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Chemical Compound Review

AGN-PC-00QXRC     [2-methoxy-3-[oxido-[2-(1,3- thiazol-3...

Synonyms: CHEMBL295212, AG-H-45346, SureCN8701203, C7238_SIGMA, CV-3988, ...
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Disease relevance of [2-methoxy-3-(octadecylcarbamoyloxy)propoxy]-(2-thiazol-3-ylethoxy)phosphinic acid

  • Pretreatment with CV 3988 attenuated systemic hypotension, preserved hypoxic pulmonary vasoconstriction, and prolonged survival of awake catheter-implanted endotoxin-treated (20 mg/kg) rats [1].
  • In vivo, two structurally different PAF receptor antagonists WEB 2170 and CV 3988 significantly reduced the formation of new vessels in a tumor induced by subcutaneous implantation of MDA-MB231 cells into SCID mice [2].
  • In rats with two-kidney, one clip hypertension, the initial rapid decrease in blood pressure seen after unclipping was significantly (p less than 0.05) inhibited by CV-3988 infusion as compared with that by vehicle infusion [3].
  • These results strongly suggest that PAF may play a lethal role in anaphylactic shock and that CV-3988 may be an effective preventing agent [4].
  • However, the intravenous administration of BN 52021 (5 and 10 mg/kg) and CV-3988 (5 mg/kg) had no effect on functional recovery (regional segment shortening) in the stunned myocardium after brief occlusion and reperfusion [5].
 

High impact information on [2-methoxy-3-(octadecylcarbamoyloxy)propoxy]-(2-thiazol-3-ylethoxy)phosphinic acid

  • The prolonged hypotension and gastrointestinal damage induced by PAF or endotoxin were significantly inhibited by three structurally dissimilar PAF antagonists (CV-3988, BN-52021, and Ro-193704) [6].
  • CV-3988 (10 mg/kg) significantly (p less than 0.05) reduced both endotoxin- and PAF-induced plasma leakage in the stomach and small intestine [6].
  • To block PAF receptor-independent death pathway, we screened a panel of PAF antagonists (CV-3988, CV-6209, BN 52021, and FR 49175) [7].
  • Moreover, the IL-12-induced chemotaxis of PMN and NK cells was significantly reduced by both WEB 2170 and CV 3988, suggesting that synthesized PAF mediates the chemotactic effect of IL-12 [8].
  • Their IC50 values were in the range of 1-4 X 10(-5) M against the platelet aggregation induced by 1 X 10(-10) M 16:0 alkylacetyl-GPC, indicating that they were about 100 times weaker inhibitors than CV-3988 [9].
 

Chemical compound and disease context of [2-methoxy-3-(octadecylcarbamoyloxy)propoxy]-(2-thiazol-3-ylethoxy)phosphinic acid

 

Biological context of [2-methoxy-3-(octadecylcarbamoyloxy)propoxy]-(2-thiazol-3-ylethoxy)phosphinic acid

  • On the other hand, while CV-3988 was an effective inhibitor, a higher concentration was required and a more restricted range of activity was noted with an IC50 value of 5.9 +/- 1.3 X 10(-7) M against a challenge of 1 X 10(-10) M AGEPC in the secretion assay [14].
  • The increase in blood pressure caused by CV-3988 infusion in spontaneously hypertensive and normotensive control rats was significant (p less than 0.01 and p less than 0.001, respectively, at 60 min) compared with that caused by vehicle infusion [3].
  • The inhibitory effect of CV-6209 on the PAF-induced rabbit platelet aggregation was 104, 9, 8 and 3 times more potent than the PAF antagonists CV-3988, ONO-6240, Ginkgolide B and etizolam, respectively [15].
  • The related histology showed an improvement with CV-3988 [4].
  • In contrast, treatment of the spermatozoa with 10(-5) CV-3988 caused a significant decrease in human sperm penetration of zona-free hamster oocytes and adversely affected sperm motility after 24 h of incubation [16].
 

