메뉴 건너뛰기




Volumn 18, Issue 12, 2005, Pages 1955-1966

The carcinogenic significance of reactive intermediates derived from 3-acetoxy- and 5-acetoxy-2-hydroxy-N-nitrosomorpholine

Author keywords

[No Author keywords available]

Indexed keywords

1,N2 GLYOXAL; 2 ACETOXYACETALDEHYDE; 2 AMINOPURINE; 2 HYDROXYETHYLVINYLNITROSAMINE; 3 ACETOXY 2 HYDROXY N NITROSOMORPHOLINE; 5 ACETOXY 2 HYDROXY N NITROSOMORPHOLINE; 6 O HYDROXYETHYLGUANINE; 7 (2 HYDROXYETHYL)GUANINE; ACETAL; ACETALDEHYDE; ACETIC ACID; ACETIC ACID ESTER; ALDEHYDE; ALPHA ACETOXYNITROSAMINE; ALPHA HYDROXYNITROSAMINE; BASE; BIS(2 HYDROXYETHYL)NITROSAMINE; CARCINOGEN; CYTOCHROME P450; DEOXYGUANOSINE; DIAZONIUM COMPOUND; ESTER; ETHYLENE GLYCOL; GLYCOL ALDEHYDE; GLYOXAL; GUANINE DERIVATIVE; N NITROSO 2,3 DEHYDROMORPHOLINE; NITROSAMINE; NITROSOMORPHOLINE; PERACETIC ACID; UNCLASSIFIED DRUG;

EID: 29644439704     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0502037     Document Type: Article
Times cited : (14)

References (51)
  • 1
    • 0019791454 scopus 로고
    • Metabolic α-hydroxylation of N-nitrosomorpholine and 3,3,5,5-tetradeutero-N-nitrosomorpholine in the F344 rat
    • Hecht, S. S., and Young, R. (1981) Metabolic α-hydroxylation of N-nitrosomorpholine and 3,3,5,5-tetradeutero-N-nitrosomorpholine in the F344 rat. Cancer Res. 41, 5039-5043.
    • (1981) Cancer Res. , vol.41 , pp. 5039-5043
    • Hecht, S.S.1    Young, R.2
  • 2
    • 0020456826 scopus 로고
    • On the metabolic activation of N-nitrosomorpholine and N-nitrosonornicotine: Effects of deuterium substitution
    • Hecht, S. S., Young, R., Rivenson, A., and Hoffmann, D. (1982) On the metabolic activation of N-nitrosomorpholine and N-nitrosonornicotine: effects of deuterium substitution. IARC Sci. Publ. 41, 499-507.
    • (1982) IARC Sci. Publ. , vol.41 , pp. 499-507
    • Hecht, S.S.1    Young, R.2    Rivenson, A.3    Hoffmann, D.4
  • 3
    • 0021701815 scopus 로고
    • N-Nitroso-2-hydroxymorpholine, a mutagenic metabolite of N-nitrosodiethanolamine
    • Hecht, S. S. (1984) N-Nitroso-2-hydroxymorpholine, a mutagenic metabolite of N-nitrosodiethanolamine. Carcinogenesis (London) 5, 1745-1747.
    • (1984) Carcinogenesis (London) , vol.5 , pp. 1745-1747
    • Hecht, S.S.1
  • 4
    • 0020962446 scopus 로고
    • Identification of an acidic metabolite of W-nitrosodiethanolamine isolated from rat urine
    • Airoldi, L., Bonfanti, M., Benfenati, E., Tavecchia, P., and Fanelli, R. (1983) Identification of an acidic metabolite of W-nitrosodiethanolamine isolated from rat urine. Biomed. Mass Spectrom. 10, 334-337.
    • (1983) Biomed. Mass Spectrom. , vol.10 , pp. 334-337
    • Airoldi, L.1    Bonfanti, M.2    Benfenati, E.3    Tavecchia, P.4    Fanelli, R.5
  • 5
    • 0021253768 scopus 로고
    • Identification of a nitrosamino aldehyde and a nitrosamino acid resulting from β-oxidation of N-nitrosodiethanolamine
    • Airoldi, L., Bonfanti, M., Fanelli, R., Bove, B., Benfenati, E., and Gariboldi, P. (1984) Identification of a nitrosamino aldehyde and a nitrosamino acid resulting from β-oxidation of N-nitrosodiethanolamine. Chem.-Biol. Interact. 51, 103-113.
