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Volumn 9, Issue 1, 1996, Pages 12-15

Mechanism of reaction of β-(aryloxy)acroleins with nucleosides

Author keywords

[No Author keywords available]

Indexed keywords

3 (4 NITROPHENOXY)ACROLEIN; ACROLEIN; GUANOSINE; UNCLASSIFIED DRUG;

EID: 0030031323     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx950105t     Document Type: Article
Times cited : (18)

References (36)
  • 1
    • 0028690470 scopus 로고
    • DNA Adducts of α,β-unsaturated aldehydes and dicarbonyl compounds
    • (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartsch, H.,Eds.) IARC Scientific Publication No. 125, International Agency for Research on Cancer, Lyon
    • Marnett, L. J. (1994) DNA Adducts of α,β-unsaturated aldehydes and dicarbonyl 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.) IARC Scientific Publication No. 125, pp 151-163, International Agency for Research on Cancer, Lyon.
    • (1994) DNA Adducts: Identification and Biological Significance , pp. 151-163
    • Marnett, L.J.1
  • 2
    • 0021253232 scopus 로고
    • Molecular requirements for the mutagenicity of malondialdehyde and related acroleins
    • Basu, A. K., and Marnett, L. J. (1984) Molecular requirements for the mutagenicity of malondialdehyde and related acroleins. Cancer Res. 44, 2848-2854.
    • (1984) Cancer Res. , vol.44 , pp. 2848-2854
    • Basu, A.K.1    Marnett, L.J.2
  • 3
    • 0017290002 scopus 로고
    • Mutagenicity of malondialdehyde, a decomposition product of peroxidized polyunsaturated fatty acids
    • Mukai, F. H., and Goldstein, B. D. (1976) Mutagenicity of malondialdehyde, a decomposition product of peroxidized polyunsaturated fatty acids Science 191, 868-869.
    • (1976) Science , vol.191 , pp. 868-869
    • Mukai, F.H.1    Goldstein, B.D.2
  • 4
    • 0020030204 scopus 로고
    • Structure-mutagenicity relationship in alpha.beta-unsaturated carbonylic compounds and their corresponding allylic alcohols
    • Lutz, D., Eder, E., Neudecker, T., and Henschler, D. (1982) Structure-mutagenicity relationship in alpha.beta-unsaturated carbonylic compounds and their corresponding allylic alcohols. Mutat. Res. 93, 305-315.
    • (1982) Mutat. Res. , vol.93 , pp. 305-315
    • Lutz, D.1    Eder, E.2    Neudecker, T.3    Henschler, D.4
  • 5
    • 0020615703 scopus 로고
    • Unequivocal demonstration that malondialdehyde is a mutagen
    • Basu, A. K., and Marnett, L. J. (1983) Unequivocal demonstration that malondialdehyde is a mutagen. Carcinogenesis 4, 331-333.
    • (1983) Carcinogenesis , vol.4 , pp. 331-333
    • Basu, A.K.1    Marnett, L.J.2
  • 6
    • 0021163945 scopus 로고
    • Dissociation of malondialdehyde mutagenicity in Salmonella typhimurium from its ability to induce interstrand DNA cross-links
    • Basu, A. K., Marnett, L. J., and Romano, L. J. (1984) Dissociation of malondialdehyde mutagenicity in Salmonella typhimurium from its ability to induce interstrand DNA cross-links. Mutat. Res. 129, 39-46.
    • (1984) Mutat. Res. , vol.129 , pp. 39-46
    • Basu, A.K.1    Marnett, L.J.2    Romano, L.J.3
  • 7
    • 0021963042 scopus 로고
    • Naturally occurring carbonyl compounds are mutagens in Salmonella tester strain TA104
    • Marnett, L. J., Hurd, H. K., Hollstein, M. C., Levin, D. E., Esterbauer, H., and Ames, B. N. (1985) Naturally occurring carbonyl compounds are mutagens in Salmonella tester strain TA104. Mutat. Res. 148, 25-34.
    • (1985) Mutat. Res. , vol.148 , pp. 25-34
    • Marnett, L.J.1    Hurd, H.K.2    Hollstein, M.C.3    Levin, D.E.4    Esterbauer, H.5    Ames, B.N.6
  • 9
    • 0023202624 scopus 로고
    • Mutagenicity and toxicity studies of several α,β-unsaturated aldehydes in the Salmonella typhimurium mutagenicity assays
