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5.05420

BMP Inhibitor III, LDN-212854

Name: BMP Inhibitor III, LDN-212854
Brand: MM

Synonym(s):

BMP Inhibitor III, LDN-212854, Abl Inhibitor V, LDN212854, Bone Morphogenetic Protein Inhibitor III, 5-(6-(4-(Piperazin-1-yl)phenyl)pyrazolo[1,5-a]pyrimidin-3-yl)quinoline, PDGFR Tyrosine Kinase Inhibitor XXIV, RIP2 Inhibitor I, RIPK2 Inhibitor I

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About This Item

Empirical Formula (Hill Notation):

C₂₅H₂₂N₆

Molecular Weight:

406.48

MDL number:

MFCD28099808

UNSPSC Code:

12352200

NACRES:

NA.77

PubChem Substance ID:

60182388

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Properties

assay

≥98% (HPLC)

Quality Segment

100

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze, protect from light

color

pale yellow

solubility

DMSO: 25 mg/mL

storage temp.

2-8°C

SMILES string

C1CN(CCN1)C2=CC=C(C=C2)C3=CN4C(=C(C=N4)C5=C6C=CC=NC6=CC=C5)N=C3

InChI

1S/C25H22N6/c1-3-21(22-4-2-10-27-24(22)5-1)23-16-29-31-17-19(15-28-25(23)31)18-6-8-20(9-7-18)30-13-11-26-12-14-30/h1-10,15-17,26H,11-14H2

InChI key

BBDGBGOVJPEFBT-UHFFFAOYSA-N

Description

General description

A cell-permeable pyrazolopyrimidinylquinoline that is superior to Dorsomorphin (Cat. Nos. 171260 and 171261) and DMH1 (Cat. No. 203646) as an ATP-site-targeting, ALK1/2 inhibitor (IC₅₀ = 2.40 and 1.30 nM, respectively; [ATP] = 6 µM) with respect to both potency and selectivity over ALK3/4/5 (IC₅₀ = 0.858, 2.133, and 9.276 µM, respectively). Also a potent RIPK2 inhibitor (IC₅₀ = 6 nM) with reduced potency against ABL1/c-abl, PDGFR-β, ALK3, and PDGFR-α (IC₅₀ = 40, 68, 85.8, and 650 nM, respectively), while displaying much reduced or no inhibitory activity toward a panel of more than 190 kinases. Selectively blocks BMP7-induced/ALK2-mediated SMAD1/5/8 activation in BMPR2^-/- PASMC, but not TGF-β1-induced SMAD2 activation in PASMC. Effectively inhibits ALK2- and ALK3-mediated C2C12 osteogenic differentiation (IC₅₀ = 10 and 40.5 nM upon stimulation with respective ligand BMP6 and BMP4) in vitro and prevents constitutively active ALK2 Q207D mutation-induced heterotopic ossification in mice (6 mg/kg/12 h via i.p.) in vivo. A good complement to the ALK4/5/7-selective A-83-01 (Cat. No. 616454).

Biochem/physiol Actions

Primary Target
ALK1/2/3

Reversible: yes

Secondary Target
RIP, Abl & PDGFR

Cell permeable: yes

Packaging

Packaged under inert gas

Preparation Note

Warming may be required for complete solubilization. Material will appear as a button in the bottom of the vial.

Other Notes

Mohedas, A.H., et al. 2013. ACS Chem. Biol.8, 1291.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c