Sequence context effects on mutational properties of cis-opened benzo[c]phenanthrene diol epoxide-deoxyadenosine adducts in site-specific mutation studies.
Identifieur interne : 002652 ( PubMed/Corpus ); précédent : 002651; suivant : 002653Sequence context effects on mutational properties of cis-opened benzo[c]phenanthrene diol epoxide-deoxyadenosine adducts in site-specific mutation studies.
Auteurs : I. Pontén ; J M Sayer ; A S Pilcher ; H. Yagi ; S. Kumar ; D M Jerina ; A. DippleSource :
- Biochemistry [ 0006-2960 ] ; 1999.
English descriptors
- KwdEn :
- Bacteriophage M13 (genetics), Base Sequence, Chromatography, High Pressure Liquid, Circular Dichroism, DNA Adducts (chemistry), DNA Adducts (genetics), DNA Mutational Analysis, Deoxyadenosines (chemistry), Deoxyadenosines (genetics), Electrophoresis, Polyacrylamide Gel, Genetic Vectors, Mutagenesis, Site-Directed, Mutagens (chemistry), Oligonucleotides (chemistry), Oligonucleotides (genetics), Phenanthrenes (chemistry).
- MESH :
- chemical , chemistry : DNA Adducts, Deoxyadenosines, Mutagens, Oligonucleotides, Phenanthrenes.
- genetics : Bacteriophage M13, DNA Adducts, Deoxyadenosines, Oligonucleotides.
- Base Sequence, Chromatography, High Pressure Liquid, Circular Dichroism, DNA Mutational Analysis, Electrophoresis, Polyacrylamide Gel, Genetic Vectors, Mutagenesis, Site-Directed.
Abstract
Diastereomeric N6-substituted dAdo adducts (cis B[c]PhDE-2/1R and cis B[c]PhDE-2/1S) that correspond to cis-opening at C-1 of the enantiomeric benzo[c]phenanthrene 3,4-diol 1,2-epoxides in which the epoxide oxygen and the benzylic hydroxyl group are trans (DE-2) were synthetically incorporated into oligonucleotide 16-mers. Each adduct was placed at the fourth nucleotide from the 5'-end of each of two different oligonucleotide sequences derived from the E. coli supF gene. Each adduct was also placed in two additional oligonucleotide sequences that were constructed by interchanging the adduct site and the immediately adjacent nucleotides between the two original sequences. These oligonucleotides were designed for use in site-specific mutation studies, with a single-stranded bacteriophage M13mp7L2 vector, to determine if the effects of sequence context on types and frequencies of base substitution mutations are attributable only to nucleotides immediately adjacent to these polycyclic aromatic hydrocarbon diol epoxide-dAdo adducts, or whether more distant nucleotide residues also affect the mutagenic response. In SOS-induced Escherichia coli SMH77, total base substitution mutation frequencies for the cis B[c]PhDE-2/1R-dAdo adduct were relatively low (0.62-5.6%) compared with those for the cis B[c]PhDE-2/1S-dAdo adduct (11.9-56.5%). Depending on sequence context, cis B[c]PhDE-2/1R-dAdo gave predominantly A-->T or a more equal distribution of A-->T and A-->G mutations whereas cis B[c]PhDE-2/1S-dAdo gave either predominantly A-->T or predominantly A-->G base substitutions. Our results clearly indicate that nucleotides that are distal as well as those that are proximal to the adduct site are capable of influencing both the mutation frequency and the distribution of base substitution mutations.
