메뉴 건너뛰기




Volumn 19, Issue 6, 2006, Pages 770-778

Chemical synthesis of 2′-deoxyguanosine-C8 adducts with heterocyclic amines: An application to synthesis of oligonucleotides site-specifically adducted with 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 1 METHYL 6 PHENYLIMIDAZO[4,5 B]PYRIDINE; 2 AMINO 3 METHYLIMIDAZO[4,5 F]QUINOLINE; 2 AMINO 3,8 DIMETHYLIMIDAZO[4,5 F]QUINOXALINE; 2 AMINO 6 METHYLDIPYRIDO[1,2 A:3',2' D]IMIDAZOLE; 3 AMINO 1,4 DIMETHYL 5H PYRIDO[4,3 B]INDOLE; 9,9 DIMETHYL 4,5 BIS(DIPHENYLPHOSPHINO)XANTHENE; AMINE; BIPHENYL DERIVATIVE; CARCINOGEN; CESIUM; CESIUM CARBONATE; DEOXYGUANOSINE; DIMETHYL SULFOXIDE; HETEROCYCLIC AMINE; IMIDAZOLE DERIVATIVE; MUTAGENIC AGENT; OLIGONUCLEOTIDE; PALLADIUM COMPLEX; PHOSPHINE DERIVATIVE; PHOSPHORAMIDOUS ACID DERIVATIVE; SOLVENT; TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM; UNCLASSIFIED DRUG; XANTHENE DERIVATIVE;

EID: 33745295131     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx050296s     Document Type: Article
Times cited : (14)

References (37)
  • 2
    • 0033034183 scopus 로고    scopus 로고
    • DNA adducts of heterocyclic amine food mutagens: Implications for mutagenesis and carcinogenesis
    • Schut, H. A., and Snyderwine, E. G. (1999) DNA adducts of heterocyclic amine food mutagens: Implications for mutagenesis and carcinogenesis. Carcinogenesis 20, 353-368.
    • (1999) Carcinogenesis , vol.20 , pp. 353-368
    • Schut, H.A.1    Snyderwine, E.G.2
  • 3
    • 0036041122 scopus 로고    scopus 로고
    • N-Hydroxyarylamines
    • Guengerich, F. P. (2002) N-Hydroxyarylamines. Drug Metab. Rev. 34, 607-623.
    • (2002) Drug Metab. Rev. , vol.34 , pp. 607-623
    • Guengerich, F.P.1
  • 4
    • 0036270413 scopus 로고    scopus 로고
    • Modulation of heterocyclic amine-induced mutagenicity and carcinogenicity: An 'A-to-Z' guide to chemopreventive agents, promoters, and transgenic models
    • Dashwood, R. H. (2002) Modulation of heterocyclic amine-induced mutagenicity and carcinogenicity: An 'A-to-Z' guide to chemopreventive agents, promoters, and transgenic models. Mutat. Res. 511, 89-112.
    • (2002) Mutat. Res. , vol.511 , pp. 89-112
    • Dashwood, R.H.1
  • 5
    • 0026673950 scopus 로고
    • Characterization of DNA adducts formed in vitro by reaction of N-hydroxy-2-amino-3-methylimidazo[4,5-f]quinoline and N-hydroxy-2-amino-3,8- dimethylimidazo[4,5-f]quinoxaline at the C-8 and N2 atoms of guanine
    • Turesky, R. J., Rossi, S. C, Welti, D. H., Lay, J. O., Jr., and Kadlubar, F. F. (1992) Characterization of DNA adducts formed in vitro by reaction of N-hydroxy-2-amino-3-methylimidazo[4,5-f]quinoline and N-hydroxy-2-amino-3,8- dimethylimidazo[4,5-f]quinoxaline at the C-8 and N2 atoms of guanine. Chem. Res. Toxicol. 5, 479-490.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 479-490
    • Turesky, R.J.1    Rossi, S.C.2    Welti, D.H.3    Lay Jr., J.O.4    Kadlubar, F.F.5
  • 6
    • 0023853676 scopus 로고
    • Reaction of N-hydroxyamine and N-acetoxy derivatives of 2-amino-3-methylimidazo[4,5-f]quinoline with DNA. Synthesis and identification of N-(deoxyguanosin-8-yl)-IQ
    • Snydewine, E. G., Roller, P. P., Adamson, R. H., Sato, S., and Thorgeirssom, S. S. (1988) Reaction of N-hydroxyamine and N-acetoxy derivatives of 2-amino-3-methylimidazo[4,5-f]quinoline with DNA. Synthesis and identification of N-(deoxyguanosin-8-yl)-IQ. Carcinogenesis 9, 411-418.
