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

Antiviral Research

Volumn 29, Issue 2-3, 1996, Pages 209-219

  De Vreese, Karen ^a   Reymen, Diane ^a   Griffin, Philip ^b   Steinkasserer, Alexander ^c   Werner, Gudrun ^c   Bridger, Gary J ^d   Esté, José ^a   James, William ^b   Henson, Geoffrey W ^d   Desmyter, Jan ^a   Anné, Jozef ^a   De Clercq, Erik ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^b UNIVERSITY OF OXFORD   (United Kingdom)

^c NOVARTIS PHARMA AG   (Switzerland)

^d Johnson Matthey Pharmaceutical Res   (United States)

Author keywords

bicyclams; entry; human immunodeficiency virus

Indexed keywords

1,1' PROPYLENEBIS(1,4,8,11 TETRAAZACYCLOTETRADECANE); 1,1' [1,4 PHENYLENEBIS(METHYLENE)]BIS(1,4,8,11 TETRAAZACYCLOTETRADECANE); ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; AURINTRICARBOXYLIC ACID; BICYCLAM DERIVATIVE; DEXTRAN SULFATE; GLYCOPROTEIN GP 120; JM 2763; MONOCLONAL ANTIBODY; NEW DRUG; R 86163; TIVIRAPINE; UNCLASSIFIED DRUG; VIRUS DNA;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CROSS RESISTANCE; DRUG BINDING; DRUG MECHANISM; DRUG RESISTANCE; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL; SYNCYTIUM; VIRION; VIRUS ENVELOPE; VIRUS GENOME; VIRUS INFECTION; VIRUS INHIBITION;

COCAL VIRUS; DNA VIRUSES; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 0029939009     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/0166-3542(95)00837-3     Document Type: Article

References (20)

