SML0559

LDN193189 hydrochloride

≥98% (HPLC), powder, ALK2/3 inhibitor

• Synonym(s): 4-[6-[4-(1-Piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-quinoline hydrochloride, DM-3189
• Empirical Formula (Hill Notation): C₂₅H₂₂N₆ · xHCl
• CAS Number: 1062368-24-4
• Molecular Weight: 406.48 (free base basis)
• MDL number: MFCD17392570
• UNSPSC Code: 51111800
• PubChem Substance ID: 329825552
• NACRES: NA.77

Properties

• product name: LDN193189 hydrochloride, ≥98% (HPLC)
• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• storage condition: desiccated
• color: yellow to orange
• solubility: H₂O: 5 mg/mL, clear (warmed)
• shipped in: wet ice
• storage temp.: −20°C
• SMILES string: C(C=N1)(C2=CC=C(N3CCNCC3)C=C2)=CN4C1=C(C5=CC=NC6=C5C=CC=C6)C=N4.Cl
• InChI: 1S/C25H22N6.ClH/c1-2-4-24-22(3-1)21(9-10-27-24)23-16-29-31-17-19(15-28-25(23)31)18-5-7-20(8-6-18)30-13-11-26-12-14-30;/h1-10,15-17,26H,11-14H2;1H
• InChI key: PCCDKTWDGDFRME-UHFFFAOYSA-N

Description

Application

LDN193189 hydrochloride has been used as an ALK2/3 (type I receptor serine-threonine kinases) inhibitor, to study the effect of TGFβ1/2/3 (tumor growth factor β) and BMP (bone morphogenetic protein) signaling on spinal cord development in zebrafish. It has also been used to inhibit SMAD (homologues of the Drosophila protein, mothers against decapentaplegic), in order to prevent non neuronal differentiation.

Biochem/physiol Actions

Although LDN193189 is a structural analog of dorsomorphin, these two drugs are found to establish different cellular responses. In vitro analysis reveals that LDN193189 inhibits a number of intracellular kinases such as, mitogen activated protein kinase 14 and 8 ( p38and c-Jun N-terminal kinase respectively), as well as those associated with AKT (serine/threonine kinase) and mTOR (mammalian target of rapamycin) signaling mechanisms. LDN193189 is known to elevate the levels hemoglobin and thus helps to prevent the onset of anemia of inflammation.

LDN193189 is a derivative of dorsomorphin that is a highly selective antagonist of BMP receptor isotypes ALK2 and ALK3 (IC₅₀ of: 5 and 30 nM). The selectivity of LDN193189 for ALK2/3 is 200 fold over the TGF-B type receptors ALK4,-5 and -7. In murine smooth muscle cells, the compound inhibits BMP-4 induced phosphorylation of SMAD 1/5/8 with an IC₅₀ of 5 nM.

Preparation Note

The product is water soluble at a minimum of 5 mg/mL.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable