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Volumn 291, Issue 27, 2016, Pages 14134-14145

Structural and kinetic analysis of miscoding opposite the DNA Adduct 1,N6 -Ethenodeoxyadenosine by human translesion DNA polymerase η

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN BONDS; OLIGONUCLEOTIDES; SPECTRUM ANALYSIS;

EID: 84976877678     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M116.732487     Document Type: Article
Times cited : (12)

References (56)
  • 3
    • 0001406666 scopus 로고
    • Detection of carcinogens as mutagens in the Salmonella/microsome test: Assay of 300 chemicals
    • Mc Cann, J., Choi, E., Yamasaki, E., and Ames, B. N. (1975) Detection of carcinogens as mutagens in the Salmonella/microsome test: assay of 300 chemicals. Proc. Natl. Acad. Sci. U.S.A. 72, 5135-5139
    • (1975) Proc. Natl. Acad. Sci. U.S.A. , vol.72 , pp. 5135-5139
    • Cann, M.J.1    Choi, E.2    Yamasaki, E.3    Ames, B.N.4
  • 4
    • 0037342752 scopus 로고    scopus 로고
    • Somatic gene mutation and human disease other than cancer
    • Erickson, R. P. (2003) Somatic gene mutation and human disease other than cancer. Mutat. Res. 543, 125-136
    • (2003) Mutat. Res. , vol.543 , pp. 125-136
    • Erickson, R.P.1
  • 5
    • 34147194790 scopus 로고    scopus 로고
    • The genetics of congenital heart disease: A review of recent developments
    • Weismann, C. G., and Gelb, B. D. (2007) The genetics of congenital heart disease: a review of recent developments. Curr. Opin. Cardiol. 22, 200-206
    • (2007) Curr. Opin. Cardiol. , vol.22 , pp. 200-206
    • Weismann, C.G.1    Gelb, B.D.2
  • 6
    • 77957601615 scopus 로고    scopus 로고
    • Genetic factors in non-syndromic congenital heart malformations
    • Wessels, M. W., and Willems, P. J. (2010) Genetic factors in non-syndromic congenital heart malformations. Clin. Genet. 78, 103-123
    • (2010) Clin. Genet , vol.78 , pp. 103-123
    • Wessels, M.W.1    Willems, P.J.2
  • 8
    • 79956220155 scopus 로고    scopus 로고
    • Geacintov, N. E. , and Broyde, S. Wiley-VCH Verlag GmbH, KGaA Weinheim, Germany
    • DeMott, M. S., and Dedon, P. C. (2010) in The Chemical Biology of DNA Damage (Geacintov, N. E., and Broyde, S., eds) pp. 21-51, Wiley-VCH Verlag GmbH, KGaA Weinheim, Germany
    • (2010) The Chemical Biology of DNA Damage , pp. 21-51
    • DeMott, M.S.1    Dedon, P.C.2
  • 9
    • 79952075274 scopus 로고    scopus 로고
    • Endogenous versus exogenous DNA adducts: Their role in carcinogenesis, epidemiology, and risk assessment
    • Swenberg, J. A., Lu, K., Moeller, B. C., Gao, L., Upton, P. B., Nakamura, J., and Starr, T. B. (2011) Endogenous versus exogenous DNA adducts: their role in carcinogenesis, epidemiology, and risk assessment. Toxicol. Sci. 120, S130-S145
    • (2011) Toxicol. Sci. , vol.120 , pp. S130-S145
    • Swenberg, J.A.1    Lu, K.2    Moeller, B.C.3    Gao, L.4    Upton, P.B.5    Nakamura, J.6    Starr, T.B.7
  • 10
    • 0000168477 scopus 로고
    • Etheno-bridged nucleotides in structural diagnosis and carcinogenesis
    • Leonard, N. J. (1992) Etheno-bridged nucleotides in structural diagnosis and carcinogenesis. Chemtracts-Biochem. Mol. Biol. 3, 273-297
    • (1992) Chemtracts-Biochem. Mol. Biol. , vol.3 , pp. 273-297
    • Leonard, N.J.1
  • 12
    • 0017786671 scopus 로고
