Biologically active oligodeoxyribonucleotides—IX.1 Synthesis and anti-HIV-1 activity of hexadeoxyribonucleotides, TGGGAG, bearing 3′- and 5′-end-modification
Identifieur interne : 003C86 ( Main/Exploration ); précédent : 003C85; suivant : 003C87Biologically active oligodeoxyribonucleotides—IX.1 Synthesis and anti-HIV-1 activity of hexadeoxyribonucleotides, TGGGAG, bearing 3′- and 5′-end-modification
Auteurs : Makoto Koizumi [Japon] ; Rika Koga [Japon] ; Hitoshi Hotoda [Japon] ; Kenji Momota [Japon] ; Toshinori Ohmine [Japon] ; Hidehiko Furukawa [Japon] ; Toshinori Agatsuma [Japon] ; Takashi Nishigaki [Japon] ; Koji Abe [Japon] ; Toshiyuki Kosaka [Japon] ; Shinya Tsutsumi [Japon] ; Junko Sone [Japon] ; Masakatsu Kaneko [Japon] ; Satoshi Kimura [Japon] ; Kaoru Shimada [Japon]Source :
- Bioorganic & Medicinal Chemistry [ 0968-0896 ] ; 1997.
Descripteurs français
- KwdFr :
- Agents antiVIH (pharmacologie), Agents antiVIH (synthèse chimique), Animaux, Conformation d'acide nucléique, Dichroïsme circulaire, Humains, Lignée cellulaire, Modèles chimiques, Oligodésoxyribonucléotides (pharmacologie), Oligodésoxyribonucléotides (synthèse chimique), Rats, Souris, VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ().
- MESH :
- pharmacologie : Agents antiVIH, Oligodésoxyribonucléotides.
- synthèse chimique : Agents antiVIH, Oligodésoxyribonucléotides.
- Animaux, Conformation d'acide nucléique, Dichroïsme circulaire, Humains, Lignée cellulaire, Modèles chimiques, Rats, Souris, VIH-1 (Virus de l'Immunodéficience Humaine de type 1).
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Anti-HIV Agents, Oligodeoxyribonucleotides.
- chemical , pharmacology : Anti-HIV Agents, Oligodeoxyribonucleotides.
- drug effects : HIV-1.
- Teeft :
- Acetic anhydride, Acid hydrolysis, Alkaline conditions, Anhydride, Animals, Aqueous ammonia, Aqueous nahco3, Aromatic groups, Best candidate, Cell Line, Ch3cn, Chain length, Circular Dichroism, Column chromatography, Cpgs, Cytopathic effect, Cytotoxicity, Dichloroacetic acid, Dmtr, Dmtr group, Dmtr loading levels, Elsevier science, Enzymatic stability, Ethylene glycol, Experimental section, Furukawa, High activity, Higher activity, Hplc, Human plasma, Humans, Insoluble material, Loading level, Makoto koizumi, Mass spectroscopy, Methylphosphate group, Methylthiophosphate group, Mice, Mmol, Models, Chemical, Nucleic Acid Conformation, Nucleic acids, Odns, Open circles, Pentachlorophenyl ester, Phase hplc, Phosphate groups, Phosphorothioate bonds, Phosphorothioate modification, Pore glass, Pyridine, Quadruplex, Quadruplex structure, Rats, Reaction mixture, Retention time, Similar procedure, Snake venom phosphodiesterase, Solid squares, Succinate linker, Succinic anhydride, Succinyl anhydride, Sulfurization step, Ternary structure, Tetraethylthiuram disulfide, Tetrahedron lett, Triethylammonium acetate, Trityl cation.
Abstract
Abstract: We have determined that hexadeoxyribonucleotides (5′TGGGAG3′), with modified aromatic groups such as a trityl group at the 5′-end, have anti-HIV-1 activity in vitro. The 6-mer bearing a 3,4-dibenzyloxybenzyl (3,4-DBB) group at the 5′-end had the most potent activity and the least cytotoxicity. When the 3′-end of the 5′-(3,4-DBB)-modified 6-mer was substituted with a 2-hydroxyethylphosphate, a 2-hydroxyethylthiophosphate, or a methylphosphate group at the 3′-end, anti-HIV-1 activity increased. Moreover, among various 3′- and 5′-end-modified 6-mers that were tested, the 6-mer (R-95288) bearing a 3,4-DBB group at the 5′-end and a 2-hydroxyethylphosphate group at the 3′-end was the most stable, when incubated with mouse, rat, or human plasma. Therefore, R-95288 was chosen as the best candidate for possible use in therapy on the basis of its anti-HIV-1 activity.
