SML0559

LDN193189 hydrochloride

≥98% (HPLC), powder, ALK2/3 inhibitor

• Sinónimos: 4-[6-[4-(1-Piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-quinoline hydrochloride, DM-3189
• Fórmula empírica (notación de Hill): C₂₅H₂₂N₆ · xHCl
• Número de CAS: 1062368-24-4
• Peso molecular: 406.48 (free base basis)
• MDL number: MFCD17392570
• UNSPSC Code: 51111800
• PubChem Substance ID: 329825552
• NACRES: NA.77

Propiedades

• Nombre del producto: 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

Descripción

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.[1] It has also been used to inhibit SMAD (homologues of the Drosophila protein, mothers against decapentaplegic), in order to prevent non neuronal differentiation.[2]

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.[3] LDN193189 is known to elevate the levels hemoglobin and thus helps to prevent the onset of anemia of inflammation.[4]

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.

LDN193189 is a selective BMP receptor antagonist.

Preparation Note

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

Información de seguridad

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable