In vitro induction of human immunodeficiency virus type 1 variants resistant to phosphoralaninate prodrugs of Z-methylenecyclopropane nucleoside analogues

Antimicrobial Agents and Chemotherapy

Volumn 43, Issue 10, 1999, Pages 2479-2483

  Yoshimura, Kazuhisa ^a   Feldman, Ron ^a   Kodama, Eiichi ^a   Kavlick, Mark F ^a   Qiu, Yao Ling ^b   Zemlicka, Jiri ^b   Mitsuya, Hiroaki ^a,c,d  

^a NATIONAL CANCER INSTITUTE   (United States)

^b WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c NATIONAL CANCER INSTITUTE   (United States)

^d KUMAMOTO UNIV SCHOOL OF MEDICINE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; NUCLEOSIDE ANALOG; PRODRUG; QYL 609; QYL 685; UNCLASSIFIED DRUG;

ARTICLE; DRUG EFFECT; DRUG POTENCY; DRUG SENSITIVITY; DRUG STRUCTURE; GENE MUTATION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; PRIORITY JOURNAL; VIRUS GENE; VIRUS REPLICATION;

EID: 0032820094     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.43.10.2479     Document Type: Article

References (26)

1. Boucher, C. A. B., N. Cammack, P. Schipper, R. Schuurman, P. Rouse, M. A. Wainberg, and J. M. Cameron. 1993. 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.
2. Fitzgibbon, J. E., R. M. Howell, C. A. Harberzetti, S. J. Sperber, D. J. Gocke, and D. T. Dubin. 1992. Human immunodeficiency virus type 1 pol gene mutations which cause decreased susceptibility to 2′,3′-dideoxycytidine. Antimicroh. Agents Chemother. 36:153-157.
3. Gao, Q., Z. Gu, M. A. Parniak, J. Cameron, N. Cammack, C. Boucher, and M. A. Wainberg. 1993. The same mutation that encodes low-level human immunodeficiency virus type 1 resistance to 2′,3′-dideoxyinosine and 2′,3′-dideoxycytidine confers high-level resistance to the (-) enantiomer of 2′,3′-dideoxy-3′-thiacytidine. Antimicrob. Agents Chemother. 37:1390-1392.
4. Gu, Z., Q. Gao, H. Fang, H. Salomon, M. A. Parniak, E. Goldberg, J. Cameron, and M. A. Wainberg. 1994. Identification of a mutation at codon 65 in the IKKK motif of reverse transcriptase that encodes human immunodeficiency virus reverse transcription. Antimicrob. Agents Chemother. 38: 275-281.
5. Huang, H., R. Chopra, G. L. Verdine, and S. C. Harrison. 1998. Structure of a covalently trapped catalytic complex of HIV-1 reverse transcriptase: implications for drug resistance. Science 282:1669-1675.
6. Kavlick, M. F., T. Shirasaka, E. Kojima, J. M. Pluda, F. Hui, Jr., R. Yarchoan, and H. Mitsuya. 1995. Genotypic and phenotypic characterization of HIV-1 isolated from patients receiving (-)-2′,3′-dideoxy-3′-thiacytidine. Antivir. Res. 28:133-146.
7. Kodama, E., S. Shigeta, T. Suzuki, and E. De Clercq. 1996. Application of a gastric cancer cell line (MKN-28) for anti-adenovirus screening using the MTT method. Antivir. Res. 31:159-164.
8. Kosalaraksa, P., M. F. Kavlick, V. Maroun, R. Le, and H. Mitsuya. 1999. Comparative fitness of multi-dideoxynucleoside-resistant human immunodeficiency virus type 1 (HIV-1) in an in vitro competitive HIV-1 replication assay. J. Virol. 73:5356-5363.
9. Larder, B. A. 1994. Interactions between drug resistance mutations in human immunodeficiency virus type 1 reverse transcriptase. J. Gen. Virol. 75:951-957.
10. Larder, B. A., S. D. Kemp, and P. R. Harrigan. 1995. Potential mechanism for sustained antiretroviral efficacy of A2T-3TC combination therapy. Science 269:696-699.
11. Maeda, Y., D. J. Venzon, and H. Mitsuya. 1998. Altered drug sensitivity, fitness, and evolution of human immunodeficiency virus type 1 with pol gene mutations conferring multi-dideoxynucleoside resistance. J. Infect. Dis. 177: 1207-1213.
12. Mitsuya, H., and J. Erickson. 1999. Discovery and development of antiretroviral therapeutics for HIV infection, p. 751-780. In T. C. Merigan, J. G. Bartlet, and D. Bolognesi (ed.), Textbook of AIDS medicine. Williams & Wilkins, Baltimore, Md.
