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PMID: 6866769 Published · ppublish English Journal Article Research Support, Non-U.S. Gov't

The incorporation of O6-methyldeoxyguanosine and O4-methyldeoxythymidine monophosphates into DNA by DNA polymerases I and alpha.

Nucleic acids research ·Vol. 11 ·No. 12 ·1983-06-25 ·Pages 4185-93

Hall JA, Saffhill R

Abstract

The modified nucleoside 5'-triphosphates O6-MedGTP ad O4-MedTTP have been synthesised and their acceptability as DNA-precursors investigated using DNA polymerases I and alpha in an in vitro assay. O6-MedGMP is only incorporated into newly-synthesized DNA-like material in the presence of templates containing thymine bases. Similarly O4-MedTMP is only incorporated in the presence of templates containing guanine bases. The results confirm the promutagenic nature and base-pairing properties of O6-MeG ad O4-MeT.

MeSH Terms
DNA Polymerase I/metabolism DNA Polymerase II/metabolism DNA Replication/drug effects DNA-Directed DNA Polymerase/metabolism Deoxyguanine Nucleotides/metabolism,pharmacology Thymidine Monophosphate/metabolism Thymine Nucleotides/metabolism,pharmacology
Chemicals
Deoxyguanine Nucleotides Thymine Nucleotides Thymidine Monophosphate O(6)-methyldeoxyguanylic acid O(6)-methyldeoxyguanosine triphosphate O(4)-methylthymidine monophosphate O(4)-methylthymidine triphosphate DNA Polymerase I DNA Polymerase II DNA-Directed DNA Polymerase
Authors & Affiliations
2 authors, click to expand affiliations / ORCID
Hall J A
Saffhill R
References (21)
21 references, click to expand
  1. Possible relevance of O-6 alkylation of deoxyguanosine to the mutagenicity and carcinogenicity of nitrosamines and nitrosamides.
    Nature. 1969 Jul 12;223(5202):206-7 PMID: 5791738
  2. Synthesis and chemical properties of monomers and polymers containing 7-methylguanine and an investigation of their substrate or template properties for bacterial deoxyribonucleic acid or ribonucleic acid polymerases.
    Biochemistry. 1970 Oct 13;9(21):4141-53 PMID: 4917900
  3. The properties of O 6 -methylguanine in templates for RNA polymerase.
    Biochim Biophys Acta. 1973 May 10;308(2):310-6 PMID: 4706005
  4. Cellular reactions of O6-methylguanine, a product of some alkylating carcinogens.
    Biochem J. 1973 Oct;136(2):387-93 PMID: 4590203
  5. Reaction products from N-methyl-N-nitrosourea and deoxyribonucleic acid containing thymidine residues. Synthesis and identification of a new methylation product, O4-methylthymidine.
    Biochem J. 1973 Sep;135(1):193-201 PMID: 4798180
  6. DNA-synthesis with methylated poly(dA-dT) templates: possible role of O4-methylthymine as a pro-mutagenic base.
    Nucleic Acids Res. 1977 Mar;4(3):761-9 PMID: 325522
  7. Modified polynucleotides. I. Investigation of the enzymatic polymerization of 5-alkyl-dUTP-s.
    Nucleic Acids Res. 1977 Aug;4(8):2767-77 PMID: 333394
  8. D(M6ATP) as a probe of the fidelity of base incorporation into polynucleotides by Escherichia coli DNA polymerase I.
    J Biol Chem. 1978 Feb 10;253(3):935-9 PMID: 340462
  9. Comparative utilization of bromodeoxyuridine and iododeoxyuridine triphosphates for mammalian DNA replication in vitro.
    Biochim Biophys Acta. 1978 Mar 29;518(1):31-6 PMID: 629978
  10. Preparation and template activities of polynucleotides containing O2- and O4-alkyluridine.
    Proc Natl Acad Sci U S A. 1978 Apr;75(4):1722-6 PMID: 273902
  11. Synthesis and properties of O6-methyldeoxyguanylic acid and its copolymers with deoxycytidylic acid.
    Biochim Biophys Acta. 1978 Dec 21;521(2):770-8 PMID: 737185
  12. DNA synthesis with methylated poly(dC-dG) templates. Evidence for a competitive nature to miscoding by O(6)-methylguanine.
    Biochim Biophys Acta. 1979 Mar 28;562(1):51-61 PMID: 373805
  13. Utilization of 2'-deoxy-6-thioguanosine 5'-triphosphate in DNA synthesis in vitro by DNA polymerase alpha from calf thymus.
    Cancer Res. 1979 Oct;39(10):3955-8 PMID: 476632
  14. Metabolism of O6-alkyldeoxyguanosines and their effect on removal of O6-methylguanine from rat liver DNA.
    Biochim Biophys Acta. 1979 Dec 17;565(2):241-52 PMID: 518880
  15. Mutagenicity of carcinogenic methylating agents is associated with a specific DNA modification.
    Nature. 1980 Feb 7;283(5747):596-9 PMID: 7354843
  16. Synthesis of 8-14C-labeled O6-methyldeoxyguanosine and its deoxynucleotide copolymers.
    Biochemistry. 1980 Feb 19;19(4):643-7 PMID: 6986904
  17. The effects of methylated thymidines upon cultures of V79 cells and the mechanism of incorporation of O4-methylthymidine into their DNA.
    Carcinogenesis. 1982;3(2):219-22 PMID: 7067049
  18. Incorporation of unnatural pyrimidine bases into deoxyribonucleic acid of mammalian cells.
    Science. 1959 Jun 5;129(3362):1550-1 PMID: 13658990
  19. Enzymatic synthesis of deoxyribonucleic acid. X. Influence of bromouracil substitutions on replication.
    Proc Natl Acad Sci U S A. 1962 Mar 15;48:449-55 PMID: 13922323
  20. CONVERSION OF MONO- AND OLIGODEOXYRIBONUCLEOTIDES TO 5-TRIPHOSPHATES.
    J Am Chem Soc. 1965 Apr 20;87:1785-8 PMID: 14289336
  21. Incorporation of 6-thioguanine into nucleic acids.
    Cancer Res. 1960 Apr;20:403-8 PMID: 14415867
Article Info
Journal
Nucleic acids research
Abbr.
Nucleic Acids Res
ISSN
0305-1048
DOI
10.1093/nar/11.12.4185
Published
1983-06-25
Pages
4185-93
Language
English
Region
England
NLM ID
0411011
PMCID
PMC326033
Subset
IM
External Links
PubMed source DOI: 10.1093/nar/11.12.4185 PMC Full Text View journal details
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