Purine P1 receptor-dependent immunostimulatory effects of antiviral acyclic analogues of adenine and 2,6-diaminopurine

European Journal of Pharmacology

Volumn 530, Issue 1-2, 2006, Pages 179-187

  Kmoníčková, Eva ^a,b   Potměšil, Petr ^a   Holý, Antonín ^c   Zídek, Zdeněk ^a  

^a INSTITUTE OF EXPERIMENTAL MEDICINE   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

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

Author keywords

Acyclic nucleoside phosphonate; Adenosine receptor; Chemokine; Cytokine

Indexed keywords

2,6 DIAMINOPURINE DERIVATIVE; ACYCLIC NUCLEOSIDE; ADENINE DERIVATIVE; ADENOSINE A1 RECEPTOR; ADENOSINE A2B RECEPTOR; ADENOSINE A3 RECEPTOR; ADENOSINE RECEPTOR; ADENOSINE RECEPTOR BLOCKING AGENT; ANTIVIRUS AGENT; CHEMOKINE; CYTOKINE; INTERLEUKIN 10; MACROPHAGE INFLAMMATORY PROTEIN 1ALPHA; MESSENGER RNA; N 6 CYCLOPENTYL 9 [2 (PHOSPHONOMETHOXY)PROPYL] 2,6 DIAMINOPURINE; N 6 CYCLOPROPYL 9 [2 (PHOSPHONOMETHOXY)PROPYL] 2,6 DIAMINOPURINE; N 6 ISOBUTYL 9 [2 (PHOSPHONOMETHOXY)ETHYL] 2,6 DIAMINOPURINE; PHOSPHONIC ACID DERIVATIVE; RANTES; TENOFOVIR; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; 1,4 DIHYDRO 2 METHYL 6 PHENYL 4 (2 PHENYLETHYNYL) 3,5 PYRIDINEDICARBOXYLIC ACID 5 BENZYL 3 ETHYL ESTER; 2 AMINOPURINE; 2,6 DIAMINOPURINE; 2,6-DIAMINOPURINE; 8 (3 CHLOROSTYRYL)CAFFEINE; 8 CYCLOPENTYLTHEOPHYLLINE; 8-(3-CHLOROSTYRYL)CAFFEINE; 8-CYCLOPENTYL-1,3-DIMETHYLXANTHINE; 9 CHLORO 2 (2 FURYL) (1,2,4)TRIAZOLO(1,5 C)QUINAZOLIN 5 IMINE; 9-CHLORO-2-(2-FURYL)-(1,2,4)TRIAZOLO(1,5-C)QUINAZOLIN-5-IMINE; ADENINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; CAFFEINE; DIHYDROPYRIDINE DERIVATIVE; DRUG DERIVATIVE; IMMUNOLOGICAL ADJUVANT; ISOALLOXAZINE; LIPOPOLYSACCHARIDE; MACROPHAGE INFLAMMATORY PROTEIN 1; QUINAZOLINE DERIVATIVE; RIBOFLAVIN DERIVATIVE; THEOPHYLLINE; TRIAZOLE DERIVATIVE;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; CYTOKINE RELEASE; DRUG EFFECT; DRUG MECHANISM; FEMALE; IMMUNOSTIMULATION; MACROPHAGE; MOUSE; NONHUMAN; PRIORITY JOURNAL; RNA TRANSCRIPTION; ANIMAL; C57BL MOUSE; CELL CULTURE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; CYTOLOGY; DOSE RESPONSE; DRUG ANTAGONISM; GENETICS; HUMAN; IMMUNOLOGY; METABOLISM; PHYSIOLOGY; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; SECRETION;

