Retention of marked sensitivity to (S)-4-isopropoxycarbonyl-6-methoxy-3-(methylthiomethyl)-3,4-dihydroquinoxaline -2(1H)-thione (HBY 097) by an azidothymidine (AZT)-resistant human immunodeficiency virus type 1 (HIV-1) strain subcultured in the combined presence of quinoxaline HBY 097 and 2',3'-dideoxy-3'-thiacytidine (lamivudine)

Biochemical Pharmacology

Volumn 55, Issue 5, 1998, Pages 617-625

  Balzarini, Jan ^a   Pelemans, Heidi ^a   Riess, Gunther ^b   Roesner, Manfred ^b   Winkler, Irvin ^b   De Clercq, Erik ^a   Kleim, Jörg Peter ^b  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^b SANOFI   (France)

Author keywords

3TC; AZT; HIV 1; Nonnucleoside reverse transcriptase inhibitors (NNRTI); Quinoxalines; Resistance

Indexed keywords

LAMIVUDINE; TALVIRALINE; ZIDOVUDINE;

ARTICLE; CELL CULTURE; CONTROLLED STUDY; CULTURE MEDIUM; DRUG RESISTANCE; DRUG SENSITIVITY; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; MUTANT; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL; VIRUS REPLICATION;

EID: 0032030658     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(97)00506-6     Document Type: Article

References (39)

