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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

N-methyl Leukotriene C4

Cayman Chemical Item Number 13390

N-methyl LTC4 (CAS 131391-65-6)

N-methyl Leukotriene C4 (CAS 131391-65-6)

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Description

Produced by neutrophils, macrophages, mast cells, and by transcellular metabolism in platelets, leukotriene C4 (LTC4) is the parent cysteinyl leukotriene formed by the LTC4 synthase-catalyzed conjugation of glutathione to LTA4.1 It is one of the constituents of slow-reacting substance of anaphylaxis (SRS-A) and exhibits potent smooth muscle contracting activity.2 LTC4, however, is rapidly metabolized to LTD4 and LTE4, which makes the characterization of LTC4 pharmacology difficult.3 N-methyl LTC4 is a synthetic analog of LTC4 that is not readily metabolized to LTD4 and LTE4.4It acts as a potent and selective CysLT2 receptor agonist exhibiting EC50 values of 122 and > 2,000 nM at the human CysLT2 and CysLT1 receptors, respectively.5 It has essentially the same potency as LTC4 at both the human and murine receptors CysLT2 receptors. N-methyl LTC4 is potent and active in vivo, causing vascular leak in mice overexpressing the human CysLT2 receptor but not in CysLT2 receptor knockout mice.5

1 Maclouf, J.A., and Murphy, R.C. Transcellular metabolism of neutrophil-derived leukotriene A4 by human platelets. A potential cellular source of leukotriene C4. J Biol Chem 263 174-181 (1988).

2 Piper, P.J. Formation and actions of leukotrienes. Physiol Rev 64 744-761 (1984).

3 Campbell, B.J., Baker, S.F., Shukla, S.D., et al. Bioconversion of leukotriene D4 by lung dipeptidase. Biochim Biophys Acta 1042 107-112 (1990).

4 Gareau, Y., Zamboni, R., and Wong, A.W. Total synthesis of N-methyl LTC4: A novel methodology for the monomethylation of amines. J Org Chem 58 1582-1585 (1993).

5 Yan, D., Stocco, R., Sawyer, N., et al. Differential signaling of cysteinyl leukotrienes and a novel cysteinyl leukotriene receptor 2 (CysLT2) agonist, N-methyl-leukotriene C4, in calcium reporter and beta arrestin assays. Mol Pharmacol (2010).

Synonyms
  • N-methyl LTC4
Formal Name N-​methyl-​5S-​hydroxy-​6R-​(S-​glutathionyl)-​7E,​9E,​11Z,​14Z-​eicosatetraenoic acid
CAS Number 131391-65-6
Molecular Formula C31H49N3O9S
Formula Weight 639.8
Formulation A solution in ethanol
Purity >97%
Stability 1 year
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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CCCCC/C=C\C\C=C/C=C\C=C/C(SCC(C(=O)​NCC(=O)​O)​[N]​1(NC)​C(=O)​CCC1C(=O)​O)​[C@@H]​(O)​CCCC(=O)​O
Size Price Quantity Subtotal
25 µg $134.00 $0.00
50 µg $255.00 $0.00
100 µg $482.00 $0.00
500 µg $2,144.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2012-02-11. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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