An irreversible pan-caspase inhibitor
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Boc-D-FMK

Item No. 16118

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3S-[[(1,1-dimethylethoxy)carbonyl]amino]-5-fluoro-4-oxo-pentanoic acid, methyl ester
CAS Number
187389-53-3
Synonyms
  • BAF
  • Boc-Asp(OMe)-FMK
  • Boc-D-Fluoromethyl Ketone
  • Boc-D(OMe)-FMK
Molecular Formula
C11H18FNO5
Formula Weight
263.3
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 50 mg/mlPBS (pH 7.2): 0.3 mg/ml
SMILES
FCC([C@@H](NC(OC(C)(C)C)=O)CC(OC)=O)=O
InChi Code
InChI=1S/C11H18FNO5/c1-11(2,3)18-10(16)13-7(8(14)6-12)5-9(15)17-4/h7H,5-6H2,1-4H3,(H,13,16)/t7-/m0/s1
InChi Key
MXOOUCRHWJYCAL-ZETCQYMHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $69

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    1 mg

    $106

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    5 mg

    $427

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    Product Description

    Boc-D-FMK is a cell-permeable, irreversible pan-caspase inhibitor.1,2 Also known as Boc-D(OMe)-FMK, this compound contains a methyl ester group, which facilitates uptake by cells and subsequently is removed by cytoplasmic esterases, leaving the functional inhibitor. Boc-D-FMK blocks apoptosis stimulated by TNF-α in neutrophils (IC50 = 39 µM), by bile duct ligation in hepatocytes, and by TNF-α in renal endothelial cells.3,4,5 The FMK pharmacophore is known to interact with non-caspase cysteine proteases, presumably explaining why Boc-D-FMK also inhibits cathepsins H and L.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chauvier, D., Ankri, S., Charriaut-Marlangue, C., et al. Broad-spectrum caspase inhibitors: From myth to reality? Cell Death Differ. 14(2), 387-391 (2007).

    2. Gregoli, P.A., and Bondurant, M.C. Function of caspases in regulating apoptosis caused by erythropoietin deprivation in erythroid progenitors. J. Cell Physiol. 178(2), 133-143 (1999).

    3. Cowburn, A.S., White, J.F., Deighton, J., et al. z-VAD-fmk augmentation of TNFα-stimulated neutrophil apoptosis is compound specific and does not involve the generation of reactive oxygen species. Blood 105(7), 2970-2972 (2005).

    4. Sheen-Chen, S.M., Hung, K.S., and Eng, H.L. Effect of Boc-D-Fmk on hepatocyte apoptosis after bile duct ligation in rat and survival rate after endotoxin challenge. J. Gastroenterol. Hepatol. 23(8 Pt 1), 1276-1279 (2008).

    5. Wu, X., Guo, R., Chen, P., et al. TNF induces caspase-dependent inflammation in renal endothelial cells through a Rho- and myosin light chain kinase-dependent mechanism. Am. J. Physiol. Renal. Physiol. 297(2), F316-F326 (2009).