A 6-mer (R-95288) bearing a 3,4-dibenzyloxybenzyl group at the 5′-end and a 2-hydroxyethylphosphate group at the 3′-end with anti-HIV-1 activity is described.gr1
Url:
DOI: 10.1016/S0968-0896(97)00161-2
Affiliations:
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Le document en format XML
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<term>Anti-HIV Agents (chemical synthesis)</term>
<term>Anti-HIV Agents (pharmacology)</term>
<term>Cell Line</term>
<term>Circular Dichroism</term>
<term>HIV-1 (drug effects)</term>
<term>Humans</term>
<term>Mice</term>
<term>Models, Chemical</term>
<term>Nucleic Acid Conformation</term>
<term>Oligodeoxyribonucleotides (chemical synthesis)</term>
<term>Oligodeoxyribonucleotides (pharmacology)</term>
<term>Rats</term>
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<keywords scheme="KwdFr" xml:lang="fr"><term>Agents antiVIH (pharmacologie)</term>
<term>Agents antiVIH (synthèse chimique)</term>
<term>Animaux</term>
<term>Conformation d'acide nucléique</term>
<term>Dichroïsme circulaire</term>
<term>Humains</term>
<term>Lignée cellulaire</term>
<term>Modèles chimiques</term>
<term>Oligodésoxyribonucléotides (pharmacologie)</term>
<term>Oligodésoxyribonucléotides (synthèse chimique)</term>
<term>Rats</term>
<term>Souris</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1) ()</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Anti-HIV Agents</term>
<term>Oligodeoxyribonucleotides</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Anti-HIV Agents</term>
<term>Oligodeoxyribonucleotides</term>
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<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>HIV-1</term>
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<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Agents antiVIH</term>
<term>Oligodésoxyribonucléotides</term>
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<term>Oligodésoxyribonucléotides</term>
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<keywords scheme="Teeft" xml:lang="en"><term>Acetic anhydride</term>
<term>Acid hydrolysis</term>
<term>Alkaline conditions</term>
<term>Anhydride</term>
<term>Animals</term>
<term>Aqueous ammonia</term>
<term>Aqueous nahco3</term>
<term>Aromatic groups</term>
<term>Best candidate</term>
<term>Cell Line</term>
<term>Ch3cn</term>
<term>Chain length</term>
<term>Circular Dichroism</term>
<term>Column chromatography</term>
<term>Cpgs</term>
<term>Cytopathic effect</term>
<term>Cytotoxicity</term>
<term>Dichloroacetic acid</term>
<term>Dmtr</term>
<term>Dmtr group</term>
<term>Dmtr loading levels</term>
<term>Elsevier science</term>
<term>Enzymatic stability</term>
<term>Ethylene glycol</term>
<term>Experimental section</term>
<term>Furukawa</term>
<term>High activity</term>
<term>Higher activity</term>
<term>Hplc</term>
<term>Human plasma</term>
<term>Humans</term>
<term>Insoluble material</term>
<term>Loading level</term>
<term>Makoto koizumi</term>
<term>Mass spectroscopy</term>
<term>Methylphosphate group</term>
<term>Methylthiophosphate group</term>
<term>Mice</term>
<term>Mmol</term>
<term>Models, Chemical</term>
<term>Nucleic Acid Conformation</term>
<term>Nucleic acids</term>
<term>Odns</term>
<term>Open circles</term>
<term>Pentachlorophenyl ester</term>
<term>Phase hplc</term>
<term>Phosphate groups</term>
<term>Phosphorothioate bonds</term>
<term>Phosphorothioate modification</term>
<term>Pore glass</term>
<term>Pyridine</term>
<term>Quadruplex</term>
<term>Quadruplex structure</term>
<term>Rats</term>
<term>Reaction mixture</term>
<term>Retention time</term>
<term>Similar procedure</term>
<term>Snake venom phosphodiesterase</term>
<term>Solid squares</term>
<term>Succinate linker</term>
<term>Succinic anhydride</term>
<term>Succinyl anhydride</term>
<term>Sulfurization step</term>
<term>Ternary structure</term>
<term>Tetraethylthiuram disulfide</term>
<term>Tetrahedron lett</term>