2-AMINOPURINE; ADENINE; ADJUVANTS, IMMUNOLOGIC; ANIMALS; ANTI-HIV AGENTS; CAFFEINE; CELL SURVIVAL; CELLS, CULTURED; DIHYDROPYRIDINES; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; FLAVINS; HUMANS; INTERLEUKIN-10; LIPOPOLYSACCHARIDES; MACROPHAGE INFLAMMATORY PROTEIN-1; MACROPHAGES; MICE; MICE, INBRED C57BL; MOLECULAR STRUCTURE; PHOSPHONIC ACIDS; QUINAZOLINES; RANTES; RECEPTORS, PURINERGIC P1; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; RNA, MESSENGER; THEOPHYLLINE; TRIAZOLES; TUMOR NECROSIS FACTOR-ALPHA;

EID: 29844433151     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejphar.2005.11.037     Document Type: Article

References (29)

1. J. Balzarini, Z. Hao, D. Herdewijn, D.G. Johns, and E. DeClercq Intracellular metabolism and mechanism of anti-retrovirus action of 9-(2-phosphonylmethoxyethyl)adenine (PMEA), a potent anti-HIV compound Proc. Natl. Acad. Sci. U. S. A. 88 1991 1499 1503
2. J. Balzarini, C. Pannecouque, E. De Clercq, S. Aquaro, C.-F. Perno, H. Egberink, and A. Holý Antiretrovirus activity of a novel class of acyclic pyrimidine nucleoside phosphonates Antimicrob. Agents Chemother. 46 2002 2185 2193
3. M.G. Bouma, R.K. Stad, F.A.J.M. van den Wildenberg, and W.A. Buurman Differential regulatory effects of adenosine on cytokine release by activated human monocytes J. Immunol. 153 1994 4159 4186
4. S. Crowe New reverse transcriptase inhibitors Adv. Exp. Med. Biol. 458 1999 183 197
5. J.A. Fotheringham, M.B. Mayne, J.A. Grant, and J.D. Geiger Activation of adenosine receptors inhibits tumor necrosis factor-alpha release by decrasing TNF-alpha mRNA stability and p38 activity Eur. J. Pharmacol. 497 2004 87 95
6. G. Haskó, C. Szabó, Z.H. Németh, V. Kvetan, S.M. Pastores, and E.S. Vizi 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 1996 4634 4640
7. 3 receptors decreases interleukin-12 and interferon-γ production and prevents lethality in endotoxemic mice Eur. J. Pharmacol. 358 1998 261 268
8. H.-T. Ho, K.L. Woods, S.K. Konrad, H. DeBoeck, and J.M. Hitchcock Cellular metabolism and enzymatic phosphorylation of 9-(2- phosphonylmethoxyethyl) guanine (PMEG), a potent antiviral agent T.M. Block Innovations in Antiviral Development and the Detection of Virus Infection 1992 Plenum Press New York, NY 159 166
9. A. Holý Phosphonomethoxyalkyl analogs of nucleotides Curr. Pharm. Des. 9 2003 2567 2592
10. A. Holý, I. Votruba, A. Merta, J. Černý, J. Veselý, J. Vlach, K. Šedivá, I. Rosenberg, M. Otmar, H. Hřebabecký, M. Trávníček, V. Vonka, R. Snoeck, and E. De Clercq Acyclic nucleotide analogues: synthesis, antiviral activity and inhibitory effects on some cellular and virus-encoded enzymes in vitro Antivir. Res. 13 1990 295 311
11. A. Holý, I. Votruba, E. Tloušt'ová, and M. Masojídková Synthesis and cytostatic activity of N-[2-(phosphonomethoxy)alkyl] derivatives of N6-substituted adenines, 2,6-diaminopurines and related compounds Collect. Czech. Chem. Commun. 66 2001 1545 1592
12. A. Holý, I. Votruba, M. MasojIdková, G. Andrei, R. Snoeck, L. Naesens, E. De Clercq, and J. Balzarini 6-[2-(Phosphonomethoxy)alkoxyl] pyrimidines with antiviral activity J. Med. Chem. 45 2002 1918 1929
