Comparative study of the anti-human cytomegalovirus activities and toxicities of a tetrahydrofuran phosphonate analogue of guanosine and cidofovir

Antimicrobial Agents and Chemotherapy

Volumn 43, Issue 3, 1999, Pages 557-567

  Bedard, Jean ^a   May, Suzanne ^a   Lis, Martin ^a   Tryphonas, Leander ^b   Drach, John ^c   Huffman, John ^d   Sidwell, Robert ^d   Chan, Laval ^a   Bowlin, Terry ^a   Rando, Robert ^a  

^a Shire Canada   (Canada)

^b CPT Inc   (Canada)

^c UNIVERSITY OF MICHIGAN   (United States)

^d UTAH STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CIDOFOVIR; DNA POLYMERASE; GANCICLOVIR; GUANOSINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; TETRAHYDROFURAN;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ANIMAL EXPERIMENT; APOPTOSIS; ARTICLE; CYTOMEGALOVIRUS INFECTION; CYTOTOXICITY; DISEASE SEVERITY; ENZYME ACTIVITY; GENE EXPRESSION; GUINEA PIG; INCIDENCE; NONHUMAN; PRIORITY JOURNAL; RETINITIS; RISK FACTOR; SWINE;

EID: 0032979644     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.43.3.557     Document Type: Article

References (51)

