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Chemical Compound Review

Leukotriene C1     (5S,6R,7E,9E,11Z,14Z)-6- [(2S)-2-[[(4S)-4...

Synonyms: Leucotriene C4, leukotriene C4, LTC4, BSPBio_001366, CHEBI:16978, ...
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Disease relevance of leukotriene C4

  • The importance of EPX and LTC4/D4 in the characterization of chronic symptomatic rhinitis was also observed [1].
  • These results suggest that renal production of LTC4 and LTB4 is increased in MRL-lpr/lpr mice with nephritis, and that enhanced production of peptidoleukotrienes causes reversible renal dysfunction [2].
  • LTC4 was detected in samples of NPS obtained in the acute phase of illness from 67% of infants with bronchiolitis due to RSV and in 33% of samples of NPS obtained during the same interval from infants with upper respiratory illness alone (p less than 0.025) [3].
  • In surviving patients, LTC4 concentrations correlated with sepsis severity score [4].
  • In patients who did not survive, the low LTC4 generation persisted throughout the observation period, whereas in surviving patients, its formation was normalized during convalescence [4].

High impact information on leukotriene C4


Chemical compound and disease context of leukotriene C4

  • In mouse mastocytoma ABMC-7 cells cultured chronically with CP-24879, there was a concentration-dependent inhibition of desaturase activity that correlated with the degree of depletion of AA and decreased production of leukotriene C4 (LTC4) [10].
  • In contrast to PMO from naive gerbils, PMO from animals with amoebic liver abscesses at 10, 20 and 30 days post-infection (p.i.) released high basal levels of PGE2 and LTC4 [11].
  • Azelastine shows anti-inflammatory properties in therapeutically relevant concentrations as assessed by its ability to reduce TNF alpha release as well as its ability to inhibit LTC4 production in allergically stimulated human nasal polyp cells [12].

Biological context of leukotriene C4

  • In rat basophilic leukemia-2H3 cells, Lyn thus plays a dual role by positively regulating Fc epsilonRI phosphorylation and degranulation while negatively regulating LTC4 production [13].
  • Both histamine and LTC4 release was inhibited by staurosporine and K-252a with an IC50 of 50 nM for both compounds [14].
  • CGS 8515 inhibited ovalbumen-induced decreases in cardiac developed tension at 0.3 and 1.0 microM, but did not antagonize coronary vasoconstriction induced by synthetic LTC4 [15].
  • 5. Indomethacin, the leukotriene C4/D4 (LTC4/D4) antagonist FPL 55712 or the blocker of nerve conduction, tetrodotoxin, had no effect on the contractile phase [16].
  • In vivo, LTC4 injection caused a pronounced but transient increase in pulmonary arterial pressure and pulmonary arterial wedge pressure (Ppw), with a smaller effect on left ventricular end-diastolic pressure [17].

Anatomical context of leukotriene C4


Associations of leukotriene C4 with other chemical compounds

  • Eosinophils exposed to 1,000 pM IL-3 for 30 min or cultured in 10 pM IL-3 for 7 d generated approximately threefold more leukotriene C4 (LTC4) in response to calcium ionophore than freshly isolated cells [8].
  • In contrast, LTC4 and LTD4 induced concentration-dependent contractions in atherosclerotic coronary arteries [18].
  • The present study compares prostaglandin E2 (PGE2), leukotriene C4 (LTC4), and LTB4 release by splenic and resident peritoneal M phi in 89Sr-treated mice and 88Sr controls following in vivo CP and in vitro incubation with zymosan, calcium ionophore A23187, or phorbol ester (PMA) [22].
  • The effect of GM-CSF on arachidonic acid metabolism to LTC4 reached a plateau with 60 min of incubation before stimulation with ionophore, and was characterized by an initial augmentation of the intracellular level of LTC4 and a subsequent increment in extracellular LTC4 [23].
  • Rolipram, an inhibitor of the low Km cAMP-specific PDE (PDE IV), inhibited the release of both histamine and LTC4 from activated basophils and increased cAMP levels in these cells [24].

Gene context of leukotriene C4

  • It has been demonstrated that extracellular signal-regulated kinases (ERK1/2) specifically regulate the pathway for LTC4 generation, but not for histamine release and interleukin-4 production [25].
  • These results, together with previous findings that both DNP-SG and LTC4 are good ligands for MRP, suggest that MRP is responsible for the unidirectional, energy-dependent efflux of organic anions from the brain into the circulating blood across the BBB [26].
  • Furthermore, etoposide inhibited LTC4 efflux, confirming the involvement of cMOAT [27].
  • A typical late phase kinetic was observed for IL-5, MCP-1, eotaxin, sVCAM-1, and LTC4 [28].
  • We conclude that in MCII mast cells cPLA2 is activated by kinase-dependent mechanisms and may be responsible for Fc epsilon RI-induced mobilization of arachidonic acid for the generation of LTC4 [29].