    • (1988) Carcinogenesis , vol.9 , pp. 411-418
    • Snydewine, E.G.1    Roller, P.P.2    Adamson, R.H.3    Sato, S.4    Thorgeirssom, S.S.5
  • 7
    • 4344631345 scopus 로고    scopus 로고
    • Synthesis of DNA adducts of two heterocyclic amines, 2-amino-3-methyl-9H- pyrido[2,3-b]indole (MeAαC) and 2-amino-9H-pyrido[2,3-b]indole (AαC) and identification of DNA adducts in organs from rats dosed with MeAαC
    • Frederiksen, H., Frandsen, H., and Pfau, W. (2004) Synthesis of DNA adducts of two heterocyclic amines, 2-amino-3-methyl-9H-pyrido[2,3-b]indole (MeAαC) and 2-amino-9H-pyrido[2,3-b]indole (AαC) and identification of DNA adducts in organs from rats dosed with MeAαC. Carcinogenesis 25, 1525-1533.
    • (2004) Carcinogenesis , vol.25 , pp. 1525-1533
    • Frederiksen, H.1    Frandsen, H.2    Pfau, W.3
  • 8
    • 0026783540 scopus 로고
    • Identification of N-(deoxyguanosin-8-yl)-2-amino-1-methyl-6-phenylimidazo [4,5-b]pyridine as the major adduct formed by the food-borne carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, with DNA
    • Lin, D., Kaderlik, K. R., Turesky, R. J., Miller, D. W., Lay, J. O., Jr., and Kadlubar, F. F. (1992) Identification of N-(deoxyguanosin-8-yl)-2-amino-1- methyl-6-phenylimidazo [4,5-b]pyridine as the major adduct formed by the food-borne carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, with DNA. Chem. Res. Toxicol. 5, 691-697.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 691-697
    • Lin, D.1    Kaderlik, K.R.2    Turesky, R.J.3    Miller, D.W.4    Lay Jr., J.O.5    Kadlubar, F.F.6
  • 9
    • 0035339585 scopus 로고    scopus 로고
    • Synthesis and spectroscopic characterization of site-specific 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine oligodeoxyribonucleotide adducts
    • Brown, K., Guenther, E. A., Dingley, K. H., Cosman, M., Harvey, C. A., Shields, S. J., and Turteltaub, K. W. (2001) Synthesis and spectroscopic characterization of site-specific 2-amino-1-methyl-6-phenylimidazo[4,5-b] pyridine oligodeoxyribonucleotide adducts. Nucleic Acids Res. 29, 1951-1959.
    • (2001) Nucleic Acids Res. , vol.29 , pp. 1951-1959
    • Brown, K.1    Guenther, E.A.2    Dingley, K.H.3    Cosman, M.4    Harvey, C.A.5    Shields, S.J.6    Turteltaub, K.W.7
  • 11
    • 0345830965 scopus 로고    scopus 로고
    • Structural characterization of carcinogen-modified oligodeoxynucleotide adducts using matrix-assisted laser desorption/ionization mass spectrometry
    • Brown, K., Harvey, C. A., Turteltaub, K. W., and Shields S. J. (2003) Structural characterization of carcinogen-modified oligodeoxynucleotide adducts using matrix-assisted laser desorption/ionization mass spectrometry. J. Mass Spectrom. 38, 68-79.
