Mutational consequences of replication of M13mp7L2 constructs containing cis-opened benzo[a]pyrene 7,8-diol 9, 10-epoxide-deoxyadenosine adducts.
Identifieur interne : 003796 ( Main/Exploration ); précédent : 003795; suivant : 003797Mutational consequences of replication of M13mp7L2 constructs containing cis-opened benzo[a]pyrene 7,8-diol 9, 10-epoxide-deoxyadenosine adducts.
Auteurs : J E Page [États-Unis] ; A S Pilcher ; H. Yagi ; J M Sayer ; D M Jerina ; A. DippleSource :
- Chemical research in toxicology [ 0893-228X ] ; 1999.
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 (biosynthèse), Adduits à l'ADN (génétique), Bactériophage M13 (génétique), Bactériophage M13 (métabolisme), Coliphages (génétique), Coliphages (métabolisme), Dichroïsme circulaire, Désoxyadénosine (), Escherichia coli (effets des radiations), Escherichia coli (génétique), Escherichia coli (métabolisme), Mutation, Oligonucléotides (), Rayons ultraviolets, Spectrophotométrie UV, Transfection.
- MESH :
- biosynthèse : Adduits à l'ADN.
- effets des radiations : Escherichia coli.
- génétique : Adduits à l'ADN, Bactériophage M13, Coliphages, Escherichia coli.
- métabolisme : Bactériophage M13, Coliphages, Escherichia coli.
- 7,8,8a,9a-Tétrahydro-benzo[10,11]chryséno[3,4-b]oxirène-7,8-diol, Adduits à l'ADN, Dichroïsme circulaire, Désoxyadénosine, Mutation, Oligonucléotides, Rayons ultraviolets, Spectrophotométrie UV, Transfection.
English descriptors
- KwdEn :
- 7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide (chemistry), Bacteriophage M13 (genetics), Bacteriophage M13 (metabolism), Circular Dichroism, Coliphages (genetics), Coliphages (metabolism), DNA Adducts (biosynthesis), DNA Adducts (chemistry), DNA Adducts (genetics), Deoxyadenosines (chemistry), Escherichia coli (genetics), Escherichia coli (metabolism), Escherichia coli (radiation effects), Mutation, Oligonucleotides (chemistry), Spectrophotometry, Ultraviolet, Transfection, Ultraviolet Rays.
- MESH :
- chemical , biosynthesis : DNA Adducts.
- chemical , chemistry : 7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide, DNA Adducts, Deoxyadenosines, Oligonucleotides.
- genetics : Bacteriophage M13, Coliphages, DNA Adducts, Escherichia coli.
- metabolism : Bacteriophage M13, Coliphages, Escherichia coli.
- radiation effects : Escherichia coli.
- Circular Dichroism, Mutation, Spectrophotometry, Ultraviolet, Transfection, Ultraviolet Rays.
Abstract
The four adducts that arise by cis ring opening of the four optically active benzo[a]pyrene diol epoxides by the exocyclic N6-amino group of deoxyadenosine were incorporated synthetically into each of two different oligonucleotide 16-mers, 5'-TTTXGAGTCTGCTCCC-3' [context I(A)] and 5'-CAGXTTTAGAGTCTGC-3' [context II(A)], at the X position. The eight resultant oligonucleotides were separately ligated into bacteriophage M13mp7L2 and replicated in Escherichia coli that had been SOS-induced, and the progeny were analyzed to evaluate the consequences of replication past these adducts. The presence of these adducts reduced plaque yields substantially. However, the progeny obtained exhibited high frequencies of base substitution mutation ranging from 9 to 68%, depending upon the individual adduct and the sequence context in which it was placed. For most of the adducts, A --> T transversion was the mutation found most frequently in either sequence context, and mutation frequencies in context I(A) were always substantially greater than those in context II(A). In context I(A), adducts with an R configuration at the site of nucleoside attachment were more mutagenic than those with an S configuration. In both sequence contexts that were studied, the cis adduct arising from the (7S,8R)-diol (9S,10R)-epoxide was the most mutagenic adduct. These findings clearly show that individual mutation frequencies are determined by the combined effects of both adduct structure and sequence context.
