Antiretroviral activities of acyclic nucleoside phosphonates [9-(2- phosphonylmethoxyethyl)adenine, 9-(2-phosphonylmethoxyethyl) guanine, (R)-9- (2-phosphonylmethoxypropyl)adenine, and MDL 74,968] in cell cultures and murine sarcoma virus-infected newborn NMRI mice

Antimicrobial Agents and Chemotherapy

Volumn 41, Issue 3, 1997, Pages 611-616

  Balzarini, J ^a   Vahlenkamp, T ^b   Egberink, H ^b   Hartmann, K ^c   Witvrouw, M ^a   Pannecouque, C ^a   Casara, P ^d,e   Nave J F ^d   De Clercq, E ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^b Department of Infectious Diseases and Immunology   (Netherlands)

^c I Medizinische Tierklinik   (Germany)

^d SANOFI   (France)

^e INSTITUT DE RECHERCHES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

9 [2 METHYLIDENE 3 (PHOSPHONOMETHOXY)PROPYL]GUANINE; ANTIVIRUS AGENT; TENOFOVIR; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL MODEL; ANIMAL TISSUE; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; DRUG POTENCY; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS 2; MOUSE; NEWBORN; NONHUMAN; PRIORITY JOURNAL; RETROVIRUS; SARCOMA VIRUS; SURVIVAL TIME; VIRUS INHIBITION;

EID: 0031020488     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.41.3.611     Document Type: Article

References (34)

