Site-specific incorporation of N-(deoxyguanosin-8-yl)-2-acetylaminofluorene (dG-AAF) into oligonucleotides using modified 'ultra-mild' DNA synthesis

Nucleic Acids Research

Volumn 33, Issue 6, 2005, Pages 1961-1969

  Gillet, Ludovic C J ^a   Alzeer, Jawad ^a   Schärer, Orlando D ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DIISOPROPYLAMINE; FLUORENE DERIVATIVE; MERCAPTOETHANOL; N (2 FLUORENYL)ACETAMIDE; N (DEOXYGUANOSIN 8 YL) 2 ACETYLAMINOFLUORENE; N ACETOXY N (2 FLUORENYL)ACETAMIDE; OLIGONUCLEOTIDE; PHOSPHORAMIDOUS ACID; UNCLASSIFIED DRUG; DEOXYGUANOSINE; DRUG DERIVATIVE; N (DEOXYGUANOSIN 8 YL) 2 FLUORENYLAMINE; N (DEOXYGUANOSIN 8 YL) N (2 FLUORENYL)ACETAMIDE; N-(DEOXYGUANOSIN-8-YL)-2-AMINOFLUORENE; N-(DEOXYGUANOSIN-8-YL)ACETYLAMINOFLUORENE; OLIGODEOXYRIBONUCLEOTIDE;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DNA SEQUENCE; DNA SYNTHESIS; EXCISION REPAIR; MOLECULAR MECHANICS; MUTAGENESIS; PRIORITY JOURNAL; SEQUENCE ANALYSIS; SOLID PHASE SYNTHESIS; STRUCTURE ANALYSIS; BIOCHEMISTRY; CHEMISTRY; DNA ADDUCT; DNA REPAIR; HELA CELL; HUMAN; METHODOLOGY; SYNTHESIS;

2-ACETYLAMINOFLUORENE; BIOCHEMISTRY; DEOXYGUANOSINE; DNA ADDUCTS; DNA REPAIR; FLUORENES; HELA CELLS; HUMANS; OLIGODEOXYRIBONUCLEOTIDES;

EID: 17144362544     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gki335     Document Type: Article

References (57)