1. Aduma, P., M. C. Connelly, R. V. Srinivas, and A. Fridland. 1995. Metabolic diversity and antiviral activities of acyclic nucleoside phosphonates. Mol. Pharmacol. 47:816-822.
2. Baba, M., S. Mori, S. Shigeta, and E. DeClercq. 1987. Selective inhibitory effect of (S)-9-(3-hydroxy-2-phosphonylmethoxy-propyl)adenine and 2′-nor-cyclic GMP on adenovirus replication in vitro. Antimicrob. Agents Chemother. 31:331-339.
3. Baldanti, F., M. R. Underwood, S. C. Stanat, K. K. Biron, S. Chou, A. Sarasini, E. Silini, and G. Gerna. 1996. Single amino acid changes in the DNA polymerase confer foscarnet resistance and slow-growth phenotype, while mutations in the UL97-encoded phosphotransferase confer ganciclovir resistance in three double-resistant human cytomegalovirus strains recovered from patients with AIDS. J. Virol. 70:1390-1395.
4. Barnard, J. A., J. H. Huffman, R. W. Sidwell, and E. J. Reist. 1993. Selective inhibition of cytomegalovirus by 9-(3′-ethylphosphono-1′-propyloxy-methyl) guanine. Antivir. Res. 22:77-89.
5. Biron, K. K. 1991. Ganciclovir-resistant human cytomegalovirus clinical isolates: resistance mechanisms and in vitro susceptibility to antiviral agents. Transplant. Proc. 23:162-167.
6. Bischofberger, N., M. J. Hitchcock, M. S. Chen, D. B. Barkhimer, K. C. Cundy, K. M. Kent, S. A. Lacy, W. A. Lee, Z. H. Li, D. B. Mendel, D. F. Smee, and J. L. Smith. 1994. 1-[(S)-2-Hydroxy-2-oxo-1,4,2-dioxaphosphorinan-5-yl) methyl]cytosine, an intracellular prodrug for (S)-1-(3-hydroxy-2-phosphonyl-methoxypropyl)cytosine with improved therapeutic index in vivo. Antimicrob. Agents Chemother. 38:2387-2391.
7. Bronson, J. J., I. Ghazzouli, M. J. M. Hitchcock, R. R. Webb, E. R. Kern, and J. C. Martin. 1989. Synthesis and antiviral activity of nucleoside analogues bearing the (S)-(3-hydroxy-2-phosphonylmethoxy)propyl moiety attached to adenine, guanine, and cytosine, p. 88-102. In J. C. Martin (ed.), Nucleotide analogues as antiviral agents. American Chemical Society, Washington, D.C.
8. Chan, L., N. Turcotte, P. Nguyen-Ba, L. Yuen, D. Barbeau, J. Bedard, and M. Hamel. Identification of novel nucleotide phosphonate analogues with potent anti-HCMV activity. Submitted for publication.
9. Cherrington, J. M., S. J. W. Allen, A. S. Mulato, R. Miner, W. L. Drew, and M. S. Chen. 1998. Sensitivities of human cytomegalovirus (HCMV) clinical isolates to cidofovir. Antivir. Res. 26:A319.
10. Cherrington, J. M., R. Miner, M. J. Hitchcock, J. P. Lalezari, and W. L. Drew. 1996. Susceptibility of human cytomegalovirus to cidofovir is unchanged after limited in vivo exposure to various regiments of drug. J. Infect. Dis. 173:987-992.
11. Chou, S., A. Erice, M. C. Jordan, G. M. Vercellotti, K. R. Michels, C. L. Talarico, S. C. Stanat, and K. K. Biron. 1995. Analysis of the UL97 phosphotransferase coding sequence in clinical cytomegalovirus isolates and identification of mutations conferring ganciclovir resistance. J. Infect. Dis. 171:576-583.
12. Chrisp, P., and S. P. Clissold. 1991. Foscarnet: a review of its antiviral activity, pharmacokinetic properties and therapeutic use in immunocompromised patients with cytomegalovirus retinitis. Drugs 41:104-129.
13. Cundy, K. C., A. M. Bidgood, G. Lynch, J. P. Shaw, L. Griffin, and W. A. Lee. 1996. Pharmacokinetics, bioavailability, metabolism and tissue distribution of cidofovir (HPMPC) and cyclic HPMPC in rats. Drug Metab. Dispos. 24: 745-752.
14. Cundy, K. C., Z. H. Li, and A. Lee. 1994. Effect of concomitant probenecid on the tissue distribution and urinary excretion of HPMPC in preclinical models. Pharm. Res. 11:S449.
15. De Clercq, E. 1995. Trends in the development of new antiviral agents for the chemotherapy of infections caused by herpesviruses and retroviruses. Rev. Med. Virol. 5:149-164.
16. De Clercq, E., A. Holy, I. Rosenberg, T. Sakuma, J. Balzarini, and P. C. Maudgal. 1986. A novel selective broad-spectrum anti-DNA virus agent. Nature 323:464-467.
17. Gordon, Y. J., E. Romanowski, and T. Araullo-Cruz. 1994. Topical HPMPC inhibits adenovirus type 5 in the New Zealand rabbit ocular replication model. Invest. Ophthal Vis. Sci. 35:4135-4143.
