Chemokines, nitric oxide and antiarthritic effects of 9-(2-phosphonomethoxyethyl)adenine (Adefovir)

European Journal of Pharmacology

Volumn 376, Issue 1-2, 1999, Pages 91-100

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

^a INSTITUTE OF MATHEMATICS   (Czech Republic)

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

Author keywords

Arthritis; Nitric oxide (NO); PMEA (9 (2 phosphonomethoxyethyl)adenine); PMPA (9 (2 phosphonomethoxypropyl)adenine); RANTES (regulated upon activation, normal T cell expressed and secreted)

Indexed keywords

ADEFOVIR; ADEFOVIR DIPIVOXIL; CHEMOKINE; CYTOKINE; NITRIC OXIDE; PRODRUG; RANTES; TENOFOVIR;

ADJUVANT ARTHRITIS; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG EFFECT; FEMALE; LYMPHOCYTE; MACROPHAGE; NONHUMAN; PRIORITY JOURNAL; RAT; SPLENOMEGALY; SUBCUTANEOUS DRUG ADMINISTRATION;

ADENINE; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ARTHRITIS, EXPERIMENTAL; FEMALE; FIBROSIS; MACROPHAGES, PERITONEAL; NITRIC OXIDE; ORGAN SIZE; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHONIC ACIDS; PRODRUGS; RANTES; RATS; RATS, INBRED LEW; SPLEEN;

EID: 0033058887     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0014-2999(99)00343-X     Document Type: Article

References (54)