    • (1984) Chem.-Biol. Interact. , vol.51 , pp. 103-113
    • Airoldi, L.1    Bonfanti, M.2    Fanelli, R.3    Bove, B.4    Benfenati, E.5    Gariboldi, P.6
  • 6
    • 0036223206 scopus 로고    scopus 로고
    • The microsome mediated oxidation of N-nitrosodiethanolamine (NDELA), a bident carcinogen
    • Loeppky, R. N., and Goelzer, P. (2002) The microsome mediated oxidation of N-nitrosodiethanolamine (NDELA), a bident carcinogen. Chem. Res. Toxicol. 15, 457-469.
    • (2002) Chem. Res. Toxicol. , vol.15 , pp. 457-469
    • Loeppky, R.N.1    Goelzer, P.2
  • 7
    • 0024390056 scopus 로고
    • Comparative tumorigenicity of N-nitroso-2-hydroxymorpholine, N-nitrosodiethanolamine, and N-nitrosomorpholine in A/J mice and F344 rats
    • Hecht, S. S., Lijinsky, W., Kovatch, R. M., Chung, F. L., and Saavedra, J. E. (1989) Comparative tumorigenicity of N-nitroso-2-hydroxymorpholine, N-nitrosodiethanolamine, and N-nitrosomorpholine in A/J mice and F344 rats. Carcinogenesis (London) 10, 1475-1477.
    • (1989) Carcinogenesis (London) , vol.10 , pp. 1475-1477
    • Hecht, S.S.1    Lijinsky, W.2    Kovatch, R.M.3    Chung, F.L.4    Saavedra, J.E.5
  • 9
    • 0022235595 scopus 로고
    • 2-glyoxal-deoxyguanosine adduct upon reaction of N-nitroso-2-hydroxymorpholine with deoxyguanosine
    • 2-glyoxal-deoxyguanosine adduct upon reaction of N-nitroso-2- hydroxymorpholine with deoxyguanosine. Carcinogenesis (London) 6, 1671-1673.
    • (1985) Carcinogenesis (London) , vol.6 , pp. 1671-1673
    • Chung, F.L.1    Hecht, S.S.2
  • 10
    • 0023189688 scopus 로고
    • Nitroso transfer from α-nitrosamino aldehydes: Implications for carcinogenesis
    • Loeppky, R. N., Tomasik, W., and Kerrick, B. E. (1987) Nitroso transfer from α-nitrosamino aldehydes: implications for carcinogenesis. Carcinogenesis (London) 8, 941-946.
    • (1987) Carcinogenesis (London) , vol.8 , pp. 941-946
    • Loeppky, R.N.1    Tomasik, W.2    Kerrick, B.E.3
  • 12
    • 0026041693 scopus 로고
    • Mutagenicity, DNA damage and DNA adduct formation by N-nitroso-2- hydroxyalkylamine and corresponding aldehydes
    • Scherer, G., Ludeke, B., Kleihues, P., Loeppky, R. N., and Eisenbrand, G. (1991) Mutagenicity, DNA damage and DNA adduct formation by N-nitroso-2-hydroxyalkylamine and corresponding aldehydes. IARC Sci. Publ. 105, 339-342.
    • (1991) IARC Sci. Publ. , vol.105 , pp. 339-342
    • Scherer, G.1    Ludeke, B.2    Kleihues, P.3    Loeppky, R.N.4    Eisenbrand, G.5
  • 13
    • 0001843367 scopus 로고
    • Putative proximate carcinogens derived from ethanolnitrosamines: Chemical properties
    • (Bartsch, H., and O'Neill, I., Eds.), IARC, Lyon, France
    • Loeppky, R. N., Srinivasan, A., and Erb, E. (1992) Putative proximate carcinogens derived from ethanolnitrosamines: chemical properties. In Nitroso Compounds: Biological Mechanisms, Exposures and Cancer Etiology (Bartsch, H., and O'Neill, I., Eds.) pp 42a-42b, IARC, Lyon, France.
