A TACE inhibitor
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TAPI-1

Item No. 18505

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-[2-(hydroxyamino)-2-oxoethyl]-4-methyl-1-oxopentyl]-3-(2-naphthalenyl)-L-alanyl-N-(2-aminoethyl)- (9CI)L-alaninamide
CAS Number
171235-71-5
Synonyms
  • TAPI
Molecular Formula
C26H37N5O5
Formula Weight
499.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mLDMSO: 30 mg/mLEthanol: 30 mg/mLPBS (pH 7.2): 10 mg/mL
λmax
224, 282 nm
SMILES
O=C([C@H](CC1=CC2=CC=CC=C2C=C1)NC(C(CC(C)C)CC(NO)=O)=O)N[C@H](C(NCCN)=O)C
InChi Code
InChI=1S/C26H37N5O5/c1-16(2)12-21(15-23(32)31-36)25(34)30-22(26(35)29-17(3)24(33)28-11-10-27)14-18-8-9-19-6-4-5-7-20(19)13-18/h4-9,13,16-17,21-22,36H,10-12,14-15,27H2,1-3H3,(H,28,33)(H,29,35)(H,30,34)(H,31,32)/t17-,21?,22-/m0/s1
InChi Key
AWNBSWDIOCXWJW-OWHMDLSXSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $164

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    1 mg

    $279

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    5 mg

    $984

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    Product Description

    TAPI-1, known in the earlier literature as just TAPI, is an inhibitor of TACE that inhibits the cleavage of TNF-α, TNFRI (p60), and TNFRII (p80) with IC50 values ranging from 5-100 µM.1,2,3 It also blocks the shedding of other TACE-dependent proteins, including IL-6R and Klotho, and may inhibit metalloproteases other than TACE.4,5,6 TAPI-1 differs from TAPI-0 (Item No. 14694), structurally, by the presence of an aminoethyl addition at the alanyl group, and is generally more stable in tissue culture and in vivo.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mohler, K.M., Sleath, P.R., Fitzner, J.N., et al. Protection against a lethal dose of endotoxin by an inhibitor of tumour necrosis factor processing. Nature 370(6486), 218-220 (1994).

    2. Crowe, P.D., Walter, B.N., Mohler, K.M., et al. A metalloprotease inhibitor blocks shedding of the 80-kD TNF receptor and TNF processing in T lymphocytes. J. Exp. Med. 181(3), 1502-1210 (1995).

    3. Hooper, N.M., Karran, E.H., and Turner, A.J. Membrane protein secretases. Biochem. J. 321(2), 265-279 (1997).

    4. Müllberg, J., Durie, F.H., Otten-Evans, C., et al. A metalloprotease inhibitor blocks shedding of the IL-6 receptor and the p60 TNF receptor. J. Immunol. 155(11), 5198-5205 (1995).

    5. Chen, C.D., Podvin, S., Gillespie, E., et al. Insulin stimulates the cleavage and release of the extracellular domain of klotho by ADAM10 and ADAM17. Proc. Natl. Acad. Sci. USA 104(50), 19796-19801 (2007).

    6. Yamamoto, K., Miyazaki, K., and Higashi, S. Pericellular proteolysis by matrix metalloproteinase-7 is differentially modulated by cholesterol sulfate, sulfatide, and cardiolipin. FEBS J. 281(15), 3346-3356 (2014).