    • 2,3-ethenoguanine. Synthesis and comparison of the electronic spectral properties of these linear and angular triheterocycles related to the Y bases
    • Sattsangi, P. D., Leonard, N. J., and Frihart, C. R. (1977) 1,N2 -Ethenoguanine and N2 ,3-ethenoguanine. Synthesis and comparison of the electronic spectral properties of these linear and angular triheterocycles related to the Y bases. J. Org. Chem. 42, 3292-3296
    • (1977) J. Org. Chem. , vol.42 , pp. 3292-3296
    • Sattsangi, P.D.1    Leonard, N.J.2    Frihart, C.R.3
  • 13
    • 0015504246 scopus 로고
    • Fluorescent modification of adenosine-containing coenzymes. Biological activities and spectroscopic properties
    • Secrist, J. A., 3rd., Barrio, J. R., Leonard, N. J., and Weber, G. (1972) Fluorescent modification of adenosine-containing coenzymes. Biological activities and spectroscopic properties. Biochemistry 11, 3499-3506
    • (1972) Biochemistry , vol.11 , pp. 3499-3506
    • Secrist, A.J.1    Barrio, J.R.2    Leonard, N.J.3    Weber, G.4
  • 14
    • 0021295867 scopus 로고
    • Etheno-substituted nucleotides and coenzymes: Fluorescence and biological activity
    • Leonard, N. J. (1984) Etheno-substituted nucleotides and coenzymes: fluorescence and biological activity. CRC Crit. Rev. Biochem. 15, 125-199
    • (1984) CRC Crit. Rev. Biochem. , vol.15 , pp. 125-199
    • Leonard, N.J.1
  • 15
    • 0011386991 scopus 로고
    • Etheno-bridged nucleotides in enzyme reactions and protein binding
    • Leonard, N. J. (1993) Etheno-bridged nucleotides in enzyme reactions and protein binding. Chemtracts-Biochem. Mol. Biol. 4, 251-284
    • (1993) Chemtracts-Biochem. Mol. Biol. , vol.4 , pp. 251-284
    • Leonard, N.J.1
  • 17
    • 0019481444 scopus 로고
    • DNA alkylation by vinyl chloride metabolites: Etheno derivatives or 7-alkylation of guanine?
    • Laib, R. J., Gwinner, L. M., and Bolt, H. M. (1981) DNA alkylation by vinyl chloride metabolites: etheno derivatives or 7-alkylation of guanine? Chem. Biol. Interact. 37, 219-231
    • (1981) Chem.Biol. Interact , vol.37 , pp. 219-231
    • Laib, R.J.1    Gwinner, L.M.2    Bolt, H.M.3
  • 18
    • 0025469065 scopus 로고
    • 2,3-ethenoguanine in rat tissue DNA
    • Fedtke, N., Boucheron, J. A., Walker, V. E., and Swenberg, J. A. (1990) Vinyl chloride-induced DNA adducts. II. Formation and persistence of 7-(2'-oxoethyl)guanine and N2 ,3-ethenoguanine in rat tissue DNA. Carcinogenesis 11, 1287-1292
    • (1990) Carcinogenesis , vol.11 , pp. 1287-1292
    • Fedtke, N.1    Boucheron, J.A.2    Walker, V.E.3    Swenberg, J.A.4
  • 19
    • 0033377954 scopus 로고    scopus 로고
    • Covalent modifications to 2'-deoxyguanosine by 4-oxo-2-nonenal, a novel product of lipid peroxidation
    • Rindgen, D., Nakajima, M., Wehrli, S., Xu, K., and Blair, I. A. (1999) Covalent modifications to 2'-deoxyguanosine by 4-oxo-2-nonenal, a novel product of lipid peroxidation. Chem. Res. Toxicol. 12, 1195-1204
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 1195-1204
    • Rindgen, D.1    Nakajima, M.2    Wehrli, S.3    Xu, K.4    Blair, I.A.5
  • 21
    • 0000892916 scopus 로고
    • Formation of etheno adducts of adenosine and cytidine from 1-halooxiranes. Evidence for a mechanism involving initial reaction with the endocyclic nitrogens
