Sequence context effects on mutational properties of cis-opened benzo[c]phenanthrene diol epoxide-deoxyadenosine adducts in site-specific mutation studies.
Identifieur interne : 003786 ( Main/Exploration ); précédent : 003785; suivant : 003787Sequence context effects on mutational properties of cis-opened benzo[c]phenanthrene diol epoxide-deoxyadenosine adducts in site-specific mutation studies.
Auteurs : I. Pontén [États-Unis] ; J M Sayer ; A S Pilcher ; H. Yagi ; S. Kumar ; D M Jerina ; A. DippleSource :
- Biochemistry [ 0006-2960 ] ; 1999.
Descripteurs français
- KwdFr :
- Adduits à l'ADN (), Adduits à l'ADN (génétique), Analyse de mutations d'ADN, Bactériophage M13 (génétique), Chromatographie en phase liquide à haute performance, Dichroïsme circulaire, Désoxyadénosine (), Désoxyadénosine (génétique), Mutagenèse dirigée, Mutagènes (), Oligonucléotides (), Oligonucléotides (génétique), Phénanthrènes (), Séquence nucléotidique, Vecteurs génétiques, Électrophorèse sur gel de polyacrylamide.
- MESH :
- génétique : Adduits à l'ADN, Bactériophage M13, Désoxyadénosine, Oligonucléotides.
- Adduits à l'ADN, Analyse de mutations d'ADN, Chromatographie en phase liquide à haute performance, Dichroïsme circulaire, Désoxyadénosine, Mutagenèse dirigée, Mutagènes, Oligonucléotides, Phénanthrènes, Séquence nucléotidique, Vecteurs génétiques, Électrophorèse sur gel de polyacrylamide.
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
Affiliations:
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Pontén</name><affiliation wicri:level="1"><nlm:affiliation>Chemistry of Carcinogenesis Laboratory, National Cancer Institute-Frederick Cancer Research and Development Center, Maryland 21702, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Chemistry of Carcinogenesis Laboratory, National Cancer Institute-Frederick Cancer Research and Development Center, Maryland 21702</wicri:regionArea><wicri:noRegion>Maryland 21702</wicri:noRegion></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="KwdFr" xml:lang="fr"><term>Adduits à l'ADN ()</term><term>Adduits à l'ADN (génétique)</term><term>Analyse de mutations d'ADN</term><term>Bactériophage M13 (génétique)</term><term>Chromatographie en phase liquide à haute performance</term><term>Dichroïsme circulaire</term><term>Désoxyadénosine ()</term><term>Désoxyadénosine (génétique)</term><term>Mutagenèse dirigée</term><term>Mutagènes ()</term><term>Oligonucléotides ()</term><term>Oligonucléotides (génétique)</term><term>Phénanthrènes ()</term><term>Séquence nucléotidique</term><term>Vecteurs génétiques</term><term>Électrophorèse sur gel de polyacrylamide</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" qualifier="génétique" xml:lang="fr"><term>Adduits à l'ADN</term><term>Bactériophage M13</term><term>Désoxyadénosine</term><term>Oligonucléotides</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><keywords scheme="MESH" xml:lang="fr"><term>Adduits à l'ADN</term><term>Analyse de mutations d'ADN</term><term>Chromatographie en phase liquide à haute performance</term><term>Dichroïsme circulaire</term><term>Désoxyadénosine</term><term>Mutagenèse dirigée</term><term>Mutagènes</term><term>Oligonucléotides</term><term>Phénanthrènes</term><term>Séquence nucléotidique</term><term>Vecteurs génétiques</term><term>Électrophorèse sur gel de polyacrylamide</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><affiliations><list><country><li>États-Unis</li></country></list><tree><noCountry><name sortKey="Dipple, A" sort="Dipple, A" uniqKey="Dipple A" first="A" last="Dipple">A. Dipple</name><name sortKey="Jerina, D M" sort="Jerina, D M" uniqKey="Jerina D" first="D M" last="Jerina">D M Jerina</name><name sortKey="Kumar, S" sort="Kumar, S" uniqKey="Kumar S" first="S" last="Kumar">S. Kumar</name><name sortKey="Pilcher, A S" sort="Pilcher, A S" uniqKey="Pilcher A" first="A S" last="Pilcher">A S Pilcher</name><name sortKey="Sayer, J M" sort="Sayer, J M" uniqKey="Sayer J" first="J M" last="Sayer">J M Sayer</name><name sortKey="Yagi, H" sort="Yagi, H" uniqKey="Yagi H" first="H" last="Yagi">H. Yagi</name></noCountry><country name="États-Unis"><noRegion><name sortKey="Ponten, I" sort="Ponten, I" uniqKey="Ponten I" first="I" last="Pontén">I. Pontén</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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