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C1480

Sigma-Aldrich

Z-Phe-Ala fluoromethyl ketone

≥90% (TLC), powder

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Synonym(s):
Z-FA-FMK
Linear Formula:
C21H23N2O4F
Molecular Weight:
386.42
MDL number:
MFCD00883668
UNSPSC Code:
12352209
PubChem Substance ID:
329774889
NACRES:
NA.77

Quality Level

200

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

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.

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)
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)
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)
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)
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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