An ADAM17/TACE and ADAM10 inhibitor
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GW 280264X

Item No. 31388

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(5S)-5-[[(2R,3S)-3-(formylhydroxyamino)-2-(2-methylpropyl)-1-oxohexyl]amino]-6-oxo-6-(2-thiazolylamino)hexyl]-carbamic acid, penthylmethyl ester
CAS Number
866924-39-2
Molecular Formula
C28H41N5O6S
Formula Weight
575.7
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
O=CN(O)[C@@H](CCC)[C@@H](CC(C)C)C(N[C@@H](CCCCNC(OCC1=CC=CC=C1)=O)C(NC2=NC=CS2)=O)=O
InChi Code
InChI=1S/C28H41N5O6S/c1-4-10-24(33(38)19-34)22(17-20(2)3)25(35)31-23(26(36)32-27-29-15-16-40-27)13-8-9-14-30-28(37)39-18-21-11-6-5-7-12-21/h5-7,11-12,15-16,19-20,22-24,38H,4,8-10,13-14,17-18H2,1-3H3,(H,30,37)(H,31,35)(H,29,32,36)/t22-,23+,24+/m1/s1
InChi Key
SKJLITFHSZNZMQ-SGNDLWITSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $134

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    10 mg

    $994

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    Cayman Chemical
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    Product Description

    GW 280264X is an inhibitor of disintegrin and metalloproteinase domain-containing protein 17/TNF-α converting enzyme (ADAM17/TACE) and ADAM10 (IC50s = 8 and 11.5 nM, respectively).1 It inhibits TNF-α-induced cleavage of endomucin in human umbilical vein endothelial cells (HUVECs) when used at a concentration of 10 µM.2 GW 280264X (1 and 10 µM) inhibits angiotensin-converting enzyme 2 (ACE2) ectodomain shedding induced by phorbol 12-myristate 13-acetate (PMA; Item No. 10008014) in HEK-ACE2 cells.3 It reduces ACE2 shedding and prevents severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) infection in HK-2 cells.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hundhausen, C., Misztela, D., Berkout, T.A., et al. The disintegrin-like metalloproteinase ADAM10 is involved in constitutive cleavage of CX3CL1 (fractalkine) and regulates CX3CL1-mediated cell-cell adhesion. Blood 102(4), 1186-1195 (2003).

    2. Yang, J., LeBlanc, M.E., Cano, I., et al. ADAM10 and ADAM17 proteases mediate proinflammatory cytokine-induced and constitutive cleavage of endomucin from the endothelial surface. The Journal of Biological Chemisty 295(19), 6641-6651 (2020).

    3. Lambert, D.W., Yarski, M., Warner, F.J., et al. Tumor necrosis factor-alpha convertase (ADAM17) mediates regulated ectodomain shedding of the severe-acute respiratory syndrome-coronavirus (SARS-CoV) receptor, angiotensin-converting enzyme-2 (ACE2). The Journal of Biological Chemisty 280(34), 30113-30119 (2005).

    4. Yeung, M.L., Teng, J.L.L., Jia, L., et al. Soluble ACE2-mediated cell entry of SARS-CoV-2 via interaction with proteins related to the renin-angiotensin system. Cell 184, 1-17 (2021).