32P-postlabelling of diastereomeric 7-alkylguanine adducts of butadiene monoepoxide.
Identifieur interne : 002773 ( PubMed/Curation ); précédent : 002772; suivant : 00277432P-postlabelling of diastereomeric 7-alkylguanine adducts of butadiene monoepoxide.
Auteurs : R. Kumar [Suède] ; P. Vodicka ; P. Koivisto ; K. Peltonen ; K. HemminkiSource :
- Carcinogenesis [ 0143-3334 ] ; 1996.
Descripteurs français
- KwdFr :
- ADN (), ADN (métabolisme), Adduits à l'ADN (analyse), Adduits à l'ADN (biosynthèse), Adduits à l'ADN (isolement et purification), Animaux, Composés époxy (métabolisme), Composés époxy (pharmacologie), Marquage isotopique, Modèles moléculaires, Mutagènes (isolement et purification), Mutagènes (métabolisme), Mutagènes (pharmacologie), Mâle, Nucléotide désoxyguanylique (isolement et purification), Nucléotide désoxyguanylique (métabolisme), Phosphorylation, Polynucleotide 5'-hydroxyl-kinase (métabolisme), Période, Radio-isotopes du phosphore, Saumon, Sites de fixation, Stéréoisomérie.
- MESH :
- analyse : Adduits à l'ADN.
- biosynthèse : Adduits à l'ADN.
- isolement et purification : Adduits à l'ADN, Mutagènes, Nucléotide désoxyguanylique.
- métabolisme : ADN, Composés époxy, Mutagènes, Nucléotide désoxyguanylique, Polynucleotide 5'-hydroxyl-kinase.
- pharmacologie : Composés époxy, Mutagènes.
- ADN, Animaux, Marquage isotopique, Modèles moléculaires, Mâle, Phosphorylation, Période, Radio-isotopes du phosphore, Saumon, Sites de fixation, Stéréoisomérie.
English descriptors
- KwdEn :
- Animals, Binding Sites, DNA (drug effects), DNA (metabolism), DNA Adducts (analysis), DNA Adducts (biosynthesis), DNA Adducts (isolation & purification), Deoxyguanine Nucleotides (isolation & purification), Deoxyguanine Nucleotides (metabolism), Epoxy Compounds (metabolism), Epoxy Compounds (pharmacology), Half-Life, Isotope Labeling, Male, Models, Molecular, Mutagens (isolation & purification), Mutagens (metabolism), Mutagens (pharmacology), Phosphorus Radioisotopes, Phosphorylation, Polynucleotide 5'-Hydroxyl-Kinase (metabolism), Salmon, Stereoisomerism.
- MESH :
- chemical , analysis : DNA Adducts.
- chemical , biosynthesis : DNA Adducts.
- chemical , drug effects : DNA.
- chemical , isolation & purification : DNA Adducts, Deoxyguanine Nucleotides, Mutagens.
- chemical , metabolism : DNA, Deoxyguanine Nucleotides, Epoxy Compounds, Mutagens, Polynucleotide 5'-Hydroxyl-Kinase.
- chemical , pharmacology : Epoxy Compounds, Mutagens.
- Animals, Binding Sites, Half-Life, Isotope Labeling, Male, Models, Molecular, Phosphorus Radioisotopes, Phosphorylation, Salmon, Stereoisomerism.
