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SML0420

Sigma-Aldrich

TAPI-2 acetate salt

≥98% (HPLC)

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Synonym(s):
N-(R)-(2-(Hydroxyaminocarbonyl)methyl)-4-methylpentanoyl-L-t-butyl-glycine-L-alanine 2-aminoethyl amide, Tumor necrosis factor-α protease inhibitor-2, TNF-α protease inhibitor-2
Empirical Formula (Hill Notation):
C19H37N5O5 · xC2H4O2
CAS Number:
689284-12-6
Molecular Weight:
415.53 (free base basis)
MDL number:
MFCD22666396
UNSPSC Code:
12352200
PubChem Substance ID:
329825415
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

lyophilized powder

color

white to off-white

shipped in

wet ice

storage temp.

−20°C

SMILES string

CC(O)=O.CC(C)C[C@H](CC(=O)NO)C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)NCCN)C(C)(C)C

InChI

1S/C19H37N5O5.C2H4O2/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;1-2(3)4/h11-13,15,29H,7-10,20H2,1-6H3,(H,21,26)(H,22,28)(H,23,27)(H,24,25);1H3,(H,3,4)/t12-,13+,15+;/m0./s1

InChI key

LMUSZKBIFGOFBD-RAFLFFCLSA-N

Application

TAPI-2 acetate salt has been used to inhibit protease activity in HepG2 cells.

Biochem/physiol Actions

TAPI-2 is a potent inhibitor matrix metalloproteinases and TACE (TNF-α convertase/ADAM17/α-secretase). It blocks the shedding of several cell surface proteins such as β-amyloid precursor protein, inhibits TNF-α release as well as a diverse variety of membrane-anchored cytokines, cell adhesion molecules, receptors, ligands. TAPI-2 is considered a fairly broad metalloproteinase inhibitor, but it much more selective for TACE than GM6001.

Features and Benefits

This compound is featured on the Cytokine Receptors (Tumor Necrosis Receptor Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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High-throughput protease activity cytometry reveals dose-dependent heterogeneity in PMA-mediated ADAM17 activation
Wu L, et al.
Integrative Biology : Quantitative Biosciences from Nano to Macro, 7(5), 513-524 (2015)

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