A stable LTC4 mimetic
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N-methyl Leukotriene C4

Item No. 13390

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-methyl-L-γ-glutamyl-S-[(1R,2E,4E,6Z,9Z)-1-[(1S)-4-carboxy-1-hydroxybutyl]-2,4,6,9-pentadecatetraen-1-yl]-L-cysteinyl-glycine
CAS Number
131391-65-6
Synonyms
  • N-methyl LTC4
Molecular Formula
C31H49N3O9S
Formula Weight
639.8
Purity
≥97%
Formulation (Request formulation change)
A 250 µg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlEthanol: 1 mg/mlEthanol:H20 (95:5): 2 mg/mlPBS (pH 7.2): 100 µg/ml
λmax
282 nm
SMILES
CCCCC/C=C\C/C=C\C=C\C=C\[C@@H](SC[C@H](NC(CC[C@@H](C(O)=O)NC)=O)C(NCC(O)=O)=O)[C@@H](O)CCCC(O)=O
InChi Code
InChI=1S/C31H49N3O9S/c1-3-4-5-6-7-8-9-10-11-12-13-14-17-26(25(35)16-15-18-28(37)38)44-22-24(30(41)33-21-29(39)40)34-27(36)20-19-23(32-2)31(42)43/h7-8,10-14,17,23-26,32,35H,3-6,9,15-16,18-22H2,1-2H3,(H,33,41)(H,34,36)(H,37,38)(H,39,40)(H,42,43)/b8-7-,11-10-,13-12+,17-14+/t23-,24-,25+,26+/m0/s1
InChi Key
FPLBRCJNODNRQZ-CXEWJZLJSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    25 µg

    $182

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    50 µg

    $345

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    100 µg

    $652

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    Product 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 Leukotriene C4 (N-methyl LTC4) is a synthetic analog of LTC4 that is not readily metabolized to LTD4 and LTE4.4 It 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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. The Journal of Biological Chemisty 263(1), 174-181 (1988).

    2. Piper, P.J. Formation and actions of leukotrienes. Physiol. Rev. 64(2), 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(1), 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. The Journal of Organic Chemistry 58(6), 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 andβarrestin assays. Mol. Pharmacol. 79(2), 270-278 (2010).