Synthesis, thermal stability and reactivity towards 9-aminoellipticine of double-stranded oligonucleotides containing a true abasic site.
Identifieur interne : 002A32 ( PubMed/Corpus ); précédent : 002A31; suivant : 002A33Synthesis, thermal stability and reactivity towards 9-aminoellipticine of double-stranded oligonucleotides containing a true abasic site.
Auteurs : J R Bertrand ; J J Vasseur ; B. Rayner ; J L Imbach ; J. Paoletti ; C. Paoletti ; C. MalvySource :
- Nucleic acids research [ 0305-1048 ] ; 1989.
English descriptors
- KwdEn :
- Alkaloids, Apurinic Acid, Base Sequence, Chemical Phenomena, Chemistry, Drug Stability, Electrophoresis, Polyacrylamide Gel, Ellipticines, Hot Temperature, Intercalating Agents, Kinetics, Molecular Sequence Data, Molecular Structure, Polydeoxyribonucleotides (chemical synthesis), Polynucleotides, Schiff Bases, Spectrometry, Fluorescence, Structure-Activity Relationship.
- MESH :
- chemical , chemical synthesis : Polydeoxyribonucleotides.
- chemical : Alkaloids, Apurinic Acid, Ellipticines, Intercalating Agents, Polynucleotides, Schiff Bases.
- Base Sequence, Chemical Phenomena, Chemistry, Drug Stability, Electrophoresis, Polyacrylamide Gel, Hot Temperature, Kinetics, Molecular Sequence Data, Molecular Structure, Spectrometry, Fluorescence, Structure-Activity Relationship.
Abstract
A 13 mers abasic oligonucleotide was synthetized. It was therefore possible to compare thermal stability and reactivity of duplex oligonucleotides either with an apurinic/apyrimidinic site or without any lesion. An important decrease in the melting temperature appeared for duplexes with an abasic site. The chemical reaction of these modified oligonucleotides with the intercalating agent 9-aminoellipticine was studied by gel electrophoresis and by fluorescence. The formation of a Schiff base between 9-aminoellipticine and abasic sites was rapid and complete with duplexes at 11 degrees C. Schiff base related fluorescence and beta-elimination cleavage were more important with the apyrimidinic sites than with the apurinic ones. When compared to previous results obtained with the model d(TprpT) some unexpected behaviours appeared with longer and duplex oligonucleotides. For instance only partial beta-elimination cleavage was observed. It is likely that stacking parameters in the double helix play a great role in the studied reaction.
DOI: 10.1093/nar/17.24.10307
PubMed: 2602153
Links to Exploration step
pubmed:2602153Le document en format XML
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Paoletti</name></author><author><name sortKey="Paoletti, C" sort="Paoletti, C" uniqKey="Paoletti C" first="C" last="Paoletti">C. Paoletti</name></author><author><name sortKey="Malvy, C" sort="Malvy, C" uniqKey="Malvy C" first="C" last="Malvy">C. Malvy</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="1989">1989</date><idno type="RBID">pubmed:2602153</idno><idno type="pmid">2602153</idno><idno type="doi">10.1093/nar/17.24.10307</idno><idno type="wicri:Area/PubMed/Corpus">002A32</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002A32</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Synthesis, thermal stability and reactivity towards 9-aminoellipticine of double-stranded oligonucleotides containing a true abasic site.</title><author><name sortKey="Bertrand, J R" sort="Bertrand, J R" uniqKey="Bertrand J" first="J R" last="Bertrand">J R Bertrand</name><affiliation><nlm:affiliation>Laboratoire de Biochimie-Enzymologie, UA 147 CNRS, UA 140 INSERM, Institut Gustave-Roussy, Villejuif, France.</nlm:affiliation></affiliation></author><author><name sortKey="Vasseur, J J" sort="Vasseur, J J" uniqKey="Vasseur J" first="J J" last="Vasseur">J J Vasseur</name></author><author><name sortKey="Rayner, B" sort="Rayner, B" uniqKey="Rayner B" first="B" last="Rayner">B. Rayner</name></author><author><name sortKey="Imbach, J L" sort="Imbach, J L" uniqKey="Imbach J" first="J L" last="Imbach">J L Imbach</name></author><author><name sortKey="Paoletti, J" sort="Paoletti, J" uniqKey="Paoletti J" first="J" last="Paoletti">J. Paoletti</name></author><author><name sortKey="Paoletti, C" sort="Paoletti, C" uniqKey="Paoletti C" first="C" last="Paoletti">C. Paoletti</name></author><author><name sortKey="Malvy, C" sort="Malvy, C" uniqKey="Malvy C" first="C" last="Malvy">C. Malvy</name></author></analytic><series><title level="j">Nucleic acids research</title><idno type="ISSN">0305-1048</idno><imprint><date when="1989" type="published">1989</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Alkaloids</term><term>Apurinic Acid</term><term>Base Sequence</term><term>Chemical Phenomena</term><term>Chemistry</term><term>Drug Stability</term><term>Electrophoresis, Polyacrylamide Gel</term><term>Ellipticines</term><term>Hot Temperature</term><term>Intercalating Agents</term><term>Kinetics</term><term>Molecular Sequence Data</term><term>Molecular Structure</term><term>Polydeoxyribonucleotides (chemical synthesis)</term><term>Polynucleotides</term><term>Schiff Bases</term><term>Spectrometry, Fluorescence</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Polydeoxyribonucleotides</term></keywords><keywords scheme="MESH" type="chemical" xml:lang="en"><term>Alkaloids</term><term>Apurinic Acid</term><term>Ellipticines</term><term>Intercalating Agents</term><term>Polynucleotides</term><term>Schiff Bases</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Base