Anatomical context of [2-methoxy-3-(octadecylcarbamoyloxy)propoxy]-(2-thiazol-3-ylethoxy)phosphinic acid

  • The hetrazepines BN 50727 and BN 50730 and the PAF structural analogues CV 3988 and CV 6209 competitively inhibited [3H]PAF binding to corneal epithelium with similar potency [17].
  • Moreover, the Tat-induced chemotaxis of monocytes was abrogated both by WEB 2170 and by CV 3988, two chemically unrelated PAF receptor antagonists, suggesting that the synthesized PAF modulates the chemotactic response of monocytes to Tat [18].
  • While 10(-5) M CV-3988 decreased the acrosome reaction, the inhibition was also reversed by the addition of PAF [16].
  • The results suggest that PAF and CV-3988 penetrate slowly into the outer half of the lipid bilayer of plasma membranes of cells in isolated rat colon, and then rapidly diffuse laterally to associate firmly with specific binding sites [19].
  • FR-900452 and CV-3988, recently found to be antagonists of platelet activating factor, selectively blocked the contraction of rat colon induced by the active phospholipid, indicating that it induced contraction by a direct stimulatory effect on the smooth muscle of rat colon in a receptor-mediated manner [20].
 

Associations of [2-methoxy-3-(octadecylcarbamoyloxy)propoxy]-(2-thiazol-3-ylethoxy)phosphinic acid with other chemical compounds

 

Gene context of [2-methoxy-3-(octadecylcarbamoyloxy)propoxy]-(2-thiazol-3-ylethoxy)phosphinic acid

  • The presence of CV-3988 returned all valued to those obtained with IL-2 or IL-4 alone, demonstrating the specificity of PAF [26].
  • The PAF receptor antagonist CV-3988 inhibited (S)-albuterol-induced cell growth, with no effect on levalbuterol [27].
  • This enhancement was blocked by three structurally unrelated specific PAF receptor antagonists BN 52021, WEB 2170, and CV 3988 [28].
  • Also, C-PAF caused time- and concentration-dependent death of cultured retinal ECs, which was prevented by the PAF receptor antagonist CV-3988 [29].
  • TNF-alpha in the presence of WEB 2170 or CV 3988, or PAF was studied with the Greiss reagent method [30].
 

Analytical, diagnostic and therapeutic context of [2-methoxy-3-(octadecylcarbamoyloxy)propoxy]-(2-thiazol-3-ylethoxy)phosphinic acid

  • The hypotensive activity of an intravenously injected AGEPC was competitively suppressed by the intravenous infusion of 3-(N-n-octadecylcarbamoyloxy)-2-methoxypropyl-2-thiazolioethylphospha te (CV-3988) and was dose-dependent [3].
  • Infarct size was 38% +/- 5% in the saline (control) group, (n = 7), 22% +/- 5% in the BN 52021 group (n = 7), and 19% +/- 5% in the CV-3988 group (n = 8) [5].
  • Effects of platelet-activating factor antagonist CV-3988 in preservation of heart and lung for transplantation [31].
  • This substance was identified as a phospholipid, 1-O-alkyl-2-acetyl-sn-glycero-3-phosphocholine (platelet-activating factor; PAF), by thin-layer chromatography, phospholipase A2 digestion, inhibition by a specific antagonist, CV-3988, and agonist-specific refractory state [32].
  • The exudate volume was not suppressed by pretreatment with indomethacin but significantly reduced by intravenous injection of CV-3988, a novel antagonist of AGEPC [33].

