Structure-activity relationships in platelet-activating factor (PAF). 10. From PAF antagonism to inhibition of HIV-1 replication

Journal of Medicinal Chemistry

Volumn 43, Issue 11, 2000, Pages 2149-2154

  Serradji, Nawal ^a   Bensaid, Okkacha ^a   Martin, Marc ^b   Kan, Erwan ^a   Dereuddre Bosquet, Nathalie ^b,c   Redeuilh, Catherine ^a   Huet, Jack ^a   Heymans, Françoise ^a   Lamouri, Aazdine ^a   Clayette, Pascal ^b,c   Dong, Chang Zhi ^a   Dormont, Dominique ^b   Godfroid, Jean Jacques ^a  

^a Laboratoire de Pharmacochimie   (France)

^b INSTITUT DE RADIOPROTECTION ET DE SÛRETÉ NUCLÉAIRE   (France)

^c SPI BIO   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 (3 PYRIDYL) 1H,3H PYRROLO[1,2 C]THIAZOLE 7 CARBOXAMIDE; PMS 601; THROMBOCYTE ACTIVATING FACTOR; THROMBOCYTE ACTIVATING FACTOR RECEPTOR AFFECTING AGENT; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DEMENTIA; DRUG EFFECT; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; STRUCTURE ACTIVITY RELATION; VIRUS REPLICATION;

ANTI-HIV AGENTS; CELLS, CULTURED; HIV; HUMANS; INHIBITORY CONCENTRATION 50; MACROPHAGES; MICROBIAL SENSITIVITY TESTS; PIPERAZINES; PLATELET ACTIVATING FACTOR; PLATELET MEMBRANE GLYCOPROTEINS; PYRIDINES; RECEPTORS, CELL SURFACE; RECEPTORS, G-PROTEIN-COUPLED; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES; VIRUS REPLICATION;

EID: 0034213477     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9911276     Document Type: Article

References (32)

