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3. Anti-HIV-1 activity of combinations and covalent conjugates of negatively charged human serum albumins (NCAs) and AZT

Author

Kuipers, M. E., Swart, P. J., Witvrouw, M., Jose Este, Reymen, D., Clercq, E., Meijer, D. K. F., and Faculty of Science and Engineering

Subjects
ANTIVIRAL DRUGS, Aco-HSA, Suc-HSA, virus diseases, HIV, synergy, polyanion, IMMUNODEFICIENCY-VIRUS TYPE-1, ENVELOPE GLYCOPROTEIN, MEMBRANE-FUSION, SULFATED POLYSACCHARIDES, PROTEASE INHIBITORS, REVERSE-TRANSCRIPTASE, DEXTRAN SULFATE, SELECTIVE-INHIBITION, AZT, ANTI-HIV ACTIVITY
Abstract

Negatively charged albumins (NCAs, with the prototypes Suc-HSA and Aco-HSA), modified proteins with a potent anti-HIV-1 activity in the nanomolar concentration range, were studied for several aspects of their antiviral mechanism. In addition we investigated the antiviral activity of combinations and covalent conjugates of these NCAs and the reverse transcriptase inhibitor AZT. Addition of NCAs to HIV-l-infected target cells in time-of-addition experiments could be delayed for 30 min after infection before significant loss of activity occurred. Syncytium formation of HIV-infected and uninfected T-cells was inhibited by the NCAs at concentrations of 1-4 mu g/ml. The gp120-mediated virus/cell binding, however, was only inhibited by the NCAs at a 10-fold higher concentrations. The combined data are compatible with a preferential influence on virus/cell fusion. A subsynergistic activity against HIV-I was observed with the non-covalent mixture of Aco-HSA and AZT, When AZT was covalently coupled to the NCAs, and added one hour after infection of the target cells, the anti-HIV-l activity of NCA-AZTMP was diminished by only 2-6-fold, while this was diminished at least 120-fold for the NCAs, Furthermore the addition of NCA-AZTMP could be delayed up to at least 3h after infection without loss of antiviral activity. It is concluded that AZT that was coupled to the NCAs significantly contributes to the overall antiviral activity of the conjugates leading to complementary effects. These results highlight the potential of using NCA-AZTMP as dual-targeting preparations against HIV-I in which both the carrier and the coupled drug contribute to the therapeutic efficacy acting at a different level in the replication cycle. more...

Published
1999

4. Comparative activity of selected antiviral compounds against clinical isolates of varicella-zoster virus

Author

Andrei, Graciela, Snoeck, Robert, Reymen, D., Liesnard, Corinne, Goubau, Patrick, Desmyter, Jan, de Clercq, Erik, Andrei, Graciela, Snoeck, Robert, Reymen, D., Liesnard, Corinne, Goubau, Patrick, Desmyter, Jan, and de Clercq, Erik more...

Abstract

Sixteen freshly isolated varicella-zoster virus (VZV) strains were evaluated in vitro, in parallel with two reference strains expressing a functional thymidine kinase (TK+) (Oka and YS) and two thymidine kinase-deficient mutants (TK-) (07-1 and YS-R), for their susceptibility to a broad range of antiviral compounds. The following compounds were included: acyclovir (ACV), brivudine (BVDU), sorivudine (BVaraU), other BVDU congeners such as BTDU, CTDU, CVDC and CVDU, ganciclovir (GCV), FIAC, araT, araA, araC, foscarnet (PFA), phosphonoacetic acid (PAA), the acyclic nucleoside phosphonates HPMPC, cHPMPC, HPMPA, cHPMPA, HPMPc3A, PMEA and PMEDAP, the N7-isomeric acyclic nucleoside analogue N7 AP, penciclovir (PCV), compounds 882C87 and H2G and two oxetanocin derivatives OXT-A and OXT-G. Fourteen of the 16 clinical isolates displayed the following order of decreasing selectivity against VZV: BVaraU > BVDU > CVDU ∼ CVDC > H2G > N7AP } CTDU ∼ BTDU ∼ OXT-G ∼ 882C87 > ACV > FIAC ∼ araT > HPMPC ∼ cHPMPC ∼ HPMPA ∼ HPMPc3A ∼ cHPMPA > PCV ∼ GCV ∼ OXT-A > PMEDAP ∼ PMEA > PFA ∼ PAA ∼ araA > araC. Two VZV strains (isolated from the cerebrospinal fluid of an AIDS patient) that were shown to have a truncated TK were clearly resistant to all the compounds that need the viral TK for their phosphorylation, while sensitivity to the acyclic nucleoside phosphonates, PFA, PAA, OXT-A and araA, remained unchanged. A slight (5- and 10-fold) increase was noted in the 50 % inhibitory concentration of N7AP and OXT-G, respectively, for the TK- VZV strains as compared to the TK+ VZV strains. Ganciclovir and FIAC also showed a marked decrease in their activity against these two strains, but this was not as pronounced as for the other viral TK-dependent drugs. From our results, it appears that although acyclic nucleoside phosphonates may not have as favourable a therapeutic index as drugs requiring the viral TK, they should be considered for the treatment of TK- VZV life-threatening infections that are, SCOPUS: ar.j, info:eu-repo/semantics/published more...