1. Balzarini, J., D. A. Cooney, M. Dalal, G.-J. Kang, J. E. Cupp, E. De Clercq, S. Broder and D. G. Johns. 1987. 2′,3′-Dideoxycytidine: regulation of its metabolism and anti-retroviral potency by natural pyrimidine nucleosides and by inhibitors of pyrimidine nucleotide synthesis. Mol. Pharmacol. 32: 798-806.
2. Balzarini, J., M. Baba, R. Pauwels, P. Herdewijn, and E. De Clercq. 1988. Anti-retrovirus activity of 3′-fluoro-and 3′-azido-substituted pyrimidine 2′,3′-dideoxvnucleoside analogues. Biochem. Pharmacol. 37:2847-2856.
3. Balzarini, J., P. Herdewijn, and E. De Clercq. 1989. Differential patterns of intracellular metabolism of 2′,3′-didehydro-2′,3′-didcoxythymidine and 3′-azido-2′,3′-dideoxythymidine, two potent anti-human immunodeficiency virus compounds. J. Biol. Chem. 264:6127-6133.
4. Balzarini, J., L. Naesens, P. Herdewijn, I. Rosenberg, A. Holy, R. Pauwels, M. Baba, D. G. Johns, and E. De Clercq. 1989. Marked in vivo antiretrovirus activity of 9-(2-priosphonylmethoxyethyl)adenine, a selective anti-human immunodeficiency virus agent. Proc. Natl. Acad. Sci. USA 86:332-336.
5. Balzarini, J., and E. De Clercq. 1991. 5-Phosphoribosyl 1-pyrophosphate svnthetase converts the acyclic nucleoside phosphonates 9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine and 9-(2-phosphonylmethoxyethyl)adenine directly to their antivirally active diphosphate derivatives. J. Bull. Chem. 266:8686-8689.
6. Balzarini, J., A. Holý, J. Jindrich, H. Dvorakova, Z. Hao, R. Snoeck, P. Herdewijn, D. G. Johns, and E. De Clercq. 1991. 9-[(2RS)-3-Fluoro-2-phosphonylmethoxypropyl] derivatives of purines: a class of highly selective antiretroviral agents in vitro and in vivo. Proc. Natl. Acad. Sci. USA 88:4961-4965.
7. Balzarini, J., L. Naesens, J. Slachmuylders, H. Niphuis, I. Rosenberg, A. Holy, H. Schellekens, and E. De Clercq. 1991. 9-(2-Phosphonylmethoxyethyl)adenine (PMEA) effectively inhibits retrovirus replication in vitro and simian immunodeficiency virus infection in rhesus monkeys. AIDS 5:21-28.
8. Balzarini, J., A. Holy, J. Jindrich, L. Naesens, R. Snoeck, D. Schols, and E. De Clercq. 1993. Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2-phosphonomethoxypropyl)-2,6-diaminopurine. Antimicrob. Agents Chemother. 37:332-338.
9. Bridges, C. G., D. L. Taylor, P. S. Ahmed, T. M. Brennan, J.-M. Hornsperger, J.-F. Navé, P. Casara, and A. S. Tyms. 1996. MDL 74,968, a new acyclonucleotide analog: activity against human immunodeficiency virus in vitro and in the hu-PBL-SCID.beige mouse model of infection. Antimicrob. Agents Chemother. 40:1072-1077.
10. Casara, P., J.-M. Altenburger, D. L. Taylor, A. S. Tyms, M. Kenny, and J.-F. Navé. 1995. Synthesis and antiviral activity of rigid acyclonucleotide analogs. Bioorg. Med. Chem. Lett. 5:1275-1280.
11. Cerný, J., I. Votruba, V. Vonka, I. Rosenberg, M. Otmar, and A. Holý. 1990. Phosphonylmethyl ethers of acyclic nucleoside analogues: inhibitors of HSV-1 induced ribonucleotide reductase. Antivir. Res. 13:253-264.
12. De Clercq, E. 1995. Toward improved anti-HIV chemotherapy: therapeutic strategies for intervention with HIV infections. J. Med. Chem. 38:2491-2517.
13. De Clercq, E., and T. C. Merigan. 1971. Moloney sarcoma virus-induced tumors in mice: inhibition or stimulation by (poly rI):(poly rC). Proc. Soc. Exp. Biol. Med. 137:590-594.
14. Egberink, H., M. Borst, H. Niphuis, J. Balzarini, H. Neu, H. Schellekens, E. De Clercq, M. Horzinek, and M. Koolen. 1990. Suppression of feline immunodeficiency virus infection in vivo by 9-(2-phosphonomethoxyethyl)adenine. Proc. Natl. Acad. Sci. USA 87:3087-3091.
15. Eriksson, S., B. Kierdaszuk, B. Munch-Petersen, B. Öberg, and N. G. Johansson. 1991. Comparison of the substrate specificities of human thymidine kinase 1 and 2 and deoxycytidine kinase toward antiviral and cytostatic nucleoside analogs. Biochem. Biophys. Res. Commun. 176:586-592.
16. Hartmann, K., A. Donath, B. Beer, H. F. Egberink, M. C. Horzinek, H. Lutz, G. Hoffmann-Fezer, I. Thum, and S. Thefeld. 1993. Use of two virustatica (AZT, PMEA) in the treatment of FIV and of FeLV seropositive cats with clinical svmptoms. Vet. Immunol. Immunopathol. 35:167-175.