    • Cooper, K. O., Witz, G., and Witmer, C. M. (1987) Mutagenicity and toxicity studies of several α,β-unsaturated aldehydes in the Salmonella typhimurium mutagenicity assays. Environ. Mol. Mutagen. 9, 289-295.
    • (1987) Environ. Mol. Mutagen. , vol.9 , pp. 289-295
    • Cooper, K.O.1    Witz, G.2    Witmer, C.M.3
  • 10
    • 0025000792 scopus 로고
    • Molecular mechanisms of DNA damage initiated by α,β-unsaturated carbonyl compounds as criteria for genotoxicity and mutagenicity
    • Eder, E., Hoffman, C., Bastian, H., Deininger, C., and Scheckenbach, S. (1990) Molecular mechanisms of DNA damage initiated by α,β-unsaturated carbonyl compounds as criteria for genotoxicity and mutagenicity. Environ Health Perspect. 88, 99-106.
    • (1990) Environ Health Perspect. , vol.88 , pp. 99-106
    • Eder, E.1    Hoffman, C.2    Bastian, H.3    Deininger, C.4    Scheckenbach, S.5
  • 11
    • 0026090388 scopus 로고
    • DNA sequence analysis of spontaneous and β-methoxy-acrolein-induced mutations in Salmonella typhimurium hisD3052
    • O'Hara, S. M., and Marnett, L. J. (1991) DNA sequence analysis of spontaneous and β-methoxy-acrolein-induced mutations in Salmonella typhimurium hisD3052. Mutat. Res. 247, 45-56.
    • (1991) Mutat. Res. , vol.247 , pp. 45-56
    • O'Hara, S.M.1    Marnett, L.J.2
  • 12
    • 0026777081 scopus 로고
    • Mutagenicity of β-alkyl substituted acrolein congeners in the Salmonella typhimurium strain TA100 and genotoxieity testing in the SOS chromotest
    • Eder, E., Deininger, C., Neudecker, T., and Deininger, D. (1992) Mutagenicity of β-alkyl substituted acrolein congeners in the Salmonella typhimurium strain TA100 and genotoxieity testing in the SOS chromotest. Environ. Mol. Mutagen. 19, 338-345.
    • (1992) Environ. Mol. Mutagen. , vol.19 , pp. 338-345
    • Eder, E.1    Deininger, C.2    Neudecker, T.3    Deininger, D.4
  • 13
    • 0023818250 scopus 로고
    • 2-Ethenodeoxyguanosine as a potential marker for DNA adduct formation by trans-4-hydroxy-2-nonenal
    • 2-Ethenodeoxyguanosine as a potential marker for DNA adduct formation by trans-4-hydroxy-2-nonenal. Cancer Res. 48, 320-323.
    • (1988) Cancer Res. , vol.48 , pp. 320-323
    • Sodum, R.S.1    Chung, F.-L.2
  • 14
    • 0027939654 scopus 로고
    • 2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans
    • 2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans. Proc. Natl. Acad. Sci. U.S.A. 91, 7491-7495.
    • (1994) Proc. Natl. Acad. Sci. U.S.A. , vol.91 , pp. 7491-7495
    • Nath, R.G.1    Chung, F.-L.2
  • 16
    • 0020686618 scopus 로고
    • 2-adducts by reaction of deoxyguanosine with α-acetoxy-N-nitrosopyrrolidine, 4-(carbethoxynitrosamino)butanal or crotonaldehyde
    • 2-adducts by reaction of deoxyguanosine with α-acetoxy-N-nitrosopyrrolidine, 4-(carbethoxynitrosamino)butanal or crotonaldehyde. Cancer Res. 43, 1230-1235.
    • (1983) Cancer Res. , vol.43 , pp. 1230-1235
    • Chung, F.-L.1    Hecht, S.S.2
  • 17
    • 0001525324 scopus 로고
    • Reaction of malondialdehyde with nucleic acid. I. Formation of fluorescent pyrimido[1,2-α]purin-10(3H)-one nucleosides
    • Seto, H., Okuda, T., Takesue, T., and Ikemura, T. (1983) Reaction of malondialdehyde with nucleic acid. I. Formation of fluorescent pyrimido[1,2-α]purin-10(3H)-one nucleosides. Bull. Chem. Soc. Jpn 56, 1799-1802.
    • (1983) Bull. Chem. Soc. Jpn , vol.56 , pp. 1799-1802
    • Seto, H.1    Okuda, T.2    Takesue, T.3    Ikemura, T.4
  • 18
    • 0021319465 scopus 로고
    • 2-propanodeoxyguanosine adducts in DNA upon reaction with acrotein or crotonaldehyde
    • 2-propanodeoxyguanosine adducts in DNA upon reaction with acrotein 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
