Highly Stable DNA Triplexes Formed with Cationic Phosphoramidate Pyrimidine α‐Oligonucleotides
Identifieur interne : 000209 ( France/Analysis ); précédent : 000208; suivant : 000210Highly Stable DNA Triplexes Formed with Cationic Phosphoramidate Pyrimidine α‐Oligonucleotides
Auteurs : Thibaut Michel [France] ; Françoise Debart [France] ; Frédéric Heitz [France] ; Jean-Jacques Vasseur [France]Source :
- ChemBioChem [ 1439-4227 ] ; 2005-07-04.
English descriptors
- Teeft :
- Absorbance, Cacodylate, Cationic, Cationic internucleotide linkages, Cationic linkages, Cationic phosphoramidate, Centred, Chem, Chembiochem, Cytosine protonation, Debart, Duplex, Duplex target, Electrostatic repulsion, Form triplexes, Gmbh, Hairpin, Hoogsteen, Kgaa, Linkage, Mismatch, Mole fraction, Nacl, Negative band, Negative bands, Nucleic, Nucleic acids, Nucleosides nucleotides, Oligonucleotides, Phosphodiester, Phosphoramidate, Pnhdmap, Pnhdmap linkages, Positive band, Positive band centred, Purine, Purine strand, Pyrimidine, Single strands, Sodium cacodylate, Stable triplexes, Target duplex, Tetrahedron lett, Tfos, Third strand, Triplex, Triplex formation, Triplex stability, Triplexes, Unmodified, Vasseur, Verlag, Verlag gmbh, Weinheim, Weinheim chembiochem.
Abstract
The ability of cationic phosphoramidate pyrimidine α‐oligonucleotides (ONs) to form triplexes with DNA duplexes was investigated by UV melting experiments, circular dichroism spectroscopy and gel mobility shift experiments. Replacement of the phosphodiester linkages in α‐ONs with positively charged phosphoramidate linkages results in more efficient triplex formation, the triplex stability increasing with the number of positive charges. At a neutral pH and in the absence of magnesium ions, it was found that a fully cationic phosphoramidate α‐TFO (triplex‐forming oligonucleotide) forms a highly stable triplex that melts at a higher temperature than the duplex target. No hysteresis between the annealing and melting curves was noticed; this indicates fast association. Moreover, the recognition of a DNA duplex with a cationic α‐TFO through Hoogsteen base pairing is highly sequence‐specific. To the best of our knowledge, this is the first report of stable triplexes in the pyrimidine motif formed by cationic α‐oligonucleotides and duplex targets.
At physiological pH and in the absence of magnesium ions, cationic phosphoramidate α‐oligonucleotides in the pyrimidine motif (see scheme) form highly stable and sequence‐specific triplexes with DNA duplexes.
Url:
DOI: 10.1002/cbic.200400436
Affiliations:
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linkages</term><term>Cationic linkages</term><term>Cationic phosphoramidate</term><term>Centred</term><term>Chem</term><term>Chembiochem</term><term>Cytosine protonation</term><term>Debart</term><term>Duplex</term><term>Duplex target</term><term>Electrostatic repulsion</term><term>Form triplexes</term><term>Gmbh</term><term>Hairpin</term><term>Hoogsteen</term><term>Kgaa</term><term>Linkage</term><term>Mismatch</term><term>Mole fraction</term><term>Nacl</term><term>Negative band</term><term>Negative bands</term><term>Nucleic</term><term>Nucleic acids</term><term>Nucleosides nucleotides</term><term>Oligonucleotides</term><term>Phosphodiester</term><term>Phosphoramidate</term><term>Pnhdmap</term><term>Pnhdmap linkages</term><term>Positive band</term><term>Positive band centred</term><term>Purine</term><term>Purine strand</term><term>Pyrimidine</term><term>Single strands</term><term>Sodium cacodylate</term><term>Stable triplexes</term><term>Target duplex</term><term>Tetrahedron lett</term><term>Tfos</term><term>Third strand</term><term>Triplex</term><term>Triplex formation</term><term>Triplex stability</term><term>Triplexes</term><term>Unmodified</term><term>Vasseur</term><term>Verlag</term><term>Verlag gmbh</term><term>Weinheim</term><term>Weinheim chembiochem</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The ability of cationic phosphoramidate pyrimidine α‐oligonucleotides (ONs) to form triplexes with DNA duplexes was investigated by UV melting experiments, circular dichroism spectroscopy and gel mobility shift experiments. Replacement of the phosphodiester linkages in α‐ONs with positively charged phosphoramidate linkages results in more efficient triplex formation, the triplex stability increasing with the number of positive charges. At a neutral pH and in the absence of magnesium ions, it was found that a fully cationic phosphoramidate α‐TFO (triplex‐forming oligonucleotide) forms a highly stable triplex that melts at a higher temperature than the duplex target. No hysteresis between the annealing and melting curves was noticed; this indicates fast association. Moreover, the recognition of a DNA duplex with a cationic α‐TFO through Hoogsteen base pairing is highly sequence‐specific. To the best of our knowledge, this is the first report of stable triplexes in the pyrimidine motif formed by cationic α‐oligonucleotides and duplex targets.</div><div type="abstract" xml:lang="en">At physiological pH and in the absence of magnesium ions, cationic phosphoramidate α‐oligonucleotides in the pyrimidine motif (see scheme) form highly stable and sequence‐specific triplexes with DNA duplexes.</div></front></TEI><affiliations><list><country><li>France</li></country><region><li>Languedoc-Roussillon</li><li>Occitanie (région administrative)</li></region><settlement><li>Montpellier</li></settlement><orgName><li>Université Montpellier 2</li></orgName></list><tree><country name="France"><region name="Occitanie (région administrative)"><name sortKey="Michel, Thibaut" sort="Michel, Thibaut" uniqKey="Michel T" first="Thibaut" last="Michel">Thibaut Michel</name></region><name sortKey="Debart, Francoise" sort="Debart, Francoise" uniqKey="Debart F" first="Françoise" last="Debart">Françoise Debart</name><name sortKey="Debart, Francoise" sort="Debart, Francoise" uniqKey="Debart F" first="Françoise" last="Debart">Françoise Debart</name><name sortKey="Heitz, Frederic" sort="Heitz, Frederic" uniqKey="Heitz F" first="Frédéric" last="Heitz">Frédéric Heitz</name><name sortKey="Vasseur, Jean Acques" sort="Vasseur, Jean Acques" uniqKey="Vasseur J" first="Jean-Jacques" last="Vasseur">Jean-Jacques Vasseur</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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