A fluorogenic substrate for proteasomal caspase-like activity
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Z-LLE-AMC

Item No. 10008117

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(phenylmethoxy)carbonyl]-L-leucyl-L-leucyl-N-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)-L-α-glutamine
CAS Number
348086-66-8
Synonyms
  • Z-Leu-Leu-Glu-AMC
  • Z-Leu-Leu-Glu-7-amido-4-Methylcoumarin
  • Proteasome Substrate II
Molecular Formula
C35H44N4O9
Formula Weight
664.8
Purity
≥95%
Emission
440-460 nm
Excitation
340-360 nm
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 50 mg/ml
λmax
230, 299, 328 nm
SMILES
O=C(N[C@@H](CC(C)C)C(N[C@@H](CC(C)C)C(N[C@@H](CCC(O)=O)C(NC1=CC=C(C(C)=CC(O2)=O)C2=C1)=O)=O)=O)OCC3=CC=CC=C3
InChi Code
InChI=1S/C35H44N4O9/c1-20(2)15-27(38-34(45)28(16-21(3)4)39-35(46)47-19-23-9-7-6-8-10-23)33(44)37-26(13-14-30(40)41)32(43)36-24-11-12-25-22(5)17-31(42)48-29(25)18-24/h6-12,17-18,20-21,26-28H,13-16,19H2,1-5H3,(H,36,43)(H,37,44)(H,38,45)(H,39,46)(H,40,4
InChi Key
FOYHOBVZPWIGJM-KCHLEUMXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $49

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    5 mg

    $143

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    10 mg

    $259

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    Product Description

    Z-LLE-AMC is a fluorogenic substrate for the caspase-like post-glutamate peptide hydrolase of the 26S proteasome or 20S proteolytic core.1,2 Caspase-like activity can be quantified by fluorescent detection of free AMC (also known as 7-amino-4-methylcoumarin), which is excited at 340-360 nm and emits at 440-460 nm. Z-LLE-AMC is typically used in cell lysates after experimental treatment.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Orlowski, M., Cardozo, C., Hidalgo, M.C., et al. Regulation of the peptidylglutamyl-peptide hydrolyzing activity of the pituitary multicatalytic proteinase complex. Biochem. 30(24), 5999-6005 (1991).

    2. Geier, E., Pfeifer, G., Wilm, M., et al. A giant protease with potential to substitute for some functions of the proteasome. Science 283(5404), 978-981 (1999).

    3. Hamouda, M.-A., Belhacene, N., Puissant, A., et al. The small heat shock protein B8 (HSPB8) confers resistance to bortezomib by promoting autophagic removal of misfolded proteins in multiple myeloma cells. Oncotarget 5(15), 6252-6266 (2014).

    4. Tadlock, L., Yamagiwa, Y., Hawker, J., et al. Transforming growth factor-β inhibition of proteasomal activity: A potential mechanism of growth arrest. Am. J. Physiol. Cell Physiol. 285(2), C277-C285 (2003).

    Product Citations

    Rana, P.S., Ignatz-Hoover, J.J., Guo, C., et al. Immunoproteasome activation expands the MHC Class I immunopeptidome, unmasks neoantigens, and enhances T-cell anti-myeloma activity. Mol. Cancer Ther. 23(12), 1743-1760 (2024).