Biologically Active Oligodeoxyribonucleotides. 5. 5‘-End-Substituted d(TGGGAG) Possesses Anti-Human Immunodeficiency Virus Type 1 Activity by Forming a G-Quadruplex Structure
Identifieur interne : 001299 ( Istex/Checkpoint ); précédent : 001298; suivant : 001300Biologically Active Oligodeoxyribonucleotides. 5. 5‘-End-Substituted d(TGGGAG) Possesses Anti-Human Immunodeficiency Virus Type 1 Activity by Forming a G-Quadruplex Structure
Auteurs : Hitoshi Hotoda [Japon] ; Makoto Koizumi [Japon] ; Rika Koga [Japon] ; Masakatsu Kaneko [Japon] ; Kenji Momota [Japon] ; Toshinori Ohmine [Japon] ; Hidehiko Furukawa [Japon] ; Toshinori Agatsuma [Japon] ; Takashi Nishigaki [Japon] ; Junko Sone [Japon] ; Shinya Tsutsumi [Japon] ; Toshiyuki Kosaka [Japon] ; Koji Abe [Japon] ; Satoshi Kimura [Japon] ; Kaoru Shimada [Japon]Source :
- Journal of Medicinal Chemistry [ 0022-2623 ] ; 1998.
Abstract
A series of hexadeoxyribonucleotides (6-mers), d(TGGGAG), substituted with a variety of aromatic groups at the 5‘-end were synthesized and tested for anti-human immunodeficiency virus type 1 (HIV-1) activity. While unmodified d(TGGGAG) (31) had no anti-HIV-1 activity, compound 23 with a 3,4-di(benzyloxy)benzyl (DBB) group at the 5‘-end potently inhibited the HIV-1IIIB-induced cytopathicity of MT-4 cells in vitro (IC50 = 0.37 μM) without cytotoxicity up to 40 μM. A thermal denaturation study on the 5‘-end-substituted 6-mers by means of the circular dichroism (CD) spectra demonstrated that the aromatic substituent attached at the 5‘-end of the 6-mer strongly enhanced the formation of a parallel helical structure consisting of four strands (quadruplex). On the contrary, compound 36, in which one of the guanosines of 23 was replaced by a thymidine, did not form a quadruplex, thus exhibiting no anti-HIV-1 activity. Moreover, both compound 15, with a tert-butyldiphenylsilyl group solely at its 3‘-end, and compound 21, with a relatively small substituent, a benzyl group, at the 5‘-end, formed quadruplexes but had no anti-HIV-1 activity. These findings led us to the conclusion that both the quadruplex structure and the aromatic substituent with adequate size at the 5‘-end are crucial for the interaction of the 5‘-end-substituted 6-mers with the V3 loop as well as the CD4 binding site on viral gp120, resulting in anti-HIV-1 activity.
Url:
DOI: 10.1021/jm970658w
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d(TGGGAG) Possesses Anti-Human Immunodeficiency Virus Type 1 Activity by
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wicri:rule="url">Japon</country></affiliation></author><author><name sortKey="Koizumi, Makoto" sort="Koizumi, Makoto" uniqKey="Koizumi M" first="Makoto" last="Koizumi">Makoto Koizumi</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Exploratory Chemistry Research Laboratories, Biological Research Laboratories, and Analytical and Metabolic ResearchLaboratories, Sankyo Company, Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan, and The Department ofInfectious Diseases, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName><orgName type="university">Université de Tokyo</orgName><placeName><settlement type="city">Tokyo</settlement><region type="province">Région de Kantō</region></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Koga, Rika" sort="Koga, Rika" uniqKey="Koga R" first="Rika" last="Koga">Rika Koga</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Exploratory Chemistry Research Laboratories, Biological Research Laboratories, and Analytical and Metabolic ResearchLaboratories, Sankyo Company, Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan, and The Department ofInfectious Diseases, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName><orgName type="university">Université de Tokyo</orgName><placeName><settlement type="city">Tokyo</settlement><region type="province">Région de Kantō</region></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Kaneko, Masakatsu" sort="Kaneko, Masakatsu" uniqKey="Kaneko M" first="Masakatsu" last="Kaneko">Masakatsu Kaneko</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Exploratory Chemistry Research Laboratories, Biological Research Laboratories, and Analytical and Metabolic ResearchLaboratories, Sankyo Company, Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan, and The Department ofInfectious Diseases, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName><orgName type="university">Université de Tokyo</orgName><placeName><settlement type="city">Tokyo</settlement><region type="province">Région de Kantō</region></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Momota, Kenji" sort="Momota, Kenji" uniqKey="Momota K" first="Kenji" last="Momota">Kenji Momota</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Exploratory Chemistry Research Laboratories, Biological Research Laboratories, and Analytical and Metabolic ResearchLaboratories, Sankyo Company, Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan, and The Department ofInfectious Diseases, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName><orgName type="university">Université de Tokyo</orgName><placeName><settlement