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5. Design, synthesis and structure relationships of new N,N',N',N''-tetrakis (omega-amino alkyl) tetraazamacrocycles

Author

Trabaud C, Dessolin J, Camplo M, Hantz O, Fabien Zoulim, Borel C, Meyer M, Pepe G, Jc, Chermann, and Jl, Kraus

Subjects
Aza Compounds, Magnetic Resonance Spectroscopy, Spectrometry, Mass, Fast Atom Bombardment, Virus Replication, Antiviral Agents, Cell Line, Hepatitis B Virus, Duck, Structure-Activity Relationship, Ducks, Drug Design, DNA, Viral, HIV-1, Animals, Humans, Cells, Cultured
Abstract

A number of N,N',N",N"'-tetrakis (omega-aminoalkyl) tetraazamacrocycles and related compounds were synthesized and evaluated for their inhibitory effects on human immunodeficiency virus type 1 (HIV-1) and duck hepatitis B virus (DHBV) replication. The activity of these compounds was found to be highly dependent upon structural features: (i) the length of the alkyl linker connecting the nitrogen atoms of the macrocyclic ring to the exocyclic nitrogen atoms of the terminal amino groups (five methylenes favoured antiviral activity); (ii) substitution of the terminal amino groups of the linker reduced antiviral activity; and (iii) the size of the tetraazamacrocyclic ring (14 or 15 atoms) did not markedly affect the antiviral activity. Some analogues were potent inhibitors of HIV-1 replication, with anti-HIV activity similar to that of biscyclam (JM 2763). In contrast, other analogues were found to be highly toxic in duck hepatocyte primary culture, the 2.2.15 cell line and to a lesser extent in MT-4 cells. Structural parameters, macrocyclic ring size and metal-chelating ability have been used to develop a structure-activity relationship model in order to aid the design of antiviral molecules derived from N,N',N",N"'-tetrakis (omega-aminoalkyl) tetraazamacrocycles.

Published
1999

6. 437 ANRS 12202: HEPATITIS B AND DELTA HEPATITIS IN CENTRAL AFRICAN REPUBLIC (CAR): VIROLOGICAL REASSESSMENT OF A FULMINANT HEPATITIS OUTBREAK OCCURRING IN THE MID EIGHTIES

Author

Samba, D., primary, Abdou-Chekaraou, M., additional, Gina, L., additional, Brichler, S., additional, Sholtés, C., additional, Martel, N., additional, Ouavéné, J.-O., additional, Kay, A., additional, Hantz, O., additional, Lesbordes, J.-L., additional, Trépo, C., additional, Gordien, E., additional, Zoulim, F., additional, Komas, N.P., additional, and Dény, P., additional

Published
2012
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7. ChemInform Abstract: Modelization, Synthesis and Antiviral Evaluation of New 2,3- Disubstituted Thiazolidinone Nucleoside Analogues.

Author

GRACIET, J. C., primary, NIDDAM, V., additional, GAMBERONI, M., additional, TRABAUD, C., additional, DESSOLIN, J., additional, MEDOU, M., additional, MOURIER, N., additional, ZOULIM, F., additional, BOREL, C., additional, HANTZ, O., additional, CAMPLO, M., additional, CHERMANN, J. C., additional, and KRAUS, J. L., additional

Published
2010
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15. P.158 Novel interferon alpha variant with improved inhibitory activity against HCV genotype 1 replication compared to IFN alpha-2b therapy, in a subgenomic replicon system

Author

Escuret, V., primary, Durantel, D., additional, Martin, A., additional, Parent, R., additional, Hantz, O., additional, Trépo, C., additional, Menguy, T., additional, Bottius, E., additional, Dardy, J., additional, Maral, J., additional, Escary, J., additional, and Zoulim, F., additional

Published
2006
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25. ChemInform Abstract: Synthesis and Antiviral Activity of N‐4′‐Dihydropyridinyl and Dihydroquinolinylcarbonyl‐2‐hydroxymethyl‐5‐(cytosin‐1′‐yl)‐1,3‐ oxathiolane Derivatives (V) Against Human Immunodeficiency Virus and Duck Hepatitis B Virus.

Author

CAMPLO, M., primary, CHARVET‐FAURY, A. S., additional, BOREL, C., additional, TURIN, F., additional, HANTZ, O., additional, TRABAUD, C., additional, NIDDAM, V., additional, MOURIER, N, additional, GRACIET, J. C., additional, CHERMANN, J. C., additional, and KRAUS, J. L., additional

Published
1996
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29. Synthesis and antiviral activity of N-4′-dihydropyridinyl and dihydroquinolinylcarbonyl-2-hydroxymethyl-5-[cytosin-1′-yl]-1,3-oxathiolane derivatives against human immunodeficiency virus and duck hepatitis B virus

Author

Camplo, M, primary, Charvet-Faury, AS, additional, Borel, C, additional, Turin, F, additional, Hantz, O, additional, Trabaud, C, additional, Niddam, V, additional, Mourier, N, additional, Graciet, JC, additional, Chermann, JC, additional, and Kraus, JL, additional

Published
1996
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41. Detection by immunofluorescence of a new 'core-like' Ag/Ab system in liver and serum of patients with NANB hepatitis.