18. Heijtink, R. A., J. Kruining, A. G. De Wilde, J. Bazarini, E. De Clercq, and S. W. Schalm. 1994. Inhibitory effects of acyclic nucleoside phosphonates on human hepatitis B virus and duck hepatitis virus infections in tissue culture. Antimicrob. Agents Chemother. 38:2180-2182.
19. Hitchcock, M. J. M., S. A. Lacy, J. R. Lindsey, and E. R. Kern. 1995. The cyclic congener of cidofovir has reduced nephrotoxicity in three species. Antivir. Res. 26:A358.
20. Ho, H.-T., K. L. Woods, J. J. Bronson, H. De Boeck, J. C. Martin, and M. J. Hitchcock. 1992. Intracellular metabolism of the antiherpes agent (S)-1-(3-hydroxy-2-(phosphonylmethoxy)propyl)-cytosine. Mol. Pharmacol. 41:197-202.
21. Huffman, J. H., R. W. Sidwell, D. L. Barnard, A. Morrison, M. J. Otto, C. L. Hill, and R. F. Schinazi. 1997. Influenza virus-inhibitory effects of a series of germanium and silicon centred polyoxometalates. Antivir. Chem. Chemother. 8:75-83.
22. Jacobson, M. A. 1997. Treatment of cytomegalovirus retinitis in patients with the acquired immunodeficiency syndrome. N. Engl. J. Med. 337:105-114.
23. Jacobson, M. A., and M. French. 1998. Altered natural history of AIDS-related opportunistic infections in the era of potent combination antiretroviral therapy. AIDS 12:S157-S163.
24. Jacobson, M. A., M. Zegans, P. R. Pavan, J. J. O'Donnell, F. Sattler, N. Rao, S. Owens, and R. Pollard. 1997. Cytomegalovirus retinitis after initiation of highly active antiretroviral therapy. Lancet 349:1443-1445.
25. Kimberlin, D. W., D. M. Coen, K. K. Biron, J. I. Cohen, R. A. Lamb, M. McKinlay, E. A. Emini, and R. J. Whitley. 1995. Molecular mechanisms of antiviral resistance. Antivir. Res. 26:369-401.
26. Krosky, P. M., M. N. Underwood, S. R. Turk, K. W. H. Feng, R. K. Jain, R. G. Ptark, A. C. Westerman, K. K. Biron, L. B. Townsend, and J. C. Drach. 1998. Resistance of human cytomegalovirus to benzimidazole ribonucleotides maps to two open reading frames: UL89 and UL56. J. Virol. 92:4721-4728.
27. Lewis, A. F., J. C. Drach, S. M. Fennewald, J. H. Huffman, R. G. Ptak, J. P. Sommadossi, G. R. Revankar, and R. F. Rando. 1994. Inhibition of human cytomegalovirus in culture by alkenyl guanine analogs of the thiazolo[4,5-d]pyrimidine ring system. Antimicrob. Agents Chemother. 38:2889-2895.
28. Li, S. B., Z. H. Yang, J. S. Feng, C. K. Y. Fong, H. L. Lucia, and G. D. Hsiung. 1990. Activity of (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)-cytosine (HPMPC) against guinea pig cytomegalovirus infection in cultured cells and in guinea pigs. Antivir. Res. 13:237-252.
29. Macher, A. M., C. M. Reichert, S. E. Straus, D. L. Longo, J. Parrillo, H. C. Lane, A. S. Fauci, A. H. Rook, J. F. Manischewitz, and G. V. J. Quinnan. 1983. Death in the AIDS patient: role of cytomegalovirus. N. Engl. J. Med. 309:1454.
30. Mattes, H., and C. Benezra. 1988. Synthesis of a model hapten with cyclohexanediol and alpha-methylene-gamma-butyrolactone groups, a synthetic analogue of poison ivy and tulipalin allergens connected with a carbon chain. J. Org. Chem. 53:2732-2737.
31. Meyers, J. D. 1986. Infection in bone marrow transplant recipients. Am. J. Med. 81:27-38.
32. Mulato, A. S., J. M. Cherrington, and M. S. Chen. 1996. Anti-HCMV activity of cidofovir in combination with antiviral compounds and immunosuppressive agents: in-vitro analyses. Antivir. Chem. Chemother. 7:203-208.
33. Palestine, A. G., M. A. Polis, M. D. DeSmet, B. F. Baird, J. Falloon, J. A. Kovacs, R. T. Davey, J. J. Zurlo, K. M. Zunich, and M. Davis. 1991. A randomized, controlled trial of foscarnet in the treatment of cytomegalovirus retinitis in patients with AIDS. Appl. Microbiol. 22:797-801.
34. Pertel, P., R. Hirschtick, J. Phair, L. Poggensee, and R. Murphy. 1992. Risk of developing cytomegalovirus retinitis in persons infected with the human immunodeficiency virus. J. Acquired Immune Defic. Syndr. 5:1069-1074.
35. Polis, M. A., K. M. Spooner, B. F. Baird, J. F. Manischewitz, H. S. Jaffe, P. E. Fisher, J. Falloon, R. T. J. Davey, J. A. Kovacs, R. E. Walker, S. M. Whitcup, R. B. Nussenblatt, H. C. Lane, and H. Masur. 1995. Anticytomegaloviral activity and safety of cidofovir in patients with human immunodeficiency virus infection and cytomegalovirus viruria. Antimicrob. Agents Chemother. 39:882-886.
