The effect of the 2-amino group of 7,8-dihydro-8-oxo-2′-deoxyguanosine on translesion synthesis and duplex stability

Nucleic Acids Research

Volumn 33, Issue 5, 2005, Pages 1637-1643

  Oka, Natsuhisa ^a   Greenberg, Marc M ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 HYDROXYDEOXYGUANOSINE; DEOXYADENOSINE; DEOXYCYTIDINE; DEOXYGUANOSINE; DEOXYINOSINE; DNA DIRECTED DNA POLYMERASE BETA; DOUBLE STRANDED DNA; 7,8 DIHYDRO 8 OXO 2' DEOXYINOSINE; 7,8-DIHYDRO-8-OXO-2'-DEOXYINOSINE; 8 OXO 7 HYDRODEOXYGUANOSINE; 8-OXO-7-HYDRODEOXYGUANOSINE; AMINE; DNA; DRUG DERIVATIVE; INOSINE; OLIGODEOXYRIBONUCLEOTIDE;

ARTICLE; CONTROLLED STUDY; DNA DAMAGE; DNA REPLICATION; DNA STRUCTURE; DNA SYNTHESIS; DNA TEMPLATE; MOLECULAR STABILITY; PRIORITY JOURNAL; SOLID PHASE SYNTHESIS; THERMOSTABILITY; BASE PAIRING; BIOSYNTHESIS; CHEMISTRY; DNA DENATURATION; KINETICS; METABOLISM; SYNTHESIS; TEMPERATURE;

ESCHERICHIA COLI;

AMINES; BASE PAIRING; DEOXYGUANOSINE; DNA; DNA DAMAGE; DNA POLYMERASE I; INOSINE; KINETICS; NUCLEIC ACID DENATURATION; OLIGODEOXYRIBONUCLEOTIDES; TEMPERATURE;

EID: 15044352935     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gki305     Document Type: Article

References (33)

