New anti-human immunodeficiency virus type 1 6-aminoquinolones: Mechanism of action

Antimicrobial Agents and Chemotherapy

Volumn 47, Issue 3, 2003, Pages 889-896

  Parolin, Cristina ^a   Gatto, Barbara ^a   Del Vecchio, Claudia ^a   Pecere, Teresa ^a   Tramontano, Enzo ^b   Cecchetti, Violetta ^c   Fravolini, Arnaldo ^c   Masiero, Sara ^a   Palumbo, Manlio ^a   Palù, Giorgio ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b UNIVERSITY OF CAGLIARI   (Italy)

^c UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

6 AMINO 1,4 DIHYDRO 1 METHYL 7 [4 (2 PYRIDYL) 1 PIPERAZINYL] 4 OXO 3 QUINOLINECARBOXYLIC ACID; 6 AMINOQUINOLONE; INTEGRASE; PROTEINASE; QUINOLONE DERIVATIVE; RNA DIRECTED DNA POLYMERASE; SAQUINAVIR; UNCLASSIFIED DRUG; VIRUS RNA;

ARTICLE; CONTROLLED STUDY; DISSOCIATION CONSTANT; DRUG ACTIVITY; DRUG MECHANISM; DRUG STRUCTURE; ENZYME ACTIVITY; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; IC 50; LIFE CYCLE; LONG TERMINAL REPEAT; PRIORITY JOURNAL; VIRUS REPLICATION;

AMINOQUINOLINES; ANTI-HIV AGENTS; GENES, ENV; GENETIC COMPLEMENTATION TEST; HIV INTEGRASE; HIV INTEGRASE INHIBITORS; HIV PROTEASE; HIV PROTEASE INHIBITORS; HIV-1; HIV-1 REVERSE TRANSCRIPTASE; HUMANS; JURKAT CELLS; PLAQUE ASSAY; QUINOLONES; REVERSE TRANSCRIPTASE INHIBITORS; RNA, VIRAL; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS REPLICATION;

EID: 0037416975     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.47.3.889-896.2003     Document Type: Article

References (60)