    • (1992) Nitroso Compounds: Biological Mechanisms, Exposures and Cancer Etiology
    • Loeppky, R.N.1    Srinivasan, A.2    Erb, E.3
  • 14
    • 0008855339 scopus 로고
    • The Chemistry of putative intermediates in the bioactivation of β-oxidized nitrosamines
    • (Loeppky, R. N., and Michejda, C. J., Eds.), American Chemical Society, Washington, DC
    • Loeppky, R. N., Erb, E., and Srinivasan, A. (1993) The Chemistry of putative intermediates in the bioactivation of β-oxidized nitrosamines. In The Chemistry and Biochemistry of Nitrosamines and Other N-Nitroso Compounds (Loeppky, R. N., and Michejda, C. J., Eds.) pp 334-336, American Chemical Society, Washington, DC.
    • (1993) The Chemistry and Biochemistry of Nitrosamines and Other N-Nitroso Compounds , pp. 334-336
    • Loeppky, R.N.1    Erb, E.2    Srinivasan, A.3
  • 15
    • 0003096890 scopus 로고
    • DNA modification by α-nitrosamino aldehydes
    • (Hemminki, K., and Bartsch, H., Eds.), IARC, Lyon, France
    • Loeppky, R. N., Lee, M. P., and Mueller, S. (1993) DNA modification by α-nitrosamino aldehydes. In The Chemistry of DNA Adducts (Hemminki, K., and Bartsch, H., Eds.) pp 429-432, IARC, Lyon, France.
    • (1993) The Chemistry of DNA Adducts , pp. 429-432
    • Loeppky, R.N.1    Lee, M.P.2    Mueller, S.3
  • 16
    • 0033014853 scopus 로고    scopus 로고
    • The mechanism of bioactivation of N-nitrosodiethanolamine
    • Loeppky, R. N. (1999) The mechanism of bioactivation of N-nitrosodiethanolamine. Drug Metab. Rev. 31, 175-193.
    • (1999) Drug Metab. Rev. , vol.31 , pp. 175-193
    • Loeppky, R.N.1
  • 17
    • 0034010202 scopus 로고    scopus 로고
    • In vitro DNA deamination by α-nitrosaminoaldehydes determined by GC/MS-SIM quantitation
    • Park, M., and Loeppky, R. N. (2000) In vitro DNA deamination by α-nitrosaminoaldehydes determined by GC/MS-SIM quantitation. Chem. Res. Toxicol. 13, 72-81.
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 72-81
    • Park, M.1    Loeppky, R.N.2
  • 19
    • 15344340782 scopus 로고    scopus 로고
    • 6-hydroxyethyldeoxyguanosine DNA adducts produced by nitrosamine bident carcinogens
    • 6- hydroxyethyldeoxyguanosine DNA adducts produced by nitrosamine bident carcinogens. Chem. Res. Toxicol. 18, 556-565.
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 556-565
    • Dennehy, M.K.1    Loeppky, R.N.2
  • 20
    • 0032425945 scopus 로고    scopus 로고
    • Probing the mechanism of the carcinogenic activation of N-nitrosodiethanolamine with deuterium isotope effects: In vivo induction of DNA single strand breaks and related in vitro assays
    • Loeppky, R. N., Fuchs, A., Janzowski, C., Humberd, C., Goelzer, P., Schneider, H., and Eisenbrand, G. (1998) Probing the mechanism of the carcinogenic activation of N-nitrosodiethanolamine with deuterium isotope effects: in vivo induction of DNA single strand breaks and related in vitro assays. Chem. Res. Toxicol. 11, 1556-1566.
