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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
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

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This Item
C0980C8984A3227
Z-Phe-Ala fluoromethyl ketone ≥90% (TLC), powder

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Z-Phe-Ala fluoromethyl ketone

Z-Gly-Pro-Arg 7-amido-4-trifluoromethylcoumarin trifluoroacetate salt ≥95% (HPLC), powder

Sigma-Aldrich

C0980

Z-Gly-Pro-Arg 7-amido-4-trifluoromethylcoumarin trifluoroacetate salt

Z-Leu-Leu-Leu-fluoromethyl ketone ≥90% (TLC)

Sigma-Aldrich

C8984

Z-Leu-Leu-Leu-fluoromethyl ketone

Ala-Tyr-Pro-Gly-Lys-Phe-NH2 trifluoroacetate salt ≥98% (HPLC), lyophilized powder

Sigma-Aldrich

A3227

Ala-Tyr-Pro-Gly-Lys-Phe-NH2 trifluoroacetate salt

form

powder

form

powder

form

powder

form

lyophilized powder

color

white to off-white

color

white to off-white

color

-

color

white

solubility

DMSO or DMF: 20 mM

solubility

DMSO or DMF: 20 mM

solubility

acetone: 10 mg/mL, clear, colorless

solubility

H2O: >10 mg/mL

shipped in

dry ice

shipped in

-

shipped in

-

shipped in

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

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

Certificates of Analysis (COA)

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25G
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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)
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)
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