Antiretroviral agent (R)-9-(2-phosphonomethoxypropyl) adenine stimulates cytokine and nitric oxide production

European Journal of Pharmacology

Volumn 331, Issue 2-3, 1997, Pages 245-252

  Zídek, Zdeněk ^a   Holý, Antonín ^b   Franková, Daniela ^a  

^a INSTITUTE OF MATHEMATICS   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

(R) PMPA ((R) 9 (2 phosphonomethoxypropyl)adenine; Acyclic nucleotide analog; IL 10 (interleukin 10); NO (nitric oxide); TNF (tumor necrosis factor )

Indexed keywords

ANTIRETROVIRUS AGENT; CYTOKINE; GAMMA INTERFERON; INTERLEUKIN 10; NITRIC OXIDE; TENOFOVIR; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ACTIVITY; FEMALE; IMMUNOMODULATION; MOUSE; NONHUMAN; PERITONEUM MACROPHAGE; PRIORITY JOURNAL;

ADENINE; ADJUVANTS, IMMUNOLOGIC; ANIMALS; ANTI-HIV AGENTS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CELLS, CULTURED; CULTURE MEDIA; CYTOKINES; FEMALE; IMMUNOHISTOCHEMISTRY; INDOMETHACIN; INTERFERON TYPE II; INTERLEUKIN-10; MACROPHAGES; MICE; MICE, INBRED C57BL; NITRIC OXIDE; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHODIESTERASE INHIBITORS; PHOSPHONIC ACIDS; STIMULATION, CHEMICAL; THEOPHYLLINE; TUMOR NECROSIS FACTOR-ALPHA;

EID: 0343144794     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-2999(97)01004-2     Document Type: Article

References (45)