<term>Triethylammonium acetate</term>
<term>Trityl cation</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Animaux</term>
<term>Conformation d'acide nucléique</term>
<term>Dichroïsme circulaire</term>
<term>Humains</term>
<term>Lignée cellulaire</term>
<term>Modèles chimiques</term>
<term>Rats</term>
<term>Souris</term>
<term>VIH-1 (Virus de l'Immunodéficience Humaine de type 1)</term>
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<front><div type="abstract" xml:lang="en">Abstract: We have determined that hexadeoxyribonucleotides (5′TGGGAG3′), with modified aromatic groups such as a trityl group at the 5′-end, have anti-HIV-1 activity in vitro. The 6-mer bearing a 3,4-dibenzyloxybenzyl (3,4-DBB) group at the 5′-end had the most potent activity and the least cytotoxicity. When the 3′-end of the 5′-(3,4-DBB)-modified 6-mer was substituted with a 2-hydroxyethylphosphate, a 2-hydroxyethylthiophosphate, or a methylphosphate group at the 3′-end, anti-HIV-1 activity increased. Moreover, among various 3′- and 5′-end-modified 6-mers that were tested, the 6-mer (R-95288) bearing a 3,4-DBB group at the 5′-end and a 2-hydroxyethylphosphate group at the 3′-end was the most stable, when incubated with mouse, rat, or human plasma. Therefore, R-95288 was chosen as the best candidate for possible use in therapy on the basis of its anti-HIV-1 activity.</div>
<div type="abstract">A 6-mer (R-95288) bearing a 3,4-dibenzyloxybenzyl group at the 5′-end and a 2-hydroxyethylphosphate group at the 3′-end with anti-HIV-1 activity is described.gr1 </div>
</front>
</TEI>
<affiliations><list><country><li>Japon</li>
</country>
<region><li>Région de Kantō</li>
</region>
<settlement><li>Tokyo</li>
</settlement>
<orgName><li>Université de Tokyo</li>
</orgName>
</list>
<tree><country name="Japon"><noRegion><name sortKey="Koizumi, Makoto" sort="Koizumi, Makoto" uniqKey="Koizumi M" first="Makoto" last="Koizumi">Makoto Koizumi</name>
</noRegion>
<name sortKey="Abe, Koji" sort="Abe, Koji" uniqKey="Abe K" first="Koji" last="Abe">Koji Abe</name>
<name sortKey="Agatsuma, Toshinori" sort="Agatsuma, Toshinori" uniqKey="Agatsuma T" first="Toshinori" last="Agatsuma">Toshinori Agatsuma</name>
<name sortKey="Furukawa, Hidehiko" sort="Furukawa, Hidehiko" uniqKey="Furukawa H" first="Hidehiko" last="Furukawa">Hidehiko Furukawa</name>
<name sortKey="Hotoda, Hitoshi" sort="Hotoda, Hitoshi" uniqKey="Hotoda H" first="Hitoshi" last="Hotoda">Hitoshi Hotoda</name>
<name sortKey="Kaneko, Masakatsu" sort="Kaneko, Masakatsu" uniqKey="Kaneko M" first="Masakatsu" last="Kaneko">Masakatsu Kaneko</name>
<name sortKey="Kimura, Satoshi" sort="Kimura, Satoshi" uniqKey="Kimura S" first="Satoshi" last="Kimura">Satoshi Kimura</name>
<name sortKey="Koga, Rika" sort="Koga, Rika" uniqKey="Koga R" first="Rika" last="Koga">Rika Koga</name>
<name sortKey="Koizumi, Makoto" sort="Koizumi, Makoto" uniqKey="Koizumi M" first="Makoto" last="Koizumi">Makoto Koizumi</name>
<name sortKey="Kosaka, Toshiyuki" sort="Kosaka, Toshiyuki" uniqKey="Kosaka T" first="Toshiyuki" last="Kosaka">Toshiyuki Kosaka</name>
<name sortKey="Momota, Kenji" sort="Momota, Kenji" uniqKey="Momota K" first="Kenji" last="Momota">Kenji Momota</name>
<name sortKey="Nishigaki, Takashi" sort="Nishigaki, Takashi" uniqKey="Nishigaki T" first="Takashi" last="Nishigaki">Takashi Nishigaki</name>
<name sortKey="Ohmine, Toshinori" sort="Ohmine, Toshinori" uniqKey="Ohmine T" first="Toshinori" last="Ohmine">Toshinori Ohmine</name>
<name sortKey="Shimada, Kaoru" sort="Shimada, Kaoru" uniqKey="Shimada K" first="Kaoru" last="Shimada">Kaoru Shimada</name>
<name sortKey="Sone, Junko" sort="Sone, Junko" uniqKey="Sone J" first="Junko" last="Sone">Junko Sone</name>
<name sortKey="Tsutsumi, Shinya" sort="Tsutsumi, Shinya" uniqKey="Tsutsumi S" first="Shinya" last="Tsutsumi">Shinya Tsutsumi</name>
</country>
</tree>
</affiliations>
</record>
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