Literature DB >> 5271176

Coding and conformational properties of oligonucleotides modified with the carcinogen N-2-acetylaminofluorene.

D Grunberger, J H Nelson, C R Cantor, I B Weinstein.   

Abstract

The present studies were undertaken to determine the mechanism by which attachment of the carcinogen N-2-acetylaminofluorene to guanosine residues in nucleic acids distors their structure and function. Oligonucleotides were modified with N-acetoxy-2-acetylaminofluorene, repurified, and their base compositions analyzed. Evidence is presented that acetylaminofluorene residues bound to guanosines in GpUpU, ApApG, or poly (U,G) inactivates their function in codon recognition. Circular dichroism spectra suggest that this is caused by gross conformational changes in these compounds involving both a rotation about the glycosidic bond of guanosine residues bearing N-2-acetylaminofluorene, as well as stacking interactions between the drug and bases adjacent to the substituted guanosine.

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Year:  1970        PMID： 5271176      PMCID： PMC283071          DOI： 10.1073/pnas.66.2.488

Source DB:  PubMed          Journal:  Proc Natl Acad Sci U S A        ISSN： 0027-8424            Impact factor:   11.205


  12 in total

1.  A possible role of transfer RNA in the mechanism of carcinogenesis.

Authors:  I B Weinstein
Journal:  Cancer Res       Date:  1968-09       Impact factor: 12.701

2.  Difference in binding of 2-acetylaminofluorene to rat liver deoxyribonucleic acid and ribosomal ribonucleic acid in vivo.

Authors:  E Kriek
Journal:  Biochim Biophys Acta       Date:  1968-06-18

3.  Modifications of ribonucleic acid by chemical carcinogens. I. In vitro modification of transfer ribonucleic acid by N-acetoxy-2-acetylaminofluorene.

Authors:  L M Fink; S Nishimura; I B Weinstein
Journal:  Biochemistry       Date:  1970-02-03       Impact factor: 3.162

4.  Mutations and decreases in density of transforming DNA produced by derivatives of the carcinogens 2-acetyl-aminofluorene and N-methyl-4-aminoazobenzene.

Authors:  V M Maher; E C Miller; J A Miller; W Szybalski
Journal:  Mol Pharmacol       Date:  1968-09       Impact factor: 4.436

5.  Differential responses of DNA and RNA polymerase to modifications of the template rat liver DNA caused by action of the carcinogen acetylaminofluorene in vivo and in vitro.

Authors:  W Troll; S Belman; E Berkowitz; Z F Chmielewicz; J L Ambrus; T J Bardos
Journal:  Biochim Biophys Acta       Date:  1968-03-18

6.  The binding of 2-acetylaminofluorene to rat liver ribonucleic acid in vivo.

Authors:  F Marroquin; E Farber
Journal:  Cancer Res       Date:  1965-09       Impact factor: 12.701

7.  On the significance and mechanism of the binding of 2-acetylaminofluorene and N-hydroxy-2-acetylaminofluorene to rat-liver ribonucleic acid in vivo.

Authors:  C C Irving; R A Veazey; R F Williard
Journal:  Cancer Res       Date:  1967-04       Impact factor: 12.701

8.  Nucleic acid guanine: reaction with the carcinogen N-acetoxy-2-acetylaminofluorene.

Authors:  E C Miller; U Juhl; J A Miller
Journal:  Science       Date:  1966-09-02       Impact factor: 47.728

9.  8-(N-2-fluorenylacetamido)guanosine, an arylamidation reaction product of guanosine and the carcinogen N-acetoxy-N-2-fluorenylacetamide in neutral solution.

Authors:  E Kriek; J A Miller; U Juhl; E C Miller
Journal:  Biochemistry       Date:  1967-01       Impact factor: 3.162

10.  Codon--anticodon pairing: the wobble hypothesis.

Authors:  F H Crick
Journal:  J Mol Biol       Date:  1966-08       Impact factor: 5.469
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  13 in total

Review 1.  DNA adduct structure-function relationships: comparing solution with polymerase structures.

Authors:  Suse Broyde; Lihua Wang; Ling Zhang; Olga Rechkoblit; Nicholas E Geacintov; Dinshaw J Patel
Journal:  Chem Res Toxicol       Date:  2007-12-04       Impact factor: 3.739

2.  Visualization of an AAF induced frameshift mutation: molecular views of base displacement in B-DNA from minimized potential energy calculations.

Authors:  S Broyde; B E Hingerty
Journal:  Nucleic Acids Res       Date:  1987-08-25       Impact factor: 16.971

3.  Base pair conformation-dependent excision of benzo[a]pyrene diol epoxide-guanine adducts by human nucleotide excision repair enzymes.

Authors:  M T Hess; D Gunz; N Luneva; N E Geacintov; H Naegeli
Journal:  Mol Cell Biol       Date:  1997-12       Impact factor: 4.272

4.  Studies on the conformation and dynamics of the C8-substituted guanine adduct of the carcinogen acetylaminofluorene; model for a possible Z-DNA modified structure.

Authors:  S Neidle; R Kuroda; S Broyde; B E Hingerty; R A Levine; D W Miller; F E Evans
Journal:  Nucleic Acids Res       Date:  1984-11-12       Impact factor: 16.971

5.  Crystal structures of 2-acetylaminofluorene and 2-aminofluorene in complex with T7 DNA polymerase reveal mechanisms of mutagenesis.

Authors:  Shuchismita Dutta; Ying Li; Donald Johnson; Leonid Dzantiev; Charles C Richardson; Louis J Romano; Tom Ellenberger
Journal:  Proc Natl Acad Sci U S A       Date:  2004-11-04       Impact factor: 11.205

6.  Accommodation of an N-(deoxyguanosin-8-yl)-2-acetylaminofluorene adduct in the active site of human DNA polymerase iota: Hoogsteen or Watson-Crick base pairing?

Authors:  Kerry Donny-Clark; Robert Shapiro; Suse Broyde
Journal:  Biochemistry       Date:  2009-01-13       Impact factor: 3.162

7.  Conformations of poly(dG-dC).poly(dG-dC) modified by the O-acetyl derivative of the carcinogen 4-hydroxyaminoquinoline 1-oxide.

Authors:  B Bailleul; S Galiègue-Zouitina; M H Loucheux-Lefebvre
Journal:  Nucleic Acids Res       Date:  1984-10-25       Impact factor: 16.971

8.  Replication of acetylaminofluorene-adducted plasmids in human cells: spectrum of base substitutions and evidence of excision repair.

Authors:  M C Mah; J Boldt; S J Culp; V M Maher; J J McCormick
Journal:  Proc Natl Acad Sci U S A       Date:  1991-11-15       Impact factor: 11.205

9.  Conformation of poly(dG-dC) . poly(dG-dC) modified by the carcinogens N-acetoxy-N-acetyl-2-aminofluorene and N-hydroxy-N-2-aminofluorene.

Authors:  E Sage; M Leng
Journal:  Proc Natl Acad Sci U S A       Date:  1980-08       Impact factor: 11.205

10.  N-acetoxy-2-acetylaminofluorene modification of a deoxyoligonucleotide duplex.

Authors:  D G Sanford; T R Krugh
Journal:  Nucleic Acids Res       Date:  1985-08-26       Impact factor: 16.971
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