Abstract
The reaction of 3,4-epoxy-1-butene (BMO) with deoxyguanosine-3'-monophosphate (3'-dGMP) resulted in the formation of two pairs of diastereomeric 7-alkyl-3'-dGMP derivatives corresponding to two isomers C¿-1 and C¿-2. The T4 polynucleotide kinase-mediated phosphorylation with [gamma-32P]-ATP showed preferential labelling of diastereo- mers of the C¿-1 isomer. The diastereomers 1 and 2 of the C¿-1 isomer had labelling efficiencies of 42%. However, the labelling efficiencies of diastereomers 3 and 4 of the C¿-2 isomer were 11 and 10%, respectively. The 32P-postlabelling of BMO-modified DNA yielded four isomers in the ratio of 4:4:1:1 with overall recoveries being 14%. The two isomers had a half-life of 270 min (C¿-1 isomer) and 300 min (C¿-2 isomer) which is in accordance with the stability predicted by other similar adduct experiments. The molecular modelling experiments showed more pronounced restricted rotation of butadiene residue in C¿-2 isomers due to steric interaction between butadiene residue at N-7 and O(6) atom of guanine than in C¿-1 isomer. The butadiene residue also leads to steric overcrowding at 3'-phosphate in C¿-2 isomer which probably restricts the access to the active site of T4 polynucleotide kinase.
DOI: 10.1093/carcin/17.6.1297
PubMed: 8681446
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pubmed:8681446Le document en format XML
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Peltonen</name></author><author><name sortKey="Hemminki, K" sort="Hemminki, K" uniqKey="Hemminki K" first="K" last="Hemminki">K. Hemminki</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="1996">1996</date><idno type="RBID">pubmed:8681446</idno><idno type="pmid">8681446</idno><idno type="doi">10.1093/carcin/17.6.1297</idno><idno type="wicri:Area/PubMed/Corpus">002773</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002773</idno><idno type="wicri:Area/PubMed/Curation">002773</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">002773</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">32P-postlabelling of diastereomeric 7-alkylguanine adducts of butadiene monoepoxide.</title><author><name sortKey="Kumar, R" sort="Kumar, R" uniqKey="Kumar R" first="R" last="Kumar">R. 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Hemminki</name></author></analytic><series><title level="j">Carcinogenesis</title><idno type="ISSN">0143-3334</idno><imprint><date when="1996" type="published">1996</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term><term>Binding Sites</term><term>DNA (drug effects)</term><term>DNA (metabolism)</term><term>DNA Adducts (analysis)</term><term>DNA Adducts (biosynthesis)</term><term>DNA Adducts (isolation & purification)</term><term>Deoxyguanine Nucleotides (isolation & purification)</term><term>Deoxyguanine Nucleotides (metabolism)</term><term>Epoxy Compounds (metabolism)</term><term>Epoxy Compounds (pharmacology)</term><term>Half-Life</term><term>Isotope Labeling</term><term>Male</term><term>Models, Molecular</term><term>Mutagens (isolation & purification)</term><term>Mutagens (metabolism)</term><term>Mutagens (pharmacology)</term><term>Phosphorus Radioisotopes</term><term>Phosphorylation</term><term>Polynucleotide 5'-Hydroxyl-Kinase (metabolism)</term><term>Salmon</term><term>Stereoisomerism</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>ADN ()</term><term>ADN (métabolisme)</term><term>Adduits à l'ADN (analyse)</term><term>Adduits à l'ADN (biosynthèse)</term><term>Adduits à l'ADN (isolement et purification)</term><term>Animaux</term><term>Composés époxy (métabolisme)</term><term>Composés époxy (pharmacologie)</term><term>Marquage isotopique</term><term>Modèles moléculaires</term><term>Mutagènes (isolement et purification)</term><term>Mutagènes (métabolisme)</term><term>Mutagènes (pharmacologie)</term><term>Mâle</term><term>Nucléotide désoxyguanylique (isolement et purification)</term><term>Nucléotide désoxyguanylique (métabolisme)</term><term>Phosphorylation</term><term>Polynucleotide 5'-hydroxyl-kinase (métabolisme)</term><term>Période</term><term>Radio-isotopes du phosphore</term><term>Saumon</term><term>Sites de fixation</term><term>Stéréoisomérie</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analysis" xml:lang="en"><term>DNA Adducts</term></keywords><keywords scheme="MESH" type="chemical" qualifier="biosynthesis" xml:lang="en"><term>DNA Adducts</term></keywords><keywords