trans-(NH3)(2)Pt(II)-modified deoxyoligonucleotides as potential antisense agents: cross-linking reactions between two 12-mers.
Identifieur interne : 000034 ( Ncbi/Merge ); précédent : 000033; suivant : 000035trans-(NH3)(2)Pt(II)-modified deoxyoligonucleotides as potential antisense agents: cross-linking reactions between two 12-mers.
Auteurs : M B Janik [Allemagne] ; B. LippertSource :
- Journal of biological inorganic chemistry : JBIC : a publication of the Society of Biological Inorganic Chemistry [ 0949-8257 ] ; 1999.
Descripteurs français
- KwdFr :
- ARN messager (), Cisplatine (), Cisplatine (pharmacologie), Conformation d'acide nucléique, Hybridation d'acides nucléiques, Hydrolyse, Oligodésoxyribonucléotides antisens (), Oligodésoxyribonucléotides antisens (pharmacologie), Purines (métabolisme), Réactifs réticulants (), Réactifs réticulants (pharmacologie), Réplication de l'ADN (), Spectrométrie de masse, Spectroscopie par résonance magnétique, Stéréoisomérie, Transcription génétique ().
- MESH :
- métabolisme : Purines.
- pharmacologie : Cisplatine, Oligodésoxyribonucléotides antisens, Réactifs réticulants.
- ARN messager, Cisplatine, Conformation d'acide nucléique, Hybridation d'acides nucléiques, Hydrolyse, Oligodésoxyribonucléotides antisens, Réactifs réticulants, Réplication de l'ADN, Spectrométrie de masse, Spectroscopie par résonance magnétique, Stéréoisomérie, Transcription génétique.
English descriptors
- KwdEn :
- Cisplatin (chemistry), Cisplatin (pharmacology), Cross-Linking Reagents (chemistry), Cross-Linking Reagents (pharmacology), DNA Replication (drug effects), Hydrolysis, Magnetic Resonance Spectroscopy, Mass Spectrometry, Nucleic Acid Conformation, Nucleic Acid Hybridization, Oligodeoxyribonucleotides, Antisense (chemistry), Oligodeoxyribonucleotides, Antisense (pharmacology), Purines (metabolism), RNA, Messenger (drug effects), Stereoisomerism, Transcription, Genetic (drug effects).
- MESH :
- chemical , chemistry : Cisplatin, Cross-Linking Reagents, Oligodeoxyribonucleotides, Antisense.
- chemical , drug effects : RNA, Messenger.
- chemical , metabolism : Purines.
- chemical , pharmacology : Cisplatin, Cross-Linking Reagents, Oligodeoxyribonucleotides, Antisense.
- drug effects : DNA Replication, Transcription, Genetic.
- Hydrolysis, Magnetic Resonance Spectroscopy, Mass Spectrometry, Nucleic Acid Conformation, Nucleic Acid Hybridization, Stereoisomerism.
Abstract
An approach is presented which probes the possible use of trans-[(NH3)(2)PtCl](+)-modified deoxyoligonucleotides in the antisense strategy. It consists of (1) the selective platination of an oligonucleotide containing 11 pyrimidine (T, C) bases as well as a single guanine (G) as a Pt-anchoring group at the 5'-end to give trans-[(NH3)(2)Pt¿5'-d(G(N7)T(2)C(2)T(2)C(2)T(2)C¿Cl](10-) 1 ("antisense strand") and (2) subsequent hybridization with the purine 12-mer 5'-d(GA(2)G(2)A(2)G(2)A(2)G)(11-) ("sense strand"). According to HPLC, three major species 2-4 are formed during reaction (2), all of which are cross-linking adducts between 1 and the sense strand, as confirmed by ESI MS and melting temperature measurements. Only for the major product 3 can a structure be proposed on the basis of 1D and 2D NMR spectra. According to these, G(1) of the antisense strand is cross-linked with G(20) via trans-(NH3)(2)Pt(II). The complementary overhangs of the duplex represent "sticky ends" and are, in principle, capable of associating into multimers of the duplex.