DOI: 10.1021/bi982436l
PubMed: 9894012
Links to Exploration step
pubmed:9894012Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Sequence context effects on mutational properties of cis-opened benzo[c]phenanthrene diol epoxide-deoxyadenosine adducts in site-specific mutation studies.</title><author><name sortKey="Ponten, I" sort="Ponten, I" uniqKey="Ponten I" first="I" last="Pontén">I. Pontén</name><affiliation><nlm:affiliation>Chemistry of Carcinogenesis Laboratory, National Cancer Institute-Frederick Cancer Research and Development Center, Maryland 21702, USA.</nlm:affiliation></affiliation></author><author><name sortKey="Sayer, J M" sort="Sayer, J M" uniqKey="Sayer J" first="J M" last="Sayer">J M Sayer</name></author><author><name sortKey="Pilcher, A S" sort="Pilcher, A S" uniqKey="Pilcher A" first="A S" last="Pilcher">A S Pilcher</name></author><author><name sortKey="Yagi, H" sort="Yagi, H" uniqKey="Yagi H" first="H" last="Yagi">H. Yagi</name></author><author><name sortKey="Kumar, S" sort="Kumar, S" uniqKey="Kumar S" first="S" last="Kumar">S. Kumar</name></author><author><name sortKey="Jerina, D M" sort="Jerina, D M" uniqKey="Jerina D" first="D M" last="Jerina">D M Jerina</name></author><author><name sortKey="Dipple, A" sort="Dipple, A" uniqKey="Dipple A" first="A" last="Dipple">A. Dipple</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="1999">1999</date><idno type="RBID">pubmed:9894012</idno><idno type="pmid">9894012</idno><idno type="doi">10.1021/bi982436l</idno><idno type="wicri:Area/PubMed/Corpus">002652</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002652</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Sequence context effects on mutational properties of cis-opened benzo[c]phenanthrene diol epoxide-deoxyadenosine adducts in site-specific mutation studies.</title><author><name sortKey="Ponten, I" sort="Ponten, I" uniqKey="Ponten I" first="I" last="Pontén">I. Pontén</name><affiliation><nlm:affiliation>Chemistry of Carcinogenesis Laboratory, National Cancer Institute-Frederick Cancer Research and Development Center, Maryland 21702, USA.</nlm:affiliation></affiliation></author><author><name sortKey="Sayer, J M" sort="Sayer, J M" uniqKey="Sayer J" first="J M" last="Sayer">J M Sayer</name></author><author><name sortKey="Pilcher, A S" sort="Pilcher, A S" uniqKey="Pilcher A" first="A S" last="Pilcher">A S Pilcher</name></author><author><name sortKey="Yagi, H" sort="Yagi, H" uniqKey="Yagi H" first="H" last="Yagi">H. Yagi</name></author><author><name sortKey="Kumar, S" sort="Kumar, S" uniqKey="Kumar S" first="S" last="Kumar">S. Kumar</name></author><author><name sortKey="Jerina, D M" sort="Jerina, D M" uniqKey="Jerina D" first="D M" last="Jerina">D M Jerina</name></author><author><name sortKey="Dipple, A" sort="Dipple, A" uniqKey="Dipple A" first="A" last="Dipple">A. Dipple</name></author></analytic><series><title level="j">Biochemistry</title><idno type="ISSN">0006-2960</idno><imprint><date when="1999" type="published">1999</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Bacteriophage M13 (genetics)</term><term>Base Sequence</term><term>Chromatography, High Pressure Liquid</term><term>Circular Dichroism</term><term>DNA Adducts (chemistry)</term><term>DNA Adducts (genetics)</term><term>DNA Mutational Analysis</term><term>Deoxyadenosines (chemistry)</term><term>Deoxyadenosines (genetics)</term><term>Electrophoresis, Polyacrylamide Gel</term><term>Genetic Vectors</term><term>Mutagenesis, Site-Directed</term><term>Mutagens (chemistry)</term><term>Oligonucleotides (chemistry)</term><term>Oligonucleotides (genetics)</term><term>Phenanthrenes (chemistry)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>DNA Adducts</term><term>Deoxyadenosines</term><term>Mutagens</term><term>Oligonucleotides</term><term>Phenanthrenes</term></keywords><keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>Bacteriophage M13</term><term>DNA Adducts</term><term>Deoxyadenosines</term><term>Oligonucleotides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Base Sequence</term><term>Chromatography, High Pressure Liquid</term><term>Circular Dichroism</term><term>DNA Mutational Analysis</term><term>Electrophoresis, Polyacrylamide Gel</term><term>Genetic Vectors</term><term>Mutagenesis, Site-Directed</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Diastereomeric N6-substituted dAdo adducts (cis B[c]PhDE-2/1R and cis B[c]PhDE-2/1S) that correspond to cis-opening at C-1 of the enantiomeric benzo[c]phenanthrene 3,4-diol 1,2-epoxides in which the epoxide oxygen and the benzylic hydroxyl group are trans (DE-2) were synthetically incorporated into oligonucleotide 16-mers. Each adduct was placed at the fourth nucleotide from the 5'-end of each of two different oligonucleotide sequences derived from the E. coli supF gene. Each adduct was also placed in two additional oligonucleotide sequences that were constructed by interchanging the adduct site and the immediately adjacent nucleotides between the two original sequences. These oligonucleotides were designed for use in site-specific mutation studies, with a single-stranded bacteriophage M13mp7L2 vector, to determine if the effects of sequence context on types and frequencies of base substitution mutations are attributable only to nucleotides immediately adjacent to these polycyclic aromatic hydrocarbon diol epoxide-dAdo adducts, or whether more distant nucleotide residues also affect the mutagenic response. In SOS-induced Escherichia coli SMH77, total base substitution mutation frequencies for the cis B[c]PhDE-2/1R-dAdo adduct were relatively low (0.62-5.6%) compared with those for the cis B[c]PhDE-2/1S-dAdo adduct (11.9-56.5%). Depending on sequence context, cis B[c]PhDE-2/1R-dAdo gave predominantly A-->T or a more equal distribution of A-->T and A-->G mutations whereas cis B[c]PhDE-2/1S-dAdo gave either predominantly A-->T or predominantly A-->G base substitutions. Our results clearly indicate that nucleotides that are distal as well as those that are proximal to the adduct site are capable of influencing both the mutation frequency and the distribution of base substitution mutations.