1. Beije,B. and Moller,L. (1988) 2-Nitrofluorene and related compounds: prevalence and biological effects. Mutat. Res., 196, 177-209.
2. Heflich,R.H. and Neft,R.E. (1994) Genetic toxicity of 2-acetylaminofluorene, 2-aminofluorene and some of their metabolites and model metabolites. Mutat. Res., 318, 73-174.
3. Schut,H.A.J. and Snyderwine,E.G. (1999) DNA adducts of heterocyclic amine food mutagens: Implications for mutagenesis and carcinogenesis. Carcinogenesis, 20, 353-368.
4. Kriek,E., Miller,J.A., Juhl,U. and Miller,E.C. (1967) 8-(N-2-Fluorenylacetamido)guanosine, an arylamidation reaction product of guanosine and the carcinogen N-acetoxy-N-2-fluorenylacetamide in neutral solution. Biochemistry, 6, 177-182.
5. Pierce,J.R., Case,R. and Tang,M.S. (1989) Recognition and repair of 2-aminofluorene- and 2-(acetylamino)fluorene-DNA adducts by UVRABC nuclease. Biochemistry, 28, 5821-5826.
6. Hansson,J., Munn,M., Rupp,W.D., Kahn,R. and Wood,R.D. (1989) Localization of DNA repair synthesis by human cell extracts to a short region at the site of a lesion. J. Biol. Chem., 264, 21788-21792.
7. Gupta,P.K., Pandrangi,R.G., Lee,M.-S. and King,C.M. (1991) Induction of mutations by N-acetoxy-N-acetyl-2-aminofluorene modified M13 viral DNA. Carcinogenesis, 12, 819-824.
8. van Oosterwijk,M.F., Filon,R., Kalle,W.H., Mullenders,L.H. and van Zeeland,A.A. (1996) The sensitivity of human fibroblasts to N-acetoxy-2-acetylaminofluorene is determined by the extent of transcription-coupled repair, and/or their capability to counteract RNA synthesis inhibition. Nucleic Acids Res., 24, 4653-4659.
9. van Oosterwijk,M.F., Filon,R., de Groot,A.J., van Zeeland,A.A. and Mullenders,L.H. (1998) Lack of transcription-coupled repair of acetylaminofluorene DNA adducts in human fibroblasts contrasts their efficient inhibition of transcription. J. Biol. Chem., 273, 13599-13604.
10. Kriek,E. (1972) Persistent binding of a new reaction product of the carcinogen N-hydroxy-N-2-acetylaminofluorene with guanine in rat liver DNA in vivo. Cancer Res., 32, 2042-2048.
11. Fuchs,R.P. (1978) Arylamidation and arylation by the carcinogen N-2-fluorenylacetamide: A sensitive and rapid radiochemical assay. Anal. Biochem., 91, 663-673.
12. Shibutani,S., Gentles,R., Johnson,F. and Grollman,A.P. (1991) Isolation and characterization of oligodeoxynucleotides containing dG-N2-AAF and oxidation products of dG-C8-AF. Carcinogenesis, 12, 813-818.
13. Johnson,D.L., Reid,T.M., Lee,M.S., King,C.M. and Romano,L.J. (1986) Preparation and characterization of a viral DNA molecule containing a site-specific 2-aminofluorene adduct: A new probe for mutagenesis by carcinogens. Biochemistry, 25, 449-456.
14. Moriya,M., Takeshita,M., Johnson,F., Peden,K., Will,S. and Grollman,A.P. (1988) Targeted mutations induced by a single acetylaminofluorene DNA adduct in mammalian cells and bacteria. Proc. Natl Acad. Sci. USA, 85, 1586-1589.
15. Gupta,P.K., Johnson,D.L., Reid,T.M., Lee,M.S., Romano,L.J. and King,C.M. (1989) Mutagenesis by single site-specific arylamine-DNA adducts. J. Biol. Chem., 264, 20120-20130.
16. O'Handley,S.F., Sanford,D.G., Xu,R., Lester,C.C., Hingerty,B.E., Broyde,S. and Krugh,T.R. (1993) Strutural characterization of an N-acetyl-2-aminofluorene (AAF) modified DNA oligomer by NMR, energy minimization and molecular dynamics. Biochemistry, 32, 2481-2497.
17. Tang,M.S. and Lieberman,M.W. (1983) Quantification of adducts formed in DNA treated with N-acetoxy-2-acetylaminofluorene or N-hydroxy-2-aminofluorene: Comparison of trifluoroacetic acid and enzymatic degradation. Carcinogenesis, 4, 1001-1006.
18. Koehl,P., Burnouf,D. and Fuchs,R.P. (1989) Construction of plasmids containing a unique acetylaminofluorene adduct located within a mutation hot spot. A new probe for frameshift mutagenesis. J. Mol. Biol., 207, 355-364.