1. Arend W.P., Dayer J.M. Cytokines and cytokine inhibitors or antagonists in rheumatoid arthritis. Arthritis Rheum. 33:1990;305-315.
2. Bacon K.B., Premack B.A., Gardner P., Schall T.J. Activation of dual T cell signaling pathways by the chemokine RANTES. Science. 269:1995;1727-1730.
3. Balzarini J., Aquaro S., Perno C.F., Witvrouw M., Holý A., De Clercq E. Activity of the (R)-enantiomers of 9-(2-phosphonylmethoxypropyl)adenine and 9-(2-phosphonylmethoxypropyl)-2,6-diaminopurine against human immunodeficiency virus in different human cell systems. Biochem. Biophys. Res. Commun. 219:1996;337-341.
4. Barditch-Crovo P., Toole J., Hendrix C.W., Cundy K.C., Ebeling D., Jaffe H.S., Lietman P.S. Anti-human immunodeficiency virus (HIV) activity, safety, and pharmacokinetics of adefovir dipivoxil (9-[2-(bis-pivaloyloxymethyl)-phosphonylmethoxyethyl]adenine) in HIV-infected patients. J. Infect. Dis. 176:1997;406-413.
5. Barnes D.A., Tse J., Kaufhold M., Owen M., Hesselgesser J., Strieter R., Horuk R., Perez H.D. Polyclonal antibody directed against human RANTES ameliorates disease in the Lewis rat adjuvant-induced arthritis model. J. Clin. Invest. 101:1998;2910-2919.
6. Billingham M.E.J. Models of arthritis and search for antirheumatic drugs. Pharmacol. Ther. 21:1983;389-428.
7. Bischofberger N., Tsai C.-C., Sabo A., Follis K.E., Grant R.F., Beck T.W., Dailey P.J., Black R. Antiviral efficacy of PMPA in macaques chronically infected with SIV. Antiviral Res. 30:1996;A42. Abstract.
8. Borah B., Francis M.D., Hovancik K., Boyce J.T., Szeverenyi N.M. A quantitative one-dimensional magnetic resonance imaging technique in adjuvant arthritis: the assessment of disease progression and indomethacin efficacy. J. Rheumatol. 22:1995;855-862.
9. Connor J.R., Manning P.T., Settle S.L., Moore W.M., Jerome G.M., Webber R.K., Tjoeng F.S., Currie M.G. Suppression of adjuvant-induced arthritis by selective inhibition of inducible nitric oxide synthase. Eur. J. Pharmacol. 273:1995;15-24.
10. Danning C.L., Boumpas D.T. Commonly used disease-modifying antirheumatic drugs in the treatment of inflammatory arthritis: an update on mechanisms of action. Clin. Exp. Rheumatol. 16:1998;595-604.
11. De Clercq E. Broad-spectrum anti-DNA virus and anti-retrovirus activity of phosphonomethoxyalkylpurines and -pyrimidines. Biochem. Pharmacol. 42:1991;963-972.
12. Devergne O., Margaing-Koka A., Schall T.J., Leger-Ravet M.B., Sadick M., Peuchmaur M., Crevon M.C., Kim K.J. Production of RANTES chemokine in delayed-type hypersensitivity reactions: involvement of macrophages and endothelial cells. J. Exp. Med. 179:1994;1689-1694.
13. Engelhardt G., Homma D., Schnitzler C. Meloxicam: a potent inhibitor of adjuvant arthritis in the Lewis rat. Inflammation Res. 44:1995;548-555.
14. Farrell A.J., Blake D.R., Palmer R.M., Moncada S. Increased concentration of nitrite in synovial fluid and serum samples suggest increased nitric oxide synthesis in rheumatic disease. Ann. Rheum. Dis. 51:1992;1219-1222.
15. Förstermann U., Gath I., Schwarz P., Closs E.I., Kleinert H. Isoforms of nitric oxide synthase. Properties, cellular distribution and expressional control. Biochem. Pharmacol. 50:1995;1321-1332.
16. Gilkeson G.S., Mudgett J.S., Seldin M.F., Ruiz P., Alexander A.A., Misukonis M.A., Pisetsky D.S., Weinberg J.B. Clinical and serologic manifestations of autoimmune disease in MRL-lpr/lpr mice lacking nitric oxide synthase type 2. J. Exp. Med. 186:1997;365-373.
17. 6-substituted acyclic purine nucleoside phosphonates. Collect. Czech. Chem. Commun. 61:1996;182-187.
18. Kiely P.D.W. The Th1-Th2 model - what relevance to inflammatory arthritis? Ann. Rheum. Dis. 57:1998;328-330.
19. Munoz-Fernandez S., Cardenal A., Balsa A., Quiralte J., del Arco A., Pena J.M., Barbado F.J., Vazquez J.J., Gijon J. Rheumatic manifestations in 556 patients with human immunodeficiency virus infection. Semin. Arthritis Rheum. 21:1991;30-39.
20. Naesens L., Neyts J., Blazarini J., Bischofberger N., De Clercq E. In vivo antiretroviral efficacy of oral bis(POM)-PMEA, the bis(pivaloyl-oxymethyl)prodrug of 9-(2-phosphonylmethoxyethyl)adenine (PMEA). Nucleosides Nucleotides. 14:1995;767-770.
21. Naesens L., Balzarini J., Bischofberger N., De Clercq E. Antiretroviral activity and pharmacokinetics in mice of oral bis(pivaloyl-oxymethyl)-9-(2-phosphonomethoxyethyl)adenine, the bis(pivaloyloxy-methyl) ester prodrug of 9-(2-phosphonylmethoxyethyl)adenine. Antimicrob. Agents Chemother. 40:1996;22-28.
22. Naesens L., Bischofberger N., Armilli M., Kim C., De Clercq E. Anti-retrovirus activity and pharmacokinetics in mice of bis(POC)-PMPA, the bis(isopropyloxycarbonyloxymethyl) oral prodrug of PMPA. Antiviral Res. 34:1997;A50.
23. Nathan C., Xie Q.-W. Regulation of biosynthesis of nitric oxide. J. Biol. Chem. 269:1994;13725-13728.
24. Odeh M. New insights into the pathogenesis and treatment of rheumatoid arthritis. Clin. Immunol. Immunopathol. 83:1997;103-116.
25. Pearson C.M. Development of arthritis, periarthritis and periostitis in rats given adjuvant. Proc. Soc. Exp. Biol. Med. 91:1956;95-101.
26. Ramos-Ruiz R., Bernabeu C., Ariza A., Fernandez J.M., Larraga V., Lopez-Bote J.P.S.O. Arthritis transferred by cells derived from pre-inflammatory rat synovium. J. Autoimmun. 5:1992;93-106.
27. Rathanaswami P., Hachicha M., Sadick M., Schall R.J., McColl S.R. Expression of the cytokine RANTES in human rheumatoid synovial fibroblasts. J. Biol. Chem. 268:1993;5834-5839.
