Oral activity of a methylenecyclopropane analog, cyclopropavir, in animal models for cytomegalovirus infections

Antimicrobial Agents and Chemotherapy

Volumn 48, Issue 12, 2004, Pages 4745-4753

  Kern, Earl R ^a,c   Bidanset, Deborah J ^a   Hartline, Caroll B ^a   Yan, Zhaohua ^b   Zemlicka, Jiri ^b   Quenelle, Debra C ^a  

^a UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

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

^c University of Alabama at Birmingham   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

9 [2,2 BIS(HYDROXYMETHYL)CYCLOPROPYLIDENE]; ANTIVIRUS AGENT; CYCLOPROPANE; CYCLOPROPAVIR; GANCICLOVIR; METHYLENECYCLOPROPANE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTERIOR EYE CHAMBER; ARTICLE; BODY WEIGHT; COMBINED IMMUNODEFICIENCY; CYTOMEGALOVIRUS INFECTION; DISEASE SEVERITY; DRUG ACTIVITY; DRUG EFFICACY; DRUG SCREENING; FEMALE; FETUS; HUMAN; HUMAN TISSUE; IMMUNE DEFICIENCY; IN VITRO STUDY; INOCULATION; KIDNEY CAPSULE; MALE; MORTALITY; MOUSE; MOUSE STRAIN; NONHUMAN; PRIORITY JOURNAL; RETINA; VIRUS INFECTION; VIRUS REPLICATION; VIRUS STRAIN;

ANIMALS; ANTIVIRAL AGENTS; CYCLOPROPANES; CYTOMEGALOVIRUS INFECTIONS; CYTOPATHOGENIC EFFECT, VIRAL; ENDPOINT DETERMINATION; GUANINE; HUMANS; IMMUNOCOMPROMISED HOST; INJECTIONS, INTRAPERITONEAL; LIVER; MICE; MICE, INBRED BALB C; MICE, SCID; PLAQUE ASSAY; RETINA; THYMUS GLAND; VIRUS REPLICATION;

EID: 9644281600     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.48.12.4745-4753.2004     Document Type: Article

References (49)