Sequence</term><term>Chemical Phenomena</term><term>Chemistry</term><term>Drug Stability</term><term>Electrophoresis, Polyacrylamide Gel</term><term>Hot Temperature</term><term>Kinetics</term><term>Molecular Sequence Data</term><term>Molecular Structure</term><term>Spectrometry, Fluorescence</term><term>Structure-Activity Relationship</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A 13 mers abasic oligonucleotide was synthetized. It was therefore possible to compare thermal stability and reactivity of duplex oligonucleotides either with an apurinic/apyrimidinic site or without any lesion. An important decrease in the melting temperature appeared for duplexes with an abasic site. The chemical reaction of these modified oligonucleotides with the intercalating agent 9-aminoellipticine was studied by gel electrophoresis and by fluorescence. The formation of a Schiff base between 9-aminoellipticine and abasic sites was rapid and complete with duplexes at 11 degrees C. Schiff base related fluorescence and beta-elimination cleavage were more important with the apyrimidinic sites than with the apurinic ones. When compared to previous results obtained with the model d(TprpT) some unexpected behaviours appeared with longer and duplex oligonucleotides. For instance only partial beta-elimination cleavage was observed. It is likely that stacking parameters in the double helix play a great role in the studied reaction.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">2602153</PMID><DateCompleted><Year>1990</Year><Month>02</Month><Day>08</Day></DateCompleted><DateRevised><Year>2019</Year><Month>05</Month><Day>01</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0305-1048</ISSN><JournalIssue CitedMedium="Print"><Volume>17</Volume><Issue>24</Issue><PubDate><Year>1989</Year><Month>Dec</Month><Day>25</Day></PubDate></JournalIssue><Title>Nucleic acids research</Title><ISOAbbreviation>Nucleic Acids Res.</ISOAbbreviation></Journal><ArticleTitle>Synthesis, thermal stability and reactivity towards 9-aminoellipticine of double-stranded oligonucleotides containing a true abasic site.</ArticleTitle><Pagination><MedlinePgn>10307-19</MedlinePgn></Pagination><Abstract><AbstractText>A 13 mers abasic oligonucleotide was synthetized. It was therefore possible to compare thermal stability and reactivity of duplex oligonucleotides either with an apurinic/apyrimidinic site or without any lesion. An important decrease in the melting temperature appeared for duplexes with an abasic site. The chemical reaction of these modified oligonucleotides with the intercalating agent 9-aminoellipticine was studied by gel electrophoresis and by fluorescence. The formation of a Schiff base between 9-aminoellipticine and abasic sites was rapid and complete with duplexes at 11 degrees C. Schiff base related fluorescence and beta-elimination cleavage were more important with the apyrimidinic sites than with the apurinic ones. When compared to previous results obtained with the model d(TprpT) some unexpected behaviours appeared with longer and duplex oligonucleotides. For instance only partial beta-elimination cleavage was observed. It is likely that stacking parameters in the double helix play a great role in the studied reaction.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Bertrand</LastName><ForeName>J R</ForeName><Initials>JR</Initials><AffiliationInfo><Affiliation>Laboratoire de Biochimie-Enzymologie, UA 147 CNRS, UA 140 INSERM, Institut Gustave-Roussy, Villejuif, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Vasseur</LastName><ForeName>J J</ForeName><Initials>JJ</Initials></Author><Author ValidYN="Y"><LastName>Rayner</LastName><ForeName>B</ForeName><Initials>B</Initials></Author><Author ValidYN="Y"><LastName>Imbach</LastName><ForeName>J L</ForeName><Initials>JL</Initials></Author><Author ValidYN="Y"><LastName>Paoletti</LastName><ForeName>J</ForeName><Initials>J</Initials></Author><Author ValidYN="Y"><LastName>Paoletti</LastName><ForeName>C</ForeName><Initials>C</Initials></Author><Author ValidYN="Y"><LastName>Malvy</LastName><ForeName>C</ForeName><Initials>C</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D003160">Comparative Study</PublicationType><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Nucleic Acids Res</MedlineTA><NlmUniqueID>0411011</NlmUniqueID><ISSNLinking>0305-1048</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000470">Alkaloids</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D004611">Ellipticines</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D007364">Intercalating Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011089">Polydeoxyribonucleotides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011119">Polynucleotides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D012545">Schiff Bases</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C001790">apyrimidinic acid</NameOfSubstance></Chemical><Chemical><RegistryNumber>11002-22-5</RegistryNumber><NameOfSubstance UI="D001080">Apurinic Acid</NameOfSubstance></Chemical><Chemical><RegistryNumber>54779-53-2</RegistryNumber><NameOfSubstance UI="C038373">9-aminoellipticine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000470" MajorTopicYN="Y">Alkaloids</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D001080" MajorTopicYN="Y">Apurinic Acid</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D001483" 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