Nucleotide analogues with immunobiological properties: 9-[2-Hydroxy-3-(phosphonomethoxy)propyl]-adenine (HPMPA), -2,6-diaminopurine (HPMPDAP), and their N6-substituted derivatives

European Journal of Pharmacology

Volumn 540, Issue 1-3, 2006, Pages 191-199

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

^a INSTITUTE OF EXPERIMENTAL MEDICINE   (Czech Republic)

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

^c CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Acyclic nucleotide analogues; Cytokine; HPMPA (9 2 Hydroxy 3 (phosphonomethoxy)propyl adenine); Immunostimulation; Nitric oxide

Indexed keywords

6 HYDROXY 9 (3 HYDROXY 2 PHOSPHONOMETHOXYPROPYL)ADENINE; 6 HYDROXY 9 [2 HYDROXY 3 (PHOSPHONOMETHOXY)PROPYL] 2,6 DIAMINOPURINE; 6 THIO 9 [2 HYDROXY 3 (PHOSPHONOMETHOXY)PROPYL] 2,6 DIAMINOPURINE; 9 (3 HYDROXY 2 PHOSPHONOMETHOXYPROPYL)ADENINE; 9 [2 HYDROXY 3 (PHOSPHONOMETHOXY)PROPYL] 2,6 DIAMINOPURINE; CHEMOKINE; GAMMA INTERFERON; INDUCIBLE NITRIC OXIDE SYNTHASE; INTERLEUKIN 10; MACROPHAGE INFLAMMATORY PROTEIN 1ALPHA; MESSENGER RNA; N 6 (2 HYDROXYETHYL) 9 (3 HYDROXY 2 PHOSPHONOMETHOXYPROPYL)ADENINE; N 6 (2 HYDROXYETHYL) 9 [2 HYDROXY 3 (PHOSPHONOMETHOXY)PROPYL] 2,6 DIAMINOPURINE; N 6 (2 METHOXYETHYL) 9 (3 HYDROXY 2 PHOSPHONOMETHOXYPROPYL)ADENINE; N 6 (2 METHOXYETHYL) 9 [2 HYDROXY 3 (PHOSPHONOMETHOXY)PROPYL] 2,6 DIAMINOPURINE; N 6 (DIMETHYLAMINO)ETHYL 9 [2 HYDROXY 3 (PHOSPHONOMETHOXY)PROPYL] 2,6 DIAMINOPURINE; N 6 2 (DIMETHYLAMINO)ETHYL 9 (3 HYDROXY 2 PHOSPHONOMETHOXYPROPYL)ADENINE; N 6 ALLYL 9 (3 HYDROXY 2 PHOSPHONOMETHOXYPROPYL)ADENINE; N 6 ALLYL 9 [2 HYDROXY 3 (PHOSPHONOMETHOXY)PROPYL] 2,6 DIAMINOPURINE; N 6 CYCLOPROPYL 9 (3 HYDROXY 2 PHOSPHONOMETHOXYPROPYL)ADENINE; N 6 CYCLOPROPYL 9 [2 HYDROXY 3 (PHOSPHONOMETHOXY)PROPYL] 2,6 DIAMINOPURINE; N 6 DIMETHYL 9 (3 HYDROXY 2 PHOSPHONOMETHOXYPROPYL)ADENINE; N 6 DIMETHYL 9 [2 HYDROXY 3 (PHOSPHONOMETHOXY)PROPYL] 2,6 DIAMINOPURINE; N 6 PIPERIDIN 1 YL 9 (3 HYDROXY 2 PHOSPHONOMETHOXYPROPYL)ADENINE; N 6 PIPERIDIN 1 YL 9 [2 HYDROXY 3 (PHOSPHONOMETHOXY)PROPYL] 2,6 DIAMINOPURINE; NITRIC OXIDE; NUCLEOTIDE DERIVATIVE; RANTES; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; CYTOKINE PRODUCTION; CYTOKINE RELEASE; DRUG ACTIVITY; DRUG EFFECT; DRUG EFFICACY; DRUG SCREENING; FEMALE; HUMAN; HUMAN CELL; IMMUNOBIOLOGY; IMMUNOMODULATION; IMMUNOREGULATION; IMMUNOSTIMULATION; IN VITRO STUDY; MOUSE; NONHUMAN; NORMAL HUMAN; PERIPHERAL BLOOD MONONUCLEAR CELL; PERITONEUM MACROPHAGE; PRIORITY JOURNAL; PROTEIN EXPRESSION; SPLEEN CELL; T LYMPHOCYTE ACTIVATION;

