Sequence context profoundly influences the mutagenic potency of trans-opened benzo[a]pyrene 7,8-diol 9,10-epoxide-purine nucleoside adducts in site-specific mutation studies.
Identifieur interne : 003983 ( Main/Exploration ); précédent : 003982; suivant : 003984Sequence context profoundly influences the mutagenic potency of trans-opened benzo[a]pyrene 7,8-diol 9,10-epoxide-purine nucleoside adducts in site-specific mutation studies.
Auteurs : J E Page [États-Unis] ; B. Zajc ; T. Oh-Hara ; M K Lakshman ; J M Sayer ; D M Jerina ; A. DippleSource :
- Biochemistry [ 0006-2960 ] ; 1998.
Descripteurs français
- KwdFr :
- 7,8,8a,9a-Tétrahydro-benzo[10,11]chryséno[3,4-b]oxirène-7,8-diol (), Adduits à l'ADN (), Adduits à l'ADN (génétique), Bactériophage M13 (génétique), Ligands, Modèles chimiques, Mutagenèse dirigée, Mutagènes (), Nucléoside purique (), Nucléoside purique (génétique), Oligonucléotides (), Oligonucléotides (génétique), Oligonucléotides (isolement et purification), Stéréoisomérie, Séquence nucléotidique, Transfection, Vecteurs génétiques ().
- MESH :
- génétique : Adduits à l'ADN, Bactériophage M13, Nucléoside purique, Oligonucléotides.
- isolement et purification : Oligonucléotides.
- 7,8,8a,9a-Tétrahydro-benzo[10,11]chryséno[3,4-b]oxirène-7,8-diol, Adduits à l'ADN, Ligands, Modèles chimiques, Mutagenèse dirigée, Mutagènes, Nucléoside purique, Oligonucléotides, Stéréoisomérie, Séquence nucléotidique, Transfection, Vecteurs génétiques.
English descriptors
- KwdEn :
- 7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide (chemistry), Bacteriophage M13 (genetics), Base Sequence, DNA Adducts (chemistry), DNA Adducts (genetics), Genetic Vectors (chemistry), Ligands, Models, Chemical, Mutagenesis, Site-Directed, Mutagens (chemistry), Oligonucleotides (chemistry), Oligonucleotides (genetics), Oligonucleotides (isolation & purification), Purine Nucleosides (chemistry), Purine Nucleosides (genetics), Stereoisomerism, Transfection.
- MESH :
- chemical , chemistry : 7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide, DNA Adducts, Mutagens, Oligonucleotides, Purine Nucleosides.
- chemistry : Genetic Vectors.
- genetics : Bacteriophage M13, DNA Adducts, Oligonucleotides, Purine Nucleosides.
- chemical , isolation & purification : Oligonucleotides.
- Base Sequence, Ligands, Models, Chemical, Mutagenesis, Site-Directed, Stereoisomerism, Transfection.
Abstract
The postoligomerization method was used to prepare oligonucleotide 16-mers that contained dAdo or dGuo adducts, derived from trans opening of each enantiomer of the two diastereomeric benzo[a]pyrene 7,8-diol 9,10-epoxides, in two sequence contexts. These 16 oligonucleotides, along with the four corresponding oligonucleotides containing unsubstituted purines, were ligated into single-stranded DNA from bacteriophage M13mp7L2 and transfected into Escherichia coli SMH77. The mutagenic effects of replication past these adducts were then evaluated. The various adduct isomers induced point mutations at different frequencies and with different distributions of mutation types, as was anticipated. However, sequence context had the most substantial effects on mutation frequency. A high frequency of deletions of a single guanine was found in a context where the dGuo adduct was at the 3'-end of a run of five guanines, whereas no single base deletion was found in the other context studied, 5'-CGA-3'. Mutation frequencies in constructs containing dAdo adducts were much higher in a 5'-TAG-3' context (37-58%, depending on the individual isomer) than in a 5'-GAT-3' context (5-20%), and for a given adduct, mutation frequency was up to 10-fold higher in the former sequence than in the latter. These findings indicate that sequence context effects need more thorough evaluation if the goal of understanding the mechanism through which DNA adducts lead to mutation is to be achieved.