1. Wood,M.L., Esteve,A., Morningstar,M.L., Kuziemko,G.M. and Essigmann,J.M. (1992) Genetic effects of oxidative DNA damage: Comparative mutagenesis of 7,8-dihydro-8-oxoguanine and 7,8-dihydro-8-oxoadenine in [i#Escherichia coli. Nucleic Acids Res.#1i], [b#20#1b], 6023-6032.
2. Tan,X., Grollman,A.P. and Shibutani,S. (1999) Comparison of the mutagenic properties of 8-oxo-7,8-dihydro-2′-deoxyadenosine and 8-oxo-7-8-dihydro-2′-deoxyguanosine DNA lesions in mammalian cells. [i#Carcinogenesis#1i], [b#20#1b], 2287-2292.
3. Kamiya,H. (2003) Mutagenic potentials of damaged nucleic acids produced by reactive oxygen/nitrogen species: Approaches using synthetic oligonucleotides and nucleotides. [i#Nucleic Acids Res.#1i], [b#31#1b], 517-531.
4. Hsu,G.W., Ober,M., Carell,T. and Beese,L.S. (2004) Error-prone replication of oxidatively damaged DNA by a high-fidelity DNA polymerase. [i#Nature#1i], [b#431#1b], 217-221.
5. Collins,A.R., Cadet,J., Moeller,L., Poulsen,H.E. and Vina,J. (2004) Are we sure we know how to measure 8-oxo-7,8-dihydroguanine in DNA from human cells? [i#Arch. Biochem. Biophys.#1i], [b#423#1b], 57-65.
6. Spitz,M.R., Wei,Q., Dong,Q., Amos,C. and Wu,X. (2003) Genetic susceptibility to lung cancer: The role of DNA damage and repair. [i#Cancer Epidemiol. Biomarkers Prevention#1i], [b#12#1b], 689-698.
7. Wang,D., Kreutzer,D.A. and Essigmann,J.M. (1998) Mutagenicity and repair of oxidative DNA damage: Insights from studies using defined lesions. [i#Mutat. Res.#1i], [b#400#1b], 99-115.
8. Dizdaroglu,M. (2003) Substrate specificities and excision kinetics of DNA glycosylases involved in base-excision repair of oxidative DNA damage. [i#Mutat. Res.#1i], [b#531#1b], 109-126.
9. David,S.S. and Williams,S.D. (1998) Chemistry of glycosylases and endonucleases involved in base-excision repair. [i#Chem. Rev.#1i], [b#98#1b] 1221-1261.
10. Uesugi,S. and Ikehara,M. (1977) Carbon-13 magnetic resonance spectra of 8-substituted purine nucleosides. Characteristic shifts for the Syn conformation. [i#J. Am. Chem. Soc.#1i], [b#99#1b], 3250-3253.
11. Shibutani,S., Takeshita,M. and Grollman,A.P. (1991) Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-OxodG. [i#Nature#1i], [b#349#1b], 431-434.
12. McAuley-Hecht,K.E., Leonard,G.A., Gibson,N.J., Thomson,J.B., Watson,W.P., Hunter,W.N. and Brown,T. (1994) Crystal structure of a DNA duplex containing 8-hydroxydeoxyguanine-adenine base pairs. [i#Biochemistry#1i], [b#33#1b], 10266-10270.
13. Kouchakdjian,M., Bodepudi,V., Shibutani,S., Eisenberg,M., Johnson,F., Grollman,A.P. and Patel,D.J. (1991) NMR structural studies of the ionizing radiation adduct 7-dihydro-8-oxodeoxyguanosine (8-oxo-7H-dG) opposite deoxyadenosine in a DNA duplex. 8-oxo-7H-dG(syn).dA(anti) alignment at lesion site. [i#Biochemistry#1i], [b#30#1b], 1403-1412.
14. Krahn,J.M., Beard,W.A., Miller,H., Grollman,A.P. and Wilson,S.H. (2003) Structure of DNA polymerase β with the mutagenic DNA lesion 8-oxodeoxyguanine reveals structural insights into its coding potential. [i#Structure#1i], [b#11#1b], 121-127.
15. Zharkov,D.O., Rosenquist,T.A., Gerchman,S.E. and Grollman,A.P. (2000) Substrate specificity and reaction mechanism of murine 8-oxoguanine-DNA glycosylase. [i#J. Biol. Chem.#1i], [b#275#1b], 28607-28617.
16. Kamiya,H., Yakushiji,H., Dugue,L., Tanimoto,M., Pochet,S., Nakabeppu,Y. and Harashima,H. (2004) Probing the substrate recognition mechanism of the human MTH1 protein by nucleotide analogs. [i#J. Mol. Biol.#1i], [b#336#1b], 843-850.
17. Tchou,J., Bodepudi,V., Shibutani,S., Antoshechkin,I., Miller,J., Grollman,A.P. and Johnson,F. (1994) Substrate specificity of Fpg protein. Recognition and cleavage of oxidatively damaged DNA. [i#J. Biol. Chem.#1i], [b#269#1b], 15318-15324.
18. Martin,F.H., Castro,M.M., Aboul-Ela,F. and Tinoco,I.Jr. (1985) Base pairing involving deoxyinosine: Implications for probe design. [i#Nucleic Acids Res.#1i], [b#13#1b], 8927-8938.
19. Kamiya,H., Sakaguchi,T., Murata,N., Fujimuro,M., Miura,H., Ishikawa,H., Shimizu,M., Inoue,H., Nishimura,S., Matsukage,A., Masutani,C., Hanaoka,F. and Ohtsuka,E. (1992) In vitro replication study of modified bases in ras sequences. [i#Chem. Pharm. Bull#1i], [b#40#1b], 2792-2795.
20. Ciuffreda,P., Casati,S. and Santaniello,E. (1999) Lipase-catalyzed protection of the hydroxy groups of the nucleosides inosine and 2′-deoxyinosine: A new chemoenzymatic synthesis of the antiviral drug 2′,3′-dideoxyinosine. [i#Bioorg. Med. Chem. Lett.#1i], [b#9#1b], 1577-1582.
21. Goodman,M.F., Creighton,S., Bloom,L.B. and Petruska,J. (1993) Biochemical basis of DNA replication. [i#Crit. Rev. Biochem. Mol. Biol.#1i] [b#28#1b], 83-16.
22. Bodepudi,V., Shibutani,S. and Johnson,F. (1992) Synthesis of 2′-deoxy-7,8-dihydro-8-oxoguanosine and 2′-deoxy-7,8-dihydro-8-oxoadenosine and their incorporation into oligomeric DNA. [i#Chem. Res. Toxicol.#1i], [b#5#1b], 608-617.
23. Eason,R.G., Burkhardt,D.M., Phillips,S.J., Smith,D.P. and David,S.S. (1996) Synthesis and characterization of 8-methoxy-2′-deoxyadenosine-containing oligonucleotides to probe the syn glycosidic conformation of 2′-deoxyadenosine within DNA. [i#Nucleic Acids Res.#1i], [b#24#1b], 890-897.
24. Koizume,S., Kamiya,H., Inoue,H. and Ohtsuka,E. (1994) Synthesis and thermodynamic stabilities of damaged DNA involving 8-hydroxyguanine (7,8-dihydro-8-oxoguanine) in a ras-gene fragment. [i#Nucleosides Nucleotides#1i], [b#13#1b], 1517-1534.
25. Plum,G.E., Grollman,A.P., Johnson,F. and Breslauer,K.J. (1995) Influence of the oxidatively damaged adduct 8-oxodeoxygunosine on the conformation energetics, and thermodynamic stabilty of a DNA duplex. [i#Biochemistry#1i] [b#34#1b], 16148-16160.
26. Kool,E.T. (2002) Active site tightness and substrate fit in DNA replication. [i#Ann. Rev. Biochemistry#1i], [b#71#1b], 191-219.
27. Creighton,S., Bloom,L.B. and Goodman,M.F. (1995) Gel fidelity assay measuring nucleotide misinsertion, exonucleolytic proofreading, and lesion bypass efficiencies. [i#Methods Enzymol.#1i], [b#262#1b], 232-256.
28. Mendelman,L.V., Pefuska,J. and Goodman,M.F. (1990) Base mispair extension kinetics. [i#J. Biol. Chem.#1i], [b#265#1b], 2338-2345.
29. Randall,S.K., Eritja,R., Kaplan,B.E., Petruska,J. and Goodman,M.F. (1987) Nucleotide insertion kinetics opposite abasic lesions in DNA. [i#J. Biol. Chem.#1i], [b#262#1b], 6864-6870.
30. - to misincorporate deoxyadenosine. [i#J. Am. Chem. Soc.#1i], [b#124#1b], 7278-7279.
31. Hill-Perkins,M., Jones,M.D. and Karran,P. (1986) Site-specific mutagenesis in vivo by single methylated or deaminated purine base. [i#Mutat. Res.#1i], [b#162#1b], 153-163.
32. Lowe,L.G. and Guengerich,F.P. (1996) Steady-state and pre-steady-state kinetic analysis of dNTP insertion opposite 8-oxo-7,8-dihydroguanine by [i#E. coli#1i]: Polymerases I exo- and II exo-. [i#Biochemistry#1i], [b#35#1b] 9840-9849.
33. Hoffmann,R., Minkin,V.I. and Carpenter,B.K. (1996) Ockham's razor and chemistry. [i#Bull. Soc. Chin. France#1i], [b#133#1b], 117-130.