MersV1, PubMed, Checkpoint, bibRecord, 002554

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 : 002554 ( PubMed/Checkpoint ); précédent : 002553; suivant : 002555

Biologically active oligodeoxyribonucleotides. 5. 5'-End-substituted d(TGGGAG) possesses anti-human immunodeficiency virus type 1 activity by forming a G-quadruplex structure.

Auteurs : H. Hotoda [Japon] ; M. Koizumi ; R. Koga ; M. Kaneko ; K. Momota ; T. Ohmine ; H. Furukawa ; T. Agatsuma ; T. Nishigaki ; J. Sone ; S. Tsutsumi ; T. Kosaka ; K. Abe ; S. Kimura ; K. Shimada

Source :

Journal of medicinal chemistry [ 0022-2623 ] ; 1998.

RBID : pubmed:9733490

Descripteurs français

English descriptors

KwdEn :
- Anti-HIV Agents (blood), Anti-HIV Agents (chemical synthesis), Anti-HIV Agents (chemistry), Anti-HIV Agents (pharmacology), Cell Line, Transformed, Circular Dichroism, Drug Stability, HIV-1 (drug effects), Humans, Molecular Conformation, Oligodeoxyribonucleotides (blood), Oligodeoxyribonucleotides (chemical synthesis), Oligodeoxyribonucleotides (chemistry), Oligodeoxyribonucleotides (pharmacology), Solutions, Structure-Activity Relationship.
MESH :
- chemical , blood : Anti-HIV Agents, Oligodeoxyribonucleotides.
- chemical , chemical synthesis : Anti-HIV Agents, Oligodeoxyribonucleotides.
- chemical , chemistry : Anti-HIV Agents, Oligodeoxyribonucleotides.
- chemical , pharmacology : Anti-HIV Agents, Oligodeoxyribonucleotides.
- drug effects : HIV-1.
- Cell Line, Transformed, Circular Dichroism, Drug Stability, Humans, Molecular Conformation, Solutions, Structure-Activity Relationship.

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 microM) without cytotoxicity up to 40 microM. 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.

DOI: 10.1021/jm970658w
PubMed: 9733490

Affiliations:

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pubmed:9733490

Le document en format XML

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<front><div type="abstract" xml:lang="en">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 microM) without cytotoxicity up to 40 microM. 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>
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<Abstract><AbstractText>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 microM) without cytotoxicity up to 40 microM. 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.</AbstractText>
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<name sortKey="Kimura, S" sort="Kimura, S" uniqKey="Kimura S" first="S" last="Kimura">S. Kimura</name>
<name sortKey="Koga, R" sort="Koga, R" uniqKey="Koga R" first="R" last="Koga">R. Koga</name>
<name sortKey="Koizumi, M" sort="Koizumi, M" uniqKey="Koizumi M" first="M" last="Koizumi">M. Koizumi</name>
<name sortKey="Kosaka, T" sort="Kosaka, T" uniqKey="Kosaka T" first="T" last="Kosaka">T. Kosaka</name>
<name sortKey="Momota, K" sort="Momota, K" uniqKey="Momota K" first="K" last="Momota">K. Momota</name>
<name sortKey="Nishigaki, T" sort="Nishigaki, T" uniqKey="Nishigaki T" first="T" last="Nishigaki">T. Nishigaki</name>
<name sortKey="Ohmine, T" sort="Ohmine, T" uniqKey="Ohmine T" first="T" last="Ohmine">T. Ohmine</name>
<name sortKey="Shimada, K" sort="Shimada, K" uniqKey="Shimada K" first="K" last="Shimada">K. Shimada</name>
<name sortKey="Sone, J" sort="Sone, J" uniqKey="Sone J" first="J" last="Sone">J. Sone</name>
<name sortKey="Tsutsumi, S" sort="Tsutsumi, S" uniqKey="Tsutsumi S" first="S" last="Tsutsumi">S. Tsutsumi</name>
</noCountry>
<country name="Japon"><region name="Région de Kantō"><name sortKey="Hotoda, H" sort="Hotoda, H" uniqKey="Hotoda H" first="H" last="Hotoda">H. Hotoda</name>
</region>
</country>
</tree>
</affiliations>
</record>

Pour manipuler ce document sous Unix (Dilib)

EXPLOR_STEP=$WICRI_ROOT/Sante/explor/MersV1/Data/PubMed/Checkpoint

HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 002554 | SxmlIndent | more

HfdSelect -h $EXPLOR_AREA/Data/PubMed/Checkpoint/biblio.hfd -nk 002554 | SxmlIndent | more

Pour mettre un lien sur cette page dans le réseau Wicri

{{Explor lien
   |wiki=    Sante
   |area=    MersV1
   |flux=    PubMed
   |étape=   Checkpoint
   |type=    RBID
   |clé=     pubmed:9733490
   |texte=   Biologically active oligodeoxyribonucleotides. 5. 5'-End-substituted d(TGGGAG) possesses anti-human immunodeficiency virus type 1 activity by forming a G-quadruplex structure.
}}

Pour générer des pages wiki

HfdIndexSelect -h $EXPLOR_AREA/Data/PubMed/Checkpoint/RBID.i   -Sk "pubmed:9733490" \
       | HfdSelect -Kh $EXPLOR_AREA/Data/PubMed/Checkpoint/biblio.hfd   \
       | NlmPubMed2Wicri -a MersV1

This area was generated with Dilib version V0.6.33.
Data generation: Mon Apr 20 23:26:43 2020. Site generation: Sat Mar 27 09:06:09 2021

	Serveur d'exploration MERS
	Attention, ce site est en cours de développement ! Attention, site généré par des moyens informatiques à partir de corpus bruts. Les informations ne sont donc pas validées.

Serveur d'exploration MERS

Biologically active oligodeoxyribonucleotides. 5. 5'-End-substituted d(TGGGAG) possesses anti-human immunodeficiency virus type 1 activity by forming a G-quadruplex structure.

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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Pour manipuler ce document sous Unix (Dilib)

Pour mettre un lien sur cette page dans le réseau Wicri

Pour générer des pages wiki