TAPI-2

The extracellular domains of many different types of transmembrane proteins, including growth factors, growth factor receptors and cell adhesion molecules, are proteolytically released (shed) in response to environmental cues. TNF protease inhibitor 2 (TAPI-2) is a broad-spectrum inhibitor of TNF-alpha converting enzyme (TACE), other ADAMs (a disintegrin and metalloproteinases), and other matrix metalloproteinases. It inhibits phorbol-12-myristate-13-acetate-induced (PMA) shedding of various cell surface proteins, such as TGF-alpha, beta amyloid precursor protein, L-selectin, and IL-6 receptor alpha subunit, with an IC50 value of 10 µM. TAPI-2 inhibits ADAM8, 10, 12, and TACE with Ki values of 10, 3, 100, and 0.12 µM, respectively. In T4-2 breast cancer cells, 20 µM TAPI-2 prevented mobilization of the growth factors TGF-alpha and amphiregulin leading to reversion of the malignant cellular phenotype.Formal Name: N-[2-[2-(hydroxyamino)-2-oxoethyl]-4-methyl-1-oxopentyl]-3-methyl-L-valyl-N-(2-aminoethyl)-L-alaninamide. CAS Number: 187034-31-7. Synonyms: TNF Protease Inhibitor 2. Molecular Formula: C19H37N5O5. Formula Weight: 415.5. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: Ethanol: 5 mg/ml, Water: 5 mg/ml. SMILES: ONC(CC(CC(C)C)C(N[C@@H](C(C)(C)C)C(N[C@@H](C)C(NCCN)=O)=O)=O)=O. InChi Code: InChI=1S/C19H37N5O5/c1-11(2)9-13(10-14(25)24-29)17(27)23-15(19(4,5)6)18(28)22-12(3)16(26)21-8-7-20/h11-13,15,29H,7-10,20H2,1-6H3,(H,21,26)(H,22,28)(H,23,27)(H,24,25)/t12-,13?,15+/m0/s1. InChi Key: LMIQCBIEAHJAMZ-RMTCENKZSA-N.