DOI: 10.1021/tx980244l
PubMed: 10077488
Affiliations:
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Le document en format XML
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Yagi</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">Chemical research in toxicology</title><idno type="ISSN">0893-228X</idno><imprint><date when="1999" type="published">1999</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>Bacteriophage M13 (metabolism)</term><term>Circular Dichroism</term><term>Coliphages (genetics)</term><term>Coliphages (metabolism)</term><term>DNA Adducts (biosynthesis)</term><term>DNA Adducts (chemistry)</term><term>DNA Adducts (genetics)</term><term>Deoxyadenosines (chemistry)</term><term>Escherichia coli (genetics)</term><term>Escherichia coli (metabolism)</term><term>Escherichia coli (radiation effects)</term><term>Mutation</term><term>Oligonucleotides (chemistry)</term><term>Spectrophotometry, Ultraviolet</term><term>Transfection</term><term>Ultraviolet Rays</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 (biosynthèse)</term><term>Adduits à l'ADN (génétique)</term><term>Bactériophage M13 (génétique)</term><term>Bactériophage M13 (métabolisme)</term><term>Coliphages (génétique)</term><term>Coliphages (métabolisme)</term><term>Dichroïsme circulaire</term><term>Désoxyadénosine ()</term><term>Escherichia coli (effets des radiations)</term><term>Escherichia coli (génétique)</term><term>Escherichia coli (métabolisme)</term><term>Mutation</term><term>Oligonucléotides ()</term><term>Rayons ultraviolets</term><term>Spectrophotométrie UV</term><term>Transfection</term></keywords><keywords scheme="MESH" type="chemical" qualifier="biosynthesis" xml:lang="en"><term>DNA Adducts</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>Deoxyadenosines</term><term>Oligonucleotides</term></keywords><keywords scheme="MESH" qualifier="biosynthèse" xml:lang="fr"><term>Adduits à l'ADN</term></keywords><keywords scheme="MESH" qualifier="effets des radiations" xml:lang="fr"><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>Bacteriophage M13</term><term>Coliphages</term><term>DNA Adducts</term><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>Adduits à l'ADN</term><term>Bactériophage M13</term><term>Coliphages</term><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>Bacteriophage M13</term><term>Coliphages</term><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Bactériophage M13</term><term>Coliphages</term><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="radiation effects" xml:lang="en"><term>Escherichia coli</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Circular Dichroism</term><term>Mutation</term><term>Spectrophotometry, Ultraviolet</term><term>Transfection</term><term>Ultraviolet Rays</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>Dichroïsme circulaire</term><term>Désoxyadénosine</term><term>Mutation</term><term>Oligonucléotides</term><term>Rayons ultraviolets</term><term>Spectrophotométrie UV</term><term>Transfection</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The four adducts that arise by cis ring opening of the four optically active benzo[a]pyrene diol epoxides by the exocyclic N6-amino group of deoxyadenosine were incorporated synthetically into each of two different oligonucleotide 16-mers, 5'-TTTXGAGTCTGCTCCC-3' [context I(A)] and 5'-CAGXTTTAGAGTCTGC-3' [context II(A)], at the X position. The eight resultant oligonucleotides were separately ligated into bacteriophage M13mp7L2 and replicated in Escherichia coli that had been SOS-induced, and the progeny were analyzed to evaluate the consequences of replication past these adducts. The presence of these adducts reduced plaque yields substantially. However, the progeny obtained exhibited high frequencies of base substitution mutation ranging from 9 to 68%, depending upon the individual adduct and the sequence context in which it was placed. For most of the adducts, A --> T transversion was the mutation found most frequently in either sequence context, and mutation frequencies in context I(A) were always substantially greater than those in context II(A). In context I(A), adducts with an R configuration at the site of nucleoside attachment were more mutagenic than those with an S configuration. In both sequence contexts that were studied, the cis adduct arising from the (7S,8R)-diol (9S,10R)-epoxide was the most mutagenic adduct. These findings clearly show that individual mutation frequencies are determined by the combined effects of both adduct structure and sequence context.</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="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="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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