Published
1995

5. Meningoradiculoneuritis due to acyclovir‐resistant varicella zoster virus in an acquired immune deficiency syndrome patient

Author

Snoeck, Robert, Rentier, Bernard, Clumeck, Nathan, de Clercq, Erik, Gérard, Melanie, Sadzot-Delvaux, Catherine, Andrei, Graciela, Balzarini, Jan, Reymen, D., Ahadi, N., De Bruyne, Jean Marc, Piette, Jacques, Snoeck, Robert, Rentier, Bernard, Clumeck, Nathan, de Clercq, Erik, Gérard, Melanie, Sadzot-Delvaux, Catherine, Andrei, Graciela, Balzarini, Jan, Reymen, D., Ahadi, N., De Bruyne, Jean Marc, and Piette, Jacques more...

Abstract

Varicella zoster virus (VZV) is recognized as one of the major viral pathogens reactivated in patients with the acquired immune deficiency syndrome (AIDS). We report the case of meningora‐diculoneuritis in an AIDS patient, associated with the isolation in the cerebrospinal fluid (CSF) of a thymidine kinase (TK)‐deficient, acyclovir (ACV)‐resistant strain of VZV. Although the virus was sensitive in vitro to phosphonoformate (PFA), the patient did not improve during PFA therapy and finally died. Several VZV strains isolated from this patient (including two isolates from the patient's CSF) were analyzed for their TK activity and subsequently the viral TK gene was sequenced showing a major deletion leading to a truncated protein. Their susceptibility to several antiviral agents including ACV, PFA, (E)‐5‐(2‐bro‐movinyl)‐2′‐deoxyuridine (BVDU), 9‐β‐D‐ara‐binofuranosyladenine (vidarabine), (S)‐1‐(3‐hy‐droxy ‐ 2 ‐ phosphonylmethoxypropyl) cytosine (HPMPC), and (S)‐9‐(3‐hydroxy‐2‐phosphonyl‐methoxypropyl)adenine (HPMPA) was evaluated. All the virus strains isolated from this patient remained sensitive to HPMPA and HPMPC, pointing to the potential usefulness of these acyclic nucleoside phosphonates for the treatment of ACV‐resistant VZV infections in immunocom‐promised patients. © 1994 Wiley‐Liss, Inc. Copyright © 1994 Wiley‐Liss, Inc. A Wiley Company, SCOPUS: ar.j, FLWNA, info:eu-repo/semantics/published more...

Published
1994

6. Meningoradiculoneuritis Due to Acyclovir-Resistant Varicella-Zoster Virus in a Patient with AIDS

Author

Snoeck, Robert, de Clercq, Erik, Gérard, Melanie, Sadzot-Delvaux, Catherine, Andrei, Graciela, Balzarini, Jan, Reymen, D., Piette, Jacques, Rentier, Bernard, Clumeck, Nathan, Snoeck, Robert, de Clercq, Erik, Gérard, Melanie, Sadzot-Delvaux, Catherine, Andrei, Graciela, Balzarini, Jan, Reymen, D., Piette, Jacques, Rentier, Bernard, and Clumeck, Nathan more...