    • Guengerich, F. P., and Raney, V. M. (1992) Formation of etheno adducts of adenosine and cytidine from 1-halooxiranes. Evidence for a mechanism involving initial reaction with the endocyclic nitrogens. J. Am. Chem. Soc. 114, 1074-1080
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 1074-1080
    • Guengerich, F.P.1    Raney, M.2
  • 22
    • 0026572753 scopus 로고
    • Etheno adducts formed in DNA of vinyl chloride-exposed rats are highly persistent in liver
    • Swenberg, J. A., Fedtke, N., Ciroussel, F., Barbin, A., and Bartsch, H. (1992) Etheno adducts formed in DNA of vinyl chloride-exposed rats are highly persistent in liver. Carcinogenesis 13, 727-729
    • (1992) Carcinogenesis , vol.13 , pp. 727-729
    • Swenberg, J.A.1    Fedtke, N.2    Ciroussel, F.3    Barbin, A.4    Bartsch, H.5
  • 23
    • 0023648312 scopus 로고
    • 6-ethenoadenine: Synthesis, physical characterization, and incorporation into a duplex bacteriophage M13 genome as part of an amber codon
    • Basu, A. K., Niedernhofer, L. J., and Essigmann, J. M. (1987) Deoxyhexanucleotide containing a vinyl chloride induced DNA lesion, 1,N6 -ethenoadenine: synthesis, physical characterization, and incorporation into a duplex bacteriophage M13 genome as part of an amber codon. Biochemistry 26, 5626-5635
    • (1987) Biochemistry , vol.26 , pp. 5626-5635
    • Basu, A.K.1    Niedernhofer, L.J.2    Essigmann, J.M.3
  • 24
    • 0029665327 scopus 로고    scopus 로고
    • 6-Ethenodoexyadenosine, a DNA adduct highly mutagenic in mammalian cells
    • Pandya, G. A., and Moriya, M. (1996) 1,N6 -Ethenodoexyadenosine, a DNA adduct highly mutagenic in mammalian cells. Biochemistry 35, 11487-11492
    • (1996) Biochemistry , vol.35 , pp. 11487-11492
    • Pandya, G.A.1    Moriya, M.2
  • 27
    • 0033254076 scopus 로고    scopus 로고
    • Exocyclic DNA adducts in mutagenesis and carcinogenesis
    • Singer, B., and Bartsch, H. Int. Agency Res. Cancer Scientific Publications, Lyon, France
    • Moriya, M., Pandya, G. A., Johnson, F., and Grollman, A. P. (1999) in Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis (Singer, B., and Bartsch, H., eds) IARC Sci. Publication No. 150, pp. 263-270, Int. Agency Res. Cancer Scientific Publications, Lyon, France
    • (1999) IARC Sci. Publication , vol.150 , pp. 263-270
    • Moriya, M.1    Pandya, G.A.2    Johnson, F.3    Grollman, A.P.4
  • 28
    • 40249093087 scopus 로고    scopus 로고
    • 6 -ethenoadenine and 8-oxoguanine in human cell extracts
    • Tolentino, J. H., Burke, T. J., Mukhopadhyay, S., Mc Gregor, W. G., and Basu, A. K. (2008) Inhibition of DNA replication fork progression and mutagenic potential of 1,N6 -ethenoadenine and 8-oxoguanine in human cell extracts. Nucleic Acids Res. 36, 1300-1308
    • (2008) Nucleic Acids Res. , vol.36 , pp. 1300-1308
    • Tolentino, J.H.1    Burke, T.J.2    Mukhopadhyay, S.3    Gregor, M.W.G.4    Basu, A.K.5
  • 29
    • 0025851827 scopus 로고
    • 6-ethenodeoxyadenosine adduct (ϵdA) opposite thymidine in a DNA duplex. Nonplanar alignment of ϵdA(anti) and dT(anti) at the lesion site
    • Kouchakdjian, M., Eisenberg, M., Yarema, K., Basu, A., Essigmann, J., and Patel, D. J. (1991) NMR studies of the exocyclic 1,N6 -ethenodeoxyadenosine adduct (ϵdA) opposite thymidine in a DNA duplex. Nonplanar alignment of ϵdA(anti) and dT(anti) at the lesion site. Biochemistry 30, 1820-1828