ADENINE; ANIMALS; CAFFEINE; CELL SURVIVAL; CYTOKINES; DIHYDROPYRIDINES; DOSE-RESPONSE RELATIONSHIP, DRUG; FEMALE; GENE EXPRESSION; INTERFERON TYPE II; INTERFERON-GAMMA; LIPOPOLYSACCHARIDES; MACROPHAGES, PERITONEAL; MICE; MICE, INBRED C57BL; MOLECULAR STRUCTURE; NITRIC OXIDE; NITRIC OXIDE SYNTHASE TYPE II; NUCLEOTIDES; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHONIC ACIDS; PURINERGIC P1 RECEPTOR ANTAGONISTS; QUINAZOLINES; RECEPTORS, PURINERGIC P1; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; RNA, MESSENGER; TRIAZOLES;

EID: 33745006563     PISSN: 00142999     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejphar.2006.04.018     Document Type: Article

References (46)

1. Albrecht H., Schook L.B., and Jongeneel C.V. Nuclear migration of NF-κB correlates with TNF-α mRNA accumulation. J. Inflam. 45 (1995) 64-71
2. Arenzana-Seisdedos A., Virelizier J.L., Rousset, Clark-Lewis I., Loescher P., Moser B., and Baggiolini M. HIV blocked by chemokine antagonist. Nature 383 (1996) 400
3. Baba M., Konno K., Shigeta S., and De Clercq E. In vitro activity of (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine against newly isolated clinical varicella-zoster virus strains. Eur. J. Clin. Microbiol. Infect. Dis. 6 (1987) 158-160
4. Bodaghi B., Goureau O., Zipeto D., Laurent L., Virelizier J.-L., and Michelson S. Role of IFN-γ-induced indoleamine 2,3 dioxygenase and inducible nitric oxide synthase in the replication of human cytomegalovirus in retinal pigment epithelial cells. J. Immunol. 162 (1999) 957-964
5. Bogdan C., Röllinghof M., Vodovotz Y., Xie Q.W., and Nathan C. Regulation of inducible nitric oxide synthase in macrophages by cytokines and microbial products. In: Masihi K.N. (Ed). Immunotherapy of Infections (1994), Marcel Dekker, Inc., New York, NY 37-54
6. Botros S., William S., Hammam O., Zídek Z., and Holý A. Activity of 9-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]adenine against Schistosomiasis mansoni in mice. Antimicrob. Agents Chemother. 47 (2003) 3853-3858
7. Ciesielski C.J., Andreakos E., Foxwell B.M.J., and Feldmann M. TNF-α-induced macrophage chemokine secretion is more dependent on NF-κB expression than lipopolysaccharides-induced macrophage chemokine secretion. Eur. J. Immunol. 32 (2002) 2037-2045
8. Crowe S. New reverse transcriptase inhibitors. Adv. Exp. Med. Biol. 458 (1999) 183-197
9. De Clercq E., Holý A., Rosenberg I., Sakuma T., Balzarini J., and Maudgal P.C. A novel selective broad-spectrum anti-DNA virus agent. Nature 323 (1986) 464-467
10. de Vries E., Stam J.G., Franssen F.F., Nieuwenhuijs H., Chavalitshewinkoon P., de Clercq E., Overdulve J.P., and van der Vliet P.C. Inhibition of the growth of Plasmodium falciparum and Plasmodium berghei by the DNA polymerase inhibitor HPMPA. Mol. Biochem. Parasitol. 47 (1991) 43-50
11. Deng H., Liu R., Ellmeier W., Choe S., Unutmaz D., Burkhart M., Di Marzio P., Marmon S., Sutton R.E., Hill C.M., Davis C.B., Peiper S.C., Schall T.J., Littman D.R., and Landau N.R. Identification of a major co-receptor for primary isolates of HIV-1. Nature 381 (1996) 661-666
12. Dimitrov D.S., Norwood D., Stantchev T.S., Feng Y., Xiao X., and Broder C.C. A mechanism of resistance to HIV-1 entry: inefficient interactions of CXCR4 with CD4 and gp120 in macrophages. Virology 259 (1999) 1-6
13. Ding A.H., Nathan C.F., and Stuehr D.J. Release of reactive nitrogen intermediates and reactive oxygen intermediates from mouse peritoneal macrophages. Comparison of activating cytokines and evidence for independent production. J. Immunol. 141 (1988) 2407-2412
