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Original Articles

Synthesis of the Fully Protected Phosphoramidite of the Benzene-DNA Adduct, N2-(4-Hydroxyphenyl)-2′-Deoxyguanosine and Incorporation of the Later into DNA Oligomers

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Pages 979-991 | Received 12 Dec 2007, Accepted 08 Apr 2008, Published online: 11 Aug 2008

REFERENCES

  • 1986 . NTP Toxicology and Carcinogenesis Studies of Benzene (CAS No. 71-43-2) in F344/N Rats and B6C3F1 Mice (Gavage Studies) . Natl. Toxicol. Program Tech. Rep. Ser. , 289 : 1 – 277 .
  • IARC . 1982 . IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans. Some industrial chemicals and dyestuffs , Vol. 29 , Lyon, , France : International Agency for Research on Cancer .
  • NTP . 2005 . 11th Report on carcinogens , Atlanta, GA : U.S. Department of Health and Human Services, National Toxicology Program .
  • Yin , S.-N. , Hayes , R. , Linet , M. , Li , G. , Dosemeci , M. , Travis , L. , Zhang , Z. , Li , D. , Chow , W. , Wacholder , S. and Blot , W. 1996 . Recent studies of human exposure to benzene in China and Europe An expanded cohort study of cancer among benzene-exposed workers in China . Environ. Health Perspect. , : 1339 – 1341 .
  • Glass , D.C. , Gray , C.N. , Jolley , D.J. , Gibbons , C. , Sim , M.R. , Fritschi , L. , Adams , G.G. , Bisby , J.A. and Manuell , R. 2003 . Leukemia risk associated with low-level benzene exposure . Epidemiology , 14 : 569 – 577 .
  • Snyder , R. and Hedli , C.C. 1996 . An overview of benzene metabolism . Environ. Health Perspect. , 104 ( Suppl. 6 ) : 1165 – 1171 .
  • Lovern , M.R. , Cole , C.E. and Schlosser , P.M. 2001 . A review of quantitative studies of benzene metabolism . Crit. Rev. Toxicol. , 31 : 285 – 311 .
  • Whysner , J. , Reddy , M.V. , Ross , P.M. , Mohan , M. and Lax , E.A. 2004 . Genotoxicity of benzene and its metabolites . Mutat. Res. , 566 : 99 – 130 .
  • Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis . Proceedings of the 2nd international conference . September 1998 , Heidelberg, Germany. Vol. 150 , pp. 1 – 361 . IARC Sci Publ .
  • Zheng , J. and Hanzlik , R.P. 1992 . Dihydroxylated mercapturic acid metabolites of bromobenzene . Chem. Res. Toxicol. , 5 : 561 – 567 .
  • Pascoe , G.A. , Calleman , C.J. and Baille , T.A. 1988 . Identification of S-(2,5-dihydroxyphenyl)-cysteine and S-(2,5-dihydroxyphenyl)-N-acetyl-cysteine as urinary metabolites of acetaminophen in the mouse. Evidence for p-benzoquinone as a reactive intermediate in acetaminophen metabolism . Chem. Biol. Interact. , 68 : 85 – 98 .
  • McDonald , T.A. , Waidyanatha , S. and Rappaport , S.M. 1993 . Measurement of adducts of benzoquinone with hemoglobin and albumin . Carcinogenesis , 14 : 1927 – 1932 .
  • Jowa , L. , Winkle , S. , Kalf , G. , Witz , G. and Snyder , R. 1986 . Deoxyguanosine adducts formed from benzoquinone and hydroquinone . Adv. Exp. Med. Biol. , 197 : 825 – 832 .
  • Jowa , L. , Witz , G. , Snyder , R. , Winkle , S. and Kalf , G.F. 1990 . Synthesis and characterization of deoxyguanosine-benzoquinone adducts . J. Appl. Toxicol. , 10 : 47 – 54 .
  • Pongracz , K. and Bodell , W.J. 1991 . Detection of 3′-hydroxy-1,N6-benzetheno-2′-deoxyadenosine 3′-phosphate by 32P postlabeling of DNA reacted with p-benzoquinone . Chem. Res. Toxicol. , 4 : 199 – 202 .
  • Pongracz , K. , Kaur , S. , Burlingame , A.L. and Bodell , W.J. 1990 . Detection of (3′-hydroxy)-3,N4-benzetheno-2′-deoxycytidine-3′-phosphate by 32P-postlabeling of DNA reacted with p-benzoquinone . Carcinogenesis , 11 : 1469 – 1472 .