References

  1. Platelet-activating factor mediates hemodynamic changes and lung injury in endotoxin-treated rats. Chang, S.W., Feddersen, C.O., Henson, P.M., Voelkel, N.F. J. Clin. Invest. (1987) [Pubmed]
  2. PAF produced by human breast cancer cells promotes migration and proliferation of tumor cells and neo-angiogenesis. Bussolati, B., Biancone, L., Cassoni, P., Russo, S., Rola-Pleszczynski, M., Montrucchio, G., Camussi, G. Am. J. Pathol. (2000) [Pubmed]
  3. Role of acetyl glyceryl ether phosphorylcholine in blood pressure regulation in rats. Masugi, F., Ogihara, T., Saeki, S., Otsuka, A., Kumahara, Y. Hypertension (1985) [Pubmed]
  4. A lethal role of platelet activating factor in anaphylactic shock in mice. Terashita, Z., Imura, Y., Shino, A., Nishikawa, K. J. Pharmacol. Exp. Ther. (1987) [Pubmed]
  5. Evidence for a role of platelet activating factor in the pathogenesis of irreversible but not reversible myocardial injury after reperfusion in dogs. Maruyama, M., Farber, N.E., Vercellotti, G.M., Jacob, H.S., Gross, G.J. Am. Heart J. (1990) [Pubmed]
  6. Evidence for platelet-activating factor as a mediator of endotoxin-induced gastrointestinal damage in the rat. Effects of three platelet-activating factor antagonists. Wallace, J.L., Steel, G., Whittle, B.J., Lagente, V., Vargaftig, B. Gastroenterology (1987) [Pubmed]
  7. Anti-apoptotic actions of the platelet-activating factor acetylhydrolase I alpha2 catalytic subunit. Bonin, F., Ryan, S.D., Migahed, L., Mo, F., Lallier, J., Franks, D.J., Arai, H., Bennett, S.A. J. Biol. Chem. (2004) [Pubmed]
  8. Platelet-activating factor synthesized by IL-12-stimulated polymorphonuclear neutrophils and NK cells mediates chemotaxis. Bussolati, B., Mariano, F., Cignetti, A., Guarini, A., Cambi, V., Foà, R., Piccoli, G., Camussi, G. J. Immunol. (1998) [Pubmed]
  9. Existence of endogenous inhibitors of platelet-activating factor (PAF) with PAF in rat uterus. Nakayama, R., Yasuda, K., Saito, K. J. Biol. Chem. (1987) [Pubmed]
  10. Effects of the platelet-activating factor antagonists CV-6209 and CV-3988 on nephrotoxic serum nephritis in the rat. Iida, H., Fujita, M., Izumino, K., Asaka, M., Entani, C., Takata, M., Sasayama, S. Nephron (1992) [Pubmed]
  11. The effects of platelet-activating factor (PAF) and a PAF antagonist (CV-3988) on smoke inhalation injury in an ovine model. Ikeuchi, H., Sakano, T., Sanchez, J., Mason, A.D., Pruitt, B.A. The Journal of trauma. (1992) [Pubmed]
  12. Gastrointestinal plasma leakage in endotoxic shock. Inhibition by prostaglandin E2 and by a platelet-activating factor antagonist. Wallace, J.L., Steel, G., Whittle, B.J. Can. J. Physiol. Pharmacol. (1987) [Pubmed]
  13. Platelet-activating factor contributes to postischemic vasospasm. Wang, W.Z., Guo, S.Z., Tsai, T.M., Anderson, G.L., Miller, F.N. J. Surg. Res. (2000) [Pubmed]
  14. Structural analogs of alkylacetylglycerophosphocholine inhibitory behavior on platelet activation. Tokumura, A., Homma, H., Hanahan, D.J. J. Biol. Chem. (1985) [Pubmed]
  15. CV-6209, a highly potent antagonist of platelet activating factor in vitro and in vivo. Terashita, Z., Imura, Y., Takatani, M., Tsushima, S., Nishikawa, K. J. Pharmacol. Exp. Ther. (1987) [Pubmed]
  16. Effects of platelet activating factor on human sperm function in vitro. Sengoku, K., Tamate, K., Takaoka, Y., Ishikawa, M. Hum. Reprod. (1993) [Pubmed]
  17. PAF binding to a single receptor in corneal epithelium plasma membrane. Hurst, J., Ma, X., Bazan, H.E. Invest. Ophthalmol. Vis. Sci. (1999) [Pubmed]
