using isotope dilution-capillary LC/MS/MS and its application to human brain tissue
    • Liu, X., Lovell, M. A., and Lynn, B. C. (2005) Development of a method for quantification of acrolein-deoxyguanosine adducts in DNA using isotope dilution-capillary LC/MS/MS and its application to human brain tissue Anal. Chem. 77, 5982-5989
    • (2005) Anal. Chem. , vol.77 , pp. 5982-5989
    • Liu, X.1    Lovell, M.A.2    Lynn, B.C.3
  • 39
    • 34248524522 scopus 로고    scopus 로고
    • 2- propanodeoxyguanosine adducts in human lung by liquid chromatography- electrospray ionization-tandem mass spectrometry
    • 2-propanodeoxyguanosine adducts in human lung by liquid chromatography-electrospray ionization-tandem mass spectrometry Chem. Res. Toxicol. 20, 565-571
    • (2007) Chem. Res. Toxicol. , vol.20 , pp. 565-571
    • Zhang, S.1    Villalta, P.W.2    Wang, M.3    Hecht, S.S.4
  • 40
    • 0000063228 scopus 로고    scopus 로고
    • Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide (Part Two)
    • International Agency for Research on Cancer. IARC, Lyon, France
    • International Agency for Research on Cancer. ((1999) Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide (Part Two), in IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol. 71, pp 1223 - 1230, IARC, Lyon, France.
    • (1999) IARC Monographs on the Evaluation of Carcinogenic Risks to Humans , vol.71 , pp. 1223-1230
  • 41
    • 34547638065 scopus 로고    scopus 로고
    • Quantitation of acrolein-derived 3-hydroxypropylmercapturic acid in human urine by liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry: Effects of cigarette smoking
    • Carmella, S. G., Chen, M., Zhang, Y., Zhang, S., Hatsukami, D. K., and Hecht, S. S. (2007) Quantitation of acrolein-derived 3-hydroxypropylmercapturic acid in human urine by liquid chromatography-atmospheric pressure chemical ionization-tandem mass spectrometry: effects of cigarette smoking Chem. Res. Toxicol. 20, 986-990
    • (2007) Chem. Res. Toxicol. , vol.20 , pp. 986-990
    • Carmella, S.G.1    Chen, M.2    Zhang, Y.3    Zhang, S.4    Hatsukami, D.K.5    Hecht, S.S.6
  • 43
    • 0037683511 scopus 로고    scopus 로고
    • Sensitive method for the quantification of urinary pyrimidine metabolites in healthy adults by gas chromatography-tandem mass spectrometry
    • Hormann, U., Schwab, M., Seefried, S., Marx, C., Zanger, U. M., Eichelbaum, M., and Mürdter, T. E. (2003) Sensitive method for the quantification of urinary pyrimidine metabolites in healthy adults by gas chromatography-tandem mass spectrometry J. Chromatogr., B 791, 371-380
    • (2003) J. Chromatogr., B , vol.791 , pp. 371-380
    • Hormann, U.1    Schwab, M.2    Seefried, S.3    Marx, C.4    Zanger, U.M.5    Eichelbaum, M.6    Mürdter, T.E.7
  • 44
    • 0037170817 scopus 로고    scopus 로고
    • Measurement of endogenous uracil and dihydrouracil in plasma and urine of normal subjects by liquid chromatography-tandem mass spectrometry
    • Jiang, H., Jiang, J., Hu, P., and Hu, Y. (2002) Measurement of endogenous uracil and dihydrouracil in plasma and urine of normal subjects by liquid chromatography-tandem mass spectrometry J Chromatogr., B 769, 169-176
    • (2002) J Chromatogr., B , vol.769 , pp. 169-176
    • Jiang, H.1    Jiang, J.2    Hu, P.3    Hu, Y.4
  • 45
    • 0016611279 scopus 로고
    • Formation of N -nitroso compounds: Chemistry, kinetics, and in vivo occurrence
    • Mirvish, S. S. (1975) Formation of N -nitroso compounds: chemistry, kinetics, and in vivo occurrence Toxicol. Appl. Pharmacol. 31, 325-351