13. D. Kontoyiannis, A. Kotlyarov, E. Carballo, L. Alexopoulou, P.J. Blackshear, M. Gaestel, R.J. Davis, R.A. Flavell, and G. Kollias Interleukin-10 targets p38 MAPK to modulate ARE-dependent TNF mRNA translation and limit intestinal pathology EMBO J. 20 2001 3760 3770
14. P. Kramata, I. Votruba, B. Otová, and A. Holý Different inhibitory potencies of acyclic phosphonomethoxyalkyl nucleotide analogs toward DNA polymerases α, δ and ε Mol. Pharmacol. 49 1996 1005 1011
15. O. Le Moine, P. Stordeur, L. Schandané, A. Marchant, D. de Groote, M. Goldman, and J. Deviere Adenosine enhances IL-10 secretion by human monocytes J. Immunol. 1996 4408 4414
16. V. Le Vraux, Y.L. Chen, I. Masson, M. De Sousa, J.P. Giroud, I. Florentin, and L. Chauvelot-Moachon Inhibition of human monocyte TNF production by adenosine receptor agonists Life Sci. 52 1993 1917 1924
17. 2A receptors inhibits IL-12 production by human monocytes J. Immunol. 164 2000 436 442
18. C.D. McWhinney, M.W. Dudley, T.L. Bowlin, N.P. Peet, L. Schook, M. Bradshaw, M. De, D.R. Borcherding, and C.K. Edwards III Activation of adenosine A3 receptors on macrophages inhibits tumor necrosis factor-α Eur. J. Pharmacol. 310 1996 209 216
19. 2 receptors on rat Kupffer cells Hepatology 19 1994 1445 1452
20. P.K. Ritchie, B.L. Spangelo, D.K. Krzymowski, T.B. Rossiter, E. Kurth, and A.M. Judd Adenosine increases interleukin 6 release and decreases tumour necrosis factor release from rat adrenal zona glomerulosa cells, ovarian cells, anterior pituitary cells and peritoneal macrophages Cytokine 9 1997 187 198
21. F.G. Sajjadi, K. Tabayashi, A.C. Foster, R.C. Domingo, and G.S. Firestein Inhibition of TNF-a expression by adenosine: role of A3 adenosine receptors J. Immunol. 156 1996 3435 3442
22. B.D. Shames, R.C.J. McIntyre, D.D. Bensard, E.J. Pulido, C.H. Selzman, L.L. Reznikov, A.H. Harken, and X. Meng Suppression of tumor necrosis factor α production by cAMP in human monocytes: dissociation with mRNA level and independent of interleukin-10 J. Surg. Res. 99 2001 187 193
23. T.P. Shanley, G. Haskó, G. Egnaczyk, A.L. Salzman, and C. Szabó Suppression of macrophage inflammatory protein (MIP)-1 alpha production by adenosine receptor agonists in immunostimulated macrophages FASEB J. 12 1998 A766
24. C. Szabó, G.S. Scott, L. Virág, G. Egnaczyk, A.L. Salzman, T.P. Shanley, and G. Haskó Suppression of macrophage inflammatory protein (MIP)-1α production and collagen-induced arthritis by adenosine receptor agonists Br. J. Pharmacol. 125 1998 379 387
25. I. Votruba, M. Trávníček, I. Rosenberg, M. Otmar, A. Merta, H. Hřebabecký, and A. Holý Inhibition of avian myeloblastosis virus reverse transcriptase by diphosphates of acyclic phosphonylmethyl nucleotide analogues Antivir. Res. 13 1990 287 293
26. W.H. Watson, Y. Zhao, and R.K. Chawla S-adenosylmethionine attenuates the LPS-induced expression of the gene for tumour necrosis factor α Biochem. J. 342 1999 21 25
27. Z. Zídek, D. Franková, and A. Holý Macrophage activation by antiviral acyclic nucleoside phosphonates in dependence on priming immune stimuli Int. J. Immunopharmacol. 22 2000 1121 1129
28. 6-substituted adenines, and 2,6-diaminopurines Eur. J. Pharmacol. 475 2003 149 159
29. 1 receptors in upregulation of nitric oxide by acyclic nucleotide analogues Eur. J. Pharmacol. 501 2004 79 86