Analytical, diagnostic and therapeutic context of leukotriene C4


  1. Indirect evidence of nasal inflammation assessed by titration of inflammatory mediators and enumeration of cells in nasal secretions of patients with chronic rhinitis. Knani, J., Campbell, A., Enander, I., Peterson, C.G., Michel, F.B., Bousquet, J. J. Allergy Clin. Immunol. (1992) [Pubmed]
  2. Enhanced renal leukotriene production in murine lupus: role of lipoxygenase metabolites. Spurney, R.F., Ruiz, P., Pisetsky, D.S., Coffman, T.M. Kidney Int. (1991) [Pubmed]
  3. The release of leukotrienes in the respiratory tract during infection with respiratory syncytial virus: role in obstructive airway disease. Volovitz, B., Welliver, R.C., De Castro, G., Krystofik, D.A., Ogra, P.L. Pediatr. Res. (1988) [Pubmed]
  4. Cysteinyl-leukotriene generation as a biomarker for survival in the critically ill. Morlion, B.J., Torwesten, E., Kuhn, K.S., Puchstein, C., Fürst, P. Crit. Care Med. (2000) [Pubmed]
  5. Increased sensitivity to anticancer drugs and decreased inflammatory response in mice lacking the multidrug resistance-associated protein. Wijnholds, J., Evers, R., van Leusden, M.R., Mol, C.A., Zaman, G.J., Mayer, U., Beijnen, J.H., van der Valk, M., Krimpenfort, P., Borst, P. Nat. Med. (1997) [Pubmed]
  6. Interleukin 5 modifies histamine release and leukotriene generation by human basophils in response to diverse agonists. Bischoff, S.C., Brunner, T., De Weck, A.L., Dahinden, C.A. J. Exp. Med. (1990) [Pubmed]
  7. Regulation of human eosinophil degranulation and activation by endogenous phospholipase A2. White, S.R., Strek, M.E., Kulp, G.V., Spaethe, S.M., Burch, R.A., Neeley, S.P., Leff, A.R. J. Clin. Invest. (1993) [Pubmed]
  8. Human eosinophils have prolonged survival, enhanced functional properties, and become hypodense when exposed to human interleukin 3. Rothenberg, M.E., Owen, W.F., Silberstein, D.S., Woods, J., Soberman, R.J., Austen, K.F., Stevens, R.L. J. Clin. Invest. (1988) [Pubmed]
  9. Differential effects of the complement peptides, C5a and C5a des Arg on human basophil and lung mast cell histamine release. Schulman, E.S., Post, T.J., Henson, P.M., Giclas, P.C. J. Clin. Invest. (1988) [Pubmed]
  10. Identification and characterization of a novel delta6/delta5 fatty acid desaturase inhibitor as a potential anti-inflammatory agent. Obukowicz, M.G., Raz, A., Pyla, P.D., Rico, J.G., Wendling, J.M., Needleman, P. Biochem. Pharmacol. (1998) [Pubmed]
  11. Entamoeba histolytica alters arachidonic acid metabolism in macrophages in vitro and in vivo. Wang, W., Chadee, K. Immunology (1992) [Pubmed]
  12. Effects of antihistamines on leukotriene and cytokine release from dispersed nasal polyp cells. Küsters, S., Schuligoi, R., Hüttenbrink, K.B., Rudert, J., Wachs, A., Szelenyi, I., Peskar, B.A. Arzneimittel-Forschung. (2002) [Pubmed]
  13. Regulation of rat basophilic leukemia-2H3 mast cell secretion by a constitutive Lyn kinase interaction with the high affinity IgE receptor (Fc epsilon RI). Vonakis, B.M., Gibbons, S.P., Rotté, M.J., Brothers, E.A., Kim, S.C., Chichester, K., MacDonald, S.M. J. Immunol. (2005) [Pubmed]
  14. Differential inhibition of histamine release from mast cells by protein kinase C inhibitors: staurosporine and K-252a. White, J.R., Zembryki, D., Hanna, N., Mong, S. Biochem. Pharmacol. (1990) [Pubmed]
  15. Inhibition of leukotriene release in anaphylactic guinea-pig hearts by a 5-lipoxygenase inhibitor, CGS 8515. Yaacob, H.B., Piper, P.J. Br. J. Pharmacol. (1988) [Pubmed]
  16. Effects of hyperosmolarity on human isolated central airways. Jongejan, R.C., de Jongste, J.C., Raatgeep, R.C., Stijnen, T., Bonta, I.L., Kerrebijn, K.F. Br. J. Pharmacol. (1991) [Pubmed]
