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Merck

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
Assay:
≥90% (TLC)
Form:
powder
Quality level:
200

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

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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

C1480-BULK: + C1480-3MG: + C1480-3MG-PW: + C1480-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
SLCM1148
SLCD7672
SLCC3375
SLCB5115
SLBZ2518

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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)
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American journal of physiology. Gastrointestinal and liver physiology, 311(6), G1091-G1104 (2016-10-30)
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Physical forces affect tumour growth, progression and metastasis. Here, we develop polymeric mechanical amplifiers that exploit in vitro and in vivo physical forces to increase immune cytokine-mediated tumour cell apoptosis. Mechanical amplifiers, consisting of biodegradable polymeric particles tethered to the
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Journal of cellular physiology, 231(6), 1392-1404 (2015-12-08)
The transmembrane glycoprotein E11 is considered critical in early osteoblast-osteocyte transitions (osteocytogenesis), however its function and regulatory mechanisms are still unknown. Using the late osteoblast MLO-A5 cell line we reveal increased E11 protein/mRNA expression (P < 0.001) concomitant with extensive osteocyte dendrite
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