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 1556-1566
    • Loeppky, R.N.1    Fuchs, A.2    Janzowski, C.3    Humberd, C.4    Goelzer, P.5    Schneider, H.6    Eisenbrand, G.7
  • 21
    • 0007606114 scopus 로고
    • Synthesis of N-alkyl-N-(1-hydroperoxyalkyl)nitrosamines by oxygenation of lithiated dialkylnitrosamines
    • Mochizuki, M., Sone, T., Anjo, T., and Okada, M. (1980) Synthesis of N-alkyl-N-(1-hydroperoxyalkyl)nitrosamines by oxygenation of lithiated dialkylnitrosamines. Tetrahedron Lett. 21, 1765-1766.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 1765-1766
    • Mochizuki, M.1    Sone, T.2    Anjo, T.3    Okada, M.4
  • 22
    • 0000641793 scopus 로고
    • Formation of N-alkyl-N-(1-hydroperoxyalkyl)nitrosamines from N-alkyl-N-(1-acetoxyalkyl)nitrosamines
    • Mochizuki, M., Anjo, T., Wakabayashi, Y., Sone, T., and Okada, M. (1980) Formation of N-alkyl-N-(1-hydroperoxyalkyl)nitrosamines from N-alkyl-N-(1-acetoxyalkyl)nitrosamines. Tetrahedron Lett. 21, 1761-1764.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 1761-1764
    • Mochizuki, M.1    Anjo, T.2    Wakabayashi, Y.3    Sone, T.4    Okada, M.5
  • 23
    • 0001760345 scopus 로고
    • Isolation and characterization of N-alkyl-N-(hydroxymethyl)nitrosamines from N-alkyl-N-(hydroperoxymethy)nitrosamines by deoxygenation
    • Mochizuki, M., Anjo, T., and Okada, M. (1980) Isolation and characterization of N-alkyl-N-(hydroxymethyl)nitrosamines from N-alkyl-N-(hydroperoxymethy)nitrosamines by deoxygenation. Tetrahedron Lett. 21, 3693-3696.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 3693-3696
    • Mochizuki, M.1    Anjo, T.2    Okada, M.3
  • 24
    • 0029740207 scopus 로고    scopus 로고
    • Effects of structure on the reactivity of α- hydroxydialkylnitrosamines in aqueous solutions
    • Mesic, M., Revis, C., and Fishbein, J. C. (1996) Effects of structure on the reactivity of α-hydroxydialkylnitrosamines in aqueous solutions. J. Am. Chem. Soc. 118, 7412-7413.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7412-7413
    • Mesic, M.1    Revis, C.2    Fishbein, J.C.3
  • 25
    • 0033784047 scopus 로고    scopus 로고
    • Mechanisms of decomposition of α-hydroxydialkylnitrosamines in aqueous solution
    • Mesic, M., Peuralahti, J., Elans, P., and Fishbein, J. C. (2000) Mechanisms of decomposition of α-hydroxydialkylnitrosamines in aqueous solution. Chem. Res. Toxicol. 13, 983-992.
    • (2000) Chem. Res. Toxicol. , vol.13 , pp. 983-992
    • Mesic, M.1    Peuralahti, J.2    Elans, P.3    Fishbein, J.C.4
  • 26
    • 0037732819 scopus 로고    scopus 로고
    • Reexamination of the aqueous chemistry of N-nitroso-3-hydroxymorpholine, a metabolite of the carcinogen N-nitrosomorpholine
    • Kim, H.-J., and Fishbein, J. C. (2003) Reexamination of the aqueous chemistry of N-nitroso-3-hydroxymorpholine, a metabolite of the carcinogen N-nitrosomorpholine. Chem. Res. Toxicol. 16, 715-720.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 715-720
    • Kim, H.-J.1    Fishbein, J.C.2
  • 27
    • 0033538301 scopus 로고    scopus 로고
    • Cyclic α-acetoxy-nitrosamines: Mechanisms of decompostion and stablility of α-hydroxynitrosamines and nitrosiminium ion reactive intermediate
    • Chahoua, L., Cai, H., and Fishbein, J. C. (1999) Cyclic α-acetoxy-nitrosamines: mechanisms of decompostion and stablility of α-hydroxynitrosamines and nitrosiminium ion reactive intermediate. J. Am. Chem. Soc. 121, 5161-6169.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 5161-6169
    • Chahoua, L.1    Cai, H.2    Fishbein, J.C.3
  • 28
    • 0032510423 scopus 로고    scopus 로고
    • The synthesis of highly reactive multifunctional α, β-epoxy- and α-acetoxy-nitrosamines
    • Park, M., Gu, F., and Loeppky, R. N. (1998) The synthesis of highly reactive multifunctional α, β-epoxy- and α-acetoxy- nitrosamines. Tetrahedron Lett. 39, 1287-1290.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 1287-1290
    • Park, M.1    Gu, F.2    Loeppky, R.N.3
  • 29
    • 0010545937 scopus 로고
    • Acid catalyzed rearrangements of N-nitrosodehydromorpholine
    • Loeppky, R. N., and Xiong, H. (1995) Acid catalyzed rearrangements of N-nitrosodehydromorpholine. J. Org. Chem. 60, 5526-5531.