19. Seeberg,E. and Fuchs,R.P. (1990) Acetylaminofluorene bound to different guanines of the sequence -GGCGCC- is excised with different efficiencies by the UvrABC excision nuclease in a pattern not correlated to the potency of mutation induction. Proc. Natl Acad. Sci. USA, 87, 191-194.
20. Shibutani,S. and Grollman,A.P. (1993) On the mechanism of frameshift (deletion) mutagenesis in vitro. J. Biol. Chem., 268, 11703-11710.
21. Tan,X., Suzuki,N., Grollman,A.P. and Shibutani,S. (2002) Mutagenic events in Escherichia coli and mammalian cells generated in response to acetylaminofluorene-derived DNA adducts positioned in the Nar I restriction enzyme site. Biochemistry, 41, 14255-14262.
22. Belguise-Valladier,P. and Fuchs,R.P. (1991) Strong sequence-dependent polymorphism in adduct-induced DNA structure: Analysis of single N-2-acetylaminofluorene residues bound within the NarI mutation hot spot. Biochemistry, 30, 10091-10100.
23. Veaute,X. and Fuchs,R.P. (1991) Polymorphism in N-2-acetylaminofluorene induced DNA structure as revealed by DNase I footprinting. Nucleic Acids Res., 19, 5603-5606.
24. Belguise-Valladier,P. and Fuchs,R.P. (1995) N-2-Aminofluorene and N-2 acetylaminofluorene adducts: The local sequence context of an adduct and its chemical structure determine its replication properties. J. Mol. Biol., 249, 903-913.
25. Thomas,D.C., Veaute,X., Kunkel,T.A. and Fuchs,R.P. (1994) Mutagenic replication in human cell extracts of DNA containing site-specific N-2-acetylaminofluorene adducts. Proc. Natl Acad. Sci. USA, 91, 7752-7756.
26. Shibutani,S., Suzuki,N. and Grollman,A.P. (1998) Mutagenic specificity of (acetylamino)fluorene-derived DNA adducts in mammalian cells. Biochemistry, 37, 12034-12041.
27. Burnouf,D., Koehl,P. and Fuchs,R.P. (1989) Single adduct mutagenesis: strong effect of the position of a single acetylaminofluorene adduct within a mutation hot spot. Proc. Natl Acad. Sci. USA, 86, 4147-4151.
28. Lambert,I.B., Napolitano,R.L. and Fuchs,R.P. (1992) Carcinogen-induced frameshift mutagenesis in repetitive sequences. Proc. Natl Acad. Sci. USA, 89, 1310-1314.
29. Shibutani,S., Suzuki,N., Tan,X., Johnson,F. and Grollman,A.P. (2001) Influence of flanking sequence context on the mutagenicity of acetylaminofluorene-derived DNA adducts in mammalian cells. Biochemistry, 40, 3717-3722.
30. Mu,D., Bertrand-Burggraf,E., Huang,J.C., Fuchs,R.P., Sancar,A. and Fuchs,B.P. (1994) Human and E.coli excinucleases are affected differently by the sequence context of acetylaminofluorene-guanine adduct. Nucleic Acids Res., 22, 4869-4871.
31. Hess,M.T., Schwitter,U., Petretta,M., Giese,B. and Naegeli,H. (1996) Site-specific DNA substrates for human excision repair: Comparison between deoxyribose and base adducts. Chem. Biol., 3, 121-128.
32. Stöhrer,G., Osband,J.A. and Alvarado-Urbina,G. (1983) Site-specific modification of the lactose operator with acetylaminofluorene. Nucleic Acids Res., 11, 5093-5101.
33. Zhou,Y. and Romano,L.J. (1993) Solid-phase synthesis of oligonucleotides containing site-specific N-(2′-deoxyguanosin-8-yl)-2-(acetylamino)fluorene adducts using 9-fluorenylmethoxycarbonyl as the base-protecting group. Biochemistry, 32, 14043-14052.
34. Zhou,Y., Chladek,S. and Romano,L.J. (1994) Synthesis of oligonucleotides containing site-specific carcinogen adducts. Preparation of the 2-cyanoethyl N,N-diisopropylphosphoramidite of N-(2′-deoxyguanosin-8-yl)-2-(acetylamino)fluorene with Fmoc as the base-protecting group. J. Org. Chem., 59, 556-563.
35. Guo,D., Xie,Z., Shen,H., Zhao,B. and Wang,Z. (2004) Translesion synthesis of acetylaminofluorene-dG adducts by DNA polymerase zeta is stimulated by yeast Rev1 protein. Nucleic Acids Res., 32, 1122-1130.
36. de Laat,W.L., Jaspers,N.G. and Hoeijmakers,J.H.J. (1999) Molecular mechanism of nucleotide excision repair. Genes Dev., 13, 768-785.
37. Petit,C. and Sancar,A. (1999) Nucleotide excision repair: From E. coli to man. Biochimie, 81, 15-25.