1. Allen, L. B., S. X. Li, G. Arnett, B. Toyer, W. M. Shannon, and M. G. Hollingshead. 1992. Novel method for evaluating antiviral drugs against human cytomegalovirus in mice. Antimicrob. Agents Chemother. 36:206-208.
2. Baldanti, F., A. Sarasini, J. C. Drach, J. Zemlicka, and G. Gerna. 2002. Z-isomers of 2-hydroxymethylcyclopropylidenemethyl adenine (synadenol) and guanine (synguanol) are active against ganciclovir- and foscarnet-resistant human cytomegalovirus UL97 mutants. Antivir. Res. 56:273-278.
3. Balfour, H. H., Jr., B. A. Chace, J. T. Stapleton, R. L. Simmons, and D. S. Fryd. 1989. A randomized, placebo-controlled trial of oral acyclovir for the prevention of cytomegalovirus disease in recipients of renal allografts. N. Engl. J. Med. 320:1381-1387.
4. Bidanset, D. J., M. del Cerro, E. S. Lazar, O. M. Faye-Peterson, and E. R. Kern. 1999. Animal model for ocular human cytomegalovirus infection in SCID-hu mice, p. 957-962. In O. Zak and M. A. Sande (ed.), Handbook of animal models of infection. Academic Press, London, United Kingdom.
5. Bidanset, D. J., R. J. Rybak, C. B. Hartline, and E. R. Kern. 2001. Replication of human cytomegalovirus in severe combined immunodeficient mice implanted with human retinal tissue. J. Infect. Dis. 184:192-195.
6. Bidanset, D. J., C. B. Hartline, D. J. Collins, D. C. Quenelle, Y. Chen, J. Zemlicka, and E. R. Kern. 2002. In vitro and in vivo activity of the methylene-cyclopropane analog, Qyl-1064 against murine and human cytomegalovirus infections. Antivir. Res. 53:A61.
7. Bidanset, D. J., J. R. Beadle, W. B. Wan, K. Y. Hostetler, and E. R. Kern. 2004. Oral activity of ether lipid ester prodrugs of cidofovir against experimental human cytomegalovirus infections. J. Infect. Dis. 190:499-503.
8. Boivin, G., C. Gilbert, A. Gaudreau, I. Greenfield, R. Sudlow, and N. A. Roberts. 2001. Rate of emergence of cytomegalovirus (CMV) mutations in leukocytes of patients with acquired immunodeficiency syndrome who are receiving valganciclovir as induction and maintenance therapy for CMV retinitis. J. Infect. Dis. 184:1598-1602.
9. Chou, S., N. S. Lurain, K. D. Thompson, R. C. Miner, and W. L. Drew. 2003. Viral DNA polymerase mutations associated with drug resistance in human cytomegalovirus. J. Infect. Dis. 188:32-39.
10. Chulay, J., K. Biron, L. Wang, M. Underwood, S. Chamberlain, L. Frick, S. Good, M. Davis, R. Harvey, L. Townsend, J. Drach, and G. Koszalka. 1999. Development of novel benzimidazole riboside compounds for treatment of cytomegalovirus disease. Adv. Exp. Med. Biol. 458:129-134.
11. Ciesla, S. L., J. Trahan, W. B. Wan, J. R. Beadle, K. A. Aldern, G. R. Painter, and K. Y. Hostetler. 2003. Esterification of cidofovir with alkoxyalkanols increases oral bioavailability and diminishes drug accumulation in kidney. Antivir. Res. 59:163-171.
12. Crippa, F., L. Corey, E. L. Chuang, G. Sale, and M. Boeckh. 2001. Virological, clinical, and ophthalmologic features of cytomegalovirus retinitis after hematopoietic stem cell transplantation. Clin. Infect. Dis. 32:214-219.
13. Duan, J., W. Paris, P. Kibler, C. Bousquet, M. Liuzzi, and M. G. Cordingley. 1998. Dose and duration-dependence of ganciclovir treatment against murine cytomegalovirus infection in severe combined immunodeficient mice. Antivir. Res. 39:189-197.
14. Enright, H., R. Haake, D. Weisdorf, N. Ramsay, P. McGlave, J. Kersey, W. Thomas, D. McKenzie, and W. Miller. 1993. Cytomegalovirus pneumonia after bone marrow transplantation. Risk factors and response to therapy. Transplantation 55:1339-1346.
15. Erice, A., N. Borrell, W. Li, W. J. Miller, and H. H. Balfour, Jr. 1998. Ganciclovir susceptibilities and analysis of UL97 region in cytomegalovirus (CMV) isolates from bone marrow recipients with CMV disease after antiviral prophylaxis. J. Infect. Dis. 178:531-534.