    • (1995) J. Org. Chem. , vol.60 , pp. 5526-5531
    • Loeppky, R.N.1    Xiong, H.2
  • 30
    • 0013946264 scopus 로고
    • The reaction of guanine derivatives with 1,2-dicarbonyl compounds
    • Shapiro, R., and Hachmann, J. (1966) The reaction of guanine derivatives with 1,2-dicarbonyl compounds. Biochemistry 5, 2799-2807.
    • (1966) Biochemistry , vol.5 , pp. 2799-2807
    • Shapiro, R.1    Hachmann, J.2
  • 31
    • 37049053144 scopus 로고
    • The alkylation of guanosine and guanylic acid
    • Brooks, P., and Lawley, P. D. (1961) The alkylation of guanosine and guanylic acid. J. Chem. Soc., 3923-3928.
    • (1961) J. Chem. Soc. , pp. 3923-3928
    • Brooks, P.1    Lawley, P.D.2
  • 33
    • 0026616794 scopus 로고
    • 2-Ethenodeoxyguanosine: Properties and formation in chloroacetaldehyde-treated polynucleotides and DNA
    • 2- Ethenodeoxyguanosine: properties and formation in chloroacetaldehyde-treated polynucleotides and DNA. Chem. Res. Toxicol. 5, 634-638.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 634-638
    • Kusmierek, J.T.1    Singer, B.2
  • 34
    • 0007612992 scopus 로고
    • Reexamination of the mechanisms of decomposition of simple α-acetoxynitrosamines in the physiological pH range
    • Revis, C., Rajamaki, M., and Fishbein, J. C. (1995) Reexamination of the mechanisms of decomposition of simple α-acetoxynitrosamines in the physiological pH range. J. Org. Chem. 60, 7733-7738.
    • (1995) J. Org. Chem. , vol.60 , pp. 7733-7738
    • Revis, C.1    Rajamaki, M.2    Fishbein, J.C.3
  • 35
    • 0001447797 scopus 로고
    • Generation and direct measurement of the reactivity of an N-nitrosiminium cation with nucleophiles in aqueous media
    • Vigroux, A., Kresge, A. J., and Fishbein, J. C. (1995) Generation and direct measurement of the reactivity of an N-nitrosiminium cation with nucleophiles in aqueous media. J. Am. Chem. Soc. 117, 4433-4434.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 4433-4434
    • Vigroux, A.1    Kresge, A.J.2    Fishbein, J.C.3
  • 36
    • 0033541159 scopus 로고    scopus 로고
    • α-(acyloxy)dialkylnitrosamines: Effects of structure on the formation of N-nitrosiminium ions and a predicted change in mechanism
    • Cai, H., and Fishbein, J. C. (1999) α-(Acyloxy)dialkylnitrosamines: effects of structure on the formation of N-nitrosiminium ions and a predicted change in mechanism. J. Am. Chem. Soc. 121, 1826-1833.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 1826-1833
    • Cai, H.1    Fishbein, J.C.2
  • 37
    • 0030788179 scopus 로고    scopus 로고
    • Secondary α-deuterium kinetic isotope effects in the decomposition of simple α-acetoxydialkylnitrosamines: Nitrosiminium ion intermediates
    • Cai, H., and Fishbein, J. C. (1997) Secondary α-deuterium kinetic isotope effects in the decomposition of simple α- acetoxydialkylnitrosamines: nitrosiminium ion intermediates. Tetrahedron 53, 10671-10676.
    • (1997) Tetrahedron , vol.53 , pp. 10671-10676
    • Cai, H.1    Fishbein, J.C.2
  • 39
    • 0025050762 scopus 로고
    • Solvolysis of model compounds of α-hydroxylation of N′-nitrosonornicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone: Evidence for a cyclic oxonium ion intermediate in the alkylation of nucleophiles
    • Spratt, T. E., Peterson, L. A., Confer, W. L., and Hecht, S. S. (1990) Solvolysis of model compounds of α-hydroxylation of N′- nitrosonornicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone: evidence for a cyclic oxonium ion intermediate in the alkylation of nucleophiles. Chem. Res. Toxicol. 3, 350-356.
    • (1990) Chem. Res. Toxicol. , vol.3 , pp. 350-356
    • Spratt, T.E.1    Peterson, L.A.2    Confer, W.L.3    Hecht, S.S.4
  • 41
    • 29644444861 scopus 로고    scopus 로고
    • Personal communication
    • Kim, H.-J., and Fishbein, J. C. (2005) Personal communication.