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">9894012</PMID><DateCompleted><Year>1999</Year><Month>02</Month><Day>23</Day></DateCompleted><DateRevised><Year>2006</Year><Month>11</Month><Day>15</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0006-2960</ISSN><JournalIssue CitedMedium="Print"><Volume>38</Volume><Issue>3</Issue><PubDate><Year>1999</Year><Month>Jan</Month><Day>19</Day></PubDate></JournalIssue><Title>Biochemistry</Title><ISOAbbreviation>Biochemistry</ISOAbbreviation></Journal><ArticleTitle>Sequence context effects on mutational properties of cis-opened benzo[c]phenanthrene diol epoxide-deoxyadenosine adducts in site-specific mutation studies.</ArticleTitle><Pagination><MedlinePgn>1144-52</MedlinePgn></Pagination><Abstract><AbstractText>Diastereomeric N6-substituted dAdo adducts (cis B[c]PhDE-2/1R and cis B[c]PhDE-2/1S) that correspond to cis-opening at C-1 of the enantiomeric benzo[c]phenanthrene 3,4-diol 1,2-epoxides in which the epoxide oxygen and the benzylic hydroxyl group are trans (DE-2) were synthetically incorporated into oligonucleotide 16-mers. Each adduct was placed at the fourth nucleotide from the 5'-end of each of two different oligonucleotide sequences derived from the E. coli supF gene. Each adduct was also placed in two additional oligonucleotide sequences that were constructed by interchanging the adduct site and the immediately adjacent nucleotides between the two original sequences. These oligonucleotides were designed for use in site-specific mutation studies, with a single-stranded bacteriophage M13mp7L2 vector, to determine if the effects of sequence context on types and frequencies of base substitution mutations are attributable only to nucleotides immediately adjacent to these polycyclic aromatic hydrocarbon diol epoxide-dAdo adducts, or whether more distant nucleotide residues also affect the mutagenic response. In SOS-induced Escherichia coli SMH77, total base substitution mutation frequencies for the cis B[c]PhDE-2/1R-dAdo adduct were relatively low (0.62-5.6%) compared with those for the cis B[c]PhDE-2/1S-dAdo adduct (11.9-56.5%). Depending on sequence context, cis B[c]PhDE-2/1R-dAdo gave predominantly A-->T or a more equal distribution of A-->T and A-->G mutations whereas cis B[c]PhDE-2/1S-dAdo gave either predominantly A-->T or predominantly A-->G base substitutions. Our results clearly indicate that nucleotides that are distal as well as those that are proximal to the adduct site are capable of influencing both the mutation frequency and the distribution of base substitution mutations.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Pontén</LastName><ForeName>I</ForeName><Initials>I</Initials><AffiliationInfo><Affiliation>Chemistry of Carcinogenesis Laboratory, National Cancer Institute-Frederick Cancer Research and Development Center, Maryland 21702, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Sayer</LastName><ForeName>J M</ForeName><Initials>JM</Initials></Author><Author ValidYN="Y"><LastName>Pilcher</LastName><ForeName>A S</ForeName><Initials>AS</Initials></Author><Author ValidYN="Y"><LastName>Yagi</LastName><ForeName>H</ForeName><Initials>H</Initials></Author><Author ValidYN="Y"><LastName>Kumar</LastName><ForeName>S</ForeName><Initials>S</Initials></Author><Author ValidYN="Y"><LastName>Jerina</LastName><ForeName>D M</ForeName><Initials>DM</Initials></Author><Author ValidYN="Y"><LastName>Dipple</LastName><ForeName>A</ForeName><Initials>A</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013487">Research Support, U.S. Gov't, P.H.S.</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Biochemistry</MedlineTA><NlmUniqueID>0370623</NlmUniqueID><ISSNLinking>0006-2960</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D018736">DNA Adducts</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D003839">Deoxyadenosines</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009153">Mutagens</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009841">Oligonucleotides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010616">Phenanthrenes</NameOfSubstance></Chemical><Chemical><RegistryNumber>111001-48-0</RegistryNumber><NameOfSubstance UI="C090203">1,2-epoxy-3,4-dihydroxy-1,2,3,4-tetrahydrobenzo(c)phenanthrene</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D017104" MajorTopicYN="N">Bacteriophage M13</DescriptorName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001483" MajorTopicYN="N">Base Sequence</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D002851" MajorTopicYN="N">Chromatography, High Pressure Liquid</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D002942" MajorTopicYN="N">Circular Dichroism</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D018736" MajorTopicYN="N">DNA Adducts</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004252" MajorTopicYN="N">DNA Mutational Analysis</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D003839" MajorTopicYN="N">Deoxyadenosines</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000235" MajorTopicYN="N">genetics</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004591" MajorTopicYN="N">Electrophoresis, Polyacrylamide Gel</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D005822" MajorTopicYN="N">Genetic Vectors</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D016297" MajorTopicYN="Y">Mutagenesis, 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