Site-specific synthesis and reactivity of oligonucleotides containing stereochemically defined 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal.
Identifieur interne : 002299 ( PubMed/Checkpoint ); précédent : 002298; suivant : 002300Site-specific synthesis and reactivity of oligonucleotides containing stereochemically defined 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal.
Auteurs : Hao Wang [États-Unis] ; Ivan D. Kozekov ; Thomas M. Harris ; Carmelo J. RizzoSource :
- Journal of the American Chemical Society [ 0002-7863 ] ; 2003.
Descripteurs français
- KwdFr :
- ADN (), Adduits à l'ADN (), Adduits à l'ADN (synthèse chimique), Aldéhydes (), Dichroïsme circulaire, Désoxyguanosine (), Désoxyguanosine (analogues et dérivés), Oligonucléotides (), Oligonucléotides (synthèse chimique), Peroxydation lipidique, Résonance magnétique nucléaire biomoléculaire, Sites de fixation, Spécificité du substrat, Stéréoisomérie.
- MESH :
- analogues et dérivés : Désoxyguanosine.
- synthèse chimique : Adduits à l'ADN, Oligonucléotides.
- ADN, Adduits à l'ADN, Aldéhydes, Dichroïsme circulaire, Désoxyguanosine, Oligonucléotides, Peroxydation lipidique, Résonance magnétique nucléaire biomoléculaire, Sites de fixation, Spécificité du substrat, Stéréoisomérie.
English descriptors
- KwdEn :
- Aldehydes (chemistry), Binding Sites, Circular Dichroism, DNA (chemistry), DNA Adducts (chemical synthesis), DNA Adducts (chemistry), Deoxyguanosine (analogs & derivatives), Deoxyguanosine (chemistry), Lipid Peroxidation, Nuclear Magnetic Resonance, Biomolecular, Oligonucleotides (chemical synthesis), Oligonucleotides (chemistry), Stereoisomerism, Substrate Specificity.
- MESH :
- chemical , analogs & derivatives : Deoxyguanosine.
- chemical , chemical synthesis : DNA Adducts, Oligonucleotides.
- chemical , chemistry : Aldehydes, DNA, DNA Adducts, Deoxyguanosine, Oligonucleotides.
- Binding Sites, Circular Dichroism, Lipid Peroxidation, Nuclear Magnetic Resonance, Biomolecular, Stereoisomerism, Substrate Specificity.
Abstract
trans-4-Hydroxynonenal (HNE) is a major peroxidation product of omega-6 polyunsaturated fatty acids. The reaction of HNE with DNA gives four diastereomeric 1,N(2)-gamma-hydroxypropano adducts of deoxyguanosine; background levels of these adducts have been detected in animal tissue. Stereospecific syntheses of these four adducts at the nucleoside level have been accomplished. In addition, a versatile strategy for their site-specific incorporation into oligonucleotides has been developed. These adducts are destabilizing as measured by melting temperature when compared to an unadducted strand. The thermal destablization of the adducted 12-mers ranged from 5 to 16 degrees C and is dependent on the absolute stereochemistry of the adduct. The HNE adducts were also examined for their ability to form interstrand DNA-DNA cross-links when incorporated into a CpG sequence. We find that only one of the HNE stereoisomers formed interstrand DNA-DNA cross-links.