    • (2005)
    • Kim, H.-J.1    Fishbein, J.C.2
  • 42
    • 0006700842 scopus 로고    scopus 로고
    • Failure to isolate the first N-nitrosiminium cation
    • Chahoua, L., Mesic, M., and Fishbein, J. C. (1996) Failure to isolate the first N-nitrosiminium cation. J. Org. Chem. 61, 1512.
    • (1996) J. Org. Chem. , vol.61 , pp. 1512
    • Chahoua, L.1    Mesic, M.2    Fishbein, J.C.3
  • 44
    • 0027410746 scopus 로고
    • N-Nitroso-N-methylvinylamine: Reaction of the epoxide with guanyl and adenyl moieties to yield adducts derived from both parts of the molecule
    • Okazaki, O., Persmark, M., and Guengerich, F. P. (1993) N-Nitroso-N-methylvinylamine: reaction of the epoxide with guanyl and adenyl moieties to yield adducts derived from both parts of the molecule. Chem. Res. Toxicol. 6, 168-173.
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 168-173
    • Okazaki, O.1    Persmark, M.2    Guengerich, F.P.3
  • 46
    • 0030614916 scopus 로고    scopus 로고
    • 2-ethenoguanine and 5,6,7,9-tetrahydro-7- hydroxy-9-oxoimidazo[1,2-α]purine in DNA treated with 2-chlorooxirane by high performance liquid chromatography/electrospray mass spectrometry and comparison of amounts to other DNA adducts
    • 2-ethenoguanine and 5,6,7,9-tetrahydro-7-hydroxy-9- oxoimidazo[1,2-α]purine in DNA treated with 2-chlorooxirane by high performance liquid chromatography/electrospray mass spectrometry and comparison of amounts to other DNA adducts. Chem. Res. Toxicol. 10, 242-247.
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 242-247
    • Mueller, M.1    Belas, F.J.2    Blair, I.A.3    Guengerich, F.P.4
  • 48
    • 0033258305 scopus 로고    scopus 로고
    • Glyoxal-guanine DNA adducts: Detection, stability and formation from nitrosamines
    • (Singer, B., and Bartsch, H., Eds.), IARC, Lyon, France
    • Loeppky, R. N., Cui, W., Goelzer, P., Park, M., and Ye, Q. (1999) Glyoxal-guanine DNA adducts: detection, stability and formation from nitrosamines. In Cyclic DNA Adducts II (Singer, B., and Bartsch, H., Eds.) pp 155-168, IARC, Lyon, France.
    • (1999) Cyclic DNA Adducts II , pp. 155-168
    • Loeppky, R.N.1    Cui, W.2    Goelzer, P.3    Park, M.4    Ye, Q.5
  • 49
    • 0037330015 scopus 로고    scopus 로고
    • Reactions of formaldehyde plus acetaldehyde with deoxyguanosine and DNA: Formation of cyclic deoxyguanosine adducts and formaldehyde cross-links
    • Cheng, G., Shi, Y., Sturla, S. J., Jalas, J. R., McIntee, E. J., Villalta, P. W., Wang, M., and Hecht, S. S. (2003) Reactions of formaldehyde plus acetaldehyde with deoxyguanosine and DNA: formation of cyclic deoxyguanosine adducts and formaldehyde cross-links. Chem. Res. Toxicol. 16, 145-152.
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 145-152
    • Cheng, G.1    Shi, Y.2    Sturla, S.J.3    Jalas, J.R.4    McIntee, E.J.5    Villalta, P.W.6    Wang, M.7    Hecht, S.S.8
  • 50
    • 0034865489 scopus 로고    scopus 로고
    • Reactions of 2,6-dimethyl-1,3-dioxane-4-ol (aldoxane) with deoxyguanosine and DNA
    • Wang, M., McIntee, E. J., Cheng, G., Shi, Y., Villalta, P. W., and Hecht, S. S. (2001) Reactions of 2,6-dimethyl-1,3-dioxane-4-ol (aldoxane) with deoxyguanosine and DNA. Chem. Res. Toxicol. 14, 1025-1032.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 1025-1032
    • Wang, M.1    McIntee, E.J.2    Cheng, G.3    Shi, Y.4    Villalta, P.W.5    Hecht, S.S.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.