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
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About This Item
Empirical Formula (Hill Notation):
C25H22N6 · xHCl
CAS Number:
Molecular Weight:
406.48 (free base basis)
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77
Product Name
LDN193189 hydrochloride, ≥98% (HPLC)
Quality Level
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
Related Categories
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.
LDN193189 is a selective BMP receptor antagonist.
Preparation Note
The product is water soluble at a minimum of 5 mg/mL.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Differential cellular responses induced by dorsomorphin and LDN?193189 in chemotherapy?sensitive and chemotherapy?resistant human epithelial ovarian cancer cells.
Ali J L, et al.
International Journal of Cancer. Journal International Du Cancer, 136(5), E455-E469 (2015)
Oral administration of a bone morphogenetic protein type I receptor inhibitor prevents the development of anemia of inflammation.
Mayeur C, et al.
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