1. Aboul-ela, F., J. Karn, and G. Varani. 1995. The structure of the human immunodeficiency virus type 1 TAR RNA reveals principles of RNA recognition by Tat protein. J. Mol. Biol. 253:313-332.
2. Antonello, C., E. Uriarte, M. Palumbo, S. Valisena, C. Parolin, and G. Palù. 1993. Synthesis and biological activity of new quinolone derivatives. Eur. J. Med. Chem. 28:291-296.
3. Artico, M., R. Di Santo, R. Costi, E. Novellino, G. Greco, S. Massa, E. Tramontano, M. E. Marongiu, A. De Montis, and P. La Colla. 1998. Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: synthesis, biological evaluation, and molecular modeling. J. Med. Chem. 41:3948-3960.
4. Baba, M., M. Okamoto, M. Kawamura, M. Makino, M. Higashida, T. Takashi, Y. Kimura, T. Ikeuchi, T. Tetsuka, and T. Okamoto. 1998. Inhibition of human immunodeficiency virus type 1 replication and cytokine production by fluoroquinoline derivatives. Mol. Pharmacol. 53:1097-1103.
5. Baba, M., M. Okamoto, M. Makino, Y. Kimura, T. Ikeuchi, T. Sakaguchi, and T. Okamoto. 1997. Potent and selective inhibition of human immunodeficiency virus type 1 transcription by piperazinyloxoquinoline derivatives. Antimicrob. Agents Chemother. 41:1250-1255.
6. Barre-Sinoussi, F., J. C. Chermann, F. Rey, M. T. Nugeyre, S. Chamaret, J. Gruest, C. Dauget, C. Axler-Bin, F. Vezinet-Brun, C. Rouzioux, W. Rozenbaum, and L. Montagnier. 1983. Isolation of a T-lymphocyte retrovirus from a patient at risk for acquired immunodeficiency syndrome (AIDS). Science 220:868-871.
7. Bassi, G. S., N. E. Mollegaard, A. I. Murchie, and D. M. Lilley. 1999. RNA folding and misfolding of the hammerhead ribozyme. Biochemistry 38:3345-3354.
8. Bassi, G. S., N. E. Mollegaard, A. I. Murchie, E. von Kitzing, and D. M. Lilley. 1995. Ionic interactions and the global conformations of the hammerhead ribozyme. Nat. Struct. Biol. 2:45-55.
9. Cecchetti, V., C. Parolin, S. Moro, T. Pecere, E. Filipponi, A. Calistri, O. Tabarrini, B. Gatto, M. Palumbo, A. Fravolini, and G. Palù. 2000. 6-Amino quinolones as new potential anti-HIV agents. J. Med. Chem. 43:3799-3802.
10. Chun, T. W., L. Stuyver, S. B. Mizell, L. A. Ehler, J. A. Mican, M. Baseler, A. L. Lloyd, M. A. Nowak, and A. S. Fauci. 1997. Presence of an inducible HIV-1 latent reservoir during highly active antiretroviral therapy. Proc. Natl. Acad. Sci. USA 94:13193-13197.
11. Cohen, J. 1998. Exploring how to get at - and eradicate - hidden HIV. Science 279:1854-1855.
12. Collman, R., J. W. Balliet, S. A. Gregory, H. Friedman, D. L. Kolson, N. Nathanson, and A. Srinivasan. 1992. An infectious molecular clone of an unusual macrophage-tropic and highly cytopathic strain of human immunodeficiency virus type 1. J. Virol. 66:7517-7521.
13. Craig, J. C., I. B. Duncan, D. Hockley, C. Grief, N. A. Roberts, and J. S. Mills. 1991. Antiviral properties of Ro 31-8959, an inhibitor of human immunodeficiency virus (HIV) proteinase. Antivir. Res. 16:295-305.
14. Cullen, B. R. 1987. Use of eukaryotic expression technology in the functional analysis of cloned genes. Methods Enzymol. 152:684-703.
15. Doranz, B. J., J. Rucker, Y. Yi, R. J. Smyth, M. Samson, S. C. Peiper, M. Parmentier, R. G. Collman, and R. W. Doms. 1996. A dual-tropic primary HIV-1 isolate that uses fusin and the beta-chemokine receptors CKR-5, CKR-3 and CKR-2b as fusion cofactors. Cell 85:1149-1158.
16. Fauci, A., A. Macher, D. Longo, H. C. Lane, A. Rook, H. Masur, and E. Gelmann. 1984. Acquired immunodeficiency syndrome: epidemiologic, clinical, immunologic, and therapeutic considerations. Ann. Intern. Med. 100: 92-106.
17. Feng, Y., C. C. Broder, P. E. Kennedy, and E. A. Berger. 1996. HIV-1 entry cofactor: functional cDNA cloning of a seven-transmembrane, G protein-coupled receptor. Science 272:809-810.
18. + T-cells provides a mechanism for lifelong persistence of HIV-1, even in patients on effective combination therapy. Nat. Med. 5:512-517.
19. Finzi, D., M. Hermankova, T. Pierson, L. M. Carruth, C. Buck, R. E. Chaisson, T. C. Quinn, K. Chadwick, J. Margolick, R. Brookmeyer, J. Gallant, M. Markowitz, D. D. Ho, D. D. Richman, and R. F. Siciliano. 1997. Identification of a reservoir for HIV-1 in patients on highly active antiretroviral therapy. Science 278:1295-1300.
20. Gallo, R. C., S. Z. Salahuddin, M. Popovic, G. M. Shearer, M. Kaplan, B. F. Haynes, T. J. Palker, R. Redfield, J. Oleske, B. Safai, G. White, P. Foster, and P. D. Markham. 1984. Frequent detection and isolation of cytopathic retroviruses (HTLV-III) from patients with AIDS and at risk for AIDS. Science 224:500-503.