scheme="MESH" type="chemical" qualifier="drug effects" xml:lang="en"><term>DNA</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>DNA Adducts</term><term>Deoxyguanine Nucleotides</term><term>Mutagens</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>DNA</term><term>Deoxyguanine Nucleotides</term><term>Epoxy Compounds</term><term>Mutagens</term><term>Polynucleotide 5'-Hydroxyl-Kinase</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Epoxy Compounds</term><term>Mutagens</term></keywords><keywords scheme="MESH" qualifier="analyse" xml:lang="fr"><term>Adduits à l'ADN</term></keywords><keywords scheme="MESH" qualifier="biosynthèse" xml:lang="fr"><term>Adduits à l'ADN</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Adduits à l'ADN</term><term>Mutagènes</term><term>Nucléotide désoxyguanylique</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>ADN</term><term>Composés époxy</term><term>Mutagènes</term><term>Nucléotide désoxyguanylique</term><term>Polynucleotide 5'-hydroxyl-kinase</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Composés époxy</term><term>Mutagènes</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Binding Sites</term><term>Half-Life</term><term>Isotope Labeling</term><term>Male</term><term>Models, Molecular</term><term>Phosphorus Radioisotopes</term><term>Phosphorylation</term><term>Salmon</term><term>Stereoisomerism</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>ADN</term><term>Animaux</term><term>Marquage isotopique</term><term>Modèles moléculaires</term><term>Mâle</term><term>Phosphorylation</term><term>Période</term><term>Radio-isotopes du phosphore</term><term>Saumon</term><term>Sites de fixation</term><term>Stéréoisomérie</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The reaction of 3,4-epoxy-1-butene (BMO) with deoxyguanosine-3'-monophosphate (3'-dGMP) resulted in the formation of two pairs of diastereomeric 7-alkyl-3'-dGMP derivatives corresponding to two isomers C¿-1 and C¿-2. The T4 polynucleotide kinase-mediated phosphorylation with [gamma-32P]-ATP showed preferential labelling of diastereo- mers of the C¿-1 isomer. The diastereomers 1 and 2 of the C¿-1 isomer had labelling efficiencies of 42%. However, the labelling efficiencies of diastereomers 3 and 4 of the C¿-2 isomer were 11 and 10%, respectively. The 32P-postlabelling of BMO-modified DNA yielded four isomers in the ratio of 4:4:1:1 with overall recoveries being 14%. The two isomers had a half-life of 270 min (C¿-1 isomer) and 300 min (C¿-2 isomer) which is in accordance with the stability predicted by other similar adduct experiments. The molecular modelling experiments showed more pronounced restricted rotation of butadiene residue in C¿-2 isomers due to steric interaction between butadiene residue at N-7 and O(6) atom of guanine than in C¿-1 isomer. The butadiene residue also leads to steric overcrowding at 3'-phosphate in C¿-2 isomer which probably restricts the access to the active site of T4 polynucleotide kinase.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">8681446</PMID><DateCompleted><Year>1996</Year><Month>08</Month><Day>22</Day></DateCompleted><DateRevised><Year>2019</Year><Month>05</Month><Day>12</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0143-3334</ISSN><JournalIssue CitedMedium="Print"><Volume>17</Volume><Issue>6</Issue><PubDate><Year>1996</Year><Month>Jun</Month></PubDate></JournalIssue><Title>Carcinogenesis</Title><ISOAbbreviation>Carcinogenesis</ISOAbbreviation></Journal><ArticleTitle>32P-postlabelling of diastereomeric 7-alkylguanine adducts of butadiene monoepoxide.</ArticleTitle><Pagination><MedlinePgn>1297-303</MedlinePgn></Pagination><Abstract><AbstractText>The reaction of 3,4-epoxy-1-butene (BMO) with deoxyguanosine-3'-monophosphate (3'-dGMP) resulted in the formation of two pairs of diastereomeric 7-alkyl-3'-dGMP derivatives corresponding to two isomers C¿-1 and C¿-2. The T4 polynucleotide kinase-mediated phosphorylation with [gamma-32P]-ATP showed preferential labelling of diastereo- mers of the C¿-1 isomer. The diastereomers 1 and 2 of the C¿-1 isomer had labelling efficiencies of 42%. However, the labelling efficiencies of diastereomers 3 and 4 of the C¿-2 isomer were 11 and 10%, respectively. The 32P-postlabelling of BMO-modified DNA yielded four isomers in the ratio of 4:4:1:1 with overall recoveries being 14%. The two isomers had a half-life of 270 min (C¿-1 isomer) and 300 min (C¿-2 isomer) which is in accordance with the stability predicted by other similar adduct experiments. The molecular modelling experiments showed more pronounced restricted rotation of butadiene residue in C¿-2 isomers due to steric interaction between butadiene residue at N-7 and O(6) atom of guanine than in C¿-1 isomer. The butadiene residue also leads to steric overcrowding at 3'-phosphate in C¿-2 isomer which probably restricts the access to the active site of T4 polynucleotide kinase.