28. Robinson E., Keystone E.C., Schall T.J., Gillett N., Fish E.N. Chemokine expression in rheumatoid arthritis (RA): evidence of RANTES and macrophage inflammatory protein (MIP)-1 beta production by synovial T cells. Clin. Exp. Immunol. 101:1995;398-407.
29. Rosenberg Z.S., Norman A., Solomon G. Arthritis associated with HIV infection: radiographic manifestations. Radiology. 173:1989;171-176.
30. Schall T.J., Bacon K., Camp D.R., Kaspari J.W., Goeddel D.V. Human macrophage inflammatory protein a (MIP-1α) and MIP-1β chemokines attract distinct populations of lymphocytes. J. Exp. Med. 177:1993;1821-1826.
31. Schmidt H.H.H.W., Warner T.D., Nakane M., Förstermann U., Murad F. Regulation and subcellular location of nitrogen oxide synthases in RAW264.7 macrophages. Mol. Pharmacol. 41:1992;615-624.
32. Srinivas R.V., Robbins B.L., Connelly M.C., Gong Y.F., Bischofberger N., Fridland A. Metabolism and in vitro antiretroviral activities of bis(pivaloyloxymethyl) prodrugs of acyclic nucleoside phosphonates. Antimicrob. Agents Chemother. 37:1993;2247-2250.
33. Starett J.E. Jr., Tortolani D.R., Russel J., Hitchock M.J.M., Whiterock V., Martin J.C., Mansuri M.M. Synthesis, oral bioavailability determination, and in vitro evaluation of prodrugs of the antiviral agent 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA). J. Med. Chem. 37:1994;1857-1864.
34. Stefanovic-Racic M., Meyers K., Meschter C., Coffey J.W., Hoffman R.A., Evans C.H. N-monomethyl arginine, an inhibitor of nitric oxide synthase, suppresses the development of adjuvant arthritis in rats. Arthritis Rheum. 37:1994;1062-1069.
35. Stewart V.C., Giovannoni G., Land J.M., McDonald W.I., Clark J.B., Heales J.R. Pretreatment of astrocytes with interferon-α/β impairs interferon-γ induction of nitric oxide synthase. J. Neurochem. 68:1997;2547-2551.
36. Stichtenoth D.O., Gutzki F.-M., Tsikas D., Selve N., Bode-Böger S.M., Böger R.H., Frölich J.C. Increased urinary nitrate excretion in rats with adjuvant arthritis. Ann. Rheum. Dis. 53:1994;547-549.
37. Tanahashi M., Funaba Y., Itoh M., Kawabe N., Nakadate-Matsushita T. Inhibitory effects of TRK-530 on rat adjuvant arthritis. Pharmacology. 56:1998;242-251.
38. Tanaka Y., Otsuka T., Hotokebuchi T., Miyahara H., Nakashima H., Kuga S., Nemoto Y., Niiro H., Niho Y. Effect of IL-10 on collagen-induced arthritis in mice. Inflammation Res. 45:1996;283-288.
39. Tanaka S., Matsui T., Murakami T., Ishizuka T., Sugiura M., Kawashima K., Sugita T. Immunological abnormality associated with the augmented nitric oxide synthesis in adjuvant-induced arthritis. Int. J. Immunopharmacol. 20:1998;71-84.
40. Taub D.D., Turcovski-Corrales S.M., Key M.L., Longo D.L., Murphy W.J. Chemokine and T lymphocyte activation: I. β chemokines costimulate human T lymphocyte activation in vitro. J. Immunol. 156:1996;2095-2103.
41. Taurog J.D., Sandberg G.P., Mahowald M.E. The cellular basis of adjuvant arthritis: I. Enhancement of cell-mediated passive transfer by concanavalin A and by immunosuppressive pretreatment of the recipients. Cell. Immunol. 75:1983;271-283.
42. Tsai C.-C., Follis K.E., Sabo A., Beck T.W., Grant R.F., Bischofberger N., Benveniste R.E., Black R. Prevention of SIV infection in macaques by (R)-9-(2-phosphonylmethoxypropyl)adenine. Science. 270:1995;1197-1199.
43. Ueki Y., Miyake S., Tominaga Y., Eguchi K. Increased nitric oxide levels in patients with rheumatoid arthritis. J. Rheumatol. 230:1996;230-236.
44. Van Arman C.G. Pathway to adjuvant arthritis. Fed. Proc. 35:1976;2442-2446.
45. Van de Langerijt A.G.M., Volsen S.G., Hicks C.A., Craig P.J., Billingham M.E.J., Van den Berg W.B. Cell migration studies in the adoptive transfer of adjuvant arthritis in the Lewis rat. Immunology. 81:1994;414-419.
46. Van den Berg W., Van Lent P.L.E.M. The role of macrophages in chronic arthritis. Immunobiology. 195:1996;614-623.
47. Volin M.V., Shah M.R., Tokuhira M., Haines G.K., Woods J.M., Koch A.E. RANTES expression and contribution to monocyte chemotaxis in arthritis. Clin. Immunol. Immunopathol. 89:1998;44-53.
48. Wang J.H., Devalia J.L., Xia C., Sapsford R.J., Davies R.J. Expression of RANTES by human bronchial epithelial cells in vitro and in vivo and the effect of corticosteroids. Am. J. Respir. Cell Mol. Biol. 14:1996;27-35.
49. Weichman, B.N., 1989. Rat adjuvant arthritis: a model of chronic inflammation. In: Chang, J.Y. Lewis, A.J. (Eds.), Pharmacological Methods in the Control of Inflammation. Alan R. Liss, New York, NY, pp. 363-380.
50. Zídek Z., Franková D., Otová B. Lack of causal relationship between inducibility/severity of adjuvant arthritis in the rat and the disease-associated changes in production of nitric oxide by macrophages. Ann. Rheum. Dis. 54:1995;325-327.
51. Zídek Z., Holý A., Franková D., Otová B. Suppression of adjuvant arthritis by some acyclic nucleotide analogs. Eur. J. Pharmacol. 286:1995;307-310.
52. Zídek Z., Franková D., Holý A., Boubelík M., Dráber P. Inhibition of murine macrophage nitric oxide synthase expression by a pivoxil prodrug of antiviral acyclic nucleotide analogue 9-(2-phosphono-methoxyethyl)adenine. Biochem. Pharmacol. 54:1997;855-861.
53. Zídek Z., Holý A., Franková D. Immunomodulatory properties of antiviral acyclic nucleotide analogues: cytokine stimulatory and nitric oxide costimulatory effects. Int. J. Immunopharmacol. 19:1997;587-597.
54. Zídek, Z., Franková, D., Holý, A., 1999. Stimulation of cytokine and nitric oxide production by acyclic nucleoside phosphonates. Nucleosides Nucleotides, in press.