TAPI-1

TNF-alpha converting enzyme (TACE, also known as ADAM17) is a zinc metalloprotease that cleaves the membrane-bound precursor of TNF-alpha to give the mature soluble form of TNF-alpha. It also mediates the proteolytic release of several other cell-surface proteins, including TNF-alpha receptors (TNFRs). TAPI-1, known in the earlier literature as just TAPI, is an inhibitor of TACE that inhibits the cleavage of TNF-alpha, TNFRI (p60), and TNFRII (p80) with IC50 values ranging from 5-100 µM. It also blocks the shedding of other TACE-dependent proteins, including IL-6R and Klotho, and may inhibit metalloproteases other than TACE. TAPI-1 differs from TAPI-0 (Cay-14694), structurally, by the presence of an aminoethyl addition at the alanyl group, and is generally more stable in tissue culture and in vivo.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: (Request formulation change), A crystalline solid. Solubility: DMF: 30 mg/mL, DMSO: 30 mg/mL, Ethanol: 30 mg/mL, PBS (pH 7.2): 10 mg/mL. lambdamax: 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.