13. 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.
14. Qiu, Y.-L., R. G. Ptak, J. M. Breienbach, J.-S. Lin, Y.-C. Cheng, J. C. Drach, E. R. Kern, and J. Zemlicka. Synthesis and antiviral activity of phosphoralaninate prodrugs of methylenecyclopropane analogues of nucleosides. Antivir. Res., in press.
15. Qiu, Y. L., M. B. Ksebati, R. G. Ptak, B. Y. Fan, J. M. Breitenbach, J. S. Lin, Y. C. Cheng, E. R. Kern, J. C. Drach, and J. Zemlicka. 1998. (Z)- and (E)-2-((hydroxymethyl)cyclopropylidene)methyladenine and -guanine. New nucleoside analogues with a broad-spectrum antiviral activity. J. Med. Chem. 41:10-23.
16. Qiu, Y. L., R. G. Ptak, J. M. Breitenbach, J. S. Lin, Y. C. Cheng, E. R. Kern, J. C. Drach, and J. Zemlicka. 1998. (Z)- and (E)-2-(hydroxymethylcyclopropylidene)-methylpurines and pyrimidines as antiviral agents. Antivir. Chem. Chemother. 9:341-352.
17. Reed, L. J., and H. Muench. 1938. A simple method of estimating fifty percent endpoints. Am. J. Hyg. 27:493-497.
18. Schinazi, R. F., R. M. Lloyd, Jr., M.-H. Nguyen, D. L. Cannon, A. McMillan, N. Ilksoy, C. K. Chu, D. C. Liotta, H. Z. Bazmi, and J. W. Mellors. 1993. Characterization of human immunodeficiency viruses resistant to oxathiolane-cytosine nucleosides. Antimicrob. Agents Chemother. 37:875-881.
19. Schuurman, R., M. Nijhuis, R. van Leeuwen, P. Schipper, D. de Jong, P. Collis, S. A. Danner, J. Mulder, C. Loveday, and C. Christopherson. 1995. Rapid changes in human immunodeficiency virus type 1 RNA load and appearance of drug-resistant virus populations in persons treated with lami-vudine (3TC). J. Infect. Dis. 171:1411-1419.
20. Shirasaka, T., M. F. Kavlick, T. Ueno, W.-Y. Gao, E. Kojima, M. L. Alcaide, S. Chokekijchai, B. M. Roy, E. Arnold, R. Yarchoan, and H. Mitsuya. 1995. Emergence of human immunodeficiency virus type-1 variants with resistance to multiple dideoxynucleosides in patients receiving therapy with dideoxynucleosides. Proc. Natl. Acad. Sci. USA 92:2398-2402.
21. Shirasaka, T., R. Yarchoan, M. C. O'Brien, R. N. Husson, B. D. Anderson, E. Kojima, T. Shimada, S. Broder, and H. Mitsuya. 1993. Changes in drug sensitivity of human immunodeficiency virus type 1 during therapy with azidothymidine, dideoxycytidine, and dideoxyinosine: an in vitro comparative study. Proc. Natl. Acad. Sci. USA 90:562-566.
22. St. Clair, M. H., J. L. Martin, G. Tudor-Williams, M. C. Bach, C. L. Vavro, D. M. King, P. Kellam, S. D. Kemp, and B. A. Larder. 1991. Resistance to ddI and sensitivity to AZT induced by a mutation in HIV-1 reverse transcriptase. Science 253:1557-1559.
23. Tanaka, M., R. V. Srinivas, T. Ueno, M. F. Kavlick, F. K. Hui, A. Fridland, J. S. Driscoll, and H. Mitsuya. 1997. In vitro induction of human immunodeficiency virus type 1 variants resistant to 2′-beta-fluoro-2′,3′-dideoxyadenosine. Antimicrob. Agents. Chemother. 41:1313-1318.
24. Uchida, H., N. E. Kodama, K. Yoshimura, Y. Maeda, P. Kasalaraksa, V. Maroun, Y. L. Qiu, J. Zemlicka, and H. Mitsuya. 1999. In vitro anti-HIV activity of Z- and E-methylenecyclopropane nucleoside analogues and their phosphoro-L-alaninate diesters. Antimicrob. Agents Chemother. 43:1487-1490.
25. Wainberg, M. A., H. Salomon, Z. Gu, J. S. G. Montaner, T. P. Cooley, R. McCaffrey, J. Ruedy, M. H. Hilary, N. Cammack, J. Cameron, and W. Nicholson. 1995. Development of HIV-1 resistance to (-)2′-deoxy-3′-thiacytidine in patients with AIDS or advanced AIDS-related complex. AIDS 9:351-357.
26. Wain-Hobson, S., J.-P. Vartanian, M. Henry, N. Chenciner, R. Cheynier, S. Delassus, L. Martins, M. Sala, M.-T. Nugeyre, D. Guetard, D. Klatzman, J.-C. Gluckman, W. Rozenbaum, F. Barre-Sinoussi, and L. Montagnier. 1991. LAV revisited: origins of the early HIV-1 isolates from Institut Pasteur. Science 252:961-965.