SRR-SB3, a disulfide-containing macrolide that inhibits a late stage of the replicative cycle of human immunodeficiency virus

Antimicrobial Agents and Chemotherapy

Volumn 41, Issue 2, 1997, Pages 262-268

  Witvrouw, M ^a   Balzarini, J ^a   Pannecouque, C ^a   Jhaumeer Laulloo, S ^b   Este J A ^a   Schols, D ^a   Cherepanov, P ^a   Schmit, J C ^a   Debyser, Z ^a   Vandamme, A M ^a   Desmyter, J ^a   Ramadas, S R ^b   De Clercq, E ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^b UNIVERSITY OF MAURITIUS   (Mauritius)

Author keywords

[No Author keywords available]

Indexed keywords

ADEFOVIR; BENZAMIDE DERIVATIVE; MACROLIDE; PROTEINASE INHIBITOR; RITONAVIR; RNA DIRECTED DNA POLYMERASE INHIBITOR; SAQUINAVIR; STAVUDINE; ZALCITABINE; ZIDOVUDINE; ZINC FINGER PROTEIN;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; DRUG EFFICACY; DRUG MECHANISM; DRUG STRUCTURE; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; INTRAPERITONEAL DRUG ADMINISTRATION; MOLONEY MURINE SARCOMA ONCOVIRUS; MONONUCLEAR CELL; MOUSE; NONHUMAN; PRIORITY JOURNAL; SIMIAN IMMUNODEFICIENCY VIRUS; VIRUS REPLICATION;

EID: 0031046754     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.41.2.262     Document Type: Article

References (59)