14. Drapier J.-C., Wietzerbin J., and Hibbs J.B.J. Interferon-γ and tumor necrosis factor induce the l-arginine-dependent cytotoxic effector mechanism in murine macrophages. Eur. J. Immunol. 18 (1988) 587-592
15. Flodström M., Welsh N., and Eizirik D.L. Cytokines activate the nuclear factor kB (NF-κB) and induce nitric oxide production in human pancreatic islets. FEBS Lett. 385 (1996) 4-6
16. Gao X.R., Tajima M., and Sairenji T. Nitric oxide down-regulates Epstein-Barr virus reactivation in epithelial cell lines. Virology 258 (1999) 375-381
17. Guidotti L.G., McClary H., Loudis J.M., and Chisari F.V. Nitric oxide inhibits hepatitis B virus replication in the livers of transgenic mice. J. Exp. Med. 191 (2000) 1247-1252
18. Holý A., Votruba I., Merta A., Černý J., Veselý J., Vlach J., Šedivá K., Rosenberg I., Otmar M., Hřebabecký H., Trávníček M., Vonka V., Snoeck R., and De Clercq E. Acyclic nucleotide analogues: synthesis, antiviral activity and inhibitory effects on some cellular and virus-encoded enzymes in vitro. Antivir. Res. 13 (1990) 295-311
19. Hori K., Burd P.R., Furuke K., Kutza J., Weih K.A., and Clouse K.A. Human immunodeficiency virus-1-infected macrophages induce inducible nitric oxide synthase and nitric oxide (NO) production in astrocytes: astrocytic NO as a possible mediator of neural damage in acquired immunodeficiency syndrome. Blood 93 (1999) 1843-1850
20. h1 cell activity via the modulation of the induction of nitric oxide synthase in macrophages. Eur. J. Immunol. 21 (1991) 2489-2494
21. Kaminsky R., Schmid C., Grether Y., Holý A., De Clercq E., Naesens L., and Brun R. (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine [(S)-HPMPA]: a purine analogue with trypanocidal activity in vitro and in vivo. Trop. Med. Int. Health 1 (1996) 255-263
22. Karupiah G., and Harris N. Gamma interferon-induced nitric oxide in antiviral defense and immunopathology. In: Karupiah G. (Ed). Gamma Interferon in Antiviral Defense (1997), R.G. Landes Comp., Georgetown, Texas 119-142
23. Kleinert H., Euchenhofer C., Ihrig-Biedert I., and Förstermann U. Glucocorticoids inhibit the induction of nitric oxide synthase II by down-regulating cytokine-induced activity of transcription factor nuclear factor-κB. Mol. Pharmacol. 49 (1996) 15-21
24. Kmoníčková E., Potměšil P., Holý A., and Zídek Z. Purine P1 receptor-dependent immunostimulatory effects of antiviral acyclic analogues of adenine and 2,6-diaminopurine. Eur. J. Pharmacol. 530 (2006) 179-187
25. Kramata P., Votruba I., Otová B., and Holý A. Different inhibitory potencies of acyclic phosphonomethoxyalkyl nucleotide analogs toward DNA polymerases a, d and e. Mol. Pharmacol. 49 (1996) 1005-1011
26. 6-substituted adenines, 2,6-diaminopurines and related compounds. Collect. Czechoslov. Chem. Commun. 69 (2004) 1889-1913
27. Marchant A., Amraoui Z., Gueydan C., Brunys C., Le Moine O., Vandenabeele P., Fiers W., Buurman W.A., and Goldman M. Methylprednisolone differentially regulates IL-10 and tumour necrosis factor (TNF) production during murine endotoxemia. Clin. Exp. Immunol. 106 (1996) 91-96
28. Marletta M.A., Yoon P.S., Iyengar R., Leaf C.D., and Wishnok J.S. Macrophage oxidation of l-arginine to nitrite and nitrate. Biochemistry 27 (1988) 8706-8711
29. Mosmann T.R. Properties and functions of interleukin-10. Adv. Immunol. 56 (1994) 1-26
30. Nathan C.F., and Hibbs J.B. Role of nitric oxide synthesis in macrophage antimicrobial activity. Curr. Opin. Immunol. 3 (1991) 65-70
