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
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.77
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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)
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)
Transcription factor E3 protects against cadmium-induced apoptosis by maintaining the lysosomal-mitochondrial axis but not autophagic flux in Neuro-2a cells
Pi H, et al.
Toxicology Letters, 295(4), 335-350 (2018)
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)
Granulin is a soluble cofactor for toll-like receptor 9 signaling
Park B, et al.
Immunity, 34(4), 505-513 (2011)
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