1. Andrei, G., and E. De Clercq. 1990. Inhibitory effect of selected antiviral compounds on arenavirus replication in vitro. Antiviral Res. 14:287-300.
2. Baba, M., M. Ito, S. Shigeta, and E. De Clercq. 1984. Synergistic antiviral effects of antiherpes compounds and human leukocyte interferon on varicella-zoster virus in vitro. Antimicrob. Agents Chemother. 25:515-517.
3. Baba, M., D. Schols, R. Pauwels, H. Nakashima, and E. De Clercq. 1940. Sulfated polysaccharides as potent inhibitors of HIV-induced syncytium formation: a new strategy towards AIDS chemotherapy. J. Acquired Immune Defic. Syndr. 3:493-499.
4. Balzarini, J., L. Naesens, P. Herdewijn, I. Rosenberg, A. Holý, R. Pauwels, M. Baba, D. G. Johns, and E. De Clercq. 1989. Marked in vivo antiretrovirus activity of 9-(2-phosphonylmethoxyethyl)adenine, a selective anti-human immunodeficiency virus agent. Proc. Natl. Acad. Sci. USA 86:332-336.
5. Balzarini, J., A. Karlsson, M.-J. Pérez-Pérez, M.-J. Camarasa, and E. De Clercq. 1993. Knocking-out concentrations of HIV-1-specific inhibitors completely suppress HIV-1 infection and prevent the emergence of drug-resistant virus. Virology 196:576-585.
6. Balzarini, J., A. Karlsson, M.-J. Pérez-Pérez, M.-J. Camarasa, W. G. Tarpley, and E. De Clercq. 1993. Treatment of human immunodeficiency virus type 1 (HIV-1)-intected cells with combinations of HIV-1-specific inhibitors result in a different resistance pattern than does treatment with single-drug therapy. J. Virol. 67:5353-5359.
7. Balzarini, J., A. Karlsson, M.-J. Pérez-Pérez, L. Vrang, J. Walbers, H. Zhang, B. Öberg, A.-M. Vandamme, M.-J. Camarasa, and E. De Clercq. 1993. HIV-1-specific reverse transcriptase inhibitors show differential activity against HIV-1 mutant strains containing different amino acid substitutions in the reverse transcriptase. Virology 192:246-253.
8. Balzarini, J., A. Karlsson, A.-M. Vandamme, M.-J. Pérez-Pérez. H. Zhang, L. Vrang, B. Öberg, K. Bäckbro, T. Unge, A. San-Fëlix, S. Veläzquez, M.-J. Camarasa, and E. De Clercq. 1993. Human immunodeficiency virus type 1 (HIV-1) strains selected for resistance against the HIV-1-specitic [2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-spiro-5″- (4″-amino-1″,2″-oxathiole-2″,2″-dioxide)]-β- D-pentofuranosyl (TSAO) nucleosidc analogues retain sensitivity to HIV-1-specific nonnucleoside inhibitors. Proc. Natl. Acad. Sci. USA 90: 6952-6956.
9. Barré-Sinoussi, F., J. C. Chermann, F. Rey, M. T. Nugeyre, S. Chamaret, J. Gruest, C. Dauguet, C. Axler-Blin, F. Vézinet-Brun, C. Rouzioux, W. Rozenbaum, and L. Montagnier. 1983. Isolation of a T-lymphotropic retrovirus from a patient at risk for AIDS. Science 220:868-871.
10. Berg, J. M. 1986. Potential metal-binding domains in nucleic acid binding proteins. Science 232:485-487.
11. Burke, C. J., G. Sanyal, M. W. Bruner, J. A. Ryan, R. L. LaFemina, H. L. Robbins, A. S. Zeft, C. R. Middaugh, and M. G. Cordingley. 1992. Structural implications of spectroscopic characterization of a putative zinc finger peptide from HIV-1 integrase. J. Biol. Chem. 267:9639-9644.
12. Bushman, F. D., A. Engelman, I. Palmer, P. Wingfield, and R. Craigie. 1993. Domains of the integrase protein of human immunodeficiency virus type 1 responsible for polynucleotide transfer and zinc binding. Proc. Natl. Acad. Sci. USA 90:3428-3432.
13. Bushman, F. D., and R. Craigie. 1991. Activities of human immunodeficiency virus (HIV) integration protein in vitro: specific cleavage and integration of HIV DNA. Proc. Natl. Acad. Sci. USA 88:1339-1343.
