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Merck
CN

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:
329774889
UNSPSC Code:
12352209
MDL number:
MFCD00883668

Key Documents

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Product Name

Z-Phe-Ala fluoromethyl ketone, ≥90% (TLC), powder

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

SMILES string

C[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc2ccccc2)C(=O)CF

InChI key

ASXVEBPEZMSPHB-YJBOKZPZSA-N

assay

≥90% (TLC)

form

powder

color

white to off-white

solubility

DMSO or DMF: 20 mM

shipped in

dry ice

storage temp.

−20°C

Quality Level

200

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)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000270632
0000270632
SLCN7450
SLCM1148
SLCD7672

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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)
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)
Yun-Pei Zhang et al.
American journal of physiology. Gastrointestinal and liver physiology, 311(6), G1091-G1104 (2016-10-30)
LPS-induced microvascular hyperpermeability and hemorrhage play a key role in the development of sepsis, the attenuation of which might be an important strategy to prevent sepsis. However, the current clinical therapies have proven to be inefficient in improving the prognosis
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