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SML0559

Sigma-Aldrich

LDN193189 hydrochloride

≥98% (HPLC), powder, ALK2/3 inhibitor

Synonyme(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

Formule empirique (notation de Hill):
C25H22N6 · xHCl
Numéro CAS:
1062368-24-4
Poids moléculaire :
406.48 (free base basis)
Numéro MDL:
MFCD17392570
Code UNSPSC :
51111800
ID de substance PubChem :
329825552
Nomenclature NACRES :
NA.77

product name

LDN193189 hydrochloride, ≥98% (HPLC)

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

yellow to orange

Solubilité

H2O: 5 mg/mL, clear (warmed)

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

PCCDKTWDGDFRME-UHFFFAOYSA-N

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.

Actions biochimiques/physiologiques

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.

Notes préparatoires

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°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.
Haematologica, 100(2), e68-e71 (2015)
Guang Wang et al.
Molecular biology of the cell, 26(5), 978-992 (2015-01-09)
The brain and reproductive expression (BRE) gene is expressed in numerous adult tissues and especially in the nervous and reproductive systems. However, little is known about BRE expression in the developing embryo or about its role in embryonic development. In
Long-term culture of pluripotent stem-cell-derived human neurons on diamond?A substrate for neurodegeneration research and therapy.
Nistor P A, et al.
Biomaterials, 61, 139-149 (2015)
Giorgia Giacomazzi et al.
Nature communications, 8(1), 1249-1249 (2017-11-03)
Muscular dystrophies (MDs) are often characterized by impairment of both skeletal and cardiac muscle. Regenerative strategies for both compartments therefore constitute a therapeutic avenue. Mesodermal iPSC-derived progenitors (MiPs) can regenerate both striated muscle types simultaneously in mice. Importantly, MiP myogenic
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