Author

Trepo, C., Vitvitski, L., Hantz, O., Chevallier, P., Lehman, H., Schlaak, M., and Sepetjan, M.

Abstract

ABSTRACT- Using direct immunofluorescence, a nuclear antigen was found in liver of chronic hepatitis patients with circulating NANBe Ag or anti-NANBe, and selected sera from either group were used as source of conjugates. The new Ag/Ab system was designated NANBc Ag and anti-NANBc since it behaved like the core Ag of HBV. N ANBc Ag was detected in coded frozen liver biopsies from patients with chronic persistent 15/25 (60 %) or active 27/50 (54 %) hepatitis and cryptogenic cirrhosis 16/30 (53.3%) devoid of HBV markers. Only 2/30 alcoholic cirrhosis cases (7%) used as controls were positive (p≤0.001). The homologous anti-NANBc antibody was always detectable by indirect immunofluorescence in the patients' serum when N ANBc Ag was found in the liver. It was also found in 11/135 (8%) additional cases without any other NANB marker. A correlation was observed between coded detection of the NANBc Ag/Ab system by immunofluorescence and demonstration of NANBe Ag or anti-NANBe by immunodiffusion. In acute post-transfusion NANB hepatitis, anti-NANBc was first detectable 14 days after transfusion and persisted as long as ALT remained elevated, or longer. IgM anti-NANBc present at onset became associated with an increasing proportion of IgG after the 28th day. The prevalence of anti-NANBc in sporadic NANB hepatitis (11/50 = 22%) was significantly lower (p≤0.001) than in cases with parenteral exposure such as post-transfusion, occupational or drug addict hepatitis (47/72 = 65%). Immunofluorescent tests for NANBc Ag and Ab are promising assays for the serological diagnosis of NANB hepatitis. [ABSTRACT FROM AUTHOR]

Published
1981
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46. Potent Nonclassical Nucleoside Antiviral Drugs Based on the N,N-Diarylformamidine Concept

Author

Anastasi, C., Hantz, O., Clercq, E. De, Pannecouque, C., Clayette, P., Dereuddre-Bosquet, N., Dormont, D., Gondois-Rey, F., Hirsch, I., and Kraus, J.-L.

Abstract

New formamidine-3TC (3TC = 2‘,3‘-dideoxy-3‘-thiacytidine) analogues have been synthesized through various methods, and their antiviral activities (HIV, HBV) have been evaluated in vitro. Anti-HIV-1 in acutely infected MT-4 cells and peripheral blood monocellular cells (PBMCs) showed that compounds substituted by N,N-diarylformamidine side chains at the 4-N nucleic base position (compounds 3 and 8−11) had at least equivalent anti-HIV activity as 3TC (EC50 = 0.5 and 11.6 μM, respectively). Moreover, the newly synthesized compounds demonstrated higher anti-HBV activity (EC50 ranging from 0.01 to 0.05 μM) compared to the parent nucleoside 3TC (EC50 = 0.2 μM). It should be underlined that these new promising derivatives inhibited HIV in cells of a macrophage lineage, which are known to be cellular reservoir for HIV. These results were particularly of interest, since the antiviral activities appeared not to be mediated through the formamidine bond hydrolysis and consequently the release of free 3TC. These new analogue series were found to be highly stable to hydrolysis even after prolonged incubation in different biological media (t1/2 ranged from 48 to 120 h). This enzymatic stability, coupled to the fact that no delay in the antiviral response was observed compared to the free 3TC antiviral response, suggest that this new N,N-diarylformamidine nucleoside series should not be considered as classical prodrugs.

Published
2004

49. Comparison of properties of woodchuck hepatitis virus and human hepatitis B virus endogenous DNA polymerases

Author

Hantz, O, Ooka, T, Vitvitski, L, Pichoud, C, and Trepo, C

Abstract

The principal properties of the DNA polymerases of woodchuck hepatitis virus and human hepatitis B virus were compared. The enzymes of both viruses exhibited optimal activities in the same range of pH, ionic strength, and MgCl2 concentration. Like human hepatitis B virus DNA polymerase, the woodchuck hepatitis virus DNA polymerase was strongly inhibited by phosphonoformic acid but not by phosphonoacetic acid and aphidicolin. Similar inhibition patterns for both enzymes were observed with arabinofuranosyl nucleotides (9-beta-D-arabinofuranosyladenine-5'-triphosphate, 1-beta-D-arabinofuranosylcytosine-5'-triphosphate, 1-beta-D-arabinofuranosylthymine-5'-triphosphate) and dideoxythymidine triphosphate, whereas no effect was obtained with corresponding nucleosides. The therapeutic significance of these results and the relevance of the woodchuck as an experimental animal model for the study of human hepatitis B virus infections are discussed.

Published
1984
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