Misincorporation of Nucleotides opposite Five-Membered Exocyclic Ring Guanine Derivatives by Escherichia coli Polymerases in Vitro and in Vivo: 1,N2-Ethenoguanine, 5,6,7,9-Tetrahydro-9-oxoimidazo[1,2-a]purine, and 5,6,7,9-Tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine†
Identifieur interne : 003A54 ( Main/Exploration ); précédent : 003A53; suivant : 003A55Misincorporation of Nucleotides opposite Five-Membered Exocyclic Ring Guanine Derivatives by Escherichia coli Polymerases in Vitro and in Vivo: 1,N2-Ethenoguanine, 5,6,7,9-Tetrahydro-9-oxoimidazo[1,2-a]purine, and 5,6,7,9-Tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine†
Auteurs : Sophie Langouët [États-Unis, France] ; Adrienne N. Mican [États-Unis] ; Michael Müller [États-Unis, Allemagne] ; Stephen P. Fink [États-Unis] ; Lawrence J. Marnett [États-Unis] ; Steven A. Muhle [États-Unis] ; F. Peter Guengerich [États-Unis]Source :
- Biochemistry [ 0006-2960 ] ; 1998.
Abstract
A variety of exocyclic modified bases have been shown to be formed in DNA from various procarcinogens (e.g., acrolein, malonaldehyde, vinyl chloride, urethan) and are also found in untreated animals and humans, presumably arising as a result of lipid peroxidation. 1,N2-Ethenoguanine (1,N2-ε-Gua), a product known to be formed from several 2-carbon electrophiles, was placed in a known site (6256) in bacteriophage M13MB19 and mutations were analyzed in Escherichia coli, with 2.05% G→A, 0.74% G→T, and 0.09% G→C changes found in uvrA- bacteria. 5,6,7,9-Tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine (HO-ethanoGua), formally the hydrated derivative of 1,N2-ε-Gua, is a stable DNA product also derived from vinyl halides. When this base was placed in the same context, the mutation rate was 0.007−0.19% for G→A, C, or T changes. The saturated etheno ring derivative of 1,N2-ε-Gua, 5,6,7,9-tetrahydro-9-oxoimidazo[1,2-a]purine (ethanoGua) produced G→A and G→T mutations (0.71% each). All mutants were SOS-dependent and were attenuated by uvrA activity in E. coli. In vitro studies with four polymerases showed strong blocks to addition beyond the adduct site in the order ethanoGua > HO-ethanoGua > 1,N2-ε-Gua. Both E. coli polymerases (pol) I exo- and II exo- and bacteriophage pol T7 exo- showed extensive misincorporation opposite ethanoGua in vitro, with pol I exo- incorporating G and T, pol II exo- incorporating A, and pol T7 exo- incorporating A and G. All modified bases reduced the use of the minus strand bearing the modified guanine in E. coli cells. It is of interest that even though the normal base pairing site of guanine is completely blocked, all of the five-membered ring derivatives incorporate the normal base (C) in >80% of the replication events in E. coli. Major differences in blockage and misincorporation are seen due to what might appear to be relatively modest structural differences, and polymerases can differ dramatically in their selectivities.