14. Condra, J. H., W. A. Schleif, O. M. Blahy, L. J. Gabryelsky, D. J. Graham, J. C. Quintero, A. Rhodes, H. L. Robbins, E. Roth, M. Shivaprakash, D. Titus, T. Yang, H. Teppler, K. E. Squires, P. J. Deutsch, and E. A. Emini. 1995. In vivo emergence of HIV-1 variants resistant to multiple protease inhibitors. Nature (London) 374:569-571.
15. Daniel, M. D., N. L. Letvin, P. K. Sehgal, G. Hunsmann, D. K. Schmidt, N. W. King, and R. C. Desrosiers. 1987. Long-term persistent infection of macaque monkeys with the simian immunodeficiency virus. J. Gen. Virol. 68:3183-3189.
16. D'Aquila, R. T., V. A. Johnson, S. L. Welles, A. J. Japour, D. R. Kuritzkes, V. DeGruttola, P. S. Reichelderfer, R. W. Cooms, C. S. Crumpacker, J. O. Kahn, and D. D. Richmand. 1995. Zidovudine resistance and HIV-1 disease progression during antiretroviral therapy. AIDS Clinical Trials Group protocol 116B/117 Team and the Virology Committee Resistance Working Group. Ann. Intern. Med. 122:401-408.
17. De Clercq, E., and T. C. Merigan. 1971. Moloney sarcoma virus-induced tumors in mice: inhibition or stimulation by (poly rI) · (poly rC). Proc. Soc. Exp. Biol. Med. 137:590-593.
18. De Clercq, E., M. Luczak, J. C. Reepmeyer, K. L. Kirk, and L. A. Cohen. 1975. Fluoroimidazoles as antiviral agents and inhibitors of polynucleotide biosynthesis. Life Sci. 17:187-194.
19. De Clercq, E., J. Descamps, G. Verhelst, R. T. Walker, A. S. Jones, P. F. Torrence, and D. Shugar. 1980. Comparative efficacy of antiherpes drugs against different strains of herpes simplex virus. J. Infect. Dis. 141:563-574.
20. De Clercq, E., J. Balzarini, P. F. Torrence, M. P. Mertes, C. L. Schmidt, D. Shugar, P. J. Barr, A. S. Jones, G. Verhelst, and R. T. Walker. 1981. Thymidylate synthetase as a target enzyme for the inhibitory activity of 5-substituted 2′-deoxyuridines on mouse leukemia L1210 cell growth. Mol. Pharmacol. 19:321-330.
21. De Clercq, E., N. Yamamoto, R. Pauwels, M. Baba, D. Schols, H. Nakashima, J. Balzarini, Z. Debyser, B. A. Murrer, D. Schwartz, D. Thornton, G. Bridger, S. Fricker, G. Henson, M. Abrams, and D. Picker. 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.
22. De Clercq, E., N. Yamamoto, R. Pauwels, J. Balzarini, M. Witvrouw, K. De Vreese, Z. Debyser, B. Rosenwirth, P. Peichl, R. Datema, D. Thornton, R. Skerlj, F. Gaul, S. Padmanabhan, G. Bridger, G. Henson, and M. Abrams. 1994. Highly potent and selective inhibition of human immunodeficiency virus by the bicyclam derivative JM3100. Antimicrob. Agents Chemother. 38:668-674.
23. Elion, G. B., S. Singer, and G. H. Hitchings. 1954. Antagonists of nucleic acid derivatives. VIII. Synergism in combination of biochemically related antimetabolites. J. Biol. Chem. 208:477-488.
24. Ellison, V., J. Gerton, K. A. Vincent, and P. O. Brown. 1995. An essential interaction between distinct domains of HIV-1 integrase mediates assembly of the active multimer. J. Biol. Chem. 270:3320-3326.
25. Emini, E. A., V. W. Byrnes, J. H. Condra, W. A. Schleif, and V. V. Sardana. 1994. The genetic and functional basis of HIV-1 resistance to nonnucleoside reverse transcriptase inhibitors. Arch. Virol. Suppl. 9:11-17.
26. Esté, J., M. Witvrouw, J. Tu, J. Desmyter, E. De Clercq, and A.-M. Vandamme. 1996. Inhibition of HIV-1 Tat mediated transactivation by oncostatin M in HL-tat cells. AIDS Res. Hum. Retroviruses 11:1355-1358.
27. Foley, G. E., H. Lazarus, S. Farber, B. G. Uzman, B. A. Boone, and R. E. McCarthy. 1965. Continuous culture of human lymphoblasts from peripheral blood of a child with acute leukemia. Cancer 18:522-529.
28. Gallo, R. C., S. Z. Salahuddin, M. Popovic, G. M. Shearer, M. Kaplan, B. F. Haynes, T. J. Palker, R. Redlield, Oleske, J., and B. Safai. 1984. Frequent detection and isolation of cytopathic retroviruscs (HTLV-III) from patients with AIDS and at risk for AIDS. Science 224:500-503.