1. 1. De Clercq E, HIV resistance to reverse transcriptase inhibitors. Biochem Pharmacol 47: 155-169, 1993.
2. 2. De Clercq E, Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. J Med Chem 38: 2491-2517, 1995.
3. 3. Kleim J-P, Bender R, Kirsch R, Meichsner C, Paessens A, Rösner M, Rübsamen-Waigmann H, Kaiser R, Wichers M, Schneweis KE, Winkler I and Riess G, Preclinical evaluation of HBY 097, a new nonnucleoside reverse transcriptase inhibitor of human immunodeficiency virus type 1 replication. Antimicrob Agents Chemother 39: 2253-2257, 1995.
4. 4. Kleim J-P, Rösner M, Winkler I, Paessens A, Kirsch R, Hsiou Y, Arnold E and Riess G, Selective pressure of a quinoxaline nonnucleoside inhibitor of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) on HIV-1 replication results in the emergence of nucleoside RT-inhibitor-specific (RT Leu-74 → Val or Ile and Val-75 → Leu or Ile) HIV-1 mutants. Proc Natl Acad Sci USA 93: 34-38, 1996.
5. 5. Balzarini J, Karlsson A, Pérez-Pérez M-J, Camarasa M-J, Tarpley WG and De Clercq E, 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, 1993.
6. 6. Kleim J-P, Bender R, Billhardt U-M, Meichsner C, Riess G, Rösner M, Winkler I and Paessens A, Activity of a novel quinoxaline derivative against human immunodeficiency virus type 1 reverse transcriptase and viral replication. Antimicrob Agents Chemother 37: 1659-1664, 1993.
7. 7. Kleim J-P, Bender R, Kirsch R, Meichsner C, Paessens A and Riess G, Mutational analysis of residue 190 of human immunodeficiency virus type 1 reverse transcriptase. Virology 200: 696-701, 1994.
8. 8. Coates JAV, Cammack N, Jenkinson HJ, Mutton IM, Pearson BA, Storer R, Cameron JM and Penn CR, The separated enantiomers of 2′-deoxy-3′-thiacytidine (BCH 189) both inhibit human immunodeficiency virus replication in vitro. Antimicrob Agents Chemother 36: 202-205, 1992.
9. 9. Lisignoli G, Facchini A, Cattini L, Monaco MCG, Degrassi A and Mariani E, In vitro toxicity of 2′,3′-dideoxy-3′-thiacytidine (BCH189/3TC), a new synthetic anti-HIV-1 nucleoside. Antiviral Chem Chemother 3: 299-303, 1992.
10. 10. Schinazi RF, Chu CK, Peck A, McMillan A, Mathis R, Cannon D, Jeong L-S, Beach JW, Choi W-B, Yeola S and Liotta DC, Activities of the four optical isomers of 2′,3′-dideoxy-3′-thiacytidine (BCH-189) against human immunodeficiency virus type 1 in human lymphocytes. Antimicrob Agents Chemother 36: 672-676, 1992.
11. 11. Sommadossi JP, Schinazi RF, Chu CK and Xie M-Y, Comparison of cytotoxicity of the (-)-and (+)-enantiomer of 2′,3′-dideoxy-3′-thiacytidine in normal human bone marrow progenitor cells. Biochem Pharmacol 44: 1921-1925, 1992.
12. 12. Soudeyns H, Yao X-J, Gao Q, Belleau B, Kraus J-L, Nguyen-Ba N, Spira B and Wainberg MA, Anti-human immunodeficiency virus type 1 activity and in vitro toxicity of 2′-deoxy-3′-thiacytidine (BCH-189), a novel heterocyclic nucleoside analog. Antimicrob Agents Chemother 35: 1386-1390, 1991.
13. 13. Gu Z, Gao Q, Li X, Parniak MA and Wainberg MA, Novel mutation in the human immunodeficiency virus type 1 reverse transcriptase gene that encodes cross-resistance to 2′,3′-dideoxyinosine and 2′,3′-dideoxycytidine. J Virol 66: 7128-7135, 1992.
14. 14. Boucher CAB, Cammack N, Schipper P, Schuurman R, Rouse P, Wainberg MA and Cameron JM, High-level resistance to (-) enantiomeric 2′-deoxy-3′-thiacytidine in vitro is due to one amino acid substitution in the catalytic site of human immunodeficiency virus type 1 reverse transcriptase. Antimicrob Agents Chemother 37: 2231-2234, 1993.
15. 15. Schinazi RF, Lloyd Jr RM, Nguyen M-H, Cannon DL, McMillan A, Ilksoy N, Chu CK, Liotta DC, Bazmi HZ and Mellors JW, Characterization of human immunodeficiency viruses resistant to oxathiolane-cytosine nucleosides. Antimicrob Agents Chemother 37: 875-881, 1993.
16. 16. Tisdale M, Kemp SD, Parry NR and Larder BA, Rapid in vitro selection of human immunodeficiency virus type 1 resistant to 3′-thiacytidine inhibitors due to a mutation in the YMDD region of reverse transcriptase. Proc Natl Acad Sci USA 90: 5653-5656, 1993.
17. 17. Mellors JW, Larder BA and Schinazi RF, Mutations in HIV-1 reverse transcriptase and protease associated with drug resistance. Inter Antiviral News 3: 8-13, 1995.
18. 18. Larder BA and Kemp SD, Multiple mutations in HIV-1 reverse transcriptase confer high-level resistance to zidovudine (AZT). Science 246: 1155-1158, 1989.
19. 19. Larder BA, Kemp SD and Harrigan PR, Potential mechanism for sustained antiretroviral efficacy of AZT-3TC combination therapy. Science 269: 696-699, 1995.
20. 20. Balzarini J, Pelemans H, Karlsson A, De Clercq E and Kleim J-P, Concomitant combination therapy for HIV infection preferable over sequential therapy with 3TC and non-nucleoside reverse transcriptase inhibitors. Proc Natl Acad Sci USA 93: 13152-13157, 1996.
21. 21. Balzarini J, Pelemans H, Pérez-Pérez M-J, San-Félix A, Camarasa M-J, De Clercq E and Karlsson A, Marked inhibitory activity of non-nucleoside reverse transcriptase inhibitors against human immunodeficiency virus type 1, when combined with (-)2′,3′-dideoxy-3′-thiacytidine (3TC). Mol Pharmacol 49: 882-890, 1996.
22. 22. Camarasa M-J, Pérez-Pérez M-J, San-Félix A, Balzarini J and De Clercq E, 3′-Spiro nucleosides, a new class of specific human immunodeficiency virus type 1 inhibitors, synthesis and antiviral activity of [2′,5′-bis-O-(tert-butyldimethylsilyl)-β-D-xylo-and -ribofuranose]-3′-spiro-5″-[4″-amino-1″,2″-oxathiole 2″,2″-dioxide] (TSAO) pyrimidine nucleosides. J Med Chem 35: 2721-2727, 1992.