16. Goodrich, J. M., R. A. Bowden, L. Fisher, C. Keller, G. Schoch, and J. D. Meyers, 1993. Ganciclovir prophylaxis to prevent cytomegalovirus disease after allogeneic marrow transplant. Ann. Intern. Med. 118:173-178.
17. Kemble, G. W., G. M. Duke, and E. S. Mocarski. 1999. Human cytomegalovirus infection of the SCID-hu (Thy/Liv) mouse, p. 951-956. In O. Zak and M. A. Sande (ed.), Handbook of animal models of infection. Academic Press, London, United Kingdom.
18. Kern, E. R. 1991. Value of animal models to evaluate agents with potential activity against human cytomegalovirus. Transplant Proc. 23:152-155.
19. Kern, E. R. 1999. Animal model for CMV infections: murine CMV, p. 927-934. In O. Zak and M. A. Sande (ed.), Handbook of animal models of infection. Academic Press. London, United Kingdom.
20. Kern, E. R., R. J. Rybak, C. B. Hartline, and D. J. Bidanset. 2001. Predictive efficacy of SCID-hu mouse models for treatment of human cytomegalovirus infections. Antivir. Chem. Chemother. 12(Suppl. 1):149-156.
21. Kern, E. R., D. J. Collins, W. B. Wan, J. R. Beadle, K. Y. Hostetler, and D. C. Quenelle. 2004. Oral treatment of murine cytomegalovirus infections with ether lipid esters of cidofovir. Antimicrob. Agents Chemother. 48:3516-3522.
22. Kern, E., N. Kushner, C. Hartline, S. Williams-Aziz, E. Harden, S. Zhou, J. Zemlicka, and M. Prichard. Submitted for publication.
23. Kushner, N. L., S. L. Williams, C. B. Hartline, E. A. Harden, D. J. Bidanset, X. Chen, J. Zemlicka, and E. R. Kern. 2003. Efficacy of methylenecyclopropane analogs of nucleosides against herpesvirus replication in vitro. Nucleosides Nucleotides Nucleic Acids 22:2105-2119.
24. Lalezari, J. P., and B. D. Kuppermann. 1997. Clinical experience with cidofovir in the treatment of cytomegalovirus retinitis. J. Acquir. Immune Defic. Syndr. Hum. Retrovirol. 14(Suppl. 1):S27-S31.
25. Lalezari, J. P., J. A. Aberg, L. H. Wang, M. B. Wire, R. Miner, W. Snowden, C. L. Talarico, S. Shaw, M. A. Jacobson, and W. L. Drew. 2002. Phase I dose escalation trial evaluating the pharmacokinetics, anti-human cytomegalovirus (HCMV) activity, and safety of 1263W94 in human immunodeficiency virus-infected men with asymptomatic HCMV shedding. Antimicrob. Agents Chemother. 46:2969-2976.
26. Limaye, A. P., L. Corey, D. M. Koelle, C. L. Davis, and M. Boeckh. 2000. Emergence of ganciclovir-resistant cytomegalovirus disease among recipients of solid-organ transplants. Lancet 356:645-649.
27. Limaye, A. P., G. Raghu, D. M. Koelle, J. Ferrenberg, M. L. Huang, and M. Boeckh. 2002. High incidence of ganciclovir-resistant cytomegalovirus infection among lung transplant recipients receiving preemptive therapy. J. Infect. Dis. 185:20-27.
28. Ljungman, P. 2002. β-Herpesvirus challenges in the transplant recipient. J. Infect. Dis. 186(Suppl. 1):S99-S109.
29. Lowance, D., H. H. Neumayer, C. M. Legendre, J. P. Squifflet, J. Kovarik, P. J. Brennan, D. Norman, R. Mendez, M. R. Keating, G. L. Coggon, A. Crisp, I. C. Lee, et al. 1999. Valacyclovir for the prevention of cytomegalovirus disease after renal transplantation. N. Engl. J. Med. 340:1462-1470.
30. Neyts, J., J. Balzarini, L. Naesens, and E. De Clercq. 1992. Efficacy of (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine and 9-(1,3-dihydroxy-2- propoxymethyl) guanine for the treatment of murine cytomegalovirus infection in severe combined immunodeficiency mice. J. Med. Virol. 37:67-71.
31. Pari, G. S., D. Netski, S. St Jeor, D. McCarthy, J. Smith, D. Georgio, and E. von Hofe. 1998. Generation of a nude mouse tumor model for in vivo replication of human cytomegalovirus. J. Infect. Dis. 177:523-528.
32. Paya, C. V., J. A. Wilson, M. J. Espy, I. G. Sia, M. J. DeBernardi, T. F. Smith, R. Patel, G. Jenkins, W. S. Harmsen, D. J. Vanness, and R. H. Wiesner. 2002. Preemptive use of oral ganciclovir to prevent cytomegalovirus infection in liver transplant patients: a randomized, placebo-controlled trial. J. Infect. Dis. 185:854-860.
