TAPI-2

Category	SARS-CoV
CAS	187034-31-7
Description	TAPI-2 is a broad-spectrum inhibitor of TNF-α converting enzyme (TACE; ADAM17), other ADAMs and matrix metalloproteinases (MMPs). It inhibits phorbol-12-myristate-13-acetate-induced (PMA) shedding of various cell surface proteins, such as TGF-α, β amyloid precursor protein, L-selectin, and IL-6 receptor α subunit.

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Product Information

Synonyms	TNF Protease Inhibitor 2; N-[(2S)-1-[[(2S)-1-(2-Aminoethylamino)-1-oxopropan-2-yl]amino]-3,3-dimethyl-1-oxobutan-2-yl]-N'-hydroxy-2-(2-methylpropyl)butanediamide
IUPAC Name	N-[(2S)-1-[[(2S)-1-(2-aminoethylamino)-1-oxopropan-2-yl]amino]-3,3-dimethyl-1-oxobutan-2-yl]-N'-hydroxy-2-(2-methylpropyl)butanediamide
Molecular Weight	415.5
Molecular Formula	C19H37N5O5
Canonical SMILES	CC(C)CC(CC(=O)NO)C(=O)NC(C(=O)NC(C)C(=O)NCCN)C(C)(C)C
InChI	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
InChIKey	LMIQCBIEAHJAMZ-RMTCENKZSA-N
Purity	≥95%
Density	1.1±0.1 g/cm3
Solubility	In vitro: 10 mM in DMSO
Appearance	Crystalline Solid
Storage	4°C, sealed storage, away from moisture and light * In solvent : -80°C 6 months; -20°C 1 month (sealed storage, away from moisture and light)
Complexity	574
Exact Mass	415.27946930
Index Of Refraction	1.506
In Vitro	The hydroxamate-based metalloprotease inhibitor TAPI-2 bounds to hmeprin with inhibition constants IC50 20±10 μM for hmeprin β subunit and 1.5±0.27 nM for hmeprin α subunit. Generally, hmeprin α is inhibited more strongly than the β subunit. Without affecting ADAM17 expression, TAPI-2 dramatically decreases the protein levels of NICD and its downstream target HES-1 in both HCP-1 and HT29 cells. Moreover, treating cells with TAPI-2 significantly decreases the CSC phenotype by -50% in both CRC cell lines. The dose-dependent effects of TAPI-2 on the sphere formation and protein levels of NICD and HES-1 confirm that the concentration used (20 μM) is within the effective dose range of TAPI-2 (5-40 μM).
PSA	176.61000
Target	IC50: 20±10 μM (MMP)Ki: 1.5±0.27 nM (MMPs)
XLogP3-AA	-0.1