21. Gatto, B., G. Capranico, and M. Palumbo. 1999. Drugs acting on DNA topoisomerases: recent advances and future perspectives. Curr. Pharm. Des. 5:195-215.
22. Hagihara, M., H. Kashiwase, T. Katsube, T. Kimura, T. Komai, K. Momota, T. Ohmine, T. Nishigaki, S. Kimura, and K. Shimada. 1999. Synthesis and anti-HIV activity of arylpiperazinyl fluoroquinolones: a new class of anti-HIV agents. Bioorg. Med. Chem. Lett. 9:3063-3068.
23. Helseth, E., M. Kowalski, D. Gabuzda, U. Olshevsky, W. Haseltine, and J. Sodroski. 1990. Rapid complementation assays measuring replicative potential of human immunodeficiency virus type 1 envelope glycoprotein mutants. J. Virol. 64:2416-2420.
24. Hirsch, M. S., F. Brun-Vezinet, R. T. D'Aquila, S. M. Hammer, V. A. Johnson, D. R. Kuritzkes, C. Loveday, J. W. Mellors, B. Clotet, B. Conway, L. M. Demeter, S. Vella, D. M. Jacobsen, and D. D. Richman. 2000. Antiretroviral drug resistance testing in adult HIV-infection: recommendations for an International AIDS Society-USA Panel. JAMA 282:2417-2426.
25. Hirsch, M. S., B. Conway, R. T. D'Aquila, V. A. Johnson, F. Brun-Vezinet, B. Clotet, L. M. Demeter, S. M. Hammer, D. M. Jacobsen, D. R. Kuritzkes, C. Loveday, J. W. Mellors, S. Vella, and D. D. Richman. 1998. Antiretroviral drug resistance testing in adults with HIV infection. JAMA 279:1984-1991.
26. Hui, J. O., A. G. Tomasselli, I. M. Reardon, J. M. Loll, D. P. Brunner, C. S. Tomich, and R. L. Heinrikson. 1993. Large scale purification of HIV-1 protease from Escherichia coli inclusion bodies. J. Protein Chem. 12:323-327.
27. Hwang, S., N. Tamilarasu, K. Ryan, I. Huq, S. Richter, W. C. Still, and T. M. Rana. 1999. Inhibition of gene expression in human cells through small molecule-RNA interactions. Proc. Natl. Acad. Sci. USA 96:12997-13002.
28. Ippolito, J. A., and T. A. Steitz. 1998. A 1.3-A resolution crystal structure of the HIV-1 trans-activation response region RNA stem reveals a metal ion-dependent bulge conformation. Proc. Natl. Acad. Sci. USA 95:9819-9824.
29. Kashiwase, H., K. Momota, T. Ohmine, T. Komai, T. Kimura, T. Katsube, T. Nishigaki, S. Kimura, K. Shimada, and H. Furukawa. 1999. A new fluoroquinolone derivative exhibits inhibitory activity against human immunodeficiency virus type 1 replication. Chemotherapy 45:48-55.
30. Litovchick, A., A. G. Evdokimov, and A. Lapidot. 2000. Aminoglycosidearginine conjugates that bind TAR RNA: synthesis, characterization and antiviral activity. Biochemistry. 39:2838-2852.
31. Marshall, A. G. 1978. Biophysical chemistry. Principles, techniques and applications, p. 70-72. John Wiley & Sons, New York, N.Y.
32. Maschera, B., G. Darby, G. Palh, L. L. Wright, M. Tisdale, R. Myers, E. Blaire, and E. S. Furfine. 1996. Human immunodeficiency virus. Mutations in the viral protease that confer resistance to saquinavir increase the dissociation rate constant of the protease-saquinavir complex. J. Biol. Chem. 271:33231-33235.
33. Maschera, B., E. Furfine, and E. D. Blair. 1995. Analysis of resistance to human immunodeficiency virus type 1 protease inhibitors by using matched bacterial expression and proviral infection vectors. J. Virol. 69:5431-5436.
34. Mossmann, T. 1993. Rapid colorimetric assay for cell growth and survival. Application to proliferation and cytotoxicity. J. Immunol. Methods 65:55-63.
35. Ohmine, T., T. Katsube, Y. Tsuzaki, M. Kazui, N. Kobayashi, T. Komai, M. Hagihara, T. Nishigaki, A. Iwamoto, T. Kimura, H. Kashiwase, and M. Yamashita. 2002. Anti-HIV-1 activities and pharmacokinetics of new arylpiperazinyl fluoroquinolones. Bioorg. Med. Chem. Lett. 12:739-742.
36. Okamoto, H., T. P. Cujec, M. Okamoto, B. M. Peterlin, M. Baba, and T. Okamoto. 2000. Inhibition of the RNA-dependent transactivation and replication of human immunodeficiency virus type 1 by a fluoroquinoline derivative K-37. Virology 272:402-408.
37. Okamoto, M., T. Okamoto, and M. Baba. 1999. Inhibition of human immunodeficiency virus type 1 replication by combination of transcription inhibitor K-12 and other antiretroviral agents in acutely and chronically infected cells. Antimicrob. Agents Chemother. 43:492-497.
38. Palella, F. J., Jr., K. M. Delaney, A. C. Moorman, M. O. Loveless, J. Fuhrer, G. A. Satten, D. J. Aschman, and S. D. Holmberg. 1998. Declining morbidity and mortality among patients with advanced human immunodeficiency virus infection. HIV Outpatient Study Investigators. N. Engl. J. Med. 338:853-860.