33. Prichard, M. N., and C. Shipman, Jr. 1990. A three-dimensional model to analyze drug-drug interactions. Antivir. Res. 14:181-205.
34. Quenelle, D. C., D. J. Collins, W. B. Wan, J. R. Beadle, K. Y. Hostetler, and E. R. Kern. 2004. Oral treatment of cowpox and vaccinia virus infection in mice with ether lipid esters of cidofovir. Antimicrob. Agents Chemother. 48:404-412.
35. 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.
36. 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.
37. Qiu, Y. L., R. G. Ptak, J. M. Breitenbach, J. S. Lin, Y. C. Cheng, J. C. Drach, E. R. Kern, and J. Zemlicka. 1999. Synthesis and antiviral activity of phosphoralaninate derivatives of methylenecyclopropane analogues of nucleosides. Antivir. Res. 43:37-53.
38. Ringden, O., B. Lönngvist, T. Paulin, J. Ahlmen, G. Klintmalm, B. Wahren, and J. D. 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.
39. Rybak, R. J., J. Zemlicka, Y. L. Qiu, C. B. Hartline, and E. R. Kern. 1999. Effective treatment of murine cytomegalovirus infections with methylenecyclopropane analogues of nucleosides. Antivir. Res. 43:175-188.
40. Rybak, R. J., C. B. Hartline, Y. L. Qiu, J. Zemlicka, E. Harden, G. Marshall, J. P. Sommadossi, and E. R. Kern. 2000. In vitro activities of methylenecyclopropane analogues of nucleosides and their phosphoralaninate prodrugs against cytomegalovirus and other herpesvirus infections. Antimicrob, Agents Chemother. 44:1506-1511.
41. Safrin, S., J. Cherrington, and H. S. Jaffe. 1997. Clinical uses of cidofovir. Rev. Med. Virol. 7:145-156.
42. Smee, D. F., J. L. Morris, J. A. Leonhardt, J. R. Mead, A. Holy, and R. W. Sidwell. 1992. Treatment of murine cytomegalovirus infections in severe combined immunodeficient mice with ganciclovir, (S)-1-[3-hydroxy-2- (phosphonylmethoxy)propyl] cytosine, interferon, and bropirimine. Antimicrob. Agents Chemother. 36:1837-1842.
43. Snoeck, R., T. Sakuma, E. De Clercq, I. Rosenberg, and A. Holy. 1988. (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine, a potent and selective inhibitor of human cytomegalovirus replication. Antimicrob. Agents Chemother. 32:1839-1844.
44. Wang, L. H., R. W. Peck, Y. Yin, J. Allanson, R. Wiggs, and M. B. Wire. 2003. Phase I safety and pharmacokinetic trials of 1263W94, a novel oral anti-human cytomegalovirus agent, in healthy and human immunodeficiency virus-infected subjects. Antimicrob. Agents Chemother. 47:1334-1342.
45. Weber, O., J. Reefschlager, H. Rubsamen-Waigmann, S. Raddatz, M. Hesseling, and D. Habich. 2000. A novel peptide aldehyde with activity against human cytomegalovirus in two different in vivo models. Antivir. Chem. Chemother. 11:51-59.
46. Williams, S. L., C. B. Hartline, N. L. Kushner, E. A. Harden, D. J. Bidanset, J. C. Drach, L. B. Townsend, M. R. Underwood, K. K. Biron, and E. R. Kern. 2003. In vitro activities of benzimidazole D- AND [SCAP]L-ribonucleosides against herpesviruses. Antimicrob. Agents Chemother. 47:2186-2192.
47. Winston, D. J., W. G. Ho, K. Bartoni, C. Dumond, D. F. Ebeling, W. C. Buhles, and R, E. Champlin. 1993. Ganciclovir prophylaxis of cytomegalovirus infection and disease in allogenic bone marrow transplant recipients. Results of a placebo-controlled, double-blind trial. Ann. Intern. Med. 118: 179-184.
48. Winston, D. J., A. M. Yeager, P. H. Chandrasekar, D. R. Snydman, F. B. Petersen, M. C. Territo and the Valacyclovir Cytomegalovirus Study Group. 2003. Randomized controlled trial of oral ganciclovir and intravenous ganciclovir: prevention of cytomegalovirus disease after allogeneic bone marrow transplantation. Clin. Infect. Dis. 36:749-758.
49. Zhou, S., J. M. Breitenbach, K. Z. Borysko, J. C. Drach, E. R. Kern, E. Gullen, Y. C. Cheng, and J. Zemlicka. 2004. Synthesis and antiviral activity of (Z)- and (E)-2,2-[bis(hydroxymethyl)cyclopropylidene]methylpurines and -pyrimidines: second-generation methylenecyclopropane analogues of nucleosides. J. Med. Chem. 47:566-575.