Terminally modified, short phosphorothioate oligonucleotides as inhibitors of gene expression in cells.
Identifieur interne : 001860 ( PubMed/Curation ); précédent : 001859; suivant : 001861Terminally modified, short phosphorothioate oligonucleotides as inhibitors of gene expression in cells.
Auteurs : Paul Marzenell [Allemagne] ; Helen Hagen [Allemagne] ; Jenny Blechinger [Allemagne] ; Holger Erfle [Allemagne] ; Andriy Mokhir [Allemagne]Source :
- Bioorganic & medicinal chemistry letters [ 1464-3405 ] ; 2014.
Descripteurs français
- KwdFr :
- ARN messager (antagonistes et inhibiteurs), ARN messager (génétique), Cellules HeLa, Expression des gènes (), Expression des gènes (génétique), Humains, Oligonucléotides phosphorothioates (), Oligonucléotides phosphorothioates (pharmacologie), Oligonucléotides phosphorothioates (synthèse chimique), Protéines luminescentes (antagonistes et inhibiteurs), Protéines luminescentes (génétique), Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire.
- MESH :
- antagonistes et inhibiteurs : ARN messager, Protéines luminescentes.
- génétique : ARN messager, Expression des gènes, Protéines luminescentes.
- pharmacologie : Oligonucléotides phosphorothioates.
- synthèse chimique : Oligonucléotides phosphorothioates.
- Cellules HeLa, Expression des gènes, Humains, Oligonucléotides phosphorothioates, Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire.
English descriptors
- KwdEn :
- Dose-Response Relationship, Drug, Gene Expression (drug effects), Gene Expression (genetics), HeLa Cells, Humans, Luminescent Proteins (antagonists & inhibitors), Luminescent Proteins (genetics), Molecular Structure, Phosphorothioate Oligonucleotides (chemical synthesis), Phosphorothioate Oligonucleotides (chemistry), Phosphorothioate Oligonucleotides (pharmacology), RNA, Messenger (antagonists & inhibitors), RNA, Messenger (genetics), Structure-Activity Relationship.
- MESH :
- chemical , antagonists & inhibitors : Luminescent Proteins, RNA, Messenger.
- chemical , chemical synthesis : Phosphorothioate Oligonucleotides.
- chemical , chemistry : Phosphorothioate Oligonucleotides.
- drug effects : Gene Expression.
- genetics : Gene Expression, Luminescent Proteins, RNA, Messenger.
- chemical , pharmacology : Phosphorothioate Oligonucleotides.
- Dose-Response Relationship, Drug, HeLa Cells, Humans, Molecular Structure, Structure-Activity Relationship.
Abstract
Phosphorothioates are excellent antisense inhibitors, which are active both in cells and in vivo. Since their affinity to complementary ribonucleic acids is rather low, long strands (⩾20-mers) are typically required to achieve the desired biological activity. However, mismatch discrimination of long inhibitors is reduced. In contrast, shorter phosphorothioates exhibit better sequence specificity, but have in most cases too low affinity for practical applications in cells. We screened a range of terminal modifiers of a 14-mer phosphorothioate sequence, which is complementary to mRNA of a representative gene, whose protein product is fluorescent (DsRed2) and easy to monitor in cells. We found that optimal combinations of 5'- and 3'-modifications include 5'-trimethoxystilbene with 3'-uracil(anthraquinone)-cap, 5'-chloic acid derivative with 3'-uracyl(anthraquinone)-cap and 5'-cholic acid derivative with three 3'-LNA moieties. In contrast to the LNA, stabilizing and activity-enhancing effects of other mentioned modifiers for PTO/RNA duplexes have not been previously reported. We observed that the 14-mer inhibitor carrying 5'-cholic acid derivative with three 3'-LNA moieties inhibits expression of DsRed2 in cells stronger than the unmodified 21-mer. Mismatch discrimination of this inhibitor was found to be comparable to that of the unmodified 14-mer.
DOI: 10.1016/j.bmcl.2014.08.027
PubMed: 25176331
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<term>Humans</term>
<term>Luminescent Proteins (antagonists & inhibitors)</term>
<term>Luminescent Proteins (genetics)</term>
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<term>Expression des gènes (génétique)</term>
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<term>Oligonucléotides phosphorothioates ()</term>
<term>Oligonucléotides phosphorothioates (pharmacologie)</term>
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<front><div type="abstract" xml:lang="en">Phosphorothioates are excellent antisense inhibitors, which are active both in cells and in vivo. Since their affinity to complementary ribonucleic acids is rather low, long strands (⩾20-mers) are typically required to achieve the desired biological activity. However, mismatch discrimination of long inhibitors is reduced. In contrast, shorter phosphorothioates exhibit better sequence specificity, but have in most cases too low affinity for practical applications in cells. We screened a range of terminal modifiers of a 14-mer phosphorothioate sequence, which is complementary to mRNA of a representative gene, whose protein product is fluorescent (DsRed2) and easy to monitor in cells. We found that optimal combinations of 5'- and 3'-modifications include 5'-trimethoxystilbene with 3'-uracil(anthraquinone)-cap, 5'-chloic acid derivative with 3'-uracyl(anthraquinone)-cap and 5'-cholic acid derivative with three 3'-LNA moieties. In contrast to the LNA, stabilizing and activity-enhancing effects of other mentioned modifiers for PTO/RNA duplexes have not been previously reported. We observed that the 14-mer inhibitor carrying 5'-cholic acid derivative with three 3'-LNA moieties inhibits expression of DsRed2 in cells stronger than the unmodified 21-mer. Mismatch discrimination of this inhibitor was found to be comparable to that of the unmodified 14-mer. </div>
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<Abstract><AbstractText>Phosphorothioates are excellent antisense inhibitors, which are active both in cells and in vivo. Since their affinity to complementary ribonucleic acids is rather low, long strands (⩾20-mers) are typically required to achieve the desired biological activity. However, mismatch discrimination of long inhibitors is reduced. In contrast, shorter phosphorothioates exhibit better sequence specificity, but have in most cases too low affinity for practical applications in cells. We screened a range of terminal modifiers of a 14-mer phosphorothioate sequence, which is complementary to mRNA of a representative gene, whose protein product is fluorescent (DsRed2) and easy to monitor in cells. We found that optimal combinations of 5'- and 3'-modifications include 5'-trimethoxystilbene with 3'-uracil(anthraquinone)-cap, 5'-chloic acid derivative with 3'-uracyl(anthraquinone)-cap and 5'-cholic acid derivative with three 3'-LNA moieties. In contrast to the LNA, stabilizing and activity-enhancing effects of other mentioned modifiers for PTO/RNA duplexes have not been previously reported. We observed that the 14-mer inhibitor carrying 5'-cholic acid derivative with three 3'-LNA moieties inhibits expression of DsRed2 in cells stronger than the unmodified 21-mer. Mismatch discrimination of this inhibitor was found to be comparable to that of the unmodified 14-mer. </AbstractText>
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