C1480
Z-Phe-Ala fluoromethyl ketone
≥90% (TLC), powder
Synonym(s):
Z-FA-FMK
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About This Item
Linear Formula:
C21H23N2O4F
Molecular Weight:
386.42
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352209
MDL number:
Quality Level
assay
≥90% (TLC)
form
powder
color
white to off-white
solubility
DMSO or DMF: 20 mM
shipped in
dry ice
storage temp.
−20°C
SMILES string
C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc2ccccc2)C(=O)CF
InChI
1S/C21H23FN2O4/c1-15(19(25)13-22)23-20(26)18(12-16-8-4-2-5-9-16)24-21(27)28-14-17-10-6-3-7-11-17/h2-11,15,18H,12-14H2,1H3,(H,23,26)(H,24,27)/t15-,18-/m0/s1
InChI key
ASXVEBPEZMSPHB-YJBOKZPZSA-N
Related Categories
Application
Z-Phe-Ala fluoromethyl ketone (Z-FA-FMK) has been used as a:
- cathepsin inhibitor to study its effects on dendritic cells
- papain-like cysteine protease inhibitor to study its effects on cadmium-induced mitochondrial apoptosis
- cysteine protease inhibitor to study its effects on the interaction of toll-like receptor 9 (TLR9) with granulin in RAW macrophages
Biochem/physiol Actions
Z-Phe-Ala fluoromethyl ketone (Z-FA-FMK) is an inhibitor of cysteine proteases, such as cathepsin B and L. It can also inhibit recombinant effector caspases 2, -3, -6, and -7 and not initiator caspases 8 and -10. Z-FA-FMK plays a role in blocking nuclear factor κ-light-chain-enhancer of activated B cells (NF-κB) transactivation. It exhibits therapeutic effects against rheumatoid arthritis.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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The cathepsin B inhibitor, z-FA-FMK, inhibits human T cell proliferation in vitro and modulates host response to pneumococcal infection in vivo
Lawrence C P, et al.
Journal of Immunology, 177(6), 3827-3836 (2006)
Granulin is a soluble cofactor for toll-like receptor 9 signaling
Park B, et al.
Immunity, 34(4), 505-513 (2011)
Z-FA-fmk Inhibits Effector Caspases but not Initiator Caspases 8 and 10, and Demonstrates That Novel Anticancer Retinoid-related Molecules Induce Apoptosis via the Intrinsic Pathway1
Lopez-Hernandez F J, et al.
Molecular Cancer Therapeutics, 2(3), 255-263 (2003)
Sortase-mediated modification of $\alpha$DEC205 affords optimization of antigen presentation and immunization against a set of viral epitopes
Swee L K, et al.
Proceedings of the National Academy of Sciences, 110(4), 1428-1433 (2013)
Man Kyu Shim et al.
Journal of controlled release : official journal of the Controlled Release Society, 294, 376-389 (2018-12-15)
Cancer nanomedicine using nanoparticle-based delivery systems has shown outstanding promise in recent decades for improving anticancer treatment. However, limited targeting efficiency, low drug loading efficiency and innate toxicity of nanoparticles have caused severe problems, leaving only a few available in
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