  • 19
    • 0023009007 scopus 로고
    • Formation of cyclic adducts of deoxyguanosine with the aldehydes trans-4-hydroxy-2-hexenal and trans-4-hydroxy-2-nonenal in vitro
    • Winter, C. K., Segall, H. J., and Haddon, W. F. (1986) Formation of cyclic adducts of deoxyguanosine with the aldehydes trans-4-hydroxy-2-hexenal and trans-4-hydroxy-2-nonenal in vitro. Cancer Res. 46, 5682-5686.
    • (1986) Cancer Res. , vol.46 , pp. 5682-5686
    • Winter, C.K.1    Segall, H.J.2    Haddon, W.F.3
  • 20
    • 0000929493 scopus 로고
    • Reaction of malondialdehyde with guanine nucleosides: Formation of adducts containing oxadiazabicyclononene residues in the base-pairing region
    • Marnett, L. J., Basu, A. K., O'Hara, S. M., Weller, P. E., Rahman, A. F. M. M., and Oliver, J. P. (1986) Reaction of malondialdehyde with guanine nucleosides: formation of adducts containing oxadiazabicyclononene residues in the base-pairing region. J. Am. Chem Soc. 108, 1348-1350.
    • (1986) J. Am. Chem Soc. , vol.108 , pp. 1348-1350
    • Marnett, L.J.1    Basu, A.K.2    O'Hara, S.M.3    Weller, P.E.4    Rahman, A.F.M.M.5    Oliver, J.P.6
  • 21
    • 0023925368 scopus 로고
    • Identification of adducts formed by reaction of guanine nucleosides with malondialdehyde and structurally related aldehydes
    • Basu, A. K., O'Hara, S. M., Valladier, P., Stone, K., Mols, O., and Marnett, L. J. (1988) Identification of adducts formed by reaction of guanine nucleosides with malondialdehyde and structurally related aldehydes. Chem. Res. Toxicol. 1, 53-59.
    • (1988) Chem. Res. Toxicol. , vol.1 , pp. 53-59
    • Basu, A.K.1    O'Hara, S.M.2    Valladier, P.3    Stone, K.4    Mols, O.5    Marnett, L.J.6
  • 22
    • 0025240126 scopus 로고
    • Investigation of the adducts formed by reaction of malondialdehyde with adenosme
    • Stone, K., Ksebati, M., and Marnett, L. J. (1990) Investigation of the adducts formed by reaction of malondialdehyde with adenosme. Chem. Res. Toxicol. 3, 33-38.
    • (1990) Chem. Res. Toxicol. , vol.3 , pp. 33-38
    • Stone, K.1    Ksebati, M.2    Marnett, L.J.3
  • 23
    • 0025147523 scopus 로고
    • Studies of the reaction of malondialdehyde with cytosine nucleosides
    • Stone, K., Uzieblo, A, and Marnett, L. J. (1990) Studies of the reaction of malondialdehyde with cytosine nucleosides. Chem. Res. Toxicol. 3, 467-472.
    • (1990) Chem. Res. Toxicol. , vol.3 , pp. 467-472
    • Stone, K.1    Uzieblo, A.2    Marnett, L.J.3
  • 24
    • 0026036253 scopus 로고
    • Reaction of malonaldehyde with nucleic acid. IV. Formation of pyrimido[1,2-a]purin-10(3H)-one nucleoside by thermal decomposition of diastereomers containing oxadiazabicyclononene residues linked to guanosine
    • Seto, H., Seto, T., Ohkubo, T., and Saitoh, I. (1991) Reaction of malonaldehyde with nucleic acid. IV. Formation of pyrimido[1,2-a]purin-10(3H)-one nucleoside by thermal decomposition of diastereomers containing oxadiazabicyclononene residues linked to guanosine. Chem. Pharm. Bull. 39, 515-517.
    • (1991) Chem. Pharm. Bull. , vol.39 , pp. 515-517
    • Seto, H.1    Seto, T.2    Ohkubo, T.3    Saitoh, I.4
  • 25
    • 0001231384 scopus 로고
    • Novel adducts from the modification of nucleic acid bases by malondialdehyde
    • Nair, V., Turner, G. A., and Offerman, R. J. (1984) Novel adducts from the modification of nucleic acid bases by malondialdehyde. J. Am. Chem. Soc. 106, 3370-3371.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 3370-3371
    • Nair, V.1    Turner, G.A.2    Offerman, R.J.3
  • 26
    • 0026021690 scopus 로고
    • Stereoselective formation of in vitro nucleic acid adducts by 2,3-epoxy-4-hydroxynonanal