DOI: 10.1021/ja0288800
PubMed: 12733907
Affiliations:
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Kozekov</name></author><author><name sortKey="Harris, Thomas M" sort="Harris, Thomas M" uniqKey="Harris T" first="Thomas M" last="Harris">Thomas M. Harris</name></author><author><name sortKey="Rizzo, Carmelo J" sort="Rizzo, Carmelo J" uniqKey="Rizzo C" first="Carmelo J" last="Rizzo">Carmelo J. Rizzo</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2003">2003</date><idno type="RBID">pubmed:12733907</idno><idno type="pmid">12733907</idno><idno type="doi">10.1021/ja0288800</idno><idno type="wicri:Area/PubMed/Corpus">002454</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002454</idno><idno type="wicri:Area/PubMed/Curation">002454</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">002454</idno><idno type="wicri:Area/PubMed/Checkpoint">002299</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">002299</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Site-specific synthesis and reactivity of oligonucleotides containing stereochemically defined 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal.</title><author><name sortKey="Wang, Hao" sort="Wang, Hao" uniqKey="Wang H" first="Hao" last="Wang">Hao Wang</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry and Center in Molecular Toxicology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry and Center in Molecular Toxicology, Vanderbilt University, Nashville, Tennessee 37235-1822</wicri:regionArea><wicri:noRegion>Tennessee 37235-1822</wicri:noRegion></affiliation></author><author><name sortKey="Kozekov, Ivan D" sort="Kozekov, Ivan D" uniqKey="Kozekov I" first="Ivan D" last="Kozekov">Ivan D. Kozekov</name></author><author><name sortKey="Harris, Thomas M" sort="Harris, Thomas M" uniqKey="Harris T" first="Thomas M" last="Harris">Thomas M. Harris</name></author><author><name sortKey="Rizzo, Carmelo J" sort="Rizzo, Carmelo J" uniqKey="Rizzo C" first="Carmelo J" last="Rizzo">Carmelo J. Rizzo</name></author></analytic><series><title level="j">Journal of the American Chemical Society</title><idno type="ISSN">0002-7863</idno><imprint><date when="2003" type="published">2003</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aldehydes (chemistry)</term><term>Binding Sites</term><term>Circular Dichroism</term><term>DNA (chemistry)</term><term>DNA Adducts (chemical synthesis)</term><term>DNA Adducts (chemistry)</term><term>Deoxyguanosine (analogs & derivatives)</term><term>Deoxyguanosine (chemistry)</term><term>Lipid Peroxidation</term><term>Nuclear Magnetic Resonance, Biomolecular</term><term>Oligonucleotides (chemical synthesis)</term><term>Oligonucleotides (chemistry)</term><term>Stereoisomerism</term><term>Substrate Specificity</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>ADN ()</term><term>Adduits à l'ADN ()</term><term>Adduits à l'ADN (synthèse chimique)</term><term>Aldéhydes ()</term><term>Dichroïsme circulaire</term><term>Désoxyguanosine ()</term><term>Désoxyguanosine (analogues et dérivés)</term><term>Oligonucléotides ()</term><term>Oligonucléotides (synthèse chimique)</term><term>Peroxydation lipidique</term><term>Résonance magnétique nucléaire biomoléculaire</term><term>Sites de fixation</term><term>Spécificité du substrat</term><term>Stéréoisomérie</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Deoxyguanosine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>DNA Adducts</term><term>Oligonucleotides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Aldehydes</term><term>DNA</term><term>DNA Adducts</term><term>Deoxyguanosine</term><term>Oligonucleotides</term></keywords><keywords scheme="MESH" qualifier="analogues et dérivés" xml:lang="fr"><term>Désoxyguanosine</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Adduits à l'ADN</term><term>Oligonucléotides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Binding Sites</term><term>Circular Dichroism</term><term>Lipid Peroxidation</term><term>Nuclear Magnetic Resonance, Biomolecular</term><term>Stereoisomerism</term><term>Substrate Specificity</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>ADN</term><term>Adduits à l'ADN</term><term>Aldéhydes</term><term>Dichroïsme circulaire</term><term>Désoxyguanosine</term><term>Oligonucléotides</term><term>Peroxydation lipidique</term><term>Résonance magnétique nucléaire biomoléculaire</term><term>Sites de fixation</term><term>Spécificité du substrat</term><term>Stéréoisomérie</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">trans-4-Hydroxynonenal (HNE) is a major peroxidation product of omega-6 polyunsaturated fatty acids. The reaction of HNE with DNA gives four diastereomeric 1,N(2)-gamma-hydroxypropano adducts of deoxyguanosine; background levels of these adducts have been detected in animal tissue. Stereospecific syntheses of these four adducts at the nucleoside level have been accomplished. In addition, a versatile strategy for their site-specific incorporation into oligonucleotides has been developed. These adducts are destabilizing as measured by melting temperature when compared to an unadducted strand. The thermal destablization of the adducted 12-mers ranged from 5 to 16 degrees C and is dependent on the absolute stereochemistry of the adduct. The HNE adducts were also examined for their ability to form interstrand DNA-DNA cross-links when incorporated into a CpG sequence. We find that only one of the HNE stereoisomers formed interstrand DNA-DNA cross-links.