Url:
DOI: 10.1021/bi972327r
Affiliations:
- Allemagne, France, États-Unis
- Basse-Saxe, Région Bretagne, Tennessee
- Göttingen, cedex
- Université de Göttingen
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Derivatives by <hi rend="italic">Escherichia c</hi><hi rend="italic">oli</hi> Polymerases in Vitro and in Vivo:
1,<hi rend="italic">N</hi><hi rend="superscript">2</hi>-Ethenoguanine, 5,6,7,9-Tetrahydro-9-oxoimidazo[1,2-<hi rend="italic">a</hi>]purine, and
5,6,7,9-Tetrahydro-7-hydroxy-9-oxoimidazo[1,2-<hi rend="italic">a</hi>]purine<ref type="bib" target="#bi972327rAF2"><hi rend="superscript">†</hi></ref></title><author><name sortKey="Langouet, Sophie" sort="Langouet, Sophie" uniqKey="Langouet S" first="Sophie" last="Langouët">Sophie Langouët</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Tennessee</region></placeName><wicri:cityArea>Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine,Nashville</wicri:cityArea></affiliation><affiliation wicri:level="3"><country xml:lang="fr">France</country><wicri:regionArea> Current address: INSERM U456, Faculté desSciences Pharmaceutiques et Biologiques 2, Avenue du Professeur Léon Bernard,35043Rennes cedex</wicri:regionArea><placeName><region type="region" nuts="2">Région Bretagne</region><settlement type="city">cedex</settlement></placeName></affiliation></author><author><name sortKey="Mican, Adrienne N" sort="Mican, Adrienne N" uniqKey="Mican A" first="Adrienne N." last="Mican">Adrienne N. Mican</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Tennessee</region></placeName><wicri:cityArea>Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine,Nashville</wicri:cityArea></affiliation></author><author><name sortKey="Muller, Michael" sort="Muller, Michael" uniqKey="Muller M" first="Michael" last="Müller">Michael Müller</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Tennessee</region></placeName><wicri:cityArea>Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine,Nashville</wicri:cityArea></affiliation><affiliation wicri:level="4"><country xml:lang="fr">Allemagne</country><wicri:regionArea> Current address: Abteilung Arbeits- undSozialmedizin der Georg-August-Universität Göttingen, Waldweg 37, D-37073Göttingen</wicri:regionArea><placeName><region type="land" nuts="2">Basse-Saxe</region><settlement type="city">Göttingen</settlement></placeName><orgName type="university">Université de Göttingen</orgName></affiliation></author><author><name sortKey="Fink, Stephen P" sort="Fink, Stephen P" uniqKey="Fink S" first="Stephen P." last="Fink">Stephen P. Fink</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Tennessee</region></placeName><wicri:cityArea>Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine,Nashville</wicri:cityArea></affiliation></author><author><name sortKey="Marnett, Lawrence J" sort="Marnett, Lawrence J" uniqKey="Marnett L" first="Lawrence J." last="Marnett">Lawrence J. Marnett</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Tennessee</region></placeName><wicri:cityArea>Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine,Nashville</wicri:cityArea></affiliation></author><author><name sortKey="Muhle, Steven A" sort="Muhle, Steven A" uniqKey="Muhle S" first="Steven A." last="Muhle">Steven A. Muhle</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Tennessee</region></placeName><wicri:cityArea>Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine,Nashville</wicri:cityArea></affiliation></author><author><name sortKey="Guengerich, F Peter" sort="Guengerich, F Peter" uniqKey="Guengerich F" first="F. Peter" last="Guengerich">F. Peter Guengerich</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Tennessee</region></placeName><wicri:cityArea>Department of Biochemistry and Center in Molecular Toxicology, Vanderbilt University School of Medicine,Nashville</wicri:cityArea></affiliation><affiliation wicri:level="1"><country wicri:rule="url">États-Unis</country><wicri:regionArea> Address correspondence to this author: Department ofBiochemistry, Vanderbilt University School of Medicine,638Medical Research Building I, Nashville</wicri:regionArea><wicri:noRegion>Nashville</wicri:noRegion></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Biochemistry</title><title level="j" type="abbrev">Biochemistry</title><idno type="ISSN">0006-2960</idno><idno type="eISSN">1520-4995</idno><imprint><publisher>American