23. 23. Pérez-Pérez M-J, San-Félix A, Balzarini J, De Clercq E and Camarasa M-J, TSAO analogues. Stereospecific synthesis and anti-HIV-1 activity of 1-[2′,5′-bis-O-(tert-butyldimethyl)-β-D-ribofuranosyl]-3′-spiro-5″-(4″-amino-1″,2″-oxathiole 2″,2″-dioxide) pyrimidine and pyrimidine-modified nucleosides. J Med Chem 35: 2988-2995, 1992.
24. 24. Pérez-Pérez M-J, San-Félix A, Camarasa M-J, Balzarini J and De Clercq E, Synthesis of [1-[2′,5′-bis-O-(t-butyldimethylsilyl)-β-xylo-and β-D-ribofuranosyl]thymine]-3′-spiro-5″-[4″-amino-1″,2″-oxathiole-2″,2″-dioxide] (TSAO). A novel type of specific anti-HIV agents. Tetrahedron Lett 33: 3029-3032, 1992.
25. 25. Balzarini J, Pérez-Pérez M-J, Velázquez S, San-Félix A, Camarasa M-J, De Clercq E and Karlsson A, Suppression of the breakthrough of human immunodeficiency virus type 1 (HIV-1) in cell culture by thiocarboxanilide derivatives when used individually or in combination vrith other HIV-1-specific inhibitors (i.e., TSAO derivatives). Proc Natl Acad Sci USA 92: 5470-5474, 1995.
26. 26. Kellam P, Boucher CAB and Larder BA, Fifth mutation in human immunodeficiency virus type 1 reverse transcriptase contributes to the development of high-level resistance to zidovudine. Proc Natl Acad Sci USA 89: 1934-1938, 1992.
27. 27. Albert J, Wahlberg J, Leitner T, Escanilla D and Uhlén M, Analysis of a rape case by direct sequencing of the human immunodeficiency virus type 1 pol and gag genes. J Virol 68: 5918-5924, 1994.
28. 28. Condra JH, Emini EA, Gotlib L, Graham DJ, Schlabach AJ, Wolfgang JA, Colonno RJ and Sardana VV, Identification of the human immunodeficiency virus reverse transcriptase residues that contribute to the activity of diverse nonnucleoside inhibitors. Antimicrob Agents Chemother 36: 1441-1446, 1992.
29. 29. Colonno RJ, Condra JH, Mizutani S, Callaha PL, Davies M-E and Murcko MA, Evidence for the direct involvement of the rhinovirus canyon in receptor binding. Proc Natl Acad Sci USA 85: 5449-5453, 1988.
30. 30. Sardana V, Emini EA, Gotlib L, Graham DJ, Lineberger DW, Long WJ, Schlabach AJ, Wolfgang JA and Condra JH. Functional analysis of HIV-1 reverse transcriptase amino acids involved in resistance to multiple non-nucleoside inhibitors. J Biol Chem 267: 17526-17530, 1992.
31. 31. Byrnes VW, Emini EA, Schleif WA, Condra JH, Schneider CL, Long WJ, J.A. Wolfgang JA, Graham DJ, Gotlib L, Schlabach AJ, Wolanski BS, Blahy OM, Quintero JC, Rhodes A, Roth E, Titus DL and Sardana VV, Susceptibilities of human immunodeficiency virus type 1 enzyme and viral variants expressing multiple resistance-engendering amino acid substitutions to reverse transcriptase inhibitors. Antimicrob Agents Chemother 38: 1404-1407, 1994.
32. 32. Nunberg JH, Schleif WA, Boots EJ, O'Brien JA, Quintero JC, Hoffman Jr JM, Emini EA and Goldman ME, Viral resistance to human immunodeficiency virus type 1-specific pyridinone reverse transcriptase inhibitors. J Virol 65: 4887-4892, 1991.
33. 33. Byrnes VW, Sardana VV, Schleif WA, Condra JH, Waterbury JA, Wolfgang JA, Long WJ, Schneider CL, Schlabach AJ, Wolanski BS, Graham DJ, Gotlib L, Rhodes A, Titus DL, Roth E, Blahy OM, Quintero JC, Staszewski S and Emini EA, Comprehensive mutant enzyme and viral variant assessment of human immunodeficiency virus type-1 reverse transcripase resistance to non-nucleoside inhibitors. Antimicrob Agents Chemother 37: 1576-1579, 1993.
34. 34. Saag MS, Emini EA, Laskin OL, Douglas J, Lapidus WI, Schleif WA, Whitley RJ, Hildebrand C, Byrnes VW, Kappes JC, Anderson KW, Massari FE, Shaw GM and the L-697,661 Working Group, A short-term clinical evaluation of L-697,661, a non-nucleoside inhibitor of HIV-1 reverse transcriptase. New Engl J Med 329: 1065-1072, 1993.
35. 35. Richman DD, Resistance of clinical isolates of human immunodeficiency virus to antiretroviral agents. Antimicrob Agents Chemother 37: 1207-1213, 1993.
36. 36. Balzarini J, Karlsson A, Meichsner C, Paessens A, Riess G, De Clercq E and Kleim J-P, Resistance pattern of human immunodeficiency virus type 1 reverse transcriptase to quinoxaline S-2720. J Virol 68: 7986-7992, 1994.
37. 37. Demeter L, Resnick L, Nawaz T, Timpone Jr JG, Batts D and Reichman D, Phenotypic and genotypic analysis of atevirdine (ATV) susceptibility of HIV-1 isolates obtained from patients receiving ATV monotherapy in a phase I clinical trial (ACTG 187): comparison to patients receiving combination therapy with ATV and zidovudine. Third Workshop on Viral Resistance, 1993, Gaithesburg, MD, 1993.
38. 38. Shah A, Kumor K, Sullivan J, Amand R, Cole S, Agarwal V, Krol G, Huguenel E, Suarez JR and Heller AH, Safety, tolerability and pharmacokinetics (PK) of HBY-097 in asymptomatic and mildly symptomatic HIV positive patients. XI International Conference on AIDS, Vancouver, British Columbia, Canada, July 7-12, 1996. Abstracts, 1996.
39. 39. Balzarini J, Pelemans H, Riess G, Roesner M, Winkler I, De Clercq E and Kleim J-P, Zidovudine-resistant human immunodeficiency virus type 1 strains subcultured in the presence of both lamivudine and quinoxaline HBY 097 retain marked sensitivity to HBY 097 but not to lamivudine. J Infect Dis 176: 1392-1395, 1997. Biochemical Pharmacology, Vol. 55, pp. 627-633, 1998.