  17. Comparative effects of leukotrienes on porcine pulmonary circulation in vitro and in vivo. Ohtaka, H., Tsang, J.Y., Foster, A., Hogg, J.C., Schellenberg, R.R. J. Appl. Physiol. (1987) [Pubmed]
  18. Differential leukotriene constrictor responses in human atherosclerotic coronary arteries. Allen, S., Dashwood, M., Morrison, K., Yacoub, M. Circulation (1998) [Pubmed]
  19. CD4+ T cell and eosinophil adhesion is mediated by specific ICAM-3 ligation and results in eosinophil activation. Douglas, I.S., Leff, A.R., Sperling, A.I. J. Immunol. (2000) [Pubmed]
  20. IgE immune complexes induce immediate and prolonged release of leukotriene C4 (LTC4) from rat alveolar macrophages. Rankin, J.A., Hitchcock, M., Merrill, W.W., Huang, S.S., Brashler, J.R., Bach, M.K., Askenase, P.W. J. Immunol. (1984) [Pubmed]
  21. Comitogenicity of eicosanoids and the peroxisome proliferator ciprofibrate in cultured rat hepatocytes. Hong, J.T., Glauert, H.P. J. Cell. Physiol. (1996) [Pubmed]
  22. Eicosanoid production by peritoneal and splenic macrophages in mice depleted of bone marrow by 89Sr. Shibata, Y., Bautista, A.P., Pennington, S.N., Humes, J.L., Volkman, A. Am. J. Pathol. (1987) [Pubmed]
  23. Enhancement of human eosinophil cytotoxicity and leukotriene synthesis by biosynthetic (recombinant) granulocyte-macrophage colony-stimulating factor. Silberstein, D.S., Owen, W.F., Gasson, J.C., DiPersio, J.F., Golde, D.W., Bina, J.C., Soberman, R., Austen, K.F., David, J.R. J. Immunol. (1986) [Pubmed]
  24. Preliminary identification and role of phosphodiesterase isozymes in human basophils. Peachell, P.T., Undem, B.J., Schleimer, R.P., MacGlashan, D.W., Lichtenstein, L.M., Cieslinski, L.B., Torphy, T.J. J. Immunol. (1992) [Pubmed]
  25. Phosphatidylinositol-3 kinase regulates p21ras activation during IgE-mediated stimulation of human basophils. Miura, K., MacGlashan, D.W. Blood (2000) [Pubmed]
  26. Characterization of efflux transport of organic anions in a mouse brain capillary endothelial cell line. Kusuhara, H., Suzuki, H., Naito, M., Tsuruo, T., Sugiyama, Y. J. Pharmacol. Exp. Ther. (1998) [Pubmed]
  27. Delineating the contribution of secretory transporters in the efflux of etoposide using Madin-Darby canine kidney (MDCK) cells overexpressing P-glycoprotein (Pgp), multidrug resistance-associated protein (MRP1), and canalicular multispecific organic anion transporter (cMOAT). Guo, A., Marinaro, W., Hu, P., Sinko, P.J. Drug Metab. Dispos. (2002) [Pubmed]
  28. Factors contributing to nasal allergic late phase eosinophilia. Kramer, M.F., Jordan, T.R., Klemens, C., Hilgert, E., Hempel, J.M., Pfrogner, E., Rasp, G. American journal of otolaryngology. (2006) [Pubmed]
  29. Phosphorylation and activation of Ca(2+)-sensitive cytosolic phospholipase A2 in MCII mast cells mediated by high-affinity Fc receptor for IgE. Currie, S., Roberts, E.F., Spaethe, S.M., Roehm, N.W., Kramer, R.M. Biochem. J. (1994) [Pubmed]
  30. Activation of the 5-lipoxygenase pathway in E-mast cells by peanut agglutinin. Razin, E. J. Immunol. (1985) [Pubmed]
  31. Accumulation of arachidonic acid cyclo- and lipoxygenase products in rat brain during ischemia and reperfusion: effects of treatment with GM1-lactone. Petroni, A., Bertazzo, A., Sarti, S., Galli, C. J. Neurochem. (1989) [Pubmed]
  32. Mediator release in cerebrospinal fluid of human immunodeficiency virus-positive patients with central nervous system involvement. Froldi, M., Castagna, A., Parma, M., Piona, A., Tedeschi, A., Miadonna, A., Lorini, M., Orazio, E.N., Lazzarin, A. J. Neuroimmunol. (1992) [Pubmed]
  33. Eosinophil activation and cysteinyl leukotriene production in infants with respiratory syncytial virus bronchiolitis. Dimova-Yaneva, D., Russell, D., Main, M., Brooker, R.J., Helms, P.J. Clin. Exp. Allergy (2004) [Pubmed]
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