Identification of novel thiocarboxanilide derivatives that suppress a variety of drug-resistant mutant human immunodeficiency virus type 1 strains at a potency similar to that for wild-type virus

Antimicrobial Agents and Chemotherapy

Volumn 40, Issue 6, 1996, Pages 1454-1466

  Balzarini, J ^a   Brouwer, W G ^b   Dao, D C ^b   Osika, E M ^b   De Clercq, E ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^b Uniroyal Chemical Ltd   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; N [4 CHLORO 3 (3 METHYL 2 BUTENYLOXY)PHENYL] 2 METHYL 3 FURANCARBOTHIOAMIDE; N [4 CHLORO 3 (3 METHYL 2 BUTENYLOXY)PHENYL] 2 METHYL 3 THIOPHENECARBOTHIOAMIDE; THIOCARBOXANILIDE; THIOCARBOXANILIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG EFFICACY; DRUG POTENCY; DRUG RESEARCH; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; PRIORITY JOURNAL; STRAIN DIFFERENCE; STRUCTURE ACTIVITY RELATION; VIRUS MUTATION;

EID: 0029904239     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.40.6.1454     Document Type: Article

References (26)

1. Ahgren, C., K. Backro, F. W. Bell, A. S. Canfrell, M. Clemens, J. M. Colacino, J. B. Deeter, J. E. Engelhart, M. Högberg, S. R. Jaskunas, N.-G. Johansson, C, L. Jordan, J. S. Kasher, M. D. Kinnick, P. Lind, C. Lopez, J. M. Morin, Jr., M. A. Muesing, R. Noreen, B. Öberg, C. J. Paget, J. A. Palkowitz, C. A. Parrish, P. Pranc, M. K. Rippy, C. Rydergard, C. Sahlberg, S. Swanson, R. J. Ternansky, T. Unge, R. T. Vasileff, L. Vrang, S. J. West, H. Zhang, and X.-X. Zhou. 1995. The PETT series: a new class of potent non-nucleoside inhibitors of human immunodeficiency virus type 1 reverse transcriptase. Antimicrob. Agents Chemother 39:1329-1335.
2. Baba, M., H. Tanaka, E. De Clercq, R. Pauwels, J. Balzarini, D. Schols, H. Nakashima, C.-F. Perno, R. T. Walker, and T. Miyasaka. 1989. Highly specific inhibition of human immunodeficiency virus type 1 by a novel 6-substituted acyclouridine derivative. Biochem. Biophys. Res Commun. 165: 1375-1381.
3. Bader, J. P., J. B. McMahon, R. J. Schultz, V. L. Narayanan, J. B. Pierce, W. A. Harrison, O. S. Weislow, C. F. Midelfort, S. F. Stinson, and M. R. Boyd. 1991. Oxathiin carboxanilide, a potent inhibitor of human immunodeficiency virus reproduction. Proc. Natl. Acad. Sci. USA 88:6740-6744.
4. Balzarini, J., W. G. Brouwer, E. E. Felauer, E. De Clercq, and A. Karlsson. 1995. Activity of various thiocarboxanilide derivatives against wild-type and several mutant human immunodeficiency virus type 1 strains Antivir. Res. 27:219-236
5. Balzarini, J., H. Jonckheere, W. A. Harrison, D. C. Dao, J. Anné, E. De Clercq, and A. Karlsson. 1995. Oxathiin carboxanilide derivatives: a class of non-nucleoside HIV-1-specific reverse transcriptase inhibitors (NNRTIs) that are active against mutant HIV-1 strains resistant to other NNRTIs. Antivir Chem. Chemother. 6:169-178.
6. Balzarini, J., A. Karlsson, and E. De Clercq. 1993. Human immunodeficiency virus type 1 drug-resistance patterns with different 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives. Mol. Pharmacol. 44:694-701.
7. 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)-infected cells with combinations of HIV-1-specific inhibitors results in a different resistance pattern than does treatment with single-drug therapy. J. Virol. 67:5353-5359.
8. 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
9. Balzarini, J., A. Karlsson, A.-M. Vandamme, M.-J. Pérez-Pérez, H. Zhang, L. Vrang, B. Öberg, K. Bäckbro, T. Unge, A. San-Félix, S. Velázquez, M.-J. Camarasa, and E. De Clercq. 1993. Human immunodeficiency virus type 1 (HIV-1) strains selected for resistance against the HIV-1-specific [2′,5′-bis-O-(tert-butyldimethylsilyl)-3′-spiro-5″- (4″-amino-1″,2″-oxathiole-2″,2″-dioxide)]-β- D-pentofuranosyl (TSAO) nucleoside analogues retain sensitivity to HIV-1-specific nonnucleoside inhibitors Proc Natl. Acad. Sci. USA 90: 6952-6956.
10. Balzarini, J., M.-J. Pérez-Pérez, S. Velázquez, A. San-Félix, M.-J. Camarasa, E. De Clercq, and A. Karlsson. 1995. Suppression of the breakthrough of human immunodeficiency virus type 1 (HIV-1) in cell culture by thiocarboxanilide derivatives when used individually or in combination with other HIV-1-specific inhibitors (i e., TSAO derivatives) Proc. Natl. Acad. Sci USA 92:5470-5474.
11. De Clercq, E. 1993. HIV-1-specific RT inhibitors highly selective inhibitors of human immunodeficiency virus type 1 that are specifically targeted at the viral reverse transcriptase. Med. Res. Rev. 13:229-258.