38. Batty,D.P. and Wood,R.D. (2000) Damage recognition in nucleotide excision repair of DNA. Gene, 241, 193-204.
39. Gillet,L.C.J. and Schärer,O.D. (2002) Preparation of C8-amine and acetylamine adducts of 2′-deoxyguanosine suitably protected for DNA synthesis. Org. Lett., 4, 4205-4208.
40. Wang,Z. and Rizzo,C.J. (2001) Synthesis of the C8-deoxyguanosine adduct of the food mutagen IQ. Org. Lett., 3, 565-568.
41. Elmquist,C.E., Stover,J.S., Wang,Z. and Rizzo,C.J. (2004) Site-specific synthesis and properties of oligonucleotides containing C8-deoxyguanosine adducts of the dietary mutagen IQ. J. Am. Chem. Soc., 126, 11189-11201.
42. Reese,C.B., Stewart,J.C.M., van Boom,J.H., de Leeuw,H.P.M., Nagel,J. and de Rooy,J.F.M. (1975) The synthesis of oligoribonucleotides. Part XI. Preparation of ribonucleoside 2-acetal 3-esters by selective deacylation. J. Chem. Soc. Perkin Trans., 1, 934-942.
43. Shibutani,S., Gentles,R. and Johnson,F. (1990) Aerial oxidation of acetylaminofluorene-derived DNA adducts. In Howard,P.C., Hecht,S.S. and Beland,F.A. (eds), Nitroarenes. Plenum Press, New York, pp. 135-147.
44. Johnson,F., Huang,C.Y. and Yu,P.L. (1994) Synthetic and oxidative studies on 8-(arylamino)-2′-deoxyguanosine and -guanosine derivatives. Environ. Health Perspect., 102(Suppl. 6), 143-149.
45. Shivji,M.K., Moggs,J.G., Kuraoka,I. and Wood,R.D. (1999) Dual-incision assays for nucleotide excision repair using DNA with a lesion at a specific site. Methods Mol. Biol., 113, 373-392.
46. Biggerstaff,M. and Wood,R.D. (1999) Assay for nucleotide excision repair protein activity using fractionated cell extracts and UV-damaged plasmid DNA. Methods Mol. Biol., 113, 357-372.
47. Schulhof,J.C., Molko,D. and Teoule,R. (1987) The final deprotection step in oligonucleotide synthesis is reduced to a mild and rapid ammonia treatment by using labile base-protecting group. Nucleic Acids Res., 15, 397-416.
48. Zhu,Q., Delaney,M.O. and Greenberg,M.M. (2001) Observation and elimination of N-acetylation of oligonucleotides prepared using fast-deprotecting phosphoramidites and ultra-mild deprotection. Bioorg. Med. Chem. Lett., 11, 1105-1107.
49. Pon,R.T. and Yu,S. (1997) Hydroquinone-O,O′-diacetic acid as a more labile replacement for succinic acid linkers in solid-phase oligonucleotide synthesis. Tetrahedron Lett., 38, 3327-3330.
50. Johnson,F., Habus,I., Gentles,R., Shibutani,S., Lee,H., Iden,C. and Rieger,R. (1992) Site-specific adduct formation in oligomeric DNA using a new protecting group. J. Am. Chem. Soc., 114, 4923-4924.
51. Huang,J.C. and Sancar,A. (1994) Determination of minimum substrate size for human excinuclease. J. Biol. Chem., 269, 19034-19040.
52. Huang,J.C., Svoboda,D.L., Reardon,J.T. and Sancar,A. (1992) Human nucleotide excision nuclease removes thymine dimers from DNA by incising the 22nd phosphodiester bond 5′ and the 6th phosphodiester bond 3′ to the photodimer. Proc. Natl Acad. Sci. USA, 89, 3664-3668.
53. Huang,J.C., Zamble,D.B., Reardon,J.T., Lippard,S.J. and Sancar,A. (1994) HMG-domain proteins specifically inhibit the repair of the major DNA adduct of the anticancer drug cisplatin by human excision nuclease. Proc. Natl Acad. Sci. USA, 91, 10394-10398.
54. Calsou,P., Frit,P. and Salles,B. (1996) Double strand breaks in DNA inhibit nucleotide excision repair in vitro. J. Biol. Chem., 271, 27601-27607.
55. Evans,E., Moggs,J.G., Hwang,J.R., Egly,J.M. and Wood,R.D. (1997) Mechanism of open complex and dual incision formation by human nucleotide excision repair factors. EMBO Rep., 16, 6559-6573.
56. Hess,M.T., Schwitter,U., Petretta,M., Giese,B. and Naegeli,H. (1997) Bipartite substrate discrimination by human nucleotide excision repair. Proc. Natl Acad. Sci. USA, 94, 6664-6669.
57. Gunz,D., Hess,M.T. and Naegeli,H. (1996) Recognition of DNA adducts by human nucleotide excision repair. Evidence for a thermodynamic probing mechanism. J. Biol. Chem., 271, 25089-25098.