1. Akarid, K., Sinet, M., Desforges, B., Gougerot-Pocidalo, M.A., 1995. Inhibitory effect of nitric oxide on the replication of a murine retrovirus in vitro and in vivo. J. Virol. 69, 7001-7014.
2. Akridge, R.E., Oyafuso, L.K., Reed, S.G., 1994. IL-10 is induced during HIV-1 infection and is capable of decreasing viral replication in human macrophages. J. Immunol. 153, 5782-5789.
3. Balzarini, J., Perno, C.F., Schols, D., De Clercq, E., 1991. Activity of acyclic nucleoside phosphonate analogues against human immunodeficiency virus in monocyte/macrophages and peritoneal blood lymphocytes. Biochem. Biophys. Res. Commun. 178, 329-335.
4. Balzarini, J., Aquaro, S., Perno, C.F., Witvrouw, M., Holý, A., De Clercq, E., 1996. Activity of the (R)-enantiomers of 9-(2-phosphonylmethoxypropyl)adenine and 9-(2-phosphonylmethoxypropyl)-2,6-diamino-purine against human immunodeficiency virus in different human cell systems. Biochem. Biophys. Res. Commun. 219, 337-341.
5. Barditch-Crovo, P.A., Toole, J., Burgee, M., Wachsman, M., Ebeling, D., Cundy, K.C., Jaffe, H.S., Lietman, P.S., 1995. A randomized, double-blind, placebo-controlled phase I/II evaluation of 9-[2-bis(pivaloyloxymethyl) phosphonylmethoxyethyl]adenine (bis-POM-PMEA), an orally bioavailable prodrug of the anti-HIV nucleotide, PMEA. Antiviral Res. 26, A229, (Abstract).
6. Bischofberger, N., Tsai, C.-C., Follis, K.E., Sabo, A., Grant, R.F., Beck, T.W., Dailey, P.J., Black, R., 1996. Antiviral efficacy of PMPA in macaques chronically infected with SIV. Antiviral Res. 30, A42, (Abstract).
7. Bogdan, C., Vodovotz, Y., Nathan, C., 1991. Macrophage deactivation by interleukin-10. J. Exp. Med. 174, 1549-1555.
8. Breen, E.A., Rezai, A., Nakajima, K., Beall, G., Mitsuyasu, R., Hirano, T., Kishimoto, T., Martinez-Maza, O., 1990. Infection with HIV is associated IL-6 levels and production. J. Immunol. 144, 480-484.
9. Calio, R., Villani, N., Balestra, E., Sesa, F., Holý, A., Balzarini, J., De Clercq, E., Perno, C.F., Del Gobbo, V., 1994. Enhancement of natural killer activity and interferon induction by different acyclic nucleoside phosphonates. Antiviral Res. 23, 77-89.
10. Cassatella, M.A., Meda, L., Bonora, S., Ceska, M., Constatin, G., 1993. Interleukin 10 (IL-10) inhibits the release of proinflammatory cytokines from human polymorphonuclear leukocytes. Evidence for an autocrine role of tumor necrosis factor and IL-1 beta in mediating the production of IL-8 triggered by lipopolysaccharide. J. Exp. Med. 178, 2207-2211.
11. Cherrington, J.M., Allen, S.J.W., Bischofberger, N., Chen, M.S., 1995. Kinetic interaction of the diphosphates of 9-(2-phosphonyl-methoxyethyl)adenine and other anti-HIV active purine congeners with HIV reverse transcriptase and human DNA polymerases α, β and γ. Antivir. Chem. Chemother. 6, 217-221.
12. Collier, A.C., Coombs, R.W., Nienow, J., Paradise, M., Yang, H.H., Troxel, S., Boggs, J., Ebeling, D., Jaffe, H.S., Corey, L., 1993. Phase I/II study of 9-(2-phosphonylmethoxyethyl)adenine (PMEA) in advanced HIV infection. The First National Conference on Human Retroviruses and Related Infections. Bethesda, MD.
13. Corradin, S.B., Fasel, N., Buchmüller-Rouiller, Y., Ransijn, A., Smith, J., Mauël, J., 1993. Induction of macrophage nitric oxide production by interferon-γ and tumor necrosis factor-α is enhanced by interleukin-10. Eur. J. Immunol. 23, 2045-2048.
14. Crowe, S.M., Kornbluth, R.S., 1994. Overview of HIV interactions with macrophages and dendric cells: The other infection in AIDS. J. Leukocyte Biol. 56, 215-217.
15. Cundy, K.C., Barditch-Crovo, P.A., Walker, A.C., Collier, D., Ebeling, D., Toole, J., Jaffe, H.S., 1995. Clinical pharmacokinetics of Adefovir in human immunodeficiency virus type 1-infected patients. Antimicrob. Agents Chemother. 39, 2401-2405.
16. Dereuddre-Bosquet, N., Clayette, P., Martin, M., Mabondzo, A., Frétier, P., Gras, G., Martal, J., Dormont, D., 1996. Anti-HIV potential of a new interferon, interferon-τ (thromboplastin). J. Acquired Immune Defic. Syndr. Hum. Retrovir. 11, 241-246.
17. Dhawan, S., Heredia, A., Wahl, L.M., Epstein, J.S., Meltzer, M.S., Hewlett, I.K., 1995. interferon-gamma-induced downregulation of CD4 inhibits the entry of human immunodeficiency virus type-1 in primary monocytes. Pathobiology 63, 93-99.
18. Förstermann, U., Gath, I., Schwarz, P., Closs, E.I., Kleinert, H., 1995. Isoforms of nitric oxide synthase. Properties, cellular distribution and expressional control. Biochem. Pharmacol. 50, 1321-1332.
19. Fauci, A.S., 1995. An elusive soluble suppressor. Nature 378, 561.
20. Fiorentino, D.F., Zlotnick, T., Mosmann, T., Howward, M., O'Garra, A., 1991. IL-10 inhibits cytokine production by activated macrophages. J. Immunol. 147, 3815-3822.
21. Gendelman, H.E., Baca, L.M., Turpin, J., Kalrer, D.C., Hansen, B., Orenstein, J.M., Diffenbach, C.W., Friedman, R.M., Meltzer, M.S., 1990. Regulation of HIV replication in infected monocytes by IFN-α. Mechanisms for viral restriction. J. Immunol. 145, 2669-2676.
22. Hartmann, K.A., Donath, A., Beer, B., Egberink, H.F., Horzinek, M.C., Lutz, H., Hoffmann-Fezer, G., Thum, I., Thefeld, S., 1992. Use of two virostatica (AZT, PMEA) in the treatment of FIV and of FeLV seropositive cats with clinical symptoms. Vet. Immunol. Immunopathol. 35, 167-175.