39. Palfi, G., S. Valisena, G. Ciarrocchi, B. Gatto, and M. Palumbo. 1992. Quinolone binding to DNA is mediated by magnesium ions. Proc. Natl. Acad. Sci. USA 89:9671-9675.
40. Palù, G., S. Valisena, C. Parolin, G. Ciarrocchi, B. Gatto, and M. Palumbo. 1991. Further insight into the mechanism of action of quinolones. Eur. J. Clin. Microbiol. Infect. Dis. XX(Suppl. 1):350-351.
41. Palumbo, M., B. Gatto, G. Zagotto, and G. Palù. 1993. On the mechanism of action of quinolone drugs. Trends Microbiol. 1:232-235.
42. Pley, H. W., K. M. Flaherty, and D. B. McKay. 1994. Three-dimensional structure of a hammerhead ribozyme. Nature 372:68-74.
43. Puglisi, J. D., R. Tan, B. J. Calnan, A. D. Frankel, and J. R. Williamson. 1992. Conformation of the TAR RNA-arginine complex by NMR spectroscopy. Science 257:76-80.
44. Ramratnam, B., J. E. Mittler, L. Zhang, D. Boden, A. Hurley, F. Fang, C. A. Macken, A. S. Perelson, M. Markowitz, and D. D. Ho. 2000. The decay of the latent reservoir of replication-competent HIV-1 is inversely correlated with the extent of residual viral replication during prolonged anti-retroviral therapy. Nat. Med. 6:82-85.
45. Ratner, L., W. Haseltine, R. Patarca, K. J. Livak, B. Starcich, S. J. Josephs, E. R. Doran, J. A. Rafalski, E. A. Whitehorn, K. Baumeister, L. Ivanoff, S. R. Petteway, Jr., M. L. Pearson, J. A. Lauteenberger, T. S. Papas, J. Ghrayeb, N. T. Chang, R. C. Gallo, and F. Wong-Staal. 1985. Complete nucleotide sequence of the AIDS virus, HTLV-III. Nature 313:277-283.
46. Reed, L. J., and H. Muench. 1938. A simple method of estimating fifty percent endpoints Am. J. Hyg. 27:493-497.
47. Rho, H. M., B. Poiesz, F. Ruscetti, and R. C. Gallo. 1981. Characterization of the reverse transcriptase from a new retrovirus (HTLV) produced by a human cutaneous T-cell lymphoma cell line. Virology 112:355-360.
48. Scott, W. G., J. B. Murray, J. R. Arnold, B. L. Stoddard, and A. Klug. 1996. Capturing the structure of a catalytic RNA intermediate: the hammerhead ribozyme. Science 274:2065-2069.
49. Shen, L., J. Baranowski, and A. Pernet. 1989. Mechanism of inhibition of DNA gyrase by quinolone antibacterials: specificity and cooperativity of drug binding to DNA. Biochemistry 28:3879-3885.
50. Shen, L., L. Mitscher, P. Sharma, T. O'Donnel, D. Chu, C. Cooper, T. Rosen, and A. Pernet. 1989. Mechanism of inhibition of DNA gyrase by quinolone antibacterials: a cooperative drug-DNA binding model. Biochemistry 28: 3886-3894.
51. 2+-mediated binding of 6-substituted quinolones to DNA: relevance to biological activity. Bioorg. Med. Chem. 6:1551-1561.
52. Toth, M. V., and G. R. Marshall. 1990. A simple, continuous fluorometric assay for HIV protease. Int. J. Pept. Protein Res. 36:544-550.
53. Tramontano, E., P. La Colla, and Y.-C. Cheng. 1998. Biochemical charac terization of the HIV-1 integrase 3′-processing activity and its inhibition by phosphorothioate oligonucleotides. Biochemistry 37:7237-7242.
54. Valisena, S., M. Palumbo, C. Parolin, G. Palù, and G. A. Meloni. 1990. Relevance of ionic effects on norfloxacin uptake by Escherichia coli. Biochem. Pharmacol. 40:431-436.
55. Witvrouw, M., D. Daelemans, C. Pannecouque, J. Neyts, G. Andrei, R. Snoeck, A. M. Vandamme, J. Balzarini, J. Desmyter, M. Baba, and E. De Clercq. 1998. Broad-spectrum antiviral activity and mechanism of antiviral action of the fluoroquinolone derivative K-12. Antivir. Chem. Chemother. 9:403-411.
56. Wong, J. K., M. Hezareh, H. F. Gunthard, D. V. Havlir, C. C. Ignacio, C. A. Spina, and D. D. Richman. 1997. Recovery of replication-competent HIV despite prolonged suppression of plasma viremia. Science 278:1291-1295.
57. Zacharias, M., and P. J. Hagerman. 1995. Bulge-induced bends in RNA: quantification by transient electric birefringence. J. Mol. Biol. 247:486-500.
58. Zacharias, M., and P. J. Hagerman. 1995. The bend in RNA created by the trans-activation response element bulge of human immunodeficiency virus is straightened by arginine and by Tat-derived peptide. Proc. Natl. Acad. Sci. USA 92:6052-6056.
59. Zhang, L., B. Ramratnam, K. Tenner-Racz, Y. He, M. Vesamen, S. Lewin, A. Talal, P. Racz, A. S. Perelson, B. T. Korber, M. Markowitz, and D. D. Ho. 1999. Quantifying residual HIV-1 replication in patients receiving combination antiretroviral therapy. N. Engl. J. Med. 340:1605-1613.
60. Zhou, Q., and P. A. Sharp. 1995. Novel mechanism and factor for regulation by HIV-1 Tat. EMBO J. 14:321-328.