DOI: 10.1007/s007750050388
PubMed: 10550694
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pubmed:10550694Le document en format XML
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<affiliation wicri:level="3"><nlm:affiliation>Fachbereich Chemie, Universität Dortmund Otto-Hahn-Strasse 6, D-44221 Dortmund, Germany.</nlm:affiliation>
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<term>Cross-Linking Reagents (chemistry)</term>
<term>Cross-Linking Reagents (pharmacology)</term>
<term>DNA Replication (drug effects)</term>
<term>Hydrolysis</term>
<term>Magnetic Resonance Spectroscopy</term>
<term>Mass Spectrometry</term>
<term>Nucleic Acid Conformation</term>
<term>Nucleic Acid Hybridization</term>
<term>Oligodeoxyribonucleotides, Antisense (chemistry)</term>
<term>Oligodeoxyribonucleotides, Antisense (pharmacology)</term>
<term>Purines (metabolism)</term>
<term>RNA, Messenger (drug effects)</term>
<term>Stereoisomerism</term>
<term>Transcription, Genetic (drug effects)</term>
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<keywords scheme="KwdFr" xml:lang="fr"><term>ARN messager ()</term>
<term>Cisplatine ()</term>
<term>Cisplatine (pharmacologie)</term>
<term>Conformation d'acide nucléique</term>
<term>Hybridation d'acides nucléiques</term>
<term>Hydrolyse</term>
<term>Oligodésoxyribonucléotides antisens ()</term>
<term>Oligodésoxyribonucléotides antisens (pharmacologie)</term>
<term>Purines (métabolisme)</term>
<term>Réactifs réticulants ()</term>
<term>Réactifs réticulants (pharmacologie)</term>
<term>Réplication de l'ADN ()</term>
<term>Spectrométrie de masse</term>
<term>Spectroscopie par résonance magnétique</term>
<term>Stéréoisomérie</term>
<term>Transcription génétique ()</term>
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<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Cisplatin</term>
<term>Cross-Linking Reagents</term>
<term>Oligodeoxyribonucleotides, Antisense</term>
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<term>Oligodeoxyribonucleotides, Antisense</term>
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<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>DNA Replication</term>
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<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Cisplatine</term>
<term>Oligodésoxyribonucléotides antisens</term>
<term>Réactifs réticulants</term>
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<term>Magnetic Resonance Spectroscopy</term>
<term>Mass Spectrometry</term>
<term>Nucleic Acid Conformation</term>
<term>Nucleic Acid Hybridization</term>
<term>Stereoisomerism</term>
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<keywords scheme="MESH" xml:lang="fr"><term>ARN messager</term>
<term>Cisplatine</term>
<term>Conformation d'acide nucléique</term>
<term>Hybridation d'acides nucléiques</term>
<term>Hydrolyse</term>
<term>Oligodésoxyribonucléotides antisens</term>
<term>Réactifs réticulants</term>
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<term>Spectrométrie de masse</term>
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<front><div type="abstract" xml:lang="en">An approach is presented which probes the possible use of trans-[(NH3)(2)PtCl](+)-modified deoxyoligonucleotides in the antisense strategy. It consists of (1) the selective platination of an oligonucleotide containing 11 pyrimidine (T, C) bases as well as a single guanine (G) as a Pt-anchoring group at the 5'-end to give trans-[(NH3)(2)Pt¿5'-d(G(N7)T(2)C(2)T(2)C(2)T(2)C¿Cl](10-) 1 ("antisense strand") and (2) subsequent hybridization with the purine 12-mer 5'-d(GA(2)G(2)A(2)G(2)A(2)G)(11-) ("sense strand"). According to HPLC, three major species 2-4 are formed during reaction (2), all of which are cross-linking adducts between 1 and the sense strand, as confirmed by ESI MS and melting temperature measurements. Only for the major product 3 can a structure be proposed on the basis of 1D and 2D NMR spectra. According to these, G(1) of the antisense strand is cross-linked with G(20) via trans-(NH3)(2)Pt(II). The complementary overhangs of the duplex represent "sticky ends" and are, in principle, capable of associating into multimers of the duplex.</div>
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<Abstract><AbstractText>An approach is presented which probes the possible use of trans-[(NH3)(2)PtCl](+)-modified deoxyoligonucleotides in the antisense strategy. It consists of (1) the selective platination of an oligonucleotide containing 11 pyrimidine (T, C) bases as well as a single guanine (G) as a Pt-anchoring group at the 5'-end to give trans-[(NH3)(2)Pt¿5'-d(G(N7)T(2)C(2)T(2)C(2)T(2)C¿Cl](10-) 1 ("antisense strand") and (2) subsequent hybridization with the purine 12-mer 5'-d(GA(2)G(2)A(2)G(2)A(2)G)(11-) ("sense strand"). According to HPLC, three major species 2-4 are formed during reaction (2), all of which are cross-linking adducts between 1 and the sense strand, as confirmed by ESI MS and melting temperature measurements. Only for the major product 3 can a structure be proposed on the basis of 1D and 2D NMR spectra. According to these, G(1) of the antisense strand is cross-linked with G(20) via trans-(NH3)(2)Pt(II). The complementary overhangs of the duplex represent "sticky ends" and are, in principle, capable of associating into multimers of the duplex.</AbstractText>
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