23. Haskó, G., Szabó, C., Németh, Z.H., Kvetan, V., Pastores, S.M., Vizi, E.S., 1996. Adenosine receptor agonists differentially regulate IL-10, TNF-α, and nitric oxide production in RAW 264.7 macrophages and in endotoxemic mice. J. Immunol. 157, 4634-4640.
24. Holý, A., Masojídková, M., 1995. Synthesis of enantiomeric 9-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases. 1. Stepwise approach. Collect. Czech. Chem. Commun. 60, 1196-1212.
25. Joyce, D.A., Gibbons, D.P., Green, P., Steer, J.H., Feldmann, M., Brennan, F.M., 1994. Two inhibitors of pro-inflammatory cytokine release, interleukin-10 and interleukin-4, have contrasting effects on release of soluble p75 tumor necrosis factor receptor by cultured monocytes. Eur. J. Immunol. 24, 2699-2705.
26. Kambayashi, T., Jacob, C.O., Zhou, D., Mazurek, M., Fong, M., Strassmann, G., 1995. Cyclic nucleotide phosphodiesterase type IV participates in the regulation of IL-10 and in the subsequent inhibition of TNF-α and IL-6 release by endotoxin-stimulated macrophages. J. Immunol. 155, 4909-4916.
27. Karupiah, G., Wen Xie, Q., Buller, R.M.L., Nathan, C., Duarte, C., MacMicking, J.D., 1993. Inhibition of viral replication by interferon-γ-induced nitric oxide synthase. Science 261, 1445-1448.
28. Kootstra, N.A., van't Wout, A.B., Huisman, J.G., Miedema, F., Schuitemaker, H., 1994. Interference of IL-10 with HIV-1 replication in primary monocyte derived macrophages. J. Virol. 68, 6967-6975.
29. Kramata, P., Votruba, I., Otová, B., Holý, A., 1996. Different inhibitory potencies of acyclic phosphonomethoxyalkyl nucleotide analogs toward DNA polymerases α, δ and ε. Mol. Pharmacol. 49, 1005-1011.
30. Le Moine, O., Stordeur, P., Schandené, L., Marchant, A., de Groote, D., Goldman, M., Deviere, J., 1996. Adenosine enhances IL-10 secretion by human monocytes. J. Immunol. 156, 4408-4414.
31. Lepe-Zuniga, J.L., Mansel, P.W.A., Hersh, E.M., 1987. Idiophatic production of interleukin 1 in the acquired immunodeficiency syndrome. J. Clin. Microbiol. 25, 1695-1700.
32. Marletta, M.A., Yoon, P.S., Iyengar, R., Leaf, C.D., Wishnok, J.S., 1988. Macrophage oxidation of L-arginine to nitrite and nitrate. Biochemistry 27, 8706-8711.
33. 2 and of agents that raise cAMP levels on macrophage activation induced by IFN-γ and TNF-α. J. Leukocyte Biol. 58, 217-224.
34. Montaner, L.J., Dozle, A.G., Collin, M., Herbein, G., Illei, P., James, W., Minty, A., Caput, D., Ferrara, P., Gordon, S.J., 1993. Interleukin 13 inhibits human immunodeficiency virus type I production in primary blood-derived human macrophages in vitro. Exp. Med. 178, 743-747.
35. Naesens, L., Balzarini, J., Bischofberger, N., De Clercq, E., 1996. Antiretroviral activity and pharmacokinetics in mice of oral bis(pivaloyloxymethyl)-9-(2-phosphonomethoxyethyl)adenine, the bis(pivaloylomethyl) ester prodrug of 9-(2-phosphonylmethoxyethyl)adenine. Antimicrob. Agents Chemother. 40, 22-28.
36. Perno, C.F., Balestra, S., Aquaro, S., Panti, S., Cenci, A., Lazzarino, G., Tavazzi, B., Dipierro, D., Balzarini, J., Calio, R., 1996. Potent inhibition of human immunodeficiency virus and herpes simplex virus type 1 by 9-(2-phosphonylmethoxyethyl)adenine in primary macrophages is determined by drug metabolism, nucleotide pools, and cytokines. Mol. Pharmacol. 50, 359-366.
37. Poli, G., Kinter, A.L., Justement, J.S., Kehrl, J.H., Bressler, P., Stanley, S., Fauci, A.S., 1990. Tumor necrosis factor α functions in an autocrine manner in the induction of human immunodeficiency virus expression. Proc. Natl. Acad. Sci. USA 87, 782-785.
38. Poli, G., Kinter, A.L., Justement, J.S., Bressler, P., Kehrl, J.H., Fauci, A.S., 1991. Transforming growth factor β suppresses human immunodeficiency virus expression and replication in infected cells of the monocyte/macrophage lineage. J. Exp. Med. 173, 589-597.
39. Sajjadi, F.G., Tabayashi, K., Foster, A.C., Domingo, R.C., Firestein, G.S., 1996. Inhibition of TNF-α expression by adenosine: Role of A3 adenosine receptors. J. Immunol. 156, 3435-3442.
40. Saville, M.W., Taga, K., Foli, A., Broder, S., Tosato, G., Yarchoan, R., 1994. Interleukin-10 suppresses human immunodeficiency virus-1 replication in vitro in cells of the monocyte/macrophage lineage. Blood 83, 3591-3599.
41. Torre, D., Ferrario, G., 1996. Immunological aspects of nitric oxide in HIV-1 infection. Med. Hypotheses 47, 405-407.
42. Tsai, C.-C., Follis, K.E., Sabo, A., Grant, R.F., Bartz, C., Notte, R.E., Benveniste, R.E., Bischofberger, N., 1994. Preexposure prophylaxis with of 9-(2-phosphonylmethoxyethyl)adenine against simian immuno-deficiency virus infection in macaques. J. Infect. Dis. 169, 260-266.
43. Tsai, C.-C., Follis, K.E., Sabo, A., Beck, T.W., Grant, R.F., Bischofberger, N., Benveniste, R.E., Black, R., 1995. Prevention of SIV infection in macaques by (R)-9-(2-phosphonylmethoxypropyl)adenine. Science 270, 1197-1199.
44. Votruba, I., Trávníček, M., Rosenberg, I., Otmar, M., Merta, A., Hřebabecký, H., Holý, A., 1990. Inhibition of avian myeloblastosis virus reverse transcriptase by diphosphates of acyclic phosphonylmethyl nucleotide analogues. Antiviral Res. 13, 287-293.
45. Walker, R.E., Vogel, S.E., Jaffe, H.S., Polis, M.A., Kovacs, J.A., Faloon, J., Davey, R.T., Ebeling, D., Cundy, K.C., Paar, D., Markowitz, N., Masur, H., Lane, H.C., 1993. A phase I/II study of PMEA in HIV infected patients. The First National Conference on Human Retroviruses and Related Infections. Bethesda, MD.