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I0536

Sigma-Aldrich

IWP-2

≥98% (HPLC)

Synonym(s):

N-(6-Methyl-2-benzothiazolyl)-2-[(3,4,6,7-tetrahydro-4-oxo-3-phenylthieno[3,2-d]pyrimidin-2-yl)thio]-acetamide

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About This Item

Empirical Formula (Hill Notation):
C22H18N4O2S3
CAS Number:
686770-61-6
Molecular Weight:
466.60
MDL number:
MFCD04457599
UNSPSC Code:
12352202
PubChem Substance ID:
329815312
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

room temp

SMILES string

Cc1ccc2nc(NC(=O)CSC3=NC4=C(SCC4)C(=O)N3c5ccccc5)sc2c1

InChI

1S/C22H18N4O2S3/c1-13-7-8-15-17(11-13)31-21(23-15)25-18(27)12-30-22-24-16-9-10-29-19(16)20(28)26(22)14-5-3-2-4-6-14/h2-8,11H,9-10,12H2,1H3,(H,23,25,27)

InChI key

WRKPZSMRWPJJDH-UHFFFAOYSA-N

Application

IWP-2 has been used to treat the cell lines L-Wnt-3a and L-Wnt-5a, to demonstrate the inhibitory effect of IWP-2. It has also been used as a Wnt signaling inhibitor to treat WT and Gja1Jrt/+ stromal cells to confirm that, theWnt/β-catenin signaling pathway pathway was not involved in the increased marker expression by Gja1Jrt/+ osteoblasts.

Biochem/physiol Actions

IWP-2 is an inactivator of Porcn function; inhibitor of Wnt production. Wnt/b-catenin (‘canonical′) pathway maintains transcriptional programs that enable stem cells to remain multipotent. Hyperactivation of the Wnt/b-catenin pathway leads to disease stage. IWP-2 inhibits Wnt production. It appears that IWP inactivates Porcn function either by directly inhibiting the Porcn active site or by modulating the function of a Porcn regulator. Porcn is a member of the membrane-bound O-acyltransferase (MBOAT) family, which adds a palmitoyl group to Wnt proteins that is essential to their signaling ability and is required for Wnt secretion. IWP-2 is useful in both regenerative medicine and anticancer efforts.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

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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Tapia-Rojas C, et al.
Journal of Neurochemistry, 139(6), 1175-1191 (2016)
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Journal of cellular biochemistry, 119(7), 5104-5117 (2017-08-18)
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