Synthesis, thermal stability and reactivity towards 9-aminoellipticine of double-stranded oligonucleotides containing a true abasic site.
Identifieur interne : 000395 ( France/Analysis ); précédent : 000394; suivant : 000396Synthesis, thermal stability and reactivity towards 9-aminoellipticine of double-stranded oligonucleotides containing a true abasic site.
Auteurs : J R Bertrand [France] ; J J Vasseur ; B. Rayner ; J L Imbach ; J. Paoletti ; C. Paoletti ; C. MalvySource :
- Nucleic acids research [ 0305-1048 ] ; 1989.
Descripteurs français
- KwdFr :
- Acide apurinique, Alcaloïdes, Bases de Schiff, Chimie, Cinétique, Données de séquences moléculaires, Ellipticines, Intercalants, Phénomènes chimiques, Polydésoxyribonucléotides (synthèse chimique), Polynucléotides, Relation structure-activité, Spectrométrie de fluorescence, Stabilité de médicament, Structure moléculaire, Séquence nucléotidique, Température élevée, Électrophorèse sur gel de polyacrylamide.
- MESH :
- synthèse chimique : Polydésoxyribonucléotides.
- Acide apurinique, Alcaloïdes, Bases de Schiff, Chimie, Cinétique, Données de séquences moléculaires, Ellipticines, Intercalants, Phénomènes chimiques, Polynucléotides, Relation structure-activité, Spectrométrie de fluorescence, Stabilité de médicament, Structure moléculaire, Séquence nucléotidique, Température élevée, Électrophorèse sur gel de polyacrylamide.
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
Affiliations:
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pubmed:2602153Le document en format XML
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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="KwdFr" xml:lang="fr"><term>Acide apurinique</term><term>Alcaloïdes</term><term>Bases de Schiff</term><term>Chimie</term><term>Cinétique</term><term>Données de séquences moléculaires</term><term>Ellipticines</term><term>Intercalants</term><term>Phénomènes chimiques</term><term>Polydésoxyribonucléotides (synthèse chimique)</term><term>Polynucléotides</term><term>Relation structure-activité</term><term>Spectrométrie de fluorescence</term><term>Stabilité de médicament</term><term>Structure moléculaire</term><term>Séquence nucléotidique</term><term>Température élevée</term><term>Électrophorèse sur gel de polyacrylamide</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" qualifier="synthèse chimique" xml:lang="fr"><term>Polydésoxyribonucléotides</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><keywords scheme="MESH" xml:lang="fr"><term>Acide apurinique</term><term>Alcaloïdes</term><term>Bases de Schiff</term><term>Chimie</term><term>Cinétique</term><term>Données de séquences moléculaires</term><term>Ellipticines</term><term>Intercalants</term><term>Phénomènes chimiques</term><term>Polynucléotides</term><term>Relation structure-activité</term><term>Spectrométrie de fluorescence</term><term>Stabilité de médicament</term><term>Structure moléculaire</term><term>Séquence nucléotidique</term><term>Température élevée</term><term>Électrophorèse sur gel de polyacrylamide</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><affiliations><list><country><li>France</li></country></list><tree><noCountry><name sortKey="Imbach, J L" sort="Imbach, J L" uniqKey="Imbach J" first="J L" last="Imbach">J L Imbach</name><name sortKey="Malvy, C" sort="Malvy, C" uniqKey="Malvy C" first="C" last="Malvy">C. Malvy</name><name sortKey="Paoletti, C" sort="Paoletti, C" uniqKey="Paoletti C" first="C" last="Paoletti">C. Paoletti</name><name sortKey="Paoletti, J" sort="Paoletti, J" uniqKey="Paoletti J" first="J" last="Paoletti">J. Paoletti</name><name sortKey="Rayner, B" sort="Rayner, B" uniqKey="Rayner B" first="B" last="Rayner">B. Rayner</name><name sortKey="Vasseur, J J" sort="Vasseur, J J" uniqKey="Vasseur J" first="J J" last="Vasseur">J J Vasseur</name></noCountry><country name="France"><noRegion><name sortKey="Bertrand, J R" sort="Bertrand, J R" uniqKey="Bertrand J" first="J R" last="Bertrand">J R Bertrand</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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