    • (2003) J. Mass Spectrom. , vol.38 , pp. 68-79
    • Brown, K.1    Harvey, C.A.2    Turteltaub, K.W.3    Shields, S.J.4
  • 12
    • 0033600909 scopus 로고    scopus 로고
    • Mutagenesis of the N-(deoxyguanosin-8-yl)-2-amino-1-methyl-6- phenylimidazo[4,5-b]pyridine DNA adduct in mammalian cells. Sequence context effects
    • Shibutani, S., Fernandes, A., Suzuki, N., Zhou, L., Johnson, F., and Grollman, A. P. (1999) Mutagenesis of the N-(deoxyguanosin-8-yl)-2-amino-1- methyl-6-phenylimidazo[4,5-b]pyridine DNA adduct in mammalian cells. Sequence context effects. J. Biol. Chem. 274, 27433-27438.
    • (1999) J. Biol. Chem. , vol.274 , pp. 27433-27438
    • Shibutani, S.1    Fernandes, A.2    Suzuki, N.3    Zhou, L.4    Johnson, F.5    Grollman, A.P.6
  • 13
    • 0032435631 scopus 로고    scopus 로고
    • An unusual DNA adduct derived from the powerfully mutagenic environmental contaminant 3-nitrobenzanthrone
    • Enya, T., Kawanishi, M., Suzuki, H., Matsui, S., and Hisamatsu, Y. (1998) An unusual DNA adduct derived from the powerfully mutagenic environmental contaminant 3-nitrobenzanthrone. Chem. Res. Toxicol. 11, 1460-1467.
    • (1998) Chem. Res. Toxicol. , vol.11 , pp. 1460-1467
    • Enya, T.1    Kawanishi, M.2    Suzuki, H.3    Matsui, S.4    Hisamatsu, Y.5
  • 14
    • 0030929002 scopus 로고    scopus 로고
    • Reactions of ester derivatives of carcinogenic N-(4-biphenyl)hydroxyamine and the corresponding hydroxamic acid with purine nucleosides
    • Kennedy, S. A., Novak, M., and Kolb, B. A. (1997) Reactions of ester derivatives of carcinogenic N-(4-biphenyl)hydroxyamine and the corresponding hydroxamic acid with purine nucleosides. J. Am. Chem. Soc. 119, 7654-7664.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 7654-7664
    • Kennedy, S.A.1    Novak, M.2    Kolb, B.A.3
  • 15
    • 0037055097 scopus 로고    scopus 로고
    • Reactivity and selectivity of the N-acetyl-Glu-P-1, N-acetyl-Glu-P-2, N-acetyl-MeIQx, and N-acetyl-IQx nitrenium ions: Comparison to carbocyclic N-arylnitrenium ions
    • Novak, M., Toth, K., Rajagopal, S., Brooks, M., Hott, L. L., and Moslener, M. (2002) Reactivity and selectivity of the N-acetyl-Glu-P-1, N-acetyl-Glu-P-2, N-acetyl-MeIQx, and N-acetyl-IQx nitrenium ions: Comparison to carbocyclic N-arylnitrenium ions. J. Am. Chem. Soc. 124, 7972-7981.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 7972-7981
    • Novak, M.1    Toth, K.2    Rajagopal, S.3    Brooks, M.4    Hott, L.L.5    Moslener, M.6
  • 16
    • 0346993059 scopus 로고    scopus 로고
    • Unusual reactions of the model carcinogen N-acetoxy-N-acetyl-2-amino- α-carboline
    • Novak, M., and Nguyen, T. M. (2003) Unusual reactions of the model carcinogen N-acetoxy-N-acetyl-2-amino-α-carboline. J. Org. Chem. 68, 9875-9881.
    • (2003) J. Org. Chem. , vol.68 , pp. 9875-9881
    • Novak, M.1    Nguyen, T.M.2
  • 17
    • 0042355859 scopus 로고    scopus 로고
    • A general method for the synthesis of the N2- and N6-carcinogenic amine adducts of 2́-deoxyguanosine and 2́-deoxyadenosine
    • De Riccardis, F., Bonola, R. R., and Johnson, F. (1999) A general method for the synthesis of the N2- and N6-carcinogenic amine adducts of 2́-deoxyguanosine and 2́-deoxyadenosine. J. Am Chem. Soc. 121, 10453-10460.