1. Baba, M., Schols, D., Pauwels, R., Nakashima, H. and De Clercq, E. (1990) Sulfated polysaccharides as potent inhibitors of HIV-induced syncytium formation: a new strategy towards AIDS chemotherapy. J. Acquir. Immun. Defic. Syndr. 3, 493-499.
2. Bridger, G.J., Skerlj, R.T., Thornton, D., Padmanabhan, S., Martellucci, S.A., Henson, G.W., Adams, M.J., Yamamoto, N., De Vreese, K., Pauwels, R. and De Clercq, E. (1995) Synthesis and structure-activity relationships of phenylenebis(methylene)-linked bis-tetraazamacrocycles that inhibit HIV replication. Effects of macrocyclic ring size and substituents on the aromatic linker. J. Med. Chem. 38, 366-378.
3. Callahan, L.N., Phelan, M., Mallinson, M. and Norcross, M.A.. (1991) Dextran sulfate blocks antibody binding to the principal neutralizing domain of human immunodeficiency virus type 1 without interfering with gp120-CD4 interactions. J. Virol. 65, 1543-1550.
4. Cushman, M., Wang, P., Stowell, J.G., Schols, D. and De Clercq, E.. (1992) Structural investigation and anti-HIV activities of high molecular weight ATA polymers. J. Org. Chem. 57, 7241-7248.
5. De Clercq, E., Yamamoto, N., Pauwels R., Baba, M., Schols, D., Nakashima, H., Balzarini, J., Debyser, Z., Murrer, B.A., Schwartz, D., Thornton, D., Bridger, G.,. Fricker, S, Henson, G., Abrams, M. and Picker, D. (1992) Potent and selective inhibition of human immunodeficiency virus (HIV)-1 and HIV-2 replication by a class of bicyclams interacting with a viral uncoating event. Proc. Natl. Acad. Sci. USA 89, 5286-5290.
6. De Clercq, E., Yamamoto, N., Pauwels, R., Balzarini, J., Witvrouw, M., De Vreese, K., Debyser, Z., Rosenwirth, B., Peichl, P., Datema, R., Thornton, D., Skerlj, R., Gaul, F., Padmanabhan, S., Bridger, G., Henson, G. and Abrams, M. (1994) Highly potent and selective inhibition of human immunodeficiency virus by the bicyclam derivative SID791. Antimicrob. Agents Chemother. 38, 668-674.
7. De Vreese, K., Kofler-Mongold, V., Leutgeb, C., Weber, V., Vermeire, K., Schacht, S., Anné, J., De Clercq, E., Datema, R. and Werner, G. (1996) The molecular target of bicyclams, potent inhibitors of human immunodeficiency virus replication. J. Virol. 70(2) 689-696.
8. Gregory, S., Collman, R., James, W., Gordon, S., Gonzalez-Scarano, F. and Nathanson, N. (1993) HIV-1 pseudotype virus containing a Cocal virus genome and an HIV envelope: construction, assay and use. J. Virol. Methods 44, 287-304.
9. Harada, S., Koyanagi, Y. and Yamamoto, N. (1985) Infection of HTLV-III/LAV in HTLV-I-carrying cells MT-2 and MT-4 and application in a plaque assay. Science 229, 563-566.
10. Harrop, H.A., Coombe, D.R. and Rider, C.C. (1994) Heparin specifically inhibits binding of V3 loop antibodies to HIV-1 gp120, an effect potentiated by CD4 binding. AIDS 8, 183-192.
11. Kikukawa, R., Koyanagi, Y., Harada, S., Kobayashi, N., Hatanaka, M. and Yamamoto, N. (1986) Differential susceptibility to the acquired immunodeficiency syndrome retrovirus in cloned cells of human leukemia T-cell line MOLT-4. J. Virol. 57, 1159-1162.
12. Levy, J.A., Hoffman, A.D., Kramer, S.M., Landis, J.A., Shimabukuro, J.M. and Oshiro, L.S. (1984) Isolation of lymphocytopathic retroviruses from San Francisco patients with AIDS. Science 225, 840-842.
13. McClure, M.O., Moore, J. P., Blanc, D. F., Scotting, P., Cook, G.M.W., Keynes, R.J., Weber, J.N., Davies, D. and Weiss, R.A. (1992) Investigations into the mechanism by which sulfated polysaccharides inhibit HIV infection in vitro. Aids Res. Hum. Retroviruses 8, 19-26.
14. Pauwels, R., Balzarini, J., Baba, M., Snoeck, R., Schols, D., Herdewijn, P., Desmyter, J. and De Clercq, E. (1988) Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds. J. Virol. Methods 20, 309-321.
15. Pleskoff, O., Seman, M. and Alizon, M. (1995) Amphotericin B derivative blocks human immunodeficiency virus type 1 entry after CD4 binding: effect on virus-cell fusion but not on cell-cell fusion. J. Virol. 69, 570-574.
16. Popovic, M., Sarngadharan, M.G., Read, E. and Gallo, R.C. (1984) Detection, isolation and continuous production of cytopathic retroviruses (HTLV-III) from patients with AIDS and pre-AIDS. Science 224, 497-500.
17. Schols, D., Baba, M., Pauwels, R. and De Clercq, E. (1989a) Flow cytometry method to demonstrate whether anti-HIV agents inhibit virion binding to T4+ cells. J. Acquir. Immun. Defic. Syndr. 2, 10-15.
18. Schols, D., Pauwels, R., Baba, M., Desmyter, J. and De Clercq, E. (1989b) Syncytium formation and destruction of bystander CD4+ cells cocultured with T cells persistently infected with human immunodeficiency virus as demonstrated by flow cytometry. J. Gen. Virol. 70, 2397-2408.
19. Schols, D., Pauwels, R., Desmyter, J. and De Clercq, E. (1990) Dextran sulfate and other polyanionic anti-HIV compounds specifically interact with the viral gp120 glycoprotein expressed by T-cells persistently infected with HIV-1. Virology 175, 556-561.
20. Steinkasserer, A., Harrison, R., Billich, A., Hammerschmid, F., Werner, G., Woltf, B., Peichl, P., Palfi, G., Schnitzel, W., Mlynar, E. and Rosenwirth, B. (1995) Mode of action of SDZ NIM 811, a nonimmunosuppressive cyclosporin A analog with activity against human immunodeficiency virus type 1 (HIV-1): interference with early and late events in HIV-1 replication. J. Virol. 69, 814-824.