DOI: 10.1021/bi980273v
PubMed: 9636059
Affiliations:
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Zajc</name></author><author><name sortKey="Oh Hara, T" sort="Oh Hara, T" uniqKey="Oh Hara T" first="T" last="Oh-Hara">T. Oh-Hara</name></author><author><name sortKey="Lakshman, M K" sort="Lakshman, M K" uniqKey="Lakshman M" first="M K" last="Lakshman">M K Lakshman</name></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="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="1998" type="published">1998</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide (chemistry)</term><term>Bacteriophage M13 (genetics)</term><term>Base Sequence</term><term>DNA Adducts (chemistry)</term><term>DNA Adducts (genetics)</term><term>Genetic Vectors (chemistry)</term><term>Ligands</term><term>Models, Chemical</term><term>Mutagenesis, Site-Directed</term><term>Mutagens (chemistry)</term><term>Oligonucleotides (chemistry)</term><term>Oligonucleotides (genetics)</term><term>Oligonucleotides (isolation & purification)</term><term>Purine Nucleosides (chemistry)</term><term>Purine Nucleosides (genetics)</term><term>Stereoisomerism</term><term>Transfection</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>7,8,8a,9a-Tétrahydro-benzo[10,11]chryséno[3,4-b]oxirène-7,8-diol ()</term><term>Adduits à l'ADN ()</term><term>Adduits à l'ADN (génétique)</term><term>Bactériophage M13 (génétique)</term><term>Ligands</term><term>Modèles chimiques</term><term>Mutagenèse dirigée</term><term>Mutagènes ()</term><term>Nucléoside purique ()</term><term>Nucléoside purique (génétique)</term><term>Oligonucléotides ()</term><term>Oligonucléotides (génétique)</term><term>Oligonucléotides (isolement et purification)</term><term>Stéréoisomérie</term><term>Séquence nucléotidique</term><term>Transfection</term><term>Vecteurs génétiques ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide</term><term>DNA Adducts</term><term>Mutagens</term><term>Oligonucleotides</term><term>Purine Nucleosides</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Genetic Vectors</term></keywords><keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>Bacteriophage M13</term><term>DNA Adducts</term><term>Oligonucleotides</term><term>Purine Nucleosides</term></keywords><keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>Adduits à l'ADN</term><term>Bactériophage M13</term><term>Nucléoside purique</term><term>Oligonucléotides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Oligonucleotides</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Oligonucléotides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Base Sequence</term><term>Ligands</term><term>Models, Chemical</term><term>Mutagenesis, Site-Directed</term><term>Stereoisomerism</term><term>Transfection</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>7,8,8a,9a-Tétrahydro-benzo[10,11]chryséno[3,4-b]oxirène-7,8-diol</term><term>Adduits à l'ADN</term><term>Ligands</term><term>Modèles chimiques</term><term>Mutagenèse dirigée</term><term>Mutagènes</term><term>Nucléoside purique</term><term>Oligonucléotides</term><term>Stéréoisomérie</term><term>Séquence nucléotidique</term><term>Transfection</term><term>Vecteurs génétiques</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The postoligomerization method was used to prepare oligonucleotide 16-mers that contained dAdo or dGuo adducts, derived from trans opening of each enantiomer of the two diastereomeric benzo[a]pyrene 7,8-diol 9,10-epoxides, in two sequence contexts. These 16 oligonucleotides, along with the four corresponding oligonucleotides containing unsubstituted purines, were ligated into single-stranded DNA from bacteriophage M13mp7L2 and transfected into Escherichia coli SMH77. The mutagenic effects of replication past these adducts were then evaluated. The various adduct isomers induced point mutations at different frequencies and with different distributions of mutation types, as was anticipated. However, sequence context had the most substantial effects on mutation frequency. A high frequency of deletions of a single guanine was found in a context where the dGuo adduct was at the 3'-end of a run of five guanines, whereas no single base deletion was found in the other context studied, 5'-CGA-3'. Mutation frequencies in constructs containing dAdo adducts were much higher in a 5'-TAG-3' context (37-58%, depending on the individual isomer) than in a 5'-GAT-3' context (5-20%), and for a given adduct, mutation frequency was up to 10-fold higher in the former sequence than in the latter. These findings indicate that sequence context effects need more thorough evaluation if the goal of understanding the mechanism through which DNA adducts lead to mutation is to be achieved.</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="Lakshman, M K" sort="Lakshman, M K" uniqKey="Lakshman M" first="M K" last="Lakshman">M K Lakshman</name><name sortKey="Oh Hara, T" sort="Oh Hara, T" uniqKey="Oh Hara T" first="T" last="Oh-Hara">T. Oh-Hara</name><name sortKey="Sayer, J M" sort="Sayer, J M" uniqKey="Sayer J" first="J M" last="Sayer">J M Sayer</name><name sortKey="Zajc, B" sort="Zajc, B" uniqKey="Zajc B" first="B" last="Zajc">B. Zajc</name></noCountry><country name="États-Unis"><noRegion><name sortKey="Page, J E" sort="Page, J E" uniqKey="Page J" first="J E" last="Page">J E Page</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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