    • (1999) J. Am Chem. Soc. , vol.121 , pp. 10453-10460
    • De Riccardis, F.1    Bonola, R.R.2    Johnson, F.3
  • 19
    • 0035932066 scopus 로고    scopus 로고
    • Synthesis of the C8-deoxyguanosine adduct of the food mutagen IQ
    • Wang, Z., and Rizzo, C. J. (2001) Synthesis of the C8-deoxyguanosine adduct of the food mutagen IQ. Org Lett. 3, 565-568.
    • (2001) Org Lett. , vol.3 , pp. 565-568
    • Wang, Z.1    Rizzo, C.J.2
  • 20
    • 33745312638 scopus 로고    scopus 로고
    • Synthesis and incorporation into DNA of the PhIP-C8-dG adduct
    • (No. 102 in Abstracts, American Chemical Society Division of Chemical Toxicology, 228th ACS International Meeting, Philadeliphia, Pennsylvania, August 22-26, 2004), and also personal communication with Bonala, R. R., and Johnson, F.
    • Bonala, R. R., and Johnson, F. (2004) Synthesis and incorporation into DNA of the PhIP-C8-dG adduct. Chem. Res. Toxicol. 17, 1780 (No. 102 in Abstracts, American Chemical Society Division of Chemical Toxicology, 228th ACS International Meeting, Philadeliphia, Pennsylvania, August 22-26, 2004), and also personal communication with Bonala, R. R., and Johnson, F.
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 1780
    • Bonala, R.R.1    Johnson, F.2
  • 21
    • 0037191621 scopus 로고    scopus 로고
    • Preparation of C8-amine and acetylamine adducts of 2́- deoxyguanosine suitably protected for DNA synthesis
    • Gillet, L. C., and Scharer, O. D. (2002) Preparation of C8-amine and acetylamine adducts of 2́-deoxyguanosine suitably protected for DNA synthesis. Org. Lett. 4, 4205-4208.
    • (2002) Org. Lett. , vol.4 , pp. 4205-4208
    • Gillet, L.C.1    Scharer, O.D.2
  • 22
    • 0036246044 scopus 로고    scopus 로고
    • Highly efficient synthesis of a phosphoramidite building block of C8-deoxyguanosine adducts of aromatic amines
    • Meier, C., and Gräsel, S. (2002) Highly efficient synthesis of a phosphoramidite building block of C8-deoxyguanosine adducts of aromatic amines. Synlett, 802-804.
    • (2002) Synlett , pp. 802-804
    • Meier, C.1    Gräsel, S.2
  • 23
    • 0037629746 scopus 로고    scopus 로고
    • A practical approach for the chemical synthesis of 2′- deoxyguanosine-C8 adducts with mutagenic/carcinogenic amino-and nitro-arenes
    • Takamura-Enya, T., Ishikawa, S., Mochizuki, M., and Wakabayashi, K. (2003) A practical approach for the chemical synthesis of 2′- deoxyguanosine-C8 adducts with mutagenic/carcinogenic amino-and nitro-arenes. Tetrahedron Lett. 44, 5969-5973.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 5969-5973
    • Takamura-Enya, T.1    Ishikawa, S.2    Mochizuki, M.3    Wakabayashi, K.4
  • 24
    • 0142181204 scopus 로고    scopus 로고
    • Development for an efficient synthesis method of 2′-deoxyguanosine- C8 adducts with several amino/nitro arenes
    • Takamura-Enya, T., Ishikawa, S., Mochizuki, M., and Wakabayashi, K. (2003) Development for an efficient synthesis method of 2′-deoxyguanosine- C8 adducts with several amino/nitro arenes. Nucleic Acid Res. Suppl. 3, 23-24.
