Polyanion Inhibitors of HIV and Other Viruses. 7. Polyanionic Compounds and Polyzwitterionic Compounds Derived from Cyclodextrins as Inhibitors of HIV Transmission
Identifieur interne : 001A52 ( Main/Exploration ); précédent : 001A51; suivant : 001A53Polyanion Inhibitors of HIV and Other Viruses. 7. Polyanionic Compounds and Polyzwitterionic Compounds Derived from Cyclodextrins as Inhibitors of HIV Transmission
Auteurs : Alain Leydet [Belgique] ; Céline Moullet [Belgique] ; Jean Pierre Roque [Belgique] ; Myriam Witvrouw [Belgique] ; Christophe Pannecouque [Belgique] ; Graciela Andrei [Belgique] ; Robert Snoeck [Belgique] ; Johan Neyts [Belgique] ; Dominique Schols [Belgique] ; Erik De Clercq [Belgique]Source :
- Journal of Medicinal Chemistry [ 0022-2623 ] ; 1998.
Abstract
New polyanionic compounds were obtained from radical addition of thiomalic acid and mercaptopropionic acid onto perallylated cyclodextrins (CDs) under UV irradiation with a catalytic amount of α,α‘-azobis(isobutyronitrile). All these polyanions, bearing 18−48 carboxylate groups, inhibited human immunodeficiency virus type 1 (HIV-1) strain IIIB replication in MT-4 cells at a 50% inhibitory concentration (IC50) of 0.1−2.9 μM, while not being toxic to the host cells at concentrations up to 62 μM. These compounds were also active against a clinical HIV-1 isolate (HE) at ≥4-fold higher concentrations. Only some compounds showed activity against the two HIV-2 strains (ROD and EHO) but at higher concentrations than those required to inhibit HIV-1 (IIIB and HE) replication. In addition, these compounds were not active against the M-tropic HIV-1 strain BaL but were active against simian immunodeficiency virus [SIV (MAC251)]. These compounds were also inhibitory to the replication of human cytomegalovirus at an IC50 of 1−10 μM, but not herpes simplex virus (type 1 and type 2) or other (picorna-, toga-, reo-, orthomyxo-, paramyxo-, bunya-, rhabdo-, and poxvirus) viruses. Radical addition on perallylated CDs of a protected cysteine gave polyzwitterionic compounds. None of these last compounds proved inhibitory to the replication of HIV-1, HIV-2, or any of the other viruses tested.
Url:
DOI: 10.1021/jm970661f
Affiliations:
- Belgique
- Languedoc-Roussillon, Occitanie (région administrative)
- Montpellier
- Université Montpellier 2
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Bataillon, 34095 Montpellier Cedex 5, France,and Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven</wicri:regionArea><orgName type="university">Université Montpellier 2</orgName><placeName><settlement type="city">Montpellier</settlement><region type="region" nuts="2">Occitanie (région administrative)</region><region type="old region" nuts="2">Languedoc-Roussillon</region></placeName></affiliation><affiliation></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" when="1998-11-13">1998</date><date when="1998-12-03">1998</date><biblScope unit="vol">41</biblScope><biblScope unit="issue">25</biblScope><biblScope unit="page" from="4927">4927</biblScope><biblScope unit="page" to="4932">4932</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">New polyanionic compounds were obtained from radical addition of thiomalic acid and mercaptopropionic acid onto perallylated cyclodextrins (CDs) under UV irradiation with a catalytic amount of α,α‘-azobis(isobutyronitrile). All these polyanions, bearing 18−48 carboxylate groups, inhibited human immunodeficiency virus type 1 (HIV-1) strain IIIB replication in MT-4 cells at a 50% inhibitory concentration (IC50) of 0.1−2.9 μM, while not being toxic to the host cells at concentrations up to 62 μM. These compounds were also active against a clinical HIV-1 isolate (HE) at ≥4-fold higher concentrations. Only some compounds showed activity against the two HIV-2 strains (ROD and EHO) but at higher concentrations than those required to inhibit HIV-1 (IIIB and HE) replication. In addition, these compounds were not active against the M-tropic HIV-1 strain BaL but were active against simian immunodeficiency virus [SIV (MAC251)]. These compounds were also inhibitory to the replication of human cytomegalovirus at an IC50 of 1−10 μM, but not herpes simplex virus (type 1 and type 2) or other (picorna-, toga-, reo-, orthomyxo-, paramyxo-, bunya-, rhabdo-, and poxvirus) viruses. Radical addition on perallylated CDs of a protected cysteine gave polyzwitterionic compounds. None of these last compounds proved inhibitory to the replication of HIV-1, HIV-2, or any of the other viruses tested.</div></front></TEI><affiliations><list><country><li>Belgique</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="Belgique"><region name="Occitanie (région administrative)"><name sortKey="Leydet, Alain" sort="Leydet, Alain" uniqKey="Leydet A" first="Alain" last="Leydet">Alain Leydet</name></region><name sortKey="Andrei, Graciela" sort="Andrei, Graciela" uniqKey="Andrei G" first="Graciela" last="Andrei">Graciela Andrei</name><name sortKey="De Clercq, Erik" sort="De Clercq, Erik" uniqKey="De Clercq E" first="Erik" last="De Clercq">Erik De Clercq</name><name sortKey="Moullet, Celine" sort="Moullet, Celine" uniqKey="Moullet C" first="Céline" last="Moullet">Céline Moullet</name><name sortKey="Neyts, Johan" sort="Neyts, Johan" uniqKey="Neyts J" first="Johan" last="Neyts">Johan Neyts</name><name sortKey="Pannecouque, Christophe" sort="Pannecouque, Christophe" uniqKey="Pannecouque C" first="Christophe" last="Pannecouque">Christophe Pannecouque</name><name sortKey="Roque, Jean Pierre" sort="Roque, Jean Pierre" uniqKey="Roque J" first="Jean Pierre" last="Roque">Jean Pierre Roque</name><name sortKey="Schols, Dominique" sort="Schols, Dominique" uniqKey="Schols D" first="Dominique" last="Schols">Dominique Schols</name><name sortKey="Snoeck, Robert" sort="Snoeck, Robert" uniqKey="Snoeck R" first="Robert" last="Snoeck">Robert Snoeck</name><name sortKey="Witvrouw, Myriam" sort="Witvrouw, Myriam" uniqKey="Witvrouw M" first="Myriam" last="Witvrouw">Myriam Witvrouw</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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