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Kumar</LastName><ForeName>R</ForeName><Initials>R</Initials><AffiliationInfo><Affiliation>Center for Nutrition and Toxicology, Karolinska Institute, Huddinge, Sweden.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Vodicka</LastName><ForeName>P</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Koivisto</LastName><ForeName>P</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Peltonen</LastName><ForeName>K</ForeName><Initials>K</Initials></Author><Author ValidYN="Y"><LastName>Hemminki</LastName><ForeName>K</ForeName><Initials>K</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Carcinogenesis</MedlineTA><NlmUniqueID>8008055</NlmUniqueID><ISSNLinking>0143-3334</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D018736">DNA Adducts</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D003848">Deoxyguanine Nucleotides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D004852">Epoxy Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009153">Mutagens</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D010761">Phosphorus Radioisotopes</NameOfSubstance></Chemical><Chemical><RegistryNumber>478ERR5NKR</RegistryNumber><NameOfSubstance UI="C024370">3,4-epoxy-1-butene</NameOfSubstance></Chemical><Chemical><RegistryNumber>6220-62-8</RegistryNumber><NameOfSubstance UI="C034009">2'-deoxyguanosine 3'-phosphate</NameOfSubstance></Chemical><Chemical><RegistryNumber>9007-49-2</RegistryNumber><NameOfSubstance UI="D004247">DNA</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 2.7.1.78</RegistryNumber><NameOfSubstance UI="D011116">Polynucleotide 5'-Hydroxyl-Kinase</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000818" MajorTopicYN="N">Animals</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D001665" MajorTopicYN="N">Binding Sites</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004247" MajorTopicYN="N">DNA</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D018736" MajorTopicYN="N">DNA Adducts</DescriptorName><QualifierName UI="Q000032" MajorTopicYN="N">analysis</QualifierName><QualifierName UI="Q000096" MajorTopicYN="N">biosynthesis</QualifierName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D003848" MajorTopicYN="N">Deoxyguanine Nucleotides</DescriptorName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D004852" MajorTopicYN="N">Epoxy Compounds</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006207" MajorTopicYN="N">Half-Life</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D007553" MajorTopicYN="N">Isotope Labeling</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008297" MajorTopicYN="N">Male</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008958" MajorTopicYN="N">Models, Molecular</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D009153" MajorTopicYN="N">Mutagens</DescriptorName><QualifierName UI="Q000302" MajorTopicYN="N">isolation & purification</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D010761" MajorTopicYN="N">Phosphorus Radioisotopes</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010766" MajorTopicYN="N">Phosphorylation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011116" MajorTopicYN="N">Polynucleotide 5'-Hydroxyl-Kinase</DescriptorName><QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D012474" MajorTopicYN="N">Salmon</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>1996</Year><Month>6</Month><Day>1</Day></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>1996</Year><Month>6</Month><Day>1</Day><Hour>0</Hour><Minute>1</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>1996</Year><Month>6</Month><Day>1</Day><Hour>0</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">8681446</ArticleId><ArticleId IdType="doi">10.1093/carcin/17.6.1297</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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