Mutagenic potential of guanine N2 adducts of butadiene mono- and diolepoxide.
Identifieur interne : 002602 ( PubMed/Corpus ); précédent : 002601; suivant : 002603Mutagenic potential of guanine N2 adducts of butadiene mono- and diolepoxide.
Auteurs : J R Carmical ; M. Zhang ; L. Nechev ; C M Harris ; T M Harris ; R S LloydSource :
- Chemical research in toxicology [ 0893-228X ] ; 2000.
English descriptors
- KwdEn :
- Base Sequence, Butadienes (metabolism), Butadienes (toxicity), Codon, DNA Adducts (genetics), DNA Replication, DNA, Circular (metabolism), DNA-Directed DNA Polymerase (metabolism), Epoxy Compounds (metabolism), Epoxy Compounds (toxicity), Escherichia coli (enzymology), Escherichia coli (genetics), Escherichia coli (metabolism), Genes, ras, Glycols, Guanine (analogs & derivatives), Guanine (toxicity), Molecular Sequence Data, Mutagens (metabolism), Mutagens (toxicity), Oligonucleotides (chemical synthesis), Oligonucleotides (metabolism), Stereoisomerism, Templates, Genetic, Transfection.
- MESH :
- chemical , analogs & derivatives : Guanine.
- chemical , chemical synthesis : Oligonucleotides.
- chemical , genetics : DNA Adducts.
- chemical , metabolism : Butadienes, DNA, Circular, DNA-Directed DNA Polymerase, Epoxy Compounds, Mutagens, Oligonucleotides.
- chemical , toxicity : Butadienes, Epoxy Compounds, Guanine, Mutagens.
- enzymology : Escherichia coli.
- genetics : Escherichia coli.
- metabolism : Escherichia coli.
- Base Sequence, Codon, DNA Replication, Genes, ras, Glycols, Molecular Sequence Data, Stereoisomerism, Templates, Genetic, Transfection.
Abstract
To explore the role of guanine N(2) adducts of stereoisomeric butadiene metabolites in butadiene-induced mutagenesis, 11-mer deoxyoligonucleotides were prepared containing adducts of (R)- and (S)-monoepoxide and (R,R)- and (S,S)-diolepoxide. These adducted oligonucleotides were utilized in both in vivo and in vitro experiments designed to examine the mutagenic potency of each and their replication by Escherichia coli polymerases. Each of the four adducted deoxyoligonucleotides was ligated into a single-stranded M13mp7L2 vector and transfected into E. coli. The resulting plaques were screened for misincorporation at position 2 of the N-ras 12 codon. Although the mutagenic frequencies were low, different relative mutagenicities of the various stereoisomers were discernible. In addition, the biological effects of each adduct on the three major E. coli polymerases were determined via primer extension assays. The adducted 11-mers were ligated into a 60-mer linear DNA molecule to provide a sufficiently long template for primer elongation. All four guanine adducts were determined to be blocking to each of the three polymerases via primer extension assays.
DOI: 10.1021/tx9901332
PubMed: 10649962
Links to Exploration step
pubmed:10649962Le document en format XML
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Nechev</name></author><author><name sortKey="Harris, C M" sort="Harris, C M" uniqKey="Harris C" first="C M" last="Harris">C M Harris</name></author><author><name sortKey="Harris, T M" sort="Harris, T M" uniqKey="Harris T" first="T M" last="Harris">T M Harris</name></author><author><name sortKey="Lloyd, R S" sort="Lloyd, R S" uniqKey="Lloyd R" first="R S" last="Lloyd">R S Lloyd</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2000">2000</date><idno type="RBID">pubmed:10649962</idno><idno type="pmid">10649962</idno><idno type="doi">10.1021/tx9901332</idno><idno type="wicri:Area/PubMed/Corpus">002602</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002602</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Mutagenic potential of guanine N2 adducts of butadiene mono- and diolepoxide.</title><author><name sortKey="Carmical, J R" sort="Carmical, J R" uniqKey="Carmical J" first="J R" last="Carmical">J R Carmical</name><affiliation><nlm:affiliation>Departments of Preventative Medicine and Community Health and Sealy Center for Molecular Science, The University of Texas Medical Branch, Galveston, Texas 77555, USA.</nlm:affiliation></affiliation></author><author><name sortKey="Zhang, M" sort="Zhang, M" uniqKey="Zhang M" first="M" last="Zhang">M. Zhang</name></author><author><name sortKey="Nechev, L" sort="Nechev, L" uniqKey="Nechev L" first="L" last="Nechev">L. Nechev</name></author><author><name sortKey="Harris, C M" sort="Harris, C M" uniqKey="Harris C" first="C M" last="Harris">C M Harris</name></author><author><name sortKey="Harris, T M" sort="Harris, T M" uniqKey="Harris T" first="T M" last="Harris">T M Harris</name></author><author><name sortKey="Lloyd, R S" sort="Lloyd, R S" uniqKey="Lloyd R" first="R S" last="Lloyd">R S Lloyd</name></author></analytic><series><title level="j">Chemical research in toxicology</title><idno type="ISSN">0893-228X</idno><imprint><date when="2000" type="published">2000</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Base Sequence</term><term>Butadienes (metabolism)</term><term>Butadienes (toxicity)</term><term>Codon</term><term>DNA Adducts (genetics)</term><term>DNA Replication</term><term>DNA, Circular (metabolism)</term><term>DNA-Directed DNA Polymerase (metabolism)</term><term>Epoxy Compounds (metabolism)</term><term>Epoxy Compounds (toxicity)</term><term>Escherichia coli (enzymology)</term><term>Escherichia coli (genetics)</term><term>Escherichia coli (metabolism)</term><term>Genes, ras</term><term>Glycols</term><term>Guanine (analogs & derivatives)</term><term>Guanine (toxicity)</term><term>Molecular Sequence Data</term><term>Mutagens (metabolism)</term><term>Mutagens (toxicity)</term><term>Oligonucleotides (chemical synthesis)</term><term>Oligonucleotides (metabolism)</term><term>Stereoisomerism</term><term>Templates, Genetic</term><term>Transfection</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Guanine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Oligonucleotides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="genetics" xml:lang="en"><term>DNA Adducts</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Butadienes</term><term>DNA, Circular</term><term>DNA-Directed DNA Polymerase</term><term>Epoxy Compounds</term><term>Mutagens</term><term>Oligonucleotides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="toxicity" xml:lang="en"><term>Butadienes</term><term>Epoxy Compounds</term><term>Guanine</term><term>Mutagens</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>Escherichia coli</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Base Sequence</term><term>Codon</term><term>DNA Replication</term><term>Genes, ras</term><term>Glycols</term><term>Molecular Sequence Data</term><term>Stereoisomerism</term><term>Templates, Genetic</term><term>Transfection</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">To explore the role of guanine N(2) adducts of stereoisomeric butadiene metabolites in butadiene-induced mutagenesis, 11-mer deoxyoligonucleotides were prepared containing adducts of (R)- and (S)-monoepoxide and (R,R)- and (S,S)-diolepoxide. These adducted oligonucleotides were utilized in both in vivo and in vitro experiments designed to examine the mutagenic potency of each and their replication by Escherichia coli polymerases. Each of the four adducted deoxyoligonucleotides was ligated into a single-stranded M13mp7L2 vector and transfected into E. coli. The resulting plaques were screened for misincorporation at position 2 of the N-ras 12 codon. Although the mutagenic frequencies were low, different relative mutagenicities of the various stereoisomers were discernible. In addition, the biological effects of each adduct on the three major E. coli polymerases were determined via primer extension assays. The adducted 11-mers were ligated into a 60-mer linear DNA molecule to provide a sufficiently long template for primer elongation. All four guanine adducts were determined to be blocking to each of the three polymerases via primer extension assays.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">10649962</PMID><DateCompleted><Year>2000</Year><Month>03</Month><Day>10</Day></DateCompleted><DateRevised><Year>2019</Year><Month>09</Month><Day>21</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0893-228X</ISSN><JournalIssue CitedMedium="Print"><Volume>13</Volume><Issue>1</Issue><PubDate><Year>2000</Year><Month>Jan</Month></PubDate></JournalIssue><Title>Chemical research in toxicology</Title><ISOAbbreviation>Chem. Res. Toxicol.</ISOAbbreviation></Journal><ArticleTitle>Mutagenic potential of guanine N2 adducts of butadiene mono- and diolepoxide.</ArticleTitle><Pagination><MedlinePgn>18-25</MedlinePgn></Pagination><Abstract><AbstractText>To explore the role of guanine N(2) adducts of stereoisomeric butadiene metabolites in butadiene-induced mutagenesis, 11-mer deoxyoligonucleotides were prepared containing adducts of (R)- and (S)-monoepoxide and (R,R)- and (S,S)-diolepoxide. These adducted oligonucleotides were utilized in both in vivo and in vitro experiments designed to examine the mutagenic potency of each and their replication by Escherichia coli polymerases. Each of the four adducted deoxyoligonucleotides was ligated into a single-stranded M13mp7L2 vector and transfected into E. coli. The resulting plaques were screened for misincorporation at position 2 of the N-ras 12 codon. Although the mutagenic frequencies were low, different relative mutagenicities of the various stereoisomers were discernible. In addition, the biological effects of each adduct on the three major E. coli polymerases were determined via primer extension assays. The adducted 11-mers were ligated into a 60-mer linear DNA molecule to provide a sufficiently long template for primer elongation. All four guanine adducts were determined to be blocking to each of the three polymerases via primer extension assays.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Carmical</LastName><ForeName>J R</ForeName><Initials>JR</Initials><AffiliationInfo><Affiliation>Departments of Preventative Medicine and Community Health and Sealy Center for Molecular Science, The University of Texas Medical Branch, Galveston, Texas 77555, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhang</LastName><ForeName>M</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Nechev</LastName><ForeName>L</ForeName><Initials>L</Initials></Author><Author ValidYN="Y"><LastName>Harris</LastName><ForeName>C M</ForeName><Initials>CM</Initials></Author><Author ValidYN="Y"><LastName>Harris</LastName><ForeName>T M</ForeName><Initials>TM</Initials></Author><Author ValidYN="Y"><LastName>Lloyd</LastName><ForeName>R 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UI="D009841">Oligonucleotides</NameOfSubstance></Chemical><Chemical><RegistryNumber>17177-50-3</RegistryNumber><NameOfSubstance UI="C080053">3,4-epoxybutane-1,2-diol</NameOfSubstance></Chemical><Chemical><RegistryNumber>478ERR5NKR</RegistryNumber><NameOfSubstance UI="C024370">3,4-epoxy-1-butene</NameOfSubstance></Chemical><Chemical><RegistryNumber>5Z93L87A1R</RegistryNumber><NameOfSubstance UI="D006147">Guanine</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.7.7.7</RegistryNumber><NameOfSubstance UI="D004259">DNA-Directed DNA Polymerase</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><CommentsCorrectionsList><CommentsCorrections RefType="ErratumIn"><RefSource>Chem Res Toxicol 2000 May;13(5):430</RefSource></CommentsCorrections></CommentsCorrectionsList><MeshHeadingList><MeshHeading><DescriptorName UI="D001483" MajorTopicYN="N">Base Sequence</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D002070" 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