31. Nishio R., Matsumori A., Shioi T., Ishida H., and Sasayama S. Treatment of experimental viral myocarditis with interleukin-10. Circulation 100 (1999) 1102-1108
32. Oswald I.P., Wynn T.A., Sher A., and James S.L. Interleukin 10 inhibits macrophage microbicidal activity by blocking the endogenous production of tumor necrosis factor a required as a costimulatory factor for interferon γ-induced activation. Proc. Natl. Acad. Sci. U. S. A. 89 (1992) 8676-8680
33. Persichini T., Colasanti M., Fraziano M., Colizzi V., Ascenzi P., and Lauro G.M. Nitric oxide inhibits HIV-1 replication in human astrocytoma cells. Biochem. Biophys. Res. Commun. 254 (1999) 200-202
34. Rahhal F.M., Arevalo J.F., Chavez de la Paz E., Munguia D., Azen S.P., and Freeman W.R. Treatment of cytomegalovirus retinitis with intravitreous cidofovir in patients with AIDS. A preliminary report. Ann. Intern. Med. 125 (1996) 98-103
35. Scheinman R.I., Cogswell P.C., Lofquist A.K., and Baldwin A.S. Role of transcriptional activation of IκBa in mediation of immunosuppression by glucocorticoids. Science 270 (1995) 283-286
36. Schreck R., Meier B., Männel D.N., Dröge W., and Baeuerle P.A. Dithiocarbamates as potent inhibitors of nuclear factor κB activation in intact cells. J. Exp. Med. 175 (1992) 1181-1194
37. Shakhov A.N., Collart M.A., Vassalli P., Nedospasov S.A., and Jongeneel C.V. Kappa B-type enhancers are involved in lipopolysaccharide-mediated transcriptional activation of the tumor necrosis factor alpha gene in primary macrophages. J. Exp. Med. 171 (1990) 35-47
38. Simmons G., Clapham P.R., Picard L., Offord R.E., Rosenkilde M.M., Schwartz T.W., Buser R., Wells T.N.C., and Proudfoot A.E.I. Potent inhibition of HIV-1 infectivity in macrophages and lymphocytes by a novel CCR5 antagonist. Science 276 (1997) 276-279
39. Votruba I., Trávníček M., Rosenberg I., Otmar M., Merta A., Hřebabecký H., and Holý A. Inhibition of avian myeloblastosis virus reverse transcriptase by diphosphates of acyclic phosphonylmethyl nucleotide analogues. Antivir. Res. 13 (1990) 287-293
40. Wong G.H.W., Kamb A., and Goeddel D.V. Antiviral properties of TNF. In: Beutler B. (Ed). Tumor Necrosis Factors: The Molecules and Their Emerging Role in Medicine (1992), Raven Press Ltd, New York, NY 371-381
41. Xiao X., Wu L., Stantchev T.S., Feng Y.-R., Ugolini S., Chen H., Shen Z., Riley J.L., Broder C.C., Sattentau Q.J., and Dimitrov D.S. Constitutive cell surface association between CD4 and CCR5. Proc. Natl. Acad. Sci. U. S. A. 96 (1999) 7496-7501
42. Xie Q.-W., Kashiwabara Y., and Nathan C. Role of transcription factor NF-k B/Rel in induction of nitric oxide synthase. J. Biol. Chem. 269 (1994) 4705-4708
43. Ylisastigui L., Vizzavona J., Drakopoulou E., Paindavoine P., Calvo C.F., Parmentier M., Gluckman J.C., Vita C., and Benjouad A. Synthetic full-length and truncated RANTES inhibit human immunodeficiency virus type 1 infection of primary macrophages. AIDS 12 (1998) 977-984
44. Zídek Z., Franková D., and Holý A. Activation by 9-(R)-[2-(phosphonomethoxy)propyl]adenine of chemokine (RANTES, macrophage inflammatory protein 1a) and cytokine (tumor necrosis factor alpha, interleukin-10 [IL-10], IL-1b) production. Antimicrob. Agents Chemother. 45 (2001) 3381-3386
45. 6-substituted adenines, and 2,6-diaminopurines. Eur. J. Pharmacol. 475 (2003) 149-159
46. 1 receptors in upregulation of nitric oxide by acyclic nucleotide analogues. Eur. J. Pharmacol. 501 (2004) 79-86