    • (2003) Nucleic Acid Res. , Issue.SUPPL. 3 , pp. 23-24
    • Takamura-Enya, T.1    Ishikawa, S.2    Mochizuki, M.3    Wakabayashi, K.4
  • 25
    • 4544364941 scopus 로고    scopus 로고
    • Site-specific synthesis and properties of oligonucleotides containing C8-deoxyguanosine adducts of the dietary mutagen IQ
    • Elmquist, C. E., Stover, J. S., Wang, Z., and Rizzo, C. J. (2004) Site-specific synthesis and properties of oligonucleotides containing C8-deoxyguanosine adducts of the dietary mutagen IQ. J. Am. Chem. Soc. 126, 11189-11201.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 11189-11201
    • Elmquist, C.E.1    Stover, J.S.2    Wang, Z.3    Rizzo, C.J.4
  • 26
    • 17144362544 scopus 로고    scopus 로고
    • Site-specific incorporation of N-(deoxyguanosin-8-yl)-2- acetylaminofluorene (dG-AAF) into oligonucleotides using modified "ultra-mild' DNA synthesis
    • Gillet, L. C., Alzeer, J., and Schärer O. D. (2005) Site-specific incorporation of N-(deoxyguanosin-8-yl)-2-acetylaminofluorene (dG-AAF) into oligonucleotides using modified "ultra-mild' DNA synthesis. Nucleic Acids Res. 33, 1961-1969.
    • (2005) Nucleic Acids Res. , vol.33 , pp. 1961-1969
    • Gillet, L.C.1    Alzeer, J.2    Schärer, O.D.3
  • 27
    • 26644461954 scopus 로고    scopus 로고
    • Synthesis of oligonucleotides bearing an arylamine modification in the C8-position of 2′-deoxyguanosine
    • Meier, C., Gräsl, S., Detmer, I., and Marx, A. (2005) Synthesis of oligonucleotides bearing an arylamine modification in the C8-position of 2′-deoxyguanosine. Nucl. Nucl. Nucleic Acid. 24, 691-694.
    • (2005) Nucl. Nucl. Nucleic Acid. , vol.24 , pp. 691-694
    • Meier, C.1    Gräsl, S.2    Detmer, I.3    Marx, A.4
  • 28
    • 22544455444 scopus 로고    scopus 로고
    • Synthesis of biologically important nucleoside analogs by Palladium-catalyzed C-N bond-formation
    • Lakshman, M. K. (2005) Synthesis of biologically important nucleoside analogs by Palladium-catalyzed C-N bond-formation. Curr. Org. Synth. 2, 83-112.
    • (2005) Curr. Org. Synth. , vol.2 , pp. 83-112
    • Lakshman, M.K.1
  • 29
    • 0034712156 scopus 로고    scopus 로고
    • Simple, efficient catalyst system for the palladium-catalyzed animation of aryl chlorides, bromides, and triflates
    • Wolfe J. P., Tomori, H., Sadighi, J. P., Yin, J., and Buchwald, S. L. (2000) Simple, efficient catalyst system for the palladium-catalyzed animation of aryl chlorides, bromides, and triflates. J. Org. Chem. 65, 1158-1174.
    • (2000) J. Org. Chem. , vol.65 , pp. 1158-1174
    • Wolfe, J.P.1    Tomori, H.2    Sadighi, J.P.3    Yin, J.4    Buchwald, S.L.5
  • 30
    • 1842740801 scopus 로고    scopus 로고
    • Palladium-catalyzed amination of aryl halides: Mechanism and rational catalyst design
    • Hartwig, J. F. (1997) Palladium-catalyzed amination of aryl halides: Mechanism and rational catalyst design. Synlett, 329-340.