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">12733907</PMID><DateCompleted><Year>2003</Year><Month>07</Month><Day>02</Day></DateCompleted><DateRevised><Year>2016</Year><Month>11</Month><Day>24</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0002-7863</ISSN><JournalIssue CitedMedium="Print"><Volume>125</Volume><Issue>19</Issue><PubDate><Year>2003</Year><Month>May</Month><Day>14</Day></PubDate></JournalIssue><Title>Journal of the American Chemical Society</Title><ISOAbbreviation>J. Am. Chem. Soc.</ISOAbbreviation></Journal><ArticleTitle>Site-specific synthesis and reactivity of oligonucleotides containing stereochemically defined 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal.</ArticleTitle><Pagination><MedlinePgn>5687-700</MedlinePgn></Pagination><Abstract><AbstractText>trans-4-Hydroxynonenal (HNE) is a major peroxidation product of omega-6 polyunsaturated fatty acids. The reaction of HNE with DNA gives four diastereomeric 1,N(2)-gamma-hydroxypropano adducts of deoxyguanosine; background levels of these adducts have been detected in animal tissue. Stereospecific syntheses of these four adducts at the nucleoside level have been accomplished. In addition, a versatile strategy for their site-specific incorporation into oligonucleotides has been developed. These adducts are destabilizing as measured by melting temperature when compared to an unadducted strand. The thermal destablization of the adducted 12-mers ranged from 5 to 16 degrees C and is dependent on the absolute stereochemistry of the adduct. The HNE adducts were also examined for their ability to form interstrand DNA-DNA cross-links when incorporated into a CpG sequence. We find that only one of the HNE stereoisomers formed interstrand DNA-DNA cross-links.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Wang</LastName><ForeName>Hao</ForeName><Initials>H</Initials><AffiliationInfo><Affiliation>Department of Chemistry and Center in Molecular Toxicology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kozekov</LastName><ForeName>Ivan D</ForeName><Initials>ID</Initials></Author><Author ValidYN="Y"><LastName>Harris</LastName><ForeName>Thomas M</ForeName><Initials>TM</Initials></Author><Author ValidYN="Y"><LastName>Rizzo</LastName><ForeName>Carmelo J</ForeName><Initials>CJ</Initials></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>ES00267</GrantID><Acronym>ES</Acronym><Agency>NIEHS NIH HHS</Agency><Country>United States</Country></Grant><Grant><GrantID>ES05355</GrantID><Acronym>ES</Acronym><Agency>NIEHS NIH HHS</Agency><Country>United States</Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType><PublicationType UI="D013487">Research Support, U.S. Gov't, P.H.S.</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Am Chem Soc</MedlineTA><NlmUniqueID>7503056</NlmUniqueID><ISSNLinking>0002-7863</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C117629">8-nitro-2'-deoxyguanosine</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000447">Aldehydes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D018736">DNA Adducts</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D009841">Oligonucleotides</NameOfSubstance></Chemical><Chemical><RegistryNumber>9007-49-2</RegistryNumber><NameOfSubstance UI="D004247">DNA</NameOfSubstance></Chemical><Chemical><RegistryNumber>G9481N71RO</RegistryNumber><NameOfSubstance UI="D003849">Deoxyguanosine</NameOfSubstance></Chemical><Chemical><RegistryNumber>K1CVM13F96</RegistryNumber><NameOfSubstance UI="C027576">4-hydroxy-2-nonenal</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000447" MajorTopicYN="N">Aldehydes</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D001665" MajorTopicYN="N">Binding Sites</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D002942" MajorTopicYN="N">Circular Dichroism</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D004247" MajorTopicYN="N">DNA</DescriptorName><QualifierName UI="Q000737" 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MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D013379" MajorTopicYN="N">Substrate Specificity</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2003</Year><Month>5</Month><Day>8</Day><Hour>5</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2003</Year><Month>7</Month><Day>3</Day><Hour>5</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2003</Year><Month>5</Month><Day>8</Day><Hour>5</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">12733907</ArticleId><ArticleId IdType="doi">10.1021/ja0288800</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>États-Unis</li></country></list><tree><noCountry><name sortKey="Harris, Thomas M" sort="Harris, Thomas M" uniqKey="Harris T" first="Thomas M" last="Harris">Thomas M. Harris</name><name sortKey="Kozekov, Ivan D" sort="Kozekov, Ivan D" uniqKey="Kozekov I" first="Ivan D" last="Kozekov">Ivan D. Kozekov</name><name sortKey="Rizzo, Carmelo J" sort="Rizzo, Carmelo J" uniqKey="Rizzo C" first="Carmelo J" last="Rizzo">Carmelo J. Rizzo</name></noCountry><country name="États-Unis"><noRegion><name sortKey="Wang, Hao" sort="Wang, Hao" uniqKey="Wang H" first="Hao" last="Wang">Hao Wang</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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