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Merck

S0447

SIS3

≥98% (HPLC), TGF-β1/ALK-5 phosphorylation inhibitor, powder

Synonym(s):

(2E)-1-(6,7-Dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-3-(1-methyl-2-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-propenone hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C28H27N3O3 · HCl
CAS Number:
521984-48-5
Molecular Weight:
489.99
UNSPSC Code:
12352200
PubChem Substance ID:
24724599
NACRES:
NA.77
MDL number:
MFCD09265258

Key Documents

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Product Name

SIS3, ≥98% (HPLC), powder

SMILES string

Cl.COc1cc2CCN(Cc2cc1OC)C(=O)\C=C\c3c(-c4ccccc4)n(C)c5ncccc35

InChI key

CDKIEBFIMCSCBB-CALJPSDSSA-N

InChI

1S/C28H27N3O3.ClH/c1-30-27(19-8-5-4-6-9-19)22(23-10-7-14-29-28(23)30)11-12-26(32)31-15-13-20-16-24(33-2)25(34-3)17-21(20)18-31;/h4-12,14,16-17H,13,15,18H2,1-3H3;1H/b12-11+;

assay

≥98% (HPLC)

form

powder

color

yellow

solubility

H2O: <2 mg/mL
DMSO: >20 mg/mL

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

SIS3 is a novel specific inhibitor of TGF-β1/ALK-5 phosphorylation of Smad3
Sugar insensitive 3 (SIS3) promotes drug-induced apoptosis and hinders the function of adenosine triphosphate (ATP)-binding cassette (ABC) transporter (ABCB1) and ABCG2. It resensitizes ABCB1 and ABCG2 overexpressed in cancerous cells, which contributes to chemotherapeutics.

Application

Sugar insensitive 3 (SIS3) has been used as smad3 inhibitor in various cells.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000483098
0000483098
0000242232
0000242232
0000434978

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Ming-Heng Wu et al.
Scientific reports, 7(1), 11006-11006 (2017-09-10)
Concomitant expressions of glycan-binding proteins and their bound glycans regulate many pathophysiologic processes, but this issue has not been addressed in liver fibrosis. Activation of hepatic stellate cells (HSCs) is a rate-limiting step in liver fibrosis and is an important
Karl David Brown et al.
Investigative ophthalmology & visual science, 58(7), 3011-3017 (2017-06-13)
Fibrotic scarring after ocular surgeries and chemical burn injuries can impede clarity of the cornea and cause vision impairment. Transforming growth factor β (TGFβ) signaling pathway is known to mediate fibrotic scarring, and NADPH oxidase-derived reactive oxygen species has been
Transforming growth factor-beta2 utilizes the canonical Smad-signaling pathway to regulate tissue transglutaminase expression in human trabecular meshwork cells
Tovar-Vidales T, et al.
Experimental Eye Research, 93(4), 442-451 (2011)
Connective tissue growth factor is a Smad2 regulated amplifier of transforming growth factor beta actions in hepatocytes?But without modulating bone morphogenetic protein 7 signaling
Gressner OA, et al.
Hepatology, 49(6), 2021-2030 (2009)
The proto-oncogene tyrosine protein kinase Src is essential for macrophage-myofibroblast transition during renal scarring
Tang PMK, et al.
Kidney International, 93(1), 173-187 (2018)
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