    • (1997) Synlett , pp. 329-340
    • Hartwig, J.F.1
  • 31
    • 0026673950 scopus 로고
    • Characterization of DNA adducts in vitro by reaction of N-hydroxy-2-amino-3methylimidazo[4,5-f]quinoline and N-hydroxy-2-amino-3,8- dimethylimidazo[4,5-f]quinoxaline at the C-8 and N2 atoms of guanine
    • Turesky, R. J., Rossi, S. C., Welti, D. H., Lay, J. O., Jr., and Kadlubar, F. F. (1992) Characterization of DNA adducts in vitro by reaction of N-hydroxy-2-amino-3methylimidazo[4,5-f]quinoline and N-hydroxy-2-amino-3,8- dimethylimidazo[4,5-f]quinoxaline at the C-8 and N2 atoms of guanine. Chem. Res. Toxicol. 5, 479-490.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 479-490
    • Turesky, R.J.1    Rossi, S.C.2    Welti, D.H.3    Lay Jr., J.O.4    Kadlubar, F.F.5
  • 32
    • 0020420450 scopus 로고
    • Modification of DNA with potent mutacarcinogenic 2-amino-6- methyldipyrido[1,2-a:3′,2′-d]imidazole isolated from glutamic acid pyrolysate: Structure of the modified nucleic acid base and initial chemical event caused by the mutagen
    • Hashimoto, Y., Shudo, K., and Okamoto, T. (1982) Modification of DNA with potent mutacarcinogenic 2-amino-6-methyldipyrido[1,2-a:3′,2′-d] imidazole isolated from glutamic acid pyrolysate: Structure of the modified nucleic acid base and initial chemical event caused by the mutagen. J. Am. Chem. Soc. 104, 7636-7640.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 7636-7640
    • Hashimoto, Y.1    Shudo, K.2    Okamoto, T.3
  • 33
    • 0026783540 scopus 로고
    • Identification of N-(deoxyguanosin-8-yl)-2-amino-1-methyl-6- phenylimidazo[4,5-b]pyridine as the major adduct formed by the food-borne carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, with DNA
    • Lin, D., Kaderlik, K. R., Turesky, R. J., Miller, D. W, Lay, J. O., Jr., and Kadlubar, F. F. (1992) Identification of N-(deoxyguanosin-8-yl)-2-amino-1- methyl-6-phenylimidazo[4,5-b]pyridine as the major adduct formed by the food-borne carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine, with DNA. Chem. Res. Toxicol. 5, 691-697.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 691-697
    • Lin, D.1    Kaderlik, K.R.2    Turesky, R.J.3    Miller, D.W.4    Lay Jr., J.O.5    Kadlubar, F.F.6
  • 35
    • 0028878974 scopus 로고
    • Specific 5′-GGGA-3′ → 5′-GGA-3′ mutation of the Apc gene in rat colon tumors induced by 2-amino-1-methyl-6-phenylimidazo[4, 5-b]pyridine
    • Kakiuchi, H., Watanabe, M., Ushijima, T., Toyota, M., Imai, K., Weisburger, J. H., Sugimura, T., and Nagao, M. (1995) Specific 5′-GGGA-3′ → 5′-GGA-3′ mutation of the Apc gene in rat colon tumors induced by 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine. Proc. Natl. Acad. Sci. U.S.A. 92, 910-914.
    • (1995) Proc. Natl. Acad. Sci. U.S.A. , vol.92 , pp. 910-914
    • Kakiuchi, H.1    Watanabe, M.2    Ushijima, T.3    Toyota, M.4    Imai, K.5    Weisburger, J.H.6    Sugimura, T.7    Nagao, M.8
  • 36
    • 0025765117 scopus 로고
    • Isolation and characterization of oligodeoxynucleotides containing dG-N2-AAF and oxidation products of dG-C8-AF
    • Shibutani, S., Gentiles, R., Johnson, F., and Grollman, A. P. (1991) Isolation and characterization of oligodeoxynucleotides containing dG-N2-AAF and oxidation products of dG-C8-AF. Carcinogenesis 12, 813-818.
    • (1991) Carcinogenesis , vol.12 , pp. 813-818
    • Shibutani, S.1    Gentiles, R.2    Johnson, F.3    Grollman, A.P.4
  • 37
    • 0032569071 scopus 로고    scopus 로고
    • 6- ethano-2′-deoxyadenosine, a metabolic product of 1,3-bis(2-chloroethyl)nitrosourea, and its incorporation into oligomeric DNA
    • 6- ethano-2′-deoxyadenosine, a metabolic product of 1,3-bis(2-chloroethyl)nitrosourea, and its incorporation into oligomeric DNA. J. Org. Chem. 63, 4385-4389.
    • (1998) J. Org. Chem. , vol.63 , pp. 4385-4389
    • Maruenda, H.1    Chenna, A.2    Liem, L.-K.3    Singer, B.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.