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SML0559

Sigma-Aldrich

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:
1062368-24-4
Molecular Weight:
406.48 (free base basis)
MDL number:
MFCD17392570
UNSPSC Code:
51111800
PubChem Substance ID:
329825552
NACRES:
NA.77
Pricing and availability is not currently available.

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000390390
0000390390
0000362892
0000362891
0000362892

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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)
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
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)
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)
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
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Questions

1–3 of 3 Questions  

  1. How to interpret water content and salt content values in CoA? They are given in mols and they are huge! I need to make 5mM solution of LDN 193189, how should I take into account these values?

    1 answer

    1. The Certificate of Analysis (CoA) for LDN193189 hydrochloride, lot 0000362892 provides the information regarding water (4 mol) and salt (3.1 mol) content.

      These values are expressed in moles per mole of the compound. This means that for every mole of the compound, there are 4 moles of water and 3.1 moles of salt (likely HCl, as the compound is a hydrochloride salt). These values indicate the degree of hydration and the amount of hydrochloride associated with the compound, which is important for calculating the exact molecular weight to prepare an accurate solution.

      The molecular weight of the free base is provided as 406.48 g/mol. Add the contributions of water (18.015 g/mol per mole) and HCl (36.46 g/mol per mole):
      Adjusted Molecular Weight = 406.48 + ( 4 × 18.015) + (3.1 × 36.46)
      Calculate this value to get the total molecular weight.
      With the adjusted MW, you can prepare your desired solutions.

      Helpful?

  2. Wat is the stability of LDN193189 when lyophilized and in solution?

    1 answer

    1. Unfortunately, the solution stability of the product SML0559 has not been determined.

      Helpful?

  3. How to dilute LDN193189 hydrochloride when it has unknown number of H2O molecules. If I use free base Mw I might overdilute it

    1 answer

    1. The water and salt (HCl) content are reported in the lot specific Certificate of Analysis. The product in water soluble at a minimum of 5 mg/mL. See the link below to review a sample Certificate of Analysis.
      https://www.sigmaaldrich.com/certificates/sapfs/PROD/sap/certificate_pdfs/COFA/Q14/SML0559-5MG0000222043.pdf

      Helpful?

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