    • (1975) Toxicol. Appl. Pharmacol. , vol.31 , pp. 325-351
    • Mirvish, S.S.1
  • 46
    • 0029071838 scopus 로고
    • Role of N -nitroso compounds (NOC) and N -nitrosation in etiology of gastric, esophageal, nasopharyngeal and bladder cancer and contribution to cancer of known exposures to NOC
    • Mirvish, S. S. (1995) Role of N -nitroso compounds (NOC) and N -nitrosation in etiology of gastric, esophageal, nasopharyngeal and bladder cancer and contribution to cancer of known exposures to NOC Cancer Lett. 93, 17-48
    • (1995) Cancer Lett. , vol.93 , pp. 17-48
    • Mirvish, S.S.1
  • 47
    • 0024845312 scopus 로고
    • Human exposure to endogenous N-nitroso compounds: Quantitative estimates in subjects at high risk for cancer of the oral cavity, oesophagus, stomach and urinary bladder
    • Bartsch, H., Ohshima, H., Pignatelli, B., and Calmels, S. (1989) Human exposure to endogenous N-nitroso compounds: quantitative estimates in subjects at high risk for cancer of the oral cavity, oesophagus, stomach and urinary bladder Cancer Surv. 8, 335-362
    • (1989) Cancer Surv. , vol.8 , pp. 335-362
    • Bartsch, H.1    Ohshima, H.2    Pignatelli, B.3    Calmels, S.4
  • 49
    • 34047187041 scopus 로고    scopus 로고
    • The effect of haem in red and processed meat on the endogenous formation of N -nitroso compounds in the upper gastrointestinal tract
    • Lunn, J. C., Kuhnle, G., Mai, V., Frankenfeld, C., Shuker, D. E., Glen, R. C., Goodman, J. M., Pollock, J. R., and Bingham, S. A. (2007) The effect of haem in red and processed meat on the endogenous formation of N -nitroso compounds in the upper gastrointestinal tract Carcinogenesis 28, 685-690
    • (2007) Carcinogenesis , vol.28 , pp. 685-690
    • Lunn, J.C.1    Kuhnle, G.2    Mai, V.3    Frankenfeld, C.4    Shuker, D.E.5    Glen, R.C.6    Goodman, J.M.7    Pollock, J.R.8    Bingham, S.A.9
  • 52
    • 33750217212 scopus 로고    scopus 로고
    • 2-propanodeoxyguanosine adducts in DNA from human tissues using liquid chromatography-electrsopray ionization-tandem mass spectrometry
    • 2- propanodeoxyguanosine adducts in DNA from human tissues using liquid chromatography-electrsopray ionization-tandem mass spectrometry Chem. Res. Toxicol. 19, 1386-1392
    • (2006) Chem. Res. Toxicol. , vol.19 , pp. 1386-1392
    • Zhang, S.1    Villalta, P.W.2    Wang, M.3    Hecht, S.S.4
  • 53
    • 2942523593 scopus 로고    scopus 로고
    • Endogenous DNA damage in humans: A review of quantitative data
    • De Bont, R. and van Larebeke, N. (2004) Endogenous DNA damage in humans: a review of quantitative data Mutagenesis. 19, 169-185
    • (2004) Mutagenesis. , vol.19 , pp. 169-185
    • De Bont, R.1    Van Larebeke, N.2
  • 54
    • 70350075002 scopus 로고    scopus 로고
    • Investigating the biochemical impact of DNA damage with structure-based probes: Abasic sites, photodimers, alkylation adducts, and oxidative lesions
    • Dahlmann, H. A., Vaidyanathan, V. G., and Sturla, S. J. (2009) Investigating the biochemical impact of DNA damage with structure-based probes: abasic sites, photodimers, alkylation adducts, and oxidative lesions Biochemistry 48, 9347-9359
    • (2009) Biochemistry , vol.48 , pp. 9347-9359
    • Dahlmann, H.A.1    Vaidyanathan, V.G.2    Sturla, S.J.3
  • 55
    • 0021398955 scopus 로고
    • Mutational specificity of depurination
    • Kunkel, T. A. (1984) Mutational specificity of depurination Proc. Natl. Acad. Sci. U.S.A. 81, 1494-1498
    • (1984) Proc. Natl. Acad. Sci. U.S.A. , vol.81 , pp. 1494-1498
    • Kunkel, T.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.