Catalog Number: 3995
Chemical Name: (2R)-N-[(1S)-2,2-Dimethyl-1-[(methylamino)carbonyl]propyl]-2-[(1S)-1-(N-hydroxyformamido)ethyl]-5-phenylpentanamide
Biological Activity
Selective ADAM10 metalloprotease inhibitor; displays over 100-fold higher potency at ADAM10 compared to ADAM17. Blocks constitutive release of IL-6R, CX3CL1 and CXCL16 in cell-based cleavage experiments. Inhibits calcium ionophore-induced betacellulin shedding in IMPE cells. Prevents E-cadherin cleavage in A549 cells.
Technical Data
  • M.Wt:
    391.5
  • Formula:
    C21H33N3O4
  • Solubility:
    Soluble to 20 mM in DMSO
  • Purity:
    >98%
  • Storage:
    Store at -20°C
  • CAS No:
    260264-93-5
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis. All Tocris products are intended for laboratory research use only.
Additional Information
Licensing Caveats:
Sold for research purposes under agreement from GlaxoSmithKline.
Background References
  1. The ADAM10 prodomain is a specific inhibitor of ADAM10 proteolytic activity and inhibits cellular shedding events.
    Moss ML, Bomar M, Liu Q, Sage H, Dempsey P, Lenhart PM, Gillispie PA, Stoeck A, Wildeboer D, Bartsch JW, Palmisano R, Zhou P
    J. Biol. Chem., 2007;282(49):35712-21.
  2. Metalloprotease inhibitors for the disintegrin-like metalloproteinases ADAM10 and ADAM17 that differentially block constitutive and phorbol ester-inducible shedding of cell surface molecules.
    Ludwig et al.
    Comb.Chem.High Throughput Screen., 2005;8:161
  3. The disintegrin-like metalloproteinase ADAM10 is involved in constitutive cleavage of CX3CL1 (fractalkine) and regulates CX3CL1-mediates cell-cell adhesion.
    Hundhausen et al.
    Blood, 2003;102:1186
  4. A Staphylococcus aureus pore-forming toxin subverts the activity of ADAM10 to cause lethal infection in mice.
    Inoshima et al.
    Nat.Med., 2011;17:1310
Citations:

The citations listed below are publications that use Tocris products. Selected citations for GI 254023X include:

4 Citations: Showing 1 - 4
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  1. ADAM10 Cell Surface Expression but Not Activity Is Critical for Staphylococcus aureus α-Hemolysin-Mediated Activation of the NLRP3 Inflammasome in Human Monocytes.
    Authors: Ezekwe Et al.
    J Bone Miner Res 2016;8
  2. Fractalkine shedding is mediated by p38 and the ADAM10 protease under pro-inflammatory conditions inhuman astrocytes.
    Authors: O'Sullivan Et al.
    Journal of Neuroinflammation 2016;13:189
  3. Annexin A1-containing extracellular vesicles and polymeric nanoparticles promote epithelial wound repair.
    Authors: Leoni Et al.
    J Clin Invest 2015;125:1215
  4. Elevated serum CXCL16 is an independent predictor of poor survival in ovarian cancer and may reflect pro-metastatic ADAM protease activity.
    Authors: Gooden Et al.
    Br J Cancer 2014;110:1535

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