Lipid prodrugs of phosphonoacids: Greatly enhanced antiviral activity of 1-O-octadecyl-sn-glycero-3-phosphonoformate in HIV-1, HSV-I and HCMV-infected cells, in vitro

Antiviral Research

Volumn 31, Issue 1-2, 1996, Pages 59-67

  Hosteller, Karl Y ^a,c   Kini, Ganesh D ^a,c   Beadle, James R ^a,c   Aldern, Kathy A ^a,c   Gardner, Michael F ^a,c   Border, Richard ^a,c   Kumar, Raj ^d   Barshak, Lena ^d,e   Sridhar, C N ^d,e   Wheeler, Carl J ^d   Richman, Douglas D ^a,b,c  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c VA SAN DIEGO HEALTHCARE SYSTEM   (United States)

^d VICAL INC   (United States)

^e Chugai Biopharmaceuticals Inc   (United States)

Author keywords

Antiviral activity; Odg Paa; Odg Pfa; Phosphonoacids

Indexed keywords

BOVINAE; CUCUMBER MOSAIC VIRUS; CYTOMEGALOVIRUS; HERPES; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1; PAA; SIMPLEXVIRUS;

1 O OCTADECYLGLYCERO 3 PHOSPHONOFORMATE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOMEGALOVIRUS; DRUG METABOLISM; DRUG POTENCY; DRUG SELECTIVITY; HERPES SIMPLEX VIRUS 1; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IN VITRO STUDY; PRIORITY JOURNAL;

ANTI-HIV AGENTS; ANTIVIRAL AGENTS; CELL LINE; CYTOMEGALOVIRUS; DNA, VIRAL; FOSCARNET; HERPESVIRUS 1, HUMAN; HIV-1; HUMANS; LIPIDS; PHOSPHONOACETIC ACID; PRODRUGS;

EID: 0029931181     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/0166-3542(96)00947-3     Document Type: Article

References (22)

1. Boezi, J.A. (1979) The antiherpesvirus action of phosphonoacetate. Pharmacol. Ther. 4, 231-243.
2. Chrisp, P. and Clissold, S.P. (1991) Foscarnet. A review of its antiviral activity, pharmacokinetic properties and therapeutic use in immunocompromised patients with cytomegalovirus retinitis. Drugs 41, 104-129.
3. Dangl, J.L., Parks, D.R., Oi, V.T. and Herzenberg, L.A. (1982) Rapid isolation of cloned isotype switch variants using fluorescence activated cell sorting. Cytometry 2(6), 395-401.
4. Dankner, W.M., Scholl, D., Stanat, S.C., Martin, M., Souke, R.L. and Spector, S.A. (1990) Rapid antiviral DNA-DNA hybridization assay for human cytomegalovirus. J. Virol. Methods 28, 293-298.
5. Eriksson, B., Larsson, A., Helgstrand, E., Johansson, N.-G. and Öberg, B. (1980) Pyrophosphate analogues as inhibitors of herpes simplex virus type 1 DNA polymerase. Biochim. Biophys. Acta 607, 53-64.
6. Eriksson, B., Öberg, B. and Wahren, B. (1982) Pyrophosphate analogues as inhibitors of DNA polymerases of cytomegalovirus, herpes simplex virus and cellular origin. Biochim. Biophys. Acta 696, 115-123.
7. Folch, J., Lees, M. and Sloane-Stanley, G.H. (1957) A simple method for the isolation and purification of total lipids from animal tissues. J. Biol. Chem. 226, 497-509.
8. Helgstrand, E., Eriksson, B., Johansson, N.G., Lannerö, B., Larsson, A., Misiorny, A., Norén, J.O., Sjöberg, B., Stenberg, K., Sterling, G., Stridh, S. and Öberg, B. (1978) Trisodium phosphonoformate, a new antiviral compound. Science 201, 819-821.
9. Herrin, T.R., Fairgrieve, J.S., Bower, R.R., Shipkowitz, N.L. and Mao, J.C.-H. (1977) Synthesis and anti-herpes simplex activity of analogues of phosphonoacetic acid. J. Med. Chem. 20, 660-663.
10. Huang, E.-S. (1975) Human cytomegalovirus. IV. Specific inhibition of virus-induced DNA polymerase activity and viral DNA replication by phosphonoacetic acid. J. Virol. 16, 1560-1565.
11. Larder, B.A., Chesebro, B. and Richman, D.D. (1990) Susceptibilities of zidovudine-susceptible and -resistant human immunodeficiency virus isolates to antiviral agents determined by using a quantitative plaque reduction assay. Antimicrob. Agents Chemother. 34(3), 436-441.
12. Lowry, O.H., Rosenbrough, N.J., Farr, A.L. and Randall, R.J. (1951) Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193, 265-275.
13. 5. Chem. Lett. 435, 348.
14. Neto, C.C., Steim, J.M., Sarin, P.S., Sun, D.K., Bhongle, N.N., Piratla, R.K. and Turcotte, J.G. (1990) Lipid conjugates of antiretroviral agents. II. Disodium palmityl phosphonoformale: anti-HIV activity, physical properties, and interaction with plasma proteins. Biochem. Biophys. Res. Comm. 171, 458-464.
15. Norén, J.O., Helgstrand, E., Johansson, N.G., Misiorny, A. and Stening, G. (1983) Synthesis of esters of phosphonoformic acid and their antiherpes activity. J. Med. Chem. 26, 264-270.
16. Nylén, P. (1924) Beitrag zur Kenntnis der organischen Phosphorverbindungen. Chem. Ber. 57(1), 1023-1037.
17. Öberg, B. (1983) Antiviral effects of phosphonoformate (PFA, foscarnet sodium). Pharmacol. Ther. 19, 387-415.
18. Overall, J.C., Kern, E.R. and Glasgow, L.A. (1976) Effective antiviral chemotherapy in cytomegalovirus infection of mice. J. Infect. Dis. 133. A237-A244.
19. Reno, J.M., Lee, L.F. and Boezi, J.A. (1978) Inhibition of herpesvirus replication and herpesvirus-induced deoxyribonucleic acid polymerase by phosphonoformate. Antimicrob. Agents Chemother. 13, 188-192.
20. Sandstrom, E.G., Kaplan, J.C., Byington, R.E. and Hirsch, M.S. (1985) Inhibition of human T-cell lymphotropic virus type III in vitro by phosphonoformate. Lancet 1(8444), 1480-1482.
21. Sundquist, B. and Öberg, B. (1979) Phosphonoformate inhibits reverse transcriptase. J. Gen. Virol. 45, 273-281.
22. Vaghefi, M.M., McKernan, P.A. and Robins, R.K. (1986) Synthesis and antiviral activity of certain nucleoside 5′-phosphonoformate derivatives. J. Med. Chem. 29(8), 1389-93.