  • Gaskell , M. , Jukes , R. , Jones , D.J. , Martin , E.A. and Farmer , P.B. 2002 . Identification and characterization of (3′′,4′′-dihydroxy)-1,N2-benzetheno-2′-deoxyguanosine 3¢-monophosphate, a novel DNA adduct formed by benzene metabolites . Chem. Res. Toxicol. , 15 : 1088 – 1095 .
  • Levay , G. , Pongracz , K. and Bodell , W.J. 1991 . Detection of DNA adducts in HL-60 cells treated with hydroquinone and p-benzoquinone by 32P-postlabeling . Carcinogenesis , 12 : 1181 – 1186 .
  • Bodell , W.J. , Pathak , D.N. , Levay , G. , Ye , Q. and Pongracz , K. 1996 . Investigation of the DNA adducts formed in B6C3F1 mice treated with benzene: implications for molecular dosimetry . Environ. Health Perspect. , 104 ( Suppl. 6 ) : 1189 – 1193 .
  • Xie , Z. , Zhang , Y. , Guliaev , A.B. , Shen , H. , Hang , B. , Singer , B. and Wang , Z. 2005 . The p-benzoquinone DNA adducts derived from benzene are highly mutagenic . DNA Repair (Amst) , 4 : 1399 – 1409 .
  • Chenna , A. , Hang , B. , Rydberg , B. , Kim , E. , Pongracz , K. , Bodell , W.J. and Singer , B. 1995 . The benzene metabolite p-benzoquinone forms adducts with DNA bases that are excised by a repair activity from human cells that differs from an ethenoadenine glycosylase . Proc. Natl. Acad. Sci. USA , 92 : 5890 – 5894 .
  • Hang , B. , Chenna , A. , Fraenkel-Conrat , H. and Singer , B. 1996 . An unusual mechanism for the major human apurinic/apyrimidinic (AP) endonuclease involving 5¢ cleavage of DNA containing a benzene-derived exocyclic adduct in the absence of an AP site . Proc. Natl. Acad. Sci. USA , 93 : 13737 – 13741 .
  • Hang , B. , Chenna , A. , Sagi , J. and Singer , B. 1998 . Differential cleavage of oligonucleotides containing the benzene-derived adduct, 1,N6-benzetheno-dA, by the major human AP endonuclease HAP1 and Escherichia coli exonuclease III and endonuclease IV . Carcinogenesis , 19 : 1339 – 1343 .
  • Guliaev , A.B. , Hang , B. and Singer , B. 2004 . Structural insights by molecular dynamics simulations into specificity of the major human AP endonuclease toward the benzene-derived DNA adduct, pBQ-C . Nucleic. Acids. Res. , 32 : 2844 – 2852 .
  • Bauer , H. , Dimitriadis , E.A. and Snyder , R. 1989 . An in vivo study of benzene metabolite DNA adduct formation in liver of male New Zealand rabbits . Arch. Toxicol. , 63 : 209 – 213 .
  • Pongracz , K. and Bodell , W.J. 1996 . Synthesis of N2-(4-hydroxyphenyl)-2′-deoxyguanosine 3¢-phosphate: comparison by 32P-postlabeling with the DNA adduct formed in HL-60 cells treated with hydroquinone . Chem. Res. Toxicol. , 9 : 593 – 598 .
  • Chenna , A. and Singer , B. 1995 . Large scale synthesis of p-benzoquinone-2′-deoxycytidine and p-benzoquinone-2′-deoxyadenosine adducts and their site-specific incorporation into DNA oligonucleotides . Chem. Res. Toxicol. , 8 : 865 – 874 .
  • Chenna , A. and Singer , B. 1997 . Synthesis of a benzene metabolite adduct, 3′′-hydroxy-1,N2-benzetheno-2′-deoxyguanosine, and its site-specific incorporation into DNA oligonucleotides . Chem. Res. Toxicol. , 10 : 165 – 171 .
  • Lakshman , M.K. 2005 . Synthesis of biologically important nucleoside analogs by Palladium-catalyzed C-N bond-formation . Curr. Org. Synth. , 2 : 83 – 112 .
  • Bonala , R. , Torres , M.C. , Iden , C.R. and Johnson , F. 2006 . Synthesis of the PhIP adduct of 2′-deoxyguanosine and its incorporation into oligomeric DNA . Chem. Res. Toxicol. , 19 : 734 – 738 .
  • Harwood , E.A. , Sigurdsson , S.T. , Edfeldt , N.B.F. , Reid , B.R. and Hopkins , P.B. 1999 . Synthesis and preliminary structural characterization of nitrous acid interstrand cross-linked duplex DNA . J. Am. Chem. Soc. , 121 : 5081 – 5082 .

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