  18. The synthesis of platelet-activating factor modulates chemotaxis of monocytes induced by HIV-1 Tat. Del Sorbo, L., DeMartino, A., Biancone, L., Bussolati, B., Conaldi, P.G., Toniolo, A., Camussi, G. Eur. J. Immunol. (1999) [Pubmed]
  19. Antagonism of platelet-activating factor in isolated rat colon: possible mechanism. Tokumura, A., Yube, N., Terao, M., Tsukatani, H. Lipids (1991) [Pubmed]
  20. Study of platelet activating factor and its antagonists on rat colon strip with a new method avoiding tachyphylaxis. Tokumura, A., Terao, M., Okamoto, M., Yoshida, K., Tsukatani, H. Eur. J. Pharmacol. (1988) [Pubmed]
  21. trans-2,5-Bis-(3,4,5-trimethoxyphenyl)tetrahydrofuran. An orally active specific and competitive receptor antagonist of platelet activating factor. Hwang, S.B., Lam, M.H., Biftu, T., Beattie, T.R., Shen, T.Y. J. Biol. Chem. (1985) [Pubmed]
  22. Evaluation of PAF antagonists using human neutrophils in a microtiter plate assay. Dewald, B., Baggiolini, M. Biochem. Pharmacol. (1987) [Pubmed]
  23. Inhibition by CV-3988 of the binding of [3H]-platelet activating factor (PAF) to the platelet. Terashita, Z., Imura, Y., Nishikawa, K. Biochem. Pharmacol. (1985) [Pubmed]
  24. Specific inhibition of PAF-acether-induced platelet activation by BN 52021 and comparison with the PAF-acether inhibitors kadsurenone and CV 3988. Nunez, D., Chignard, M., Korth, R., Le Couedic, J.P., Norel, X., Spinnewyn, B., Braquet, P., Benveniste, J. Eur. J. Pharmacol. (1986) [Pubmed]
  25. 1-O-hexadec-1'-enyl-2-acetyl-sn-glycero-3-phosphocholine and its biological activity. Nakayama, R., Yasuda, K., Satouchi, K., Saito, K. Biochem. Biophys. Res. Commun. (1988) [Pubmed]
  26. Differential effects of interleukin-2 and interleukin-4 on immunomodulatory role of platelet-activating factor in human B cells. Patke, C.L., Green, C.G., Shearer, W.T. Clin. Diagn. Lab. Immunol. (1994) [Pubmed]
  27. Levalbuterol inhibits human airway smooth muscle cell proliferation: therapeutic implications in the management of asthma. Ibe, B.O., Portugal, A.M., Raj, J.U. Int. Arch. Allergy Immunol. (2006) [Pubmed]
  28. Platelet-activating factor enhances interleukin-6 production by alveolar macrophages. Thivierge, M., Rola-Pleszczynski, M. J. Allergy Clin. Immunol. (1992) [Pubmed]
  29. Platelet-activating factor in vasoobliteration of oxygen-induced retinopathy. Beauchamp, M.H., Marrache, A.M., Hou, X., Gobeil, F., Bernier, S.G., Lachapelle, P., Abran, D., Quiniou, C., Brault, S., Peri, K.G., Roberts, J., Almazan, G., Varma, D.R., Chemtob, S. Invest. Ophthalmol. Vis. Sci. (2002) [Pubmed]
  30. Role of nitric oxide and platelet-activating factor in cardiac alterations induced by tumor necrosis factor-alpha in the guinea-pig papillary muscle. Alloatti, G., Penna, C., De Martino, A., Montrucchio, G., Camussi, G. Cardiovasc. Res. (1999) [Pubmed]
  31. Effects of platelet-activating factor antagonist CV-3988 in preservation of heart and lung for transplantation. Qayumi, A.K., Jamieson, W.R., Poostizadeh, A. Ann. Thorac. Surg. (1991) [Pubmed]
  32. Cooperativity between platelet-activating factor and collagen in platelet aggregation. Kojima, S., Hagiwara, H., Soga, W., Sekiya, F., Saito, Y., Inada, Y. Biochem. Biophys. Res. Commun. (1987) [Pubmed]
  33. Inflammatory effects of acetylglycerylether phosphorylcholine: vascular permeability increase and induction of pleurisy in rats. Oh, S., Hayashi, M., Yamaki, K. Prostaglandins, leukotrienes, and medicine. (1986) [Pubmed]
 
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