Chemical Society</publisher><date type="e-published">1998</date><date type="published">1998</date><biblScope unit="vol">37</biblScope><biblScope unit="issue">15</biblScope><biblScope unit="page" from="5184">5184</biblScope><biblScope unit="page" to="5193">5193</biblScope></imprint><idno type="ISSN">0006-2960</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0006-2960</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract">A variety of exocyclic modified bases have been shown to be formed in DNA from various procarcinogens (e.g., acrolein, malonaldehyde, vinyl chloride, urethan) and are also found in untreated animals and humans, presumably arising as a result of lipid peroxidation. 1,N2-Ethenoguanine (1,N2-ε-Gua), a product known to be formed from several 2-carbon electrophiles, was placed in a known site (6256) in bacteriophage M13MB19 and mutations were analyzed in Escherichia coli, with 2.05% G→A, 0.74% G→T, and 0.09% G→C changes found in uvrA- bacteria. 5,6,7,9-Tetrahydro-7-hydroxy-9-oxoimidazo[1,2-a]purine (HO-ethanoGua), formally the hydrated derivative of 1,N2-ε-Gua, is a stable DNA product also derived from vinyl halides. When this base was placed in the same context, the mutation rate was 0.007−0.19% for G→A, C, or T changes. The saturated etheno ring derivative of 1,N2-ε-Gua, 5,6,7,9-tetrahydro-9-oxoimidazo[1,2-a]purine (ethanoGua) produced G→A and G→T mutations (0.71% each). All mutants were SOS-dependent and were attenuated by uvrA activity in E. coli. In vitro studies with four polymerases showed strong blocks to addition beyond the adduct site in the order ethanoGua > HO-ethanoGua > 1,N2-ε-Gua. Both E. coli polymerases (pol) I exo- and II exo- and bacteriophage pol T7 exo- showed extensive misincorporation opposite ethanoGua in vitro, with pol I exo- incorporating G and T, pol II exo- incorporating A, and pol T7 exo- incorporating A and G. All modified bases reduced the use of the minus strand bearing the modified guanine in E. coli cells. It is of interest that even though the normal base pairing site of guanine is completely blocked, all of the five-membered ring derivatives incorporate the normal base (C) in >80% of the replication events in E. coli. Major differences in blockage and misincorporation are seen due to what might appear to be relatively modest structural differences, and polymerases can differ dramatically in their selectivities.</div></front></TEI><affiliations><list><country><li>Allemagne</li><li>France</li><li>États-Unis</li></country><region><li>Basse-Saxe</li><li>Région Bretagne</li><li>Tennessee</li></region><settlement><li>Göttingen</li><li>cedex</li></settlement><orgName><li>Université de Göttingen</li></orgName></list><tree><country name="États-Unis"><region name="Tennessee"><name sortKey="Langouet, Sophie" sort="Langouet, Sophie" uniqKey="Langouet S" first="Sophie" last="Langouët">Sophie Langouët</name></region><name sortKey="Fink, Stephen P" sort="Fink, Stephen P" uniqKey="Fink S" first="Stephen P." last="Fink">Stephen P. Fink</name><name sortKey="Guengerich, F Peter" sort="Guengerich, F Peter" uniqKey="Guengerich F" first="F. Peter" last="Guengerich">F. Peter Guengerich</name><name sortKey="Guengerich, F Peter" sort="Guengerich, F Peter" uniqKey="Guengerich F" first="F. Peter" last="Guengerich">F. Peter Guengerich</name><name sortKey="Marnett, Lawrence J" sort="Marnett, Lawrence J" uniqKey="Marnett L" first="Lawrence J." last="Marnett">Lawrence J. Marnett</name><name sortKey="Mican, Adrienne N" sort="Mican, Adrienne N" uniqKey="Mican A" first="Adrienne N." last="Mican">Adrienne N. Mican</name><name sortKey="Muhle, Steven A" sort="Muhle, Steven A" uniqKey="Muhle S" first="Steven A." last="Muhle">Steven A. Muhle</name><name sortKey="Muller, Michael" sort="Muller, Michael" uniqKey="Muller M" first="Michael" last="Müller">Michael Müller</name></country><country name="France"><region name="Région Bretagne"><name sortKey="Langouet, Sophie" sort="Langouet, Sophie" uniqKey="Langouet S" first="Sophie" last="Langouët">Sophie Langouët</name></region></country><country name="Allemagne"><region name="Basse-Saxe"><name sortKey="Muller, Michael" sort="Muller, Michael" uniqKey="Muller M" first="Michael" last="Müller">Michael Müller</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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