type="city">Tokyo</settlement><region type="province">Région de Kantō</region></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Ohmine, Toshinori" sort="Ohmine, Toshinori" uniqKey="Ohmine T" first="Toshinori" last="Ohmine">Toshinori Ohmine</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Exploratory Chemistry Research Laboratories, Biological Research Laboratories, and Analytical and Metabolic ResearchLaboratories, Sankyo Company, Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan, and The Department ofInfectious Diseases, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName><orgName type="university">Université de Tokyo</orgName><placeName><settlement type="city">Tokyo</settlement><region type="province">Région de Kantō</region></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Furukawa, Hidehiko" sort="Furukawa, Hidehiko" uniqKey="Furukawa H" first="Hidehiko" last="Furukawa">Hidehiko Furukawa</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Exploratory Chemistry Research Laboratories, Biological Research Laboratories, and Analytical and Metabolic ResearchLaboratories, Sankyo Company, Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan, and The Department ofInfectious Diseases, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName><orgName type="university">Université de Tokyo</orgName><placeName><settlement type="city">Tokyo</settlement><region type="province">Région de Kantō</region></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Agatsuma, Toshinori" sort="Agatsuma, Toshinori" uniqKey="Agatsuma T" first="Toshinori" last="Agatsuma">Toshinori Agatsuma</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Exploratory Chemistry Research Laboratories, Biological Research Laboratories, and Analytical and Metabolic ResearchLaboratories, Sankyo Company, Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan, and The Department ofInfectious Diseases, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName><orgName type="university">Université de Tokyo</orgName><placeName><settlement type="city">Tokyo</settlement><region type="province">Région de Kantō</region></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Nishigaki, Takashi" sort="Nishigaki, Takashi" uniqKey="Nishigaki T" first="Takashi" last="Nishigaki">Takashi Nishigaki</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Exploratory Chemistry Research Laboratories, Biological Research Laboratories, and Analytical and Metabolic ResearchLaboratories, Sankyo Company, Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan, and The Department ofInfectious Diseases, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName><orgName type="university">Université de Tokyo</orgName><placeName><settlement type="city">Tokyo</settlement><region type="province">Région de Kantō</region></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Sone, Junko" sort="Sone, Junko" uniqKey="Sone J" first="Junko" last="Sone">Junko Sone</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Exploratory Chemistry Research Laboratories, Biological Research Laboratories, and Analytical and Metabolic ResearchLaboratories, Sankyo Company, Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan, and The Department ofInfectious Diseases, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName><orgName type="university">Université de Tokyo</orgName><placeName><settlement type="city">Tokyo</settlement><region type="province">Région de Kantō</region></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Tsutsumi, Shinya" sort="Tsutsumi, Shinya" uniqKey="Tsutsumi S" first="Shinya" last="Tsutsumi">Shinya Tsutsumi</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Exploratory Chemistry Research Laboratories, Biological Research Laboratories, and Analytical and Metabolic ResearchLaboratories, Sankyo Company, Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan, and The Department ofInfectious Diseases, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName><orgName type="university">Université de Tokyo</orgName><placeName><settlement type="city">Tokyo</settlement><region type="province">Région de Kantō</region></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Kosaka, Toshiyuki" sort="Kosaka, Toshiyuki" uniqKey="Kosaka T" first="Toshiyuki" last="Kosaka">Toshiyuki Kosaka</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Exploratory Chemistry Research Laboratories, Biological Research Laboratories, and Analytical and Metabolic ResearchLaboratories, Sankyo Company, Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan, and The Department ofInfectious Diseases, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName><orgName type="university">Université de Tokyo</orgName><placeName><settlement type="city">Tokyo</settlement><region type="province">Région de Kantō</region></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Abe, Koji" sort="Abe, Koji" uniqKey="Abe K" first="Koji" last="Abe">Koji Abe</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Exploratory Chemistry Research Laboratories, Biological Research Laboratories, and Analytical and Metabolic ResearchLaboratories, Sankyo