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Original Articles

Reaction of Glycidamide with 2′-Deoxyadenosine and 2′-Deoxyguanosine—Mechanism for the Amide Hydrolysis

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Pages 129-148 | Received 15 May 2006, Accepted 27 Sep 2006, Published online: 24 Jan 2007

REFERENCES

  • IARC . 1994 . IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans 389 – 433 . Lyon, , France (60, IARC)
  • Tareke , E. , Rydberg , P. , Karlsson , P. , Eriksson , S. and Törnqvist , M. 2002 . Analysis of acrylamide, a carcinogen formed in heated foodstuffs . J. Agric. Food. Chem. , 50 : 4998 – 5006 .
  • Solomon , J. J. , Fedyk , J. , Mukai , F. and Segal , A. 1985 . Direct alkylation of 2′-deoxynucleosides and DNA following in vitro reaction with acrylamide . Cancer Res. , 45 : 3465 – 3470 .
  • Besaratinia , A. and Pfeifer , G.P. 2004 . Genotoxicity of acrylamide and glycidamide . J. Natl. Cancer Inst. , 96 : 1023 – 1029 .
  • Paulsson , B. , Kotova , N. , Grawé , J. , Henderson , A. , Granath , F. , Golding , B. and Törnqvist , M. 2003 . Induction of micronuclei in mouse and rat by glycidamide, genotoxic metabolite of acrylamide . Mutation Research , 535 : 15 – 24 .
  • Ghanayem , B.I. , Witt , K.L. , Kissling , G.E. , Tice , R.R. and Recio , L. 2005 . Absence of acrylamide-induced genotoxicity in CYP2E1-null mice: Evidence consistent with a glycidamide-mediated effect . Mutation Research , 578 : 284 – 297 .
  • Segerbäck , D. , Calleman , C.J. , Schroeder , J.L. , Costa , L.G. and Faustman , E.M. 1995 . Formation of N-7-(2-carbamoyl-2-hydroxyethyl)guanine in DNA of the mouse and the rat following intraperitoneal administration of [14C]acrylamide . Carcinogenesis , 16 : 1161 – 1165 .
  • Gamboa da Costa , G. , Churchwell , M.I. , Hamilton , L.P. , Von Tungeln , L.S. , Beland , F.A. , Marques , M.M. and Doerge , D.R. 2003 . DNA Adduct formation from acrylamide via conversion to glycidamide in adult and neonatal mice . Chem. Res. Toxicol. , 16 : 1328 – 1337 .
  • Backman , J. , Sjöholm , R. and Kronberg , L. 2004 . Characterization of the adducts formed in the reactions of glycidamide with thymidine and cytidine . Chem. Res. Toxicol. , 17 : 1652 – 1658 .
  • Florea-Wang , D. , Haapala , E. , Mattinen , J. , Hakala , K. , Vilpo , J. and Hovinen , J. 2003 . Reactions of N,N-bis(2-chloroethyl)-p-aminophenylbutyric acid (chlorambucil) with 2′-deoxyadenosine . Chem. Res. Toxicol. , 16 ( 3 ) : 403 – 408 .
  • Munter , T. , Cottrell , L. , Hill , S. , Kronberg , L. , Watson , W.P. and Golding , B.T. 2002 . Identification of adducts derived from reactions of (1-chloroethenyl)oxirane with nucleosides and calf thymus DNA . Chem. Res. Toxicol. , 15 : 1549 – 1560 .
  • Olsen , R. , Molander , P. , Ovrebo , S. , Ellingsen , D.G. , Thorud , S. , Thomassen , Y. , Lundanes , E. , Greibrokk , T. , Backman , J. , Sjoeholm , R. and Kronberg , L. 2005 . Reaction of glyoxal with 2′-deoxyguanosine, 2′-deoxyadenosine, 2′-deoxycytidine, cytidine, thymidine, and calf thymus DNA: Identification of DNA adducts . Chem. Res. Toxicol. , 18 ( 4 ) : 730 – 739 .
  • Singer , B. and Grunberger , D. 1983 . Molecular Biology of Mutagens & Carcinogens , New York : Plenum Press .
  • Carrell , H.L. , Glusker , J.P. , Moschel , R.C. , Hudgins , W.R. and Dipple , A. 1981 . Crystal structure of a carcinogen: nucleoside adduct . Cancer Res. , 41 : 2230 – 2234 .
  • Macon , J.B. and Wolfenden , R. 1968 . 1-Methyladenosine. Dimroth rearrangement and reversible reduction . Biochemistry , 7 : 3453 – 3458 .
  • Fujii , T. , Saito , T. and Terahara , N. 1986 . Purines. XXVII. Hydrolytic deamination versus Dimroth rearrangement in the 9-substituted adenine ring: Effect of an omega-hydroxyalkyl group at the 1-position . Chem. Pharm. Bull. , 34 : 1094 – 1107 .
  • Solomon , J.J. 1999 . “ Cyclic adducts and intermediates induced by simple epoxides. In ” . In Exocyclic DNA Adducts in Mutagenesis and Carcinogenesis , Edited by: Singer , B. and Bartsch , H. 123 – 135 . Lyon, , France : International Agency for Research on Cancer . (IARC Scientific Publication No. 150)
  • Selzer , R.R. and Elfarra , A.A. 1996 . Characterization of N1- and N 6-adenosine adducts and N1-inosine adducts formed by the reaction of butadiene monoxide with adenosine: evidence for the N1-adenosine adducts as major initial products . Chem. Res. Toxicol. , 9 : 875 – 881 .
  • Barlow , T. , Ding , J. , Vouros , P. and Dipple , A. 1997 . Investigation of hydrolytic deamination of 1-(2-hydroxy-1-phenylethyl)adenosine . Chem. Res. Toxicol. , 10 : 1247 – 1249 .
  • Selzer , R.R. and Elfarra , A.A. 1996 . Synthesis and biochemical characterization of N1-, N2-, and N7-guanosine adducts of butadiene monoxide . Chem. Res. Toxicol. , 9 : 126 – 132 .
  • Golding , B.T. , Slaich , P.T. , Kennedy , G. , Bleasdale , C. and Watson , P.T. 1996 . Mechanisms of formation of adducts from reactions of glycidaldehyde with 2′-deoxyguanosine and/or guanosine . Chem. Res. Toxicol. , 9 : 147 – 157 .

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