1. Walh, L. M.; Corcoran, M. L.; Pyle, S. W.; Arthur, L. O.; Harel-Bellan, A.; Farrar, W. L. Human Immunodeficiency Virus Glycoprotein (gp 120) Induction of Monocyte Arachidonic Acid Metabolites and Interleukines. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 621-625.
2. Perry, S. W.; Hamilton, J. A.; Tjoelker, L. W.; Dbaibo, G.; Dzenko, K. A.; Epstein, L. G.; Hannun, Y.; Whittaker, J. S.; Dewhurst, S.; Gelbard, H. A. Platelet-Activating Factor Receptor Activation, an Initiator Step in HIV-1 Neuropathogenesis. J. Biol. Chem. 1998, 273, 17660-17664.
3. Kolson, D. L.; Lavi, E.; Gonzalez-Scarano, F. The Effects of Human Immunodeficiency Virus in the Central Nervous System. Adv. Virus Res. 1998, 50, 1-47.
4. Gelbard, H. A.; Nottet, H. S.; Swindells, S.; Jett, M.; Dzenko, K. A.; Genis, P.; White, R.; Wang, L.; Choi, Y. B.; Zhang, D.; Lipton, S. A.; Tourtellote, W. W.; Epstein, L. G.; Gendelman, H. E. Platelet-Activating Factor: a Candidate Human Immunodeficiency Virus Type 1-Induced Neurotoxin. J. Virol. 1994, 68, 4628-4635.
5. Dagenais, P.; Thivierge, M.; Parent, J.-L.; Stankova, J.; Rola-Pleszczynski, M. Augmented Expression of Platelet-Activating Factor Receptor Gene by TNF-alpha through Transcriptional Activation in Human Monocytes. J. Leukocyte Biol. 1997, 61, 106-112.
6. Rola-Pleszczynski, M. Priming of Human Monocytes with PAF Augments their Production of Tumor Necrosis Factor. J. Lipid Mediators 1990, 2, S77-S82.
7. Howard, A. D.; Erickson, K. L. The Induction and Augmentation of Macrophage Tumoricidal Responses by Platelet-Activating Factor. Cell. Immunol. 1995, 164, 105-112.
8. Enting, H. E.; Hoetelmans, R. M. W.; Lange, J. M. A.; Burger, D. M.; Beijnen, J. H.; Portegies, P. Antiretroviral Drugs and the Central Nervous System. AIDS 1998, 12, 1941-1955.
9. Weissman, D.; Poli, G.; Bousseau, A.; Fauci, A. S. A Platelet-Activating Factor Antagonist, RP 55778, Inhibits Cytokine-Dependent Induction of Human Immunodeficiency Virus Expression in Chronically Infected Promonocytic Cells. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 2537-2541.
10. Le Naour, R.; Clayette, P.; Henin, Y.; Mabondzo, A.; Raoul, H.; Bousseau, A.; Dormont, D. Infection of Human Macrophages with an Endogenous Tumor Necrosis Factor-Alpha (TNF-alpha)-Independent Human Immunodeficiency Virus Type-1 Isolate is Unresponsive to the TNF-alpha Synthesis Inhibitor RP 55778. J. Gen. Virol. 1994, 75, 1379-1388.
11. Sedivy, P.; Caillard, C. G.; Floch, A.; Folliard, F.; Mondot, S.; Robaut, C.; Terlain, B. 48740 RP, a Specific PAF-Acether Antagonist. Prostaglandins 1985, 30, 688.
12. Floch, A.; Bousseau, A.; Hetier, E.; Floch, F.; Bost, P.-E.; Cavero, I. RP 55778, a PAF Receptor Antagonist, Prevents and Reverses LPS-Induced Hemoconcentration and TNF Release. J. Lipid Mediators 1989, 1, 349-360.
13. Johnson, C. D. Platelet-Activating Factor and Platelet-Activating Factor Antagonists in Acute Pancreatitis. Dig. Surg. 1999, 16, 93-101.
14. Schifitto, G.; Sacktor, N.; Marder, K.; McDermott, M. P.; McArthur, J. C.; Kieburtz, K.; Small, S.; Epstein, L. G. Randomized Trial of the Platelet-Activating Factor Antagonist Lexipafant in HIV-Associated Cognitive Impairment. Neurological AIDS Research Consortium. Neurology 1999, 53, 391-396.
15. Lamotte-Brasseur, J.; Heymans, F.; Dive, G.; Lamouri, A.; Redeuilh, C.; Hosford, D.; Braquet, P.; Godfroid, J.-J. PAF-Receptor and the "Cache-Oreilles" Effect. Simple PAF Antagonists. Lipids 1991, 26, 1167-1171.
16. Dive, G.; Godfroid, J.-J.; Lamotte-Brasseur, J.; Batt, J.-P.; Heymans, F.; Dupond, L.; Braquet, P. PAF-Receptor. 1. "Cache-Oreilles" Effects of Selected High-Potency Platelet-Activating Factor (PAF) Antagonists. J. Lipid Mediators 1989, 1, 201-215.