Company, Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan, and The Department ofInfectious Diseases, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName><orgName type="university">Université de Tokyo</orgName><placeName><settlement type="city">Tokyo</settlement><region type="province">Région de Kantō</region></placeName></affiliation><affiliation></affiliation></author><author><name sortKey="Kimura, Satoshi" sort="Kimura, Satoshi" uniqKey="Kimura S" first="Satoshi" last="Kimura">Satoshi Kimura</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Exploratory Chemistry Research Laboratories, Biological Research Laboratories, and Analytical and Metabolic ResearchLaboratories, Sankyo Company, Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan, and The Department ofInfectious Diseases, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName><orgName type="university">Université de Tokyo</orgName><placeName><settlement type="city">Tokyo</settlement><region type="province">Région de Kantō</region></placeName></affiliation><affiliation></affiliation><affiliation wicri:level="1"><country xml:lang="fr">Japon</country><wicri:regionArea> Current address: Department of Infection Control and Prevention,The University of Tokyo Hospital, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author><author><name sortKey="Shimada, Kaoru" sort="Shimada, Kaoru" uniqKey="Shimada K" first="Kaoru" last="Shimada">Kaoru Shimada</name><affiliation wicri:level="4"><country xml:lang="fr">Japon</country><wicri:regionArea>Exploratory Chemistry Research Laboratories, Biological Research Laboratories, and Analytical and Metabolic ResearchLaboratories, Sankyo Company, Ltd., 1-2-58 Hiromachi, Shinagawa-ku, Tokyo 140-8710, Japan, and The Department ofInfectious Diseases, The Institute of Medical Science, The University of Tokyo, 4-6-1 Shirokanedai, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName><orgName type="university">Université de Tokyo</orgName><placeName><settlement type="city">Tokyo</settlement><region type="province">Région de Kantō</region></placeName></affiliation><affiliation></affiliation><affiliation wicri:level="1"><country xml:lang="fr">Japon</country><wicri:regionArea> Current address: Tokyo Senbai Hospital, 1-4-3 Mita, Minato-ku,Tokyo 108</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Journal of Medicinal Chemistry</title><title level="j" type="abbrev">J. Med. Chem.</title><idno type="ISSN">0022-2623</idno><idno type="eISSN">1520-4804</idno><imprint><publisher>American Chemical Society</publisher><date type="e-published">1998</date><date type="published">1998</date><biblScope unit="vol">41</biblScope><biblScope unit="issue">19</biblScope><biblScope unit="page" from="3655">3655</biblScope><biblScope unit="page" to="3663">3663</biblScope></imprint><idno type="ISSN">0022-2623</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0022-2623</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract">A series of hexadeoxyribonucleotides (6-mers), d(TGGGAG), substituted with a variety of aromatic groups at the 5‘-end were synthesized and tested for anti-human immunodeficiency virus type 1 (HIV-1) activity. While unmodified d(TGGGAG) (31) had no anti-HIV-1 activity, compound 23 with a 3,4-di(benzyloxy)benzyl (DBB) group at the 5‘-end potently inhibited the HIV-1IIIB-induced cytopathicity of MT-4 cells in vitro (IC50 = 0.37 μM) without cytotoxicity up to 40 μM. A thermal denaturation study on the 5‘-end-substituted 6-mers by means of the circular dichroism (CD) spectra demonstrated that the aromatic substituent attached at the 5‘-end of the 6-mer strongly enhanced the formation of a parallel helical structure consisting of four strands (quadruplex). On the contrary, compound 36, in which one of the guanosines of 23 was replaced by a thymidine, did not form a quadruplex, thus exhibiting no anti-HIV-1 activity. Moreover, both compound 15, with a tert-butyldiphenylsilyl group solely at its 3‘-end, and compound 21, with a relatively small substituent, a benzyl group, at the 5‘-end, formed quadruplexes but had no anti-HIV-1 activity. These findings led us to the conclusion that both the quadruplex structure and the aromatic substituent with adequate size at the 5‘-end are crucial for the interaction of the 5‘-end-substituted 6-mers with the V3 loop as well as the CD4 binding site on viral gp120, resulting in anti-HIV-1 activity.</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"><region name="Région de Kantō"><name sortKey="Hotoda, Hitoshi" sort="Hotoda, Hitoshi" uniqKey="Hotoda H" first="Hitoshi" last="Hotoda">Hitoshi Hotoda</name></region><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="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="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>Pour manipuler ce document sous Unix (Dilib)
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|texte= Biologically Active Oligodeoxyribonucleotides. 5. 5‘-End-Substituted d(TGGGAG) Possesses Anti-Human Immunodeficiency Virus Type 1 Activity by Forming a G-Quadruplex Structure
}}
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