    • Sodum, R. S., and Chung, F.-L. (1991) Stereoselective formation of in vitro nucleic acid adducts by 2,3-epoxy-4-hydroxynonanal. Cancer Res. 51, 137-143
    • (1991) Cancer Res. , vol.51 , pp. 137-143
    • Sodum, R.S.1    Chung, F.-L.2
  • 28
    • 0027291213 scopus 로고
    • Identification and characterization of deoxyguanosine adducts of mutagenic β-alkyl-substituted acrolein congeners
    • Eder, E., and Hoffman, C. (1993) Identification and characterization of deoxyguanosine adducts of mutagenic β-alkyl-substituted acrolein congeners. Chem. Res. Toxicol. 6, 486-494.
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 486-494
    • Eder, E.1    Hoffman, C.2
  • 29
    • 0020446036 scopus 로고
    • Mutagenic properties of allylic and alpha,beta-unsaturated compounds: Consideration of alkylating mechanisms
    • Eder, E. D., Henschler, D., and Neudecker, T. (1982) Mutagenic properties of allylic and alpha,beta-unsaturated compounds: consideration of alkylating mechanisms. Xenobiotica 12, 831-848.
    • (1982) Xenobiotica , vol.12 , pp. 831-848
    • Eder, E.D.1    Henschler, D.2    Neudecker, T.3
  • 30
    • 0003373490 scopus 로고
    • Propiolaldehyde
    • Sauer, J. C. (1956) Propiolaldehyde. Org. Synth. 36, 66-69.
    • (1956) Org. Synth. , vol.36 , pp. 66-69
    • Sauer, J.C.1
  • 31
    • 0028003694 scopus 로고
    • A simple method for N-15 labeling of exocyclic amino groups in synthetic oligodeoxynucleotides
    • Acedo, M., Fabrega, C., Avino, A., Goodman, M., Fagan, P., Wemmer, D., and Eritja, R (1994) A simple method for N-15 labeling of exocyclic amino groups in synthetic oligodeoxynucleotides. Nucleic Acids Res. 22, 2982-2989.
    • (1994) Nucleic Acids Res. , vol.22 , pp. 2982-2989
    • Acedo, M.1    Fabrega, C.2    Avino, A.3    Goodman, M.4    Fagan, P.5    Wemmer, D.6    Eritja, R.7
  • 32
    • 0016694032 scopus 로고
    • Formaldehyde as a probe of DNA structure. I Reaction with exocyclic amino groups of DNA bases
    • McGhee, J. D., and von Hippel, P. H. (1975) Formaldehyde as a probe of DNA structure. I Reaction with exocyclic amino groups of DNA bases. Biochemistry 14, 1281-1296.
    • (1975) Biochemistry , vol.14 , pp. 1281-1296
    • McGhee, J.D.1    Von Hippel, P.H.2
  • 33
    • 0023901349 scopus 로고
    • A study of reactions of α,β-unsaturated carbortyl compounds with deoxyguanosine
    • Chung, F.-L., Roy, K. R., and Hecht, S. S. (1988) A study of reactions of α,β-unsaturated carbortyl compounds with deoxyguanosine, J. Org. Chem. 53, 14-17.
    • (1988) J. Org. Chem. , vol.53 , pp. 14-17
    • Chung, F.-L.1    Roy, K.R.2    Hecht, S.S.3
  • 34
    • 0023901349 scopus 로고
    • A study of reactions of α,β-unsaturated carbonyl compounds with deoxyguanosine
    • Chung, F.-L., Roy, K. R., and Hecht, S. S. (1988) A study of reactions of α,β-unsaturated carbonyl compounds with deoxyguanosine. J. Org.Chem. 53, 14-17.
    • (1988) J. Org.Chem. , vol.53 , pp. 14-17
    • Chung, F.-L.1    Roy, K.R.2    Hecht, S.S.3
  • 35
    • 0343556549 scopus 로고
    • Nucleophilic attack on enones
    • (Patai, S., and Rappoport, Z., Eds.) John Wiley and Sons
    • Duval, D., and Geribaldi, S. (1989) Nucleophilic attack on enones. In The Chemistry of Enones (Patai, S., and Rappoport, Z., Eds.) pp 355-469, John Wiley and Sons.
    • (1989) The Chemistry of Enones , pp. 355-469
    • Duval, D.1    Geribaldi, S.2
  • 36
    • 85008133941 scopus 로고
    • Reaction of β-ethoxyacrolein and p-toluidine in benzene solution
    • Ono, M., Tanaka, H., and Tamura, S. (1982) Reaction of β-ethoxyacrolein and p-toluidine in benzene solution. Chem Pharm. Bull. 30, 1933-1941.
    • (1982) Chem Pharm. Bull. , vol.30 , pp. 1933-1941
    • Ono, M.1    Tanaka, H.2    Tamura, S.3


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