36. Prichard, M. N., and C. Shipman, Jr. 1990. A three-dimensional model to analyze drug-drug interactions. Antivir. Res. 14:181-206.
37. Ringden, O., B. Lonnqvist, T. Paulin, J. Ahlmen, G. Klintmalm, B. Wahren, and J. O. Lernestedt. 1986. Pharmacokinetics, safety and preliminary clinical experiences using foscarnet in the treatment of cytomegalovirus infections in bone marrow and renal transplant recipients. J. Antimicrob. Chemother. 17: 373-387.
38. Sarasini, A., F. Baldanti, M. Furione, E. Percevalle, R. Brerra, M. Barbi, and G. Gerna. 1995. Double resistance to ganciclovir and foscarnet of four human cytomegalovirus strains recovered from AIDS patients. J. Med. Virol. 47:237-244.
39. Sidwell, R. W., and J. H. Huffman. 1971. Use of disposable micro tissue culture plates for antiviral and interferon induction studies. Appl. Microbiol. 22:797-801.
40. Sidwell, R. W., D. F. Smee, R. P. Warren, J. H. Huffman, B. J. Gilbert, R. A. Burger, and F. C. Pearson. 1993. Murine cytomegalovirus-inhibitory effects of ImuVert. Antivir. Res. 20:279-292.
41. Smith, I. L., J. M. Cherrington, R. E. Jiles, M. D. Fuller, W. R. Freeman, and S. A. Spector. 1997. High-level resistance of cytomegalovirus to ganciclovir is associated with alterations in both the UL97 and DNA polymerase genes. J. Infect. Dis. 176:69-77.
42. Snoeck, R., G. Andrei, and E. De Clercq. 1995. Human cytomegalovirus (HCMV) strains selected under selective pressure of phosphonoformate (PFA) are resistant for both PFA and phosphonylmethoxyethyl derivatives in vitro. Antivir. Res. 26:A320.
43. Snoeck, R., M. Van Ranst, G. Andrei, E. De Clercq, S. De Wit, M. Poncin, and N. Clumeck. 1995. Treatment of anogenital papillomavirus infections with an acyclic nucleoside phosphonate analogue. N. Engl. J. Med. 333:943-944.
44. Stanat, S. C., J. E. Reardon, A. Erice, M. C. Jordan, W. L. Drew, and K. K. Biron. 1991. Ganciclovir-resistant cytomegalovirus clinical isolates: mode of resistance to ganciclovir. Antimicrob. Agents Chemother. 35:2191-2197.
45. Sullivan, V., K. K. Biron, C. Talarico, S. C. Stanat, M. Davis, L. M. Pozzi, and D. M. Coen. 1993. A point mutation in the human cytomegalovirus DNA polymerase gene confers resistance to ganciclovir and phosphonylmethoxyalkyl derivatives. Antimicrob. Agents Chemother. 37:19-25.
46. Tatarowicz, W. A., N. S. Lurain, and K. D. Thompson. 1992. A ganciclovir-resistant clinical isolate of human cytomegalovirus exhibiting cross-resistance to other DNA polymerase inhibitors. J. Infect. Dis. 166:904-907.
47. Whitley, R. J., M. A. Jacobson, D. N. Friedberg, G. N. Holland, D. A. Jabs, D. T. Dieterich, W. D. Hardy, M. A. Polis, T. A. Deutsch, J. Feinberg, S. A. Spector, S. Walmsley, W. L. Drew, W. G. Powderly, P. D. Griffiths, C. A. Benson, and H. A. Kessler. 1998. Guidelines for the treatment of cytomegalovirus diseases in patients with AIDS in the era of potent antiretroviral therapy: recommendations of an international panel. International AIDS Society-USA. Arch. Intern. Med. 158:957-969.
48. Xiong, X., J. L. Smith, C. Kim, E. Huang, and M. S. Chen. 1996. Kinetic analysis of the interaction of cidofovir diphosphate with human cytomegalovirus DNA polymerase. Biochem. Pharmacol. 51:1563-1567.
49. Yokota, T., S. Mochizuki, K. Konno, S. Mon, S. Shigeta, and E. De Clercq. 1991. Inhibitory effects of selected antiviral compounds on human hepatitis B virus DNA synthesis. Antimicrob. Agents Chemother. 35:394-397.
50. Yu, K. L., J. J. Bronson, H. Yang, A. Patick, M. Alam, V. Brankovan, R. Datema, M. J. M. Hitchcock, and J. C. Martin. 1988. Synthesis and antiviral activity of methyl derivatives of 9-[2-(phosphonomethyl)ethyl]guanine. J. Med. Chem. 35:2958-2969.
51. Zou, R., J. C. Drach, and L. B. Townsend. 1997. Design, synthesis, and antiviral evaluation of 2-substituted 4,5-dichloro- and 4,6-dichloro-1-β-D-ribofuranosylbenzimidazoles as potential agents for human cytomegalovirus infections. J. Med. Chem. 40:802-810.