    • (1991) Biochemistry , vol.30 , pp. 1820-1828
    • Kouchakdjian, M.1    Eisenberg, M.2    Yarema, K.3    Basu, A.4    Essigmann, J.5    Patel, D.J.6
  • 30
    • 0025809945 scopus 로고
    • 6 -ethenodeoxyadenosine adduct (ϵdA) opposite deoxyguanosine in a DNA duplex. ϵdA(syn)· dG(anti) pairing at the lesion site
    • de los Santos, C., Kouchakdjian, M., Yarema, K., Basu, A., Essigmann, J., and Patel, D. J. (1991) NMR studies of the exocyclic 1,N6 -ethenodeoxyadenosine adduct (ϵdA) opposite deoxyguanosine in a DNA duplex. ϵdA(syn)· dG(anti) pairing at the lesion site. Biochemistry 30, 1828-1835
    • (1991) Biochemistry , vol.30 , pp. 1828-1835
    • De los Santos, C.1    Kouchakdjian, M.2    Yarema, K.3    Basu, A.4    Essigmann, J.5    Patel, D.J.6
  • 32
    • 0021222694 scopus 로고
    • 4-methyldeoxythymidine, using polymerases of varying fidelity
    • Singer, B., Abbott, L. G., and Spengler, S. J. (1984) Assessment of mutagenic efficiency of two carcinogen-modified nucleosides, 1,N6 -ethenodeoxyadenosine and O4 -methyldeoxythymidine, using polymerases of varying fidelity. Carcinogenesis 5, 1165-1171
    • (1984) Carcinogenesis , vol.5 , pp. 1165-1171
    • Singer, B.1    Abbott, L.G.2    Spengler, S.J.3
  • 33
    • 84875474767 scopus 로고    scopus 로고
    • 4-ethenocytosine-containing RNA oligonucleotides
    • Calabretta, A., and Leumann, C. J. (2013) Base pairing and miscoding properties of 1,N6 -ethenoadenine- and 3,N4 -ethenocytosine-containing RNA oligonucleotides. Biochemistry 52, 1990-1997
    • (2013) Biochemistry , vol.52 , pp. 1990-1997
    • Calabretta, A.1    Leumann, C.J.2
  • 36
    • 67449103244 scopus 로고    scopus 로고
    • 5 -methyl-formamidopyrimidine lesion of deoxyguanosine by DNA polymerases and an improved procedure for sequence analysis of in vitro bypass products by mass spectrometry
    • Christov, P. P., Angel, K. C., Guengerich, F. P., and Rizzo, C. J. (2009) Replication past the N5 -methyl-formamidopyrimidine lesion of deoxyguanosine by DNA polymerases and an improved procedure for sequence analysis of in vitro bypass products by mass spectrometry. Chem. Res. Toxicol. 22, 1086-1095
    • (2009) Chem. Res. Toxicol. , vol.22 , pp. 1086-1095
    • Christov, P.P.1    Angel, K.C.2    Guengerich, F.P.3    Rizzo, C.J.4
  • 38
    • 33847713782 scopus 로고    scopus 로고
    • 6 -methylguanine and cytosine, but accurate bypass is preferred
    • Eoff, R. L., Irimia, A., Egli, M., and Guengerich, F. P. (2007) Sulfolobus solfataricus DNA polymerase Dpo4 is partially inhibited by wobble pairing between O6 -methylguanine and cytosine, but accurate bypass is preferred. J. Biol. Chem. 282, 1456-1467
    • (2007) J. Biol. Chem. , vol.282 , pp. 1456-1467
    • Eoff, R.L.1    Irimia, A.2    Egli, M.3    Guengerich, F.P.4
  • 39
    • 53049102355 scopus 로고    scopus 로고
    • 6 sulfonic acid
    • Yuan, B., and Wang, Y. (2008) Mutagenic and cytotoxic properties of 6-thioguanine, S6 -methylthioguanine, and guanine-S6 -sulfonic acid. J. Biol. Chem. 283, 23665-23670
    • (2008) J. Biol. Chem. , vol.283 , pp. 23665-23670
    • Yuan, B.1    Wang, Y.2
  • 41
    • 84857537972 scopus 로고    scopus 로고
    • Liquid chromatographymass spectrometry analysis of DNA polymerase reaction products
