Alkoxy propane prodrugs of foscarnet: Effect of alkyl chain length on in vitro antiviral activity in cells infected with HIV-1, HSV-1 and HCMV

Antiviral Research

Volumn 36, Issue 1, 1997, Pages 43-53

  Kini, Ganesh D ^a   Beadle, James R ^a   Xie, Hong ^a   Aldern, Kathy A ^a   Richman, Douglas D ^a,b   Y Hostetler, Karl ^a  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Alkoxy propane; Foscarnet; HCMV; HIV 1; HSV 1; Prodrugs

Indexed keywords

FOSCARNET; FOSCARNET DERIVATIVE; PRODRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HUMAN; HUMAN CELL; HUMAN CYTOMEGALOVIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANTIVIRAL AGENTS; CELL LINE; CELL SURVIVAL; CYTOMEGALOVIRUS; FOSCARNET; HERPESVIRUS 1, HUMAN; HIV-1; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PRODRUGS;

HERPES; HUMAN HERPESVIRUS 1; HUMAN HERPESVIRUS 5; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 0030869999     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-3542(97)00039-9     Document Type: Article

References (19)

1. Bakker-Woudenberg I.A.J.M., Lokerse A.F., Kate M.T. Increased efficacy of ganciclovir and foscarnet inhibition of cytomegalovirus replication in vitro by encapsulation in liposomes. Scand. J. Infect. Dis. Suppl. 74:1991;54-57.
2. Baumann W.J., Schmid H.H.O., Ulshofer H.W., Mangold H.K. Alkoxylipids IV. Synthesis and characterization of naturally occurring ethers, esters and ether esters of diols. Biochim. Biophys. Acta. 144:1967;355-365.
3. Brachwitz H., Langen P., Dube G., Schildt J., Paultauf F., Hermetter A. Halo lipids. 10. Synthesis and cytostatic activity of O-alkylglycerophospho-L-serine analogs. Chem. Phys. Lipids. 54:1990;89-98.
4. Chrisp P., Clissold S.P. Foscarnet. A review of its antiviral activity, pharmacokinetic properties and therapeutic use in immunocompromised patients with CMV retinitis. Drugs. 41:1991;104-129.
5. Dangl J.L., Parks D.R., Oi V.T., Herzenberg L.A. Rapid isolation of cloned isotype switch variants using fluorescence activated cell sorting. Cytometry. 2:1982;395-401.
6. Dusserre N., Lessard C., Paquette N., Perron S., Poulin L., Tremblay M., Beauchamp D., Désormeaux A., Bergeron M.G. Encapsulation of foscarnet in liposomes modifies drug intracellular accumulation, in vitro anti-HIV-1 activity, tissue distribution and pharmacokinetics. AIDS. 9:1995;833-841.
7. Gümbel H.O.C., Rückert D.G., Cinatl J., Rabenau H., Doerr H.W., Ohrloff C. In vitro anti-human cytomegalovirus activity of liposome-encapsulated foscarnet. German J. Ophthalmol. 3:1994;5-8.
8. Hostetler K.Y., Kini G.D., Beadle J.R., Aldern K.A., Gardner M.F., Border R., Kumar R., Barshak L., Sridhar C.N., Wheeler C.J., Richman D.D. Lipid prodrugs of phosphonoacids: Greatly enhanced antiviral activity of 1-O-Octadecyl-sn-glycero-3-phosphonoformate in HIV-1, HSV-1 and HCMV-infected cells, in vitro. Antiviral Res. 31:1996;59-67.
9. Kosar-Hashemi B., Armarego W.L.F. A convenient spectrophotometric method for measuring the kinetic parameters of glyceryl-ether monooxygenase (EC 1.14.16.5). Biol. Chem. Hoppe-Seyler. 374:1993;9-25.
10. Larder B.A., Chesbro B., Richman D.D. Susceptibilities of zidovudine-susceptible and -resistant human immunodeficiency virus isolates to antiviral agents determined using a quantitative plaque reduction assay. Antimicrob. Agents Chemother. 34:1990;436-441.
11. Mellors J.W., Bazmi H.Z., Schinazi R.F., Roy B.M., Hsiou Y., Arnold E., Weir J., Mayers D.L. Novel mutations in reverse transcriptase of human immunodeficiency virus type 1 reduce susceptibility to foscarnet in laboratory and clinical isolates. Antimicrob. Agents Chemother. 39:1995;1087-1092.
12. Öberg B. Antiviral effects of phosphonoformate (PFA, foscarnet sodium). Pharmacol. Ther. 19:1983;387-415.
13. Pascher I., Sundell S., Eibl H., Harlos K. Interactions and space requirement of the phosphate head group of membrane lipids. the single crystal structures of a triclinic and a monoclinic form of hexadecyl-2-deoxyglycerophosphone acid monohydrate. Chem. Phys. Lipids. 35:1984;103-115.
14. Polis M.A., deSmet M.D., Baird B.F., Mellow S., Faloon J., Davey R.T., Kovacs J.A., Palestine A.G., Nussenblatt R.B., Masur H.et al. Increased survival of a cohort of patients with AIDS and CMV retinitis who received sodium phosphonoformate (foscarnet). Am. J. Med. 94:1993;175-180.
15. Sandstrom E.G., Kaplan J.C., Byington R.E., Hirsch M.S. Inhibition of human T-lymphotrophic virus III by phosphonoformate. Lancet. 1(8444):1985;1480-1482.
16. Szoka F.C. Jr., Chu C.-J. Increased efficacy of phosphonoformate and phosphonoacetate inhibition of herpes simplex virus type 2 replication by encapsulation in liposomes. Antimicrobial Agents Chemotherapy. 32:1988;858-864.
17. Tachedjian G., Mellors J., Bazmi H., Birch C., Mills J. Zidovudine resistance is suppressed by mutations conferring resistance of human immunodeficiency virus type 1 to foscarnet. J. Virol. 70:1996;7171-7181.
18. Tsushima S., Yoshioka Y., Tanida S., Nomura H., Nojima S., Hozumi M. Synthesis and antimicrobial activities of alkyl lysolipids. Chem. Pharm. Bull. 30:1982;3260-3270.
19. Yoshida H., Ikeda K., Achiwa K., Hosino H. Synthesis of sulfated cerebroside analogs having mimicks of ceramide and their anti-human immunodeficiency virus type 1 activities. Chem. Pharm. Bull. 43:1995;594-602.