17. Lamouri, A.; Heymans, F.; Tavet, F.; Dive, G.; Batt, J.-P.; Blavet, N.; Braquet, P.; Godfroid, J.-J. Design and Modelling of New Platelet-Activating Factor Antagonists. 1. Synthesis and Biological Activity of 1,4-Bis(3′,4′,5′-trimethoxybenzoyl)-2-[[(substitued carbonyl and carbamoyl)oxy]methyl]piperazines. J. Med. Chem. 1993, 36, 990-1000.
18. 1. Synthesis and Biological Activity of 1,4-Bis(3′,4′,5′-trimethoxybenzoyl)-2-alkyl and 2-alkoxymethylpiperazines. J. Lipid Mediators Cell Signalling 1997, 15, 145-159.
19. Batt, J.-P.; Lamouri, A.; Tavet, F.; Heymans, F.; Dive, G.; Godfroid, J.-J. New Hypothesis on the Conformation of the PAF-Receptor from Studies on the Geometry of Selected Platelet-Activating Factor-Antagonists. J. Lipid Mediators 1991, 4, 343-346.
20. 1. Relative Importance of Hydrophobicity and Electronic Distribution in Piperazinic Series. J. Lipid Mediators Cell Signalling 1997, 15, 161-173.
21. Le Texier, L.; Favre, E.; Ronzani, N.; Massicot, F.; Blavet, N.; Pirotzky, E.; Godfroid, J.-J. Structure - Activity Relationships in Platelet-Activating Factor (PAF). 8. Tetrahydrofuran Derivatives as Dual PAF Antagonists and Acetylcholinesterase Inhibitors: Anti-Acetylcholinesterase Activity and Comparative SAR. J. Lipid Mediators Cell Signalling 1996, 13, 207-222.
22. 2 Inhibition. J. Lipid Mediators Cell Signalling 1996, 15, 125-144.
23. Rekker, R. F.; De Kort, H. M. The Hydrophobic Fragmental Constant; an Extension to a 1000 Data Point Set. Eur. J. Med. Chem. 1979, 14, 479-488.
24. Mansch, C.; Leo, A.; Hunger, S. H.; Kim, K. H.; Nikaitani, D.; Lien, E. J. "Aromatic" Substituent Constants for Structure -Activity Correlations. J. Med. Chem. 1973, 16, 1207-1216.
25. Martin, M.; Serradji, N.; Dereuddre-Bosquet, N.; Le Pavec, G.; Lamouri, A.; Heymans, F.; Godfroid, J. J.; Clayette, P.; Dormont, D. Anti-HIV-1 and Antiinflammatory Properties of a New PAF Antagonist, PMS 601. Antimicrob. Agents Chemother., submitted.
26. Bouras, A.; Boggetto, N.; Benatalah, Z.; de Rosny, E.; Sicsic, S.; Reboud-Ravaux, M. Design, Synthesis, and Evaluation of Conformationally Constrained Tongs, New Inhibitors of HIV-1 Protease Dimerization. J. Med. Chem. 1999, 42, 957-962.
27. Cazenave, J. P.; Benveniste, J.; Mustard, J. F. Aggregation of Rabbit Platelets by Platelet-Activating Factor is Independent of the Release Reaction and the Arachidonate Pathway and Inhibited by Membrane-Active Drugs. Lab. Invest. 1979, 41, 275-285.
28. Dereuddre-Bosquet, N.; Clayette, P.; Martin, M.; Benveniste, O.; Fretier, P.; Jaccard, P.; Vaslin, B.; Lebeaut, A.; Dormont, D. Lack of IL-10 Expression in Monocyte-Derived Macrophages in Response to in vitro Infection by HIV-1 Isolates. AIDS Res. Hum. Retroviruses 1997, 13, 9961-966.
29. Fidgor, C. G.; Leemans, J. M. M.; Bont, W. S.; Vries, J. E. Theory and Practice of Centrifugal Elutriation (CE). Factors Influencing the Separation of Human Blood Cells. Cell. Biophys. 1983, 5, 105-118.
30. Gartner, S.; Markovitz, P.; Markovitz, D. M.; Kaplan, M. H.; Gallo, R. C.; Popovic, M. The Role of Mononuclear Phagocytes in HTLV-III/LAV Infection. Science 1986, 233, 215-219.
31. Kärber, G. Beitrag Zur Kollektiven Behandlung Pharmakologischer Reihenversuche. Arch. Exp. Pathol. Pharmakol. 1931, 162, 956-959.
32. Rey, F.; Spire, B.; Dormont, D.; Barré-Sinoussi, F.; Montagnier, L.; Chermann, J. C. Characterization of RNA Dependent DNA Polymerase of a New Human T-Lymphotropic Retrovirus (Lymphadenopathy Associated Virus). Biochem. Biophys. Res. Commun. 1984, 121, 126-133.