    • Chapter 7, Unit 7
    • Chowdhury, G., and Guengerich, F. P. (2011) Liquid chromatographymass spectrometry analysis of DNA polymerase reaction products. Curr. Protoc. Nucleic Acid Chem. Chapter 7, Unit 7.16.1-11
    • (2011) Curr. Protoc. Nucleic Acid Chem. , vol.16 , pp. 1-11
    • Chowdhury, G.1    Guengerich, F.P.2
  • 42
    • 84920973951 scopus 로고    scopus 로고
    • Error-prone translesion synthesis past DNApeptide cross-links conjugated to the major groove of DNA via C5 of thymidine
    • Wickramaratne, S., Boldry, E. J., Buehler, C., Wang, Y. C., Distefano, M. D., and Tretyakova, N. Y. (2015) Error-prone translesion synthesis past DNApeptide cross-links conjugated to the major groove of DNA via C5 of thymidine. J. Biol. Chem. 290, 775-787
    • (2015) J. Biol. Chem. , vol.290 , pp. 775-787
    • Wickramaratne, S.1    Boldry, E.J.2    Buehler, C.3    Wang, Y.C.4    Distefano, M.D.5    Tretyakova, N.Y.6
  • 45
    • 84985741268 scopus 로고
    • Protonation and quaternization of 1,N6 -ethenoadenosine: What are the species responsible for the fluorescence of 1,N6 -ethenoadenosine?
    • Inoue, Y., and Kuramochi, T. (1979) Protonation and quaternization of 1,N6 -ethenoadenosine: what are the species responsible for the fluorescence of 1,N6 -ethenoadenosine? Biopolymers 18, 2175-2194
    • (1979) Biopolymers , vol.18 , pp. 2175-2194
    • Inoue, Y.1    Kuramochi, T.2
  • 47
    • 0029133553 scopus 로고
    • 6-ethenoadenine when present in DNA
    • Saparbaev, M., Kleibl, K., and Laval, J. (1995) Escherichia coli, Saccharomyces cerevisiae, rat and human 3-methyladenine DNA glycolases repair 1,N6 -ethenoadenine when present in DNA. Nucleic Acids Res. 23, 3750-3755
    • (1995) Nucleic Acids Res , vol.23 , pp. 3750-3755
    • Saparbaev, M.1    Kleibl, K.2    Laval, J.3
  • 48
    • 84925813561 scopus 로고    scopus 로고
    • Structural and kinetic analysis of nucleoside triphosphate incorporation opposite an abasic site by human translesion DNA polymerase &eta
    • Patra, A., Zhang, Q., Lei, L., Su, Y., Egli, M., and Guengerich, F. P. (2015) Structural and kinetic analysis of nucleoside triphosphate incorporation opposite an abasic site by human translesion DNA polymerase η. J. Biol. Chem. 290, 8028- 8038
    • (2015) J. Biol. Chem. , vol.290 , pp. 8028-8038
    • Patra, A.1    Zhang, Q.2    Lei, L.3    Su, Y.4    Egli, M.5    Guengerich, F.P.6
  • 49
    • 33745808012 scopus 로고    scopus 로고
    • 6 -ethenodeoxyadenosine lesion by human DNA polymerase ι
    • Nair, D. T., Johnson, R. E., Prakash, L., Prakash, S., and Aggarwal, A. K. (2006) Hoogsteen base pair formation promotes synthesis opposite the 1,N6 -ethenodeoxyadenosine lesion by human DNA polymerase ι. Nat. Struct. Mol. Biol. 13, 619- 625
    • (2006) Nat. Struct. Mol. Biol. , vol.13 , pp. 619-625
    • Nair, D.T.1    Johnson, R.E.2    Prakash, L.3    Prakash, S.4    Aggarwal, A.K.5
  • 51
    • 0031059866 scopus 로고    scopus 로고
    • Processing of X-ray diffraction data collected in oscillation mode
    • Otwinowski, Z., and Minor, W. (1997) Processing of X-ray diffraction data collected in oscillation mode. Methods Enzymol. 276, 307-326
    • (1997) Methods Enzymol , vol.276 , pp. 307-326
    • Otwinowski, Z.1    Minor, W.2
  • 55


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