Inhibitor of cPLA2
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Pyrrophenone

Item No. 13294

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[[(2S,4R)-1-[2-(2,4-difluorobenzoyl)benzoyl]-4-[(triphenylmethyl)thio]-2-pyrrolidinyl]methyl]-4-[(Z)-(2,4-dioxo-5-thiazolidinylidene)methyl]-benzamide
CAS Number
341973-06-6
Molecular Formula
C49H37F2N3O5S2
Formula Weight
850.0
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 12.5 mg/mlDMSO: 15 mg/mlDMSO:PBS (pH 7.2) (1:10): 0.1 mg/ml
λmax
332 nm
SMILES
FC(C=C1F)=CC=C1C(C2=CC=CC=C2C(N3[C@H](CNC(C4=CC=C(/C=C5SC(NC\5=O)=O)C=C4)=O)C[C@@H](SC(C6=CC=CC=C6)(C7=CC=CC=C7)C8=CC=CC=C8)C3)=O)=O
InChi Code
InChI=1S/C49H37F2N3O5S2/c50-36-24-25-41(42(51)27-36)44(55)39-18-10-11-19-40(39)47(58)54-30-38(28-37(54)29-52-45(56)32-22-20-31(21-23-32)26-43-46(57)53-48(59)60-43)61-49(33-12-4-1-5-13-33,34-14-6-2-7-15-34)35-16-8-3-9-17-35/h1-27,37-38H,28-30H2,(H,52,56)(H,53,57,59)/b43-26-/t37-,38+/m0/s1
InChi Key
XSCZRVUQXBBTRO-GYCZXHFISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Cayman Chemical
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    Product Description

    The group IVA phospholipase A2 (PLA2), known as calcium-dependent cytosolic PLA2 (cPLA2), selectively releases arachidonic acid (AA) from membrane phospholipids, playing a central role in initiating the synthesis of prostaglandins (PGs) and leukotrienes (LTs).1,2 Pyrrophenone inhibits cPLA2α with an IC50 of 4.2 nM in enzyme assays and potently blocks the release of AA and the production of PGE2 and LTC4 in cells (IC50 = 24, 25, and 14 nM, respectively).3 Its action is reversible and selective, as pyrrophenone inhibits the secretory type IB and IIA PLA2s with more than a hundred-fold less potency.4 Pyrrophenone has also been shown to inhibit calcium ionophore (A23187)-stimulated AA release from monocytic cells,4 interleukin-1-induced PGE2 synthesis in mesangial cells,4 and the production of PGE2, LTs, and platelet-activating factor by human neutrophils,5 always with maximal inhibition at concentrations below 1 μM.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ghosh, M., Stewart, A., Tucker, D.E., et al. Role of cytosolic phospholipase A2 in prostaglandin E2 production by lung fibroblasts. Am. J. Respir. Cell Mol. Biol. 30(1), 91-100 (2004).

    2. Liberty, I.F., Raichel, L., Hazan-Eitan, Z., et al. Cytosolic phospholipase A2 is responsible for prostaglandin E2 and leukotriene B4 formation in phagocyte-like PLB-985 cells: Studies of differentiated cPLA2-deficient PLB-985 cells. J. Leukoc. Biol. 76(1), 176-184 (2004).

    3. Seno, K., Okuno, T., Nishi, K., et al. Pyrrolidine inhibitors of human cytosolic phospholipase A2 part2: Synthesis of potent and crystallized 4-triphenylmethylthio derivative “pyrrophenone”. Bioorg. Med. Chem. Lett. 11(4), 587-590 (2001).

    4. Ono, T., Yamada, K., Chikazawa, Y., et al. Characterization of a novel inhibitor of cytosolic phospholipase A2α, pyrrophenone. Biochem. J. 363(Pt 3), 727-735 (2002).

    5. Flamand, N., Picard, S., Lemieux, L., et al. Effects of pyrrophenone, an inhibitor of group IVA phospholipase A2, on eicosanoid and PAF biosynthesis in human neutrophils. Br. J. Pharmacol. 149(4), 385-392 (2006).

    Product Citations

    Inazumi, T., Yamada, K., Shirata, N., et al. Prostaglandin E2-EP4 axis promotes lipolysis and fibrosis in adipose tissue leading to ectopic fat deposition and insulin resistance. Cell Rep. 33(2), 108265 (2020).