Abstract

SCOPUS: ar.j, info:eu-repo/semantics/published

Published
1993

9. Polyanion Inhibitors of Human Immunodeficiency Virus and Other Viruses. Part 2. Polymerized Anionic Surfactants Derived from Amino Acids and Dipeptides

Author

Leydet, A., primary, El Hachemi, H., additional, Boyer, B., additional, Lamaty, G., additional, Roque, J. P., additional, Schols, D., additional, Snoeck, R., additional, Andrei, G., additional, Ikeda, S., additional, Neyts, J., additional, Reymen, D., additional, Este, J., additional, Witvrouw, M., additional, and De Clercq, E., additional more...

Published
1996
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11. T30177, an oligonucleotide stabilized by an intramolecular guanosine octet, is a potent inhibitor of laboratory strains and clinical isolates of human immunodeficiency virus type 1

Author

Ojwang, J O, primary, Buckheit, R W, additional, Pommier, Y, additional, Mazumder, A, additional, De Vreese, K, additional, Esté, J A, additional, Reymen, D, additional, Pallansch, L A, additional, Lackman-Smith, C, additional, and Wallace, T L, additional more...

Published
1995
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12. Differential antiviral activity of derivatized dextrans

Author

Neyts, J., primary, Reymen, D., additional, Letourneur, D., additional, Jozefonvicz, J., additional, Schols, D., additional, Este, J., additional, Andrei, G., additional, McKenna, P., additional, Witvrouw, M., additional, Ikeda, S., additional, Clement, J., additional, and DE Clercq, E., additional more...

Published
1995
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18. Activity of a Sulfated Polysaccharide Extracted from the Red Seaweed Aghardhiella Tenera against Human Immunodeficiency Virus and Other Enveloped Viruses

Author

Witvrouw, M., primary, Este, J. A., additional, Mateu, M. Q., additional, Reymen, D., additional, Andrei, G., additional, Snoeck, R., additional, Ikeda, S., additional, Pauwels, R., additional, Bianchini, N. V., additional, Desmyter, J., additional, and De Clercq, E., additional more...

Published
1994
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21. Meningoradiculoneuritis due to acyclovir‐resistant varicella zoster virus in an acquired immune deficiency syndrome patient

Author

Snoeck, R., primary, Gérard, M., additional, Sadzot‐Delvaux, C., additional, Andrei, G., additional, Balzarini, J., additional, Reymen, D., additional, Ahadi, N., additional, De Bruyn, J. M., additional, Piette, J., additional, Rentier, B., additional, Clumeck, N., additional, and De Clercq, E., additional more...

Published
1994
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24. Activity of a Sulfated Polysaccharide Extracted from the Red Seaweed Aghardhiella Teneraagainst Human Immunodeficiency Virus and Other Enveloped Viruses

Author

Witvrouw, M., Este, J. A., Mateu, M. Q., Reymen, D., Andrei, G., Snoeck, R., Ikeda, S., Pauwels, R., Bianchini, N. V., Desmyter, J., and De Clercq, E.

Abstract

A galactan sulfate (GS) was isolated from an aqueous extract of the red seaweed Aghardhiella teneraand partially purified. GS inhibited the cytopathic effect of human immunodeficiency virus type 1 (HIV-1) and type 2 (HIV-2) in MT-4 cells at concentrations 10-fold higher than those required for the inhibition by dextran sulfate (MW 5000) of the cytopathic effect of HIV-1 and HIV-2 (50% inhibitory concentrations: 0.5 and 0.05 μg ml−1, respectively). GS suppressed syncytium formation between MOLT-4 cells and persistently HIV-1- or HIV-2-infected HUT-78 cells at concentrations higher than 5 μg ml−1. Like dextran sulfate (DS) and aurintricarboxylic acid (ATA), GS inhibited the binding of HIV-1 to the cells and the binding of anti-gp120 mAb to HIV-1 gp120. Like DS and ATA, GS proved active not only against HIV-1 and HIV-2 but also against other enveloped viruses, i.e. herpes-, toga-, arena-, myxo- and rhabdoviruses. GS represents a natural polysaccharide with broad-spectrum activity against a number of important viral pathogens. more...

Published
1994
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30. Anti-HIV and anti-HCMV activities of new aurintricarboxylic acid analogues

Author

Cushman, M., Wang, P., Reymen, D., Este, J., Witvrouw, M., Neyts, J., and Declercq, E.