29. Gazdar, A. F., D. N. Carney, P. A. Bunn, E. K. Russell, E. S. Jaffe, G. P. Schechter, and J. G. Guccion. 1980. Mitogen requirements for the in vitro propagation of cutaneous T-cell lymphomas. Blood 55:409-417.
30. Gozelick, R. J., I. E. Henderson, J. P. Hanser, and A. Rein. 1988. Point mutants of Moloney murine leukemia virus that fail to package viral RNA: evidence for specific RNA recognition by a "zinc finger-like" protein sequence. Proc. Natl. Acad. Sci. USA 85:8420-8424.
31. Hsu, M.-C., A. D. Schutt, M. Holly, L. W. Slice, M. I. Sherman, D. D. Richman, M. J. Potash, and D. J. Volsky. 1991. Inhibition of HIV replication in acute and chronic infections in vitro by a Tat antagonist. Science 254: 1799-1802.
32. Kawana, F., S. Shigeta, M. Hosoya, H. Suzuki, and E. De Clercq. 1987. Inhibitory effects of antiviral compounds on respiratory syncytial virus replication in vitro. Antimicrob. Agents Chemother. 31:1225-1230.
33. Larder, B. A., and S. D. Kemp. 1989. Multiple mutations in HIV-1 reverse transcriptase confer high-level resistance to zidovudinc (AZT). Science 246: 1155-1158.
34. Meric, C., and P. F. Spahr. 1986. Rous sarcoma virus nucleic acid-binding protein p12 is necessary for viral 70S RNA dimer formation and packaging. J. Virol. 60:450-459.
35. Meric, C., E. Gouilloud, and P.-F. Spahr. 1988. Mutations in Rous sarcoma virus nucleocapsid protein p12 (NC): deletions of Cys-Hyx boxes. J. Virol. 62:3328-3333.
36. Miyoshi, I., H. Tagucbi, I. Kobonishi, S. Yoshimoto, Y. Ohtsuki, Y. Shiraishi, and T. Akagi. 1982. Type C virus-producing cell lines derived from adult T cell leukemia. Gann Monogr. 28:219-228.
37. Montaner, J. S., J. Singer, M. T. Schechter, J. M. Raboud, C. Tsoukas, M. O'Shaughnessy, J. Ruedy, K. Nagai, H. Salomon, B. Spira, and M. A. Wainberg. 1993. Clinical correlates of in vitro HIV-1 resistance to zidovudine. Results of a Multicentre Canadian AZT trial. AIDS 7:189-196.
38. Otsuka, M., M. Fujita, and Y. Sugiura. 1994. Novel zinc chelators which inhibit the binding of HIV-EP1 (HIV enhancer binding protein) to NF-kappa B recognition sequence. J. Med. Chem. 37:4267-4265.
39. Pauwels, R., E. De Clercq, J. Desmyter, J. Balzarini, P. Goubau, P. Herdewijn, H. Vanderhaeghe, and M. Vandeputte. 1987. Sensitive and rapid assay on MT-4 cells for the detection of antiviral compounds against the AIDS virus. J. Virol. Methods 16:171-185.
40. Pauwels, R., J. Balzarini, M. Baba, R. Snoeck, D. Schob, P. Herdewijn, J. Desmyter, and E. De Clercq. 1988. Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds. J. Virol. Methods 28:309-321.
41. Pauwels, R., K. Andries, Z. Debyser, M. J. Kukla, D. Schols, H. J. Breslin, R. Woestenborghs, J. Desmyter, M. A. Janssen, E. De Clercq, and P. A. Janssen. 1994. New tetrahydroimidazo[4,5,1-jk][1,4]-benzodiazepin-2(1H)-one and -thione derivatives are potent inhibitors of human immunodeficiency virus type 1 replication and are synergistic with 2́,3́-dideoxynucleoside analogs. Antimicrob. Agents Chemother. 38:2863-2870.
42. Popovic, M., M. G. Sarngadharan, E. Read, and R. C. Gallo, 1984. Detection, isolation and continuous production of cytopathic retroviruses (HTLV-III) from patients with AIDS and pre-AIDS. Science 224:497-500.
43. Reed, L. J., and H. Muench. 1938. A simple method of estimating fifty percent endpoints. Am. J. Hyg. 27:493-497.
44. Rey, M. A., B. Krust, A. G. Laurent, D. Guétard, L. Montagnier, and A. G. Hovanessian. 1989. Characterization of an HIV-2-related virus with a smaller sized extracellular envelope glycoprotein. Virology 173:258-267.
45. Rice, W. G., C. A. Schaeffer, B. Harten, F. Villinger, T. L. South, M. F. Summers, L. E. Henderson, J. W. J. Bess, L. O. Arthur, J. S. McDougal, S. L. Orloff, J. Mendeleyev, and E. Kun. 1993. Inhibition of HIV-1 infectivity by zinc-ejecting aromatic C-nitroso compounds. Nature (London) 361:473-475.
46. Rice, W. G., J. G. Supko, L. Malspeis, R. W. Buckheit, Jr., D. Clanton, M. Bu, L. Graham, C. A. Schaeffer, J. A. Turpin, J. Domagala, R. Gogliotti, J. P. Bader, S. M. Halliday, L. Coren, R. C. Sowder II, L. O. Arthur, and L. E. Henderson. 1995. Inhibitors of HIV nucleocapsid protein zinc fingers as candidates for the treatment of AIDS. Science 270:1194-1197.
47. Sakaguchi, K., N. Zambrano, E. T. Baldwin, B. A. Shapiro, J. W. Erickson, J. G. Omichinski, G. M. Clore, A. M. Gronenborn, and E. Appela. 1993. Identification of a binding site for the human immunodeficiency virus type 1 nucleocapsid protein. Proc. Natl. Acad. Sci. USA 90:5219-5223.
48. Schmit, J.-C., L. Ruiz, B. Clotet, A. Raventos, J. Tor, J. Leonard, J. Desmyter, E. De Clercq, and A.-M. Vandamme. 1996. Resistance related mutations in the HIV-1 protease gene of patients treated for one year with the protease inhibitor ritonavir (ABT-538). AIDS 10:995-999.
49. + cells. J. Acquired Immune Defic. Syndr. 2:10-15.
50. Schols, D., M. Baba, R. Pauwels, J. Desmyter, and E. De Clercq. 1989. Specific interaction of aurintricarboxylic acid with the human immunodeficiency/CD4 cell receptor. Proc. Natl. Acad. Sci. USA 86:3322-3326.
51. + cells cocultured with T cells persistently infected with human immunodeficiency virus as demonstrated by flow cytometry. J. Gen. Virol. 70:2397-2408.
52. Schols, D., R. Pauwels, J. Desmyter, and E. De Clercq. 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.
53. Sherman, P. A., and J. A. Fyfe. 1990. Human immunodeficiency virus integration protein expressed in Escherichia coli possesses selective DNA cleaving activity. Proc. Natl. Acad. Sci. USA 87:5119-5123.
54. Spire, B., J. Sire, V. Zachar, F. Rey, F. Barré-Sinoussi, F. Galibert, A. Hampe, and J. C. Chermann. 1989. Nucleotide sequence of HIV1-NDK: a highly cytopathic strain of human immunodeficiency virus. Gene 81:275-284.
55. Tummino, P. J., J. D. Scholten, P. J. Harvey, T. P. Holler, L. Maloney, R. Gogliotti, J. Domagala, and D. Hupe. 1996. The in vitro ejection of zinc from human immunodeficiency virus (HIV) type 1 nucleocapsid protein by disulfide benzamides with cellular anti-HIV activity. Proc. Natl. Acad. Sci. USA 93:969-973.
56. Vandamme, A.-M., K. Fransen, L. Debaisieux, D. Marissens, S. Sprecher, D. Vaira, A. T. Vandenbroucke, C. Verhofstede, and the Belgian AIDS Reference Laboratories. 1995. Standardisation of primers and an algorithm for HIV-1 diagnostic PCR evaluated in patients harbouring strains of diverse geographical origin. J. Virol. Methods 51:305-316.
57. Vinckier, F., M. Boogaerts, D. De Clerck, and E. De Clercq. 1987. Chronic herpetic infection in an immunocompromised patient: report of a case. J. Oral Maxillofac. Surg. 45:723-728.
58. Witvrouw, M., D. Schols, G. Andrei, R. Snoeck, M. Hosoya, R. Pauwels, J. Balzarini, and E. De Clercq. 1991. Antiviral activity of low-MW dextran sulfate (derived from dextran MW 1,000) compared to dextran sulfate samples of higher MW. Antiviral Chem. Chemother. 2:171-179.
59. Witvrouw, M., R. Pauwels, A.-M. Vandamme, D. Schols, R. Reymen, N. Yamamoto, J. Desmyter, and E. De Clercq. 1992. Cell type-specific anti-human immunodeficiency virus type 1 activity of the transactivation inhibitor Ro 5-3335. Antimicrob. Agents Chemother. 36:2628-2633.