17. Hartmann, K., J. Balzarini, J. Higgins, E. De Clercq, and N. C. Pedersen. 1994. In vitro activity of acyclic nucleoside phosphonate derivatives against feline immunodeficiency virus in Crandell feline kidney cells and feline peripheral blood lymphocytes. Antivir. Chem. Chemother. 5:13-19.
18. Ho, H. T., H. De Boeck, K. L. Woods, S. A. Konrad, V. Brankovan, and M. J. M. Hitchcock. 1991. Structure and activity correlation-studies of antiHIV acyclic guanine nucleotide analogs at enzyme level. Antivir. Res. 15(Suppl. 1):95.
19. Johnson, M. A., G. Ahluwalia, M. C. Connelly, D. A. Cooney, S. Broder, D. G. Johns, and A. Fridland. 1988. Metabolic pathways for the activation of the antiretroviral agent 2′,3′-dideoxyadenosine in human lymphoid cells. J. Biol. Chem. 263:15354-15357.
20. Johnson, M. A., and A. Fridland. 1989. Phosphorylation of 2′,3′-dideoxyinosine by cytosolic 5′-nucleotidase of human lymphoid cells. Mol. Pharmacol. 36:291-295.
21. Merta, A., I. Votruba, I. Rosenberg, M. Otmar, H. Hrebabecký, R. Bernaerts, and A. Holý. 1990. Inhibition of herpes simplex virus DNA polymerasc by diphosphates of acyclic phosphonylmethoxyalkyl nucleotide analogues. Antivir. Res. 13:209-218.
22. Merta, A., I. Votruba, J. Jindrich, A. Holý, T. Cihlar, I. Rosenberg, M. Otmar, and T. Y. Herve. 1992. Phosphorylation of 9-(2-phosphonomethoxyethyl)adenine and 9-(S)-(3-hydroxy-2-phosphonomethoxypropyl)adenine by AMP(dAMP) kinase from L-1210 cells. Biochem. Pharmacol. 44:2067-2077.
23. Navé, J.-F., P. J. Casara, D. L. Taylor, A. S. Tyms, M. Kenny, and S. Halazy. 1996. Synthesis, enzymatic phosphorylation and antiviral activity of acyclic dienyl phosphonate derivatives of guanine. Bioorg. Med. Chem. Lett. 6:179-184.
24. Pauwels, R., J. Balzarini, D. Schols, M. Baba, J. Desmyter, I. Rosenberg, A. Holy, and E. De Clercq. 1988. Phosphonylmethoxyethyl purine derivatives: a new class of anti-human immunodeficiency virus agents. Antimicrob. Agents Chemother. 32:1025-1030.
25. Pauwels, R., J. Balzarini, M. Baba, R. Snoeck, D. Schols, P. Herdewijn, J. Desmyter, and E. De Clercq. 1988. Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds. J. Virol. Methods 20:309-321.
26. Robbins, B. L., and A. Fridland. 1996. Metabolism and therapeutic activity of acyclic adenine phosphonate analogues. Int. Antivir. News 4:57-58.
27. Robbins, B. L., J. Greenhaw, M. C. Connelly, and A. Fridland. 1995. Metabolic pathways for activation of the antiviral agent 9-(2-phosphonylmethoxyethyl)adenine in human lymphoid cells. Antimicrob. Agents Chemother. 39:2304-2308.
28. Rose, W. C., A. R. Crosswell, J. J. Bronson, and J. C. Martin. 1990. In vivo antitumor activity of 9-[(2-phosphonylmethoxy)ethyl]guanine and related phosphonate nucleotide analogues. J. Natl. Cancer Inst. 82:510-512.
29. Shewach, D. S., D. C. Liotta, and R. F. Schinazi. 1993. Affinity of the antiviral enantiomers of oxathiolane cytosine nucleosides for human 2′-deoxycytidine kinase. Biochem. Pharmacol. 45:1540-1543.
30. Starnes, M. C., and Y.-C. Cheng. 1987. Cellular metabolism of 2′,3′-dideoxycytidine, a compound active against human immunodeficiency virus in vitro. J. Biol. Chem. 262:988-991.
31. Tsai, C.-C., K. E. Follis, A. Sabo, R. F. Grant, C. Bartz, R. E. Nolte, R. E. Benveniste, and N. Bischofberger. 1994. Preexposure prophylaxis with 9-(2-phosphonylmethoxycthyl)adenine against simian immunodeficiency virus infection in macaques. J. Infect. Dis. 169:260-266.
32. Tsai, C.-C., K. E. Follis, A. Sabo, T. W. Beck, R. F. Grant, N. Bischofberger, R. E. Benveniste, and R. Black. 1995. Prevention of SIV infection in macaques by (R)-9-(2-phosphonylmethoxypropyl)adenine. Science 276:1197-1199.
33. Vahlenkamp, T. W., A. De Ronde, J. Balzarini, L. Naesens, E. De Clercq, M. J. T. van Eijk, M. C. Horzinek, and H. F. Egberink. 1995. (R)-9-(2-Phosphonylmethoxypropyl)-2,6-diaminopurine is a potent inhibitor of feline immunodeficiency virus infection. Antimicrob. Agents Chemother. 39:746-749.
34. Yu, K.-L., J. J. Bronson, H. Yang, A. Patick, M. Alam, V. Brankovan, R. Datema, M. J. M. Hitchcock, and J. C. Martin. 1993. Synthesis and antiviral activity of 2-substituted 9-(2-phosphonomethoxyethyl)guanine analogues. J. Med. Chem. 36:2726-2738.