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SML0559

Sigma-Aldrich

LDN193189 hydrochloride

≥98% (HPLC)

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:
Molecular Weight:
406.48 (free base basis)
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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This Item
SML2179SML1507SML0965
Sigma-Aldrich

Sigma-Aldrich

SML0965

LDN-212854

form

powder

form

powder

form

powder

form

powder

storage condition

desiccated

storage condition

protect from light

storage condition

-

storage condition

-

color

yellow to orange

color

white to beige

color

white to beige

color

white to beige

solubility

H2O: 5 mg/mL, clear (warmed)

solubility

DMSO: 2 mg/mL, clear (warmed)

solubility

H2O: 15 mg/mL, clear

solubility

DMSO: 1 mg/mL, clear (warmed)

shipped in

wet ice

shipped in

-

shipped in

-

shipped in

-

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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