12. De Clercq, E. 1994. HIV resistance to reverse transcriptase inhibitors. Biochem. Pharmacol. 47:155-169.
13. Dueweke, T. J., S. M. Poppe, D. L. Romero, S. M. Swaney, A. G. So, K. M. Downey, I. W. Althaus, F. Reusser, M. Busso, L. Resnick, D. L. Mayers, J. Lane, P. A. Aristoff, R. C. Thomas, and W. G. Tarpley. 1993. U-90152, a potent inhibitor of human immunodeficiency virus type 1 replication. Antimicrob. Agents Chemother. 37:1127-1131.
14. Goldman, M. E., J. H. Nunberg, J. A. O'Brien, J. C. Quintero, W. A. Schleif. K. F. Freund, S. L. Gaul, W. S. Saari, J. S. Wai, J. M. Hoffman, P. S. Anderson, D. J. Hupe, E. A. Emini, and A. M. Stern. 1991. Pyridinone derivatives: specific human immunodeficiency virus type 1 reverse transcriptase inhibitors with antiviral activity. Proc. Natl. Acad. Sci. USA 88: 6863-6867.
15. Jacobo-Molina, A., J. Ding, R. G. Nanni, A. D. Clark, Jr., X. Lu, C. Tantillo, R. L. Williams, G. Kamer, A. L. Ferris, P. Clark, A. Hizi, S. H. Hughes, and E. Arnold. 1993. Crystal structure of human immunodeficiency virus type 1 reverse transcriptase complexed with double-stranded DNA at 3.0 A resolution shows bent DNA Proc. Natl. Acad. Sci. USA 90:6320-6324.
16. Kleim, J.-P., R. Bender, U.-M. Billhardt, C. Meichsner, G. Riess, M. Rösner, I. Winkler, and A. Paessens. 1993. Activity of a novel quinoxaline derivative against human immunodeficiency virus type 1 reverse transcriptase and viral replication. Antimicrob Agents Chemother 37:1659-1664
17. Mellors, J. W., B. A. Larder, and R. F. Schinazi. 1994. Mutations in HIV-1 reverse transcriptase and protease associated with drug resistance. Int. Antivir. News 3:8-13.
18. Merluzzi, V. J., K. D. Hargrave, M. Labadia, K. Grozinger, M. Skoog, J. C. Wu, C.-K. Shin, K. Eckner, S. Hattox, J. Adams, A. S. Rosenthal, R. Faanes, R. J. Eckner, R. A. Koup, and J. L. Sullivan. 1990. Inhibition of HIV-1 replication by a non-nucleoside reverse transcriptase inhibitor. Science 250: 1411-1413.
19. Miyasaka, T., H. Tanaka, M. Baba, H. Hayakawa, R. T. Walker, J. Balzarini. and E. De Clercq. 1989. A novel lead for specific anti-HIV-1 agents: 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine. J. Med. Chem. 32:2507-2509.
20. Nanni, R. G., J. Ding, A. Jacobo-Molina, S. H. Hughes, and E. Arnold. 1993 Review of HIV-1 reverse transcriptase three-dimensional structure, implications for drug design. Perspect. Drug Discov. Des. 1:129-150.
21. Nunberg, J. H., W. A. Schleif, E. J. Boots, J. A. O'Brien, J. C. Quintero, J. M. Hoffman, E. A. Emini, and M. E. Goldman. 1991. Viral resistance to human immunodeficiency virus type 1-specific pyridinone reverse transcriptase inhibitors. J. Virol. 65:4887-4892.
22. Pauwels, R., K. Andries, Z. Debyser, P. Van Daele, D. Schols, P. Stoffels, K. De Vreese, R. Woestenborghs, A.-M. Vandamme, C. C. M. Janssen, J. Anné, G. Cauwenbergh, J. Desmyter, J. Heykants, M. A. C. Janssen, E. De Clercq, and P. A. J. Janssen. 1993. Potent and highly selective human immunodeficiency virus type 1 (HIV-1) inhibition by a series of α-anilinophenylacetamide derivatives targeted at HIV-1 reverse transcriptase. Proc. Natl. Acad. Sci. USA 90:1711-1715.
23. Pauwels, R., K. Andries, J. Desmyter, D. Schols, J. Kukla, H. J. Breslin, A. Raeymaeckers, J. Van Gelder, R. Woestenborghs, J. Heykants, H. Schellekens, M. A. C. Janssen, E. De Clercq, and P. A. J. Janssen. 1990. Potent and selective inhibition of HIV-1 replication in vitro by a novel series of TIBO derivatives. Nature (London) 343:470-474.
24. Ren, J., R. Esnouf, E. Garman, D. Somers, C. Ross, I. Kirby, J. Keeling, G. Darby, Y. Jones, D. Stuart, and D. Stammers. 1995. High resolution structures of HIV-1 RT from four RT-inhibitor complexes. Struc. Biol. 2:293-302.
25. Romero, D. L., M. Busso, C.-K. Tan, F. Reusser, J. R. Palmer, S. M. Poppe, P. A. Aristoff, K. M. Downey, A. G. So, L. Resnick, and W. G. Tarpley. 1991. Nonnucleoside reverse transcriptase inhibitors that potently and specifically block human immunodeficiency virus type 1 replication. Proc. Natl Acad. Sci. USA 88:8806-8810
26. Tantillo, C., J. Ding, A. Jacobo-Molina, R. G. Nanni, P. L. Boyer, S. H. Hughes, R. Pauwels, K. Andries, P. A. J. Janssen, and E. Arnold. 1994. Locations of anti-AIDS drug binding sites and resistance mutations in the three-dimensional structure of HIV-1 reverse transcriptase. J. Mol. Biol 243:369-387.