Subjects
HIV (Viruses) -- Inactivation, Herpesviruses, Antiviral agents -- Evaluation
Abstract

According to the authors' abstract of an article published in Antiviral Chemistry & Chemotherapy, "A variety of aurintricarboxylic acid (ATA) polymer analogues were prepared by substituting certain salicylic acid derivatives [...] more...

Published
1995

31. The bicyclams, a new class of potent human immunodeficiency virus inhibitors, block viral entry after binding.

Author

De Vreese K, Reymen D, Griffin P, Steinkasserer A, Werner G, Bridger GJ, Esté J, James W, Henson GW, Desmyter J, Anné J, and De Clercq I

Subjects
Antibodies, Monoclonal immunology, Base Sequence, Benzodiazepines pharmacology, Benzylamines, Cyclams, DNA Primers, DNA, Viral biosynthesis, DNA, Viral drug effects, Drug Resistance, Microbial, Giant Cells, HIV Antibodies immunology, HIV Envelope Protein gp120 immunology, HIV-1 genetics, HIV-1 pathogenicity, Humans, Imidazoles pharmacology, Molecular Sequence Data, Peptide Fragments immunology, Tumor Cells, Cultured, Antiviral Agents pharmacology, HIV-1 drug effects, Heterocyclic Compounds pharmacology
Abstract

The bicyclams represent a new class of highly potent and selective HIV inhibitors. Time-of-addition experiments have previously shown that these compounds interfere with an early event in the viral replicative cycle. Additional experiments have now been carried out in order to investigate in more detail the mechanism of action of these promising compounds. As described in this paper, PCR experiments revealed that no viral DNA was formed following viral infection, thus confining the target(s) of action of the bicyclams to an early stage of HIV infection. An assay, using pseudotype virions containing the envelope of HIV-1 and the genome of a plaque-forming virus (Cocal Virus), pointed to viral entry as the main target of the bicyclams. HIV-1 strains resistant to two prototype bicyclams, JM2763 and SID791 (JM3100), were raised. Results obtained with SID791 with respect to syncytium formation induced by SID791-sensitive and -resistant HIV-1 strains and the cross-resistance observed for dextran sulfate, suggest inhibition of binding and/or fusion as a plausible target of SID791. Additional experiments enabled us to exclude SID791 and JM2763 as binding inhibitors and to conclude that bicyclams block the entry of cell-bound virus. Furthermore, a monoclonal antibody recognising the V3 loop of wild-type gp120 did not bind to this region in the two bicyclam-resistant strains. Our results point to gp120 as a possible target for the HIV-inhibitory effects of the bicyclams. more...

Published
1996
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32. Cosalane analogues with enhanced potencies as inhibitors of HIV-1 protease and integrase.

Author

Cushman M, Golebiewski WM, Pommier Y, Mazumder A, Reymen D, De Clercq E, Graham L, and Rice WG

Subjects
Amino Acid Sequence, Aurintricarboxylic Acid chemistry, Aurintricarboxylic Acid pharmacology, Cell Line, HIV-1 enzymology, HIV-1 physiology, Herpesviridae drug effects, Humans, Integrases, Microbial Sensitivity Tests, Molecular Sequence Data, Virus Replication drug effects, Antiviral Agents pharmacology, Aurintricarboxylic Acid analogs & derivatives, DNA Nucleotidyltransferases antagonists & inhibitors, HIV Protease Inhibitors pharmacology, HIV-1 drug effects
Abstract

Several new analogues of the novel anti-HIV agent cosalane have been synthesized and evaluated as inhibitors of HIV-1 integrase and protease, HIV-1 replication, HIV-1 and HIV-2 cytopathicity, HIV-1- and HIV-2-mediated syncytium formation, and cytopathicity of a variety of human pathogenic viruses. The congeners displayed enhanced potencies relative to cosalane itself as inhibitors of HIV-1 integrase and protease. The two most potent analogues against HIV-1 integrase displayed IC50 values of 2.2 microM, while the three most potent compounds against HIV-1 protease had IC50 values in the 0.35-0.39 microM range. In addition to its activity against HIV-1 and HIV-2 cytopathicity, cosalane inhibited the cytopathic effects of herpes simplex virus-1, herpes simplex virus-2, and human cytomegalovirus at concentrations that were well below the cytotoxic concentrations. Potentially useful antiviral activities were also revealed for some of the new cosalane congeners against influenza virus, Junin virus, and Tacaribe virus. more...

Published
1995
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