LDN 193189 dihydrochloride

GMP Version Available: LDN 193189
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Description: Potent and selective ALK2 and ALK3 inhibitor; inhibits BMP4 signaling; promotes neural induction of hPSCs
Chemical Name: 4-[6-[4-(1-Piperazinyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]quinoline dihydrochloride
Purity: ≥98% (HPLC)
Citations (37)
Reviews (2)
Protocols (3)
Literature (4)
Pathways (1)

Biological Activity for LDN 193189 dihydrochloride

LDN 193189 dihydrochloride is a potent and selective ALK2 and ALK3 inhibitor (IC50 values are 5 and 30 nM, respectively); inhibits BMP4-mediated Smad1/5/8 activation. Exhibits >200-fold selectivity for BMP signaling over TGF-β signaling. Also exhibits selectivity over AMPK, PDGFR and MAPK signaling. Promotes neural induction of hPSCs in combination with SB 431542 (Cat.No. 1614). Also induces differentiation of hPSCs into nociceptive sensory neurons in combination with SB 431542 (Cat.No. 1614), SU 5402 (Cat.No.3300), CHIR 99021 (Cat.No. 4423) and DAPT (Cat.No. 2634).

LDN 193189 synthesized to cGMP guidelines also available.

For more information about how LDN 193189 dihydrochloride may be used, see our protocols: Generation of β cells from hPSCs, Generating Midbrain Dopaminergic Neurons from hPSCs, Accelerated Induction of Cortical Neurons from hiPSCs.

Scientific Data

Application of LDN 193189 in motor neurons differentiated from iPSCs. Image shows IBJ6 human fibroblast induced pluripotent stem cells which have been differentiated into motor neurons. This was performed using a combination of LDN 193189 (100 nM) and SB 431542 (Catalog # 1614, Tocris) followed by Retinoic acid (Catalog # 0695, Tocris) and Purmorphamine (Catalog # 4551, Tocris) culture on Laminin for 18 days. Commitment to the motor neuron fate was assessed using the motor neuron marker anti-Human Islet-1 (red, R&D Systems, Catalog # AF1837) and the general neuronal marker, beta III tubulin (green, R&D Systems, Catalog # MAB1195). For visualization, the neurons were stained using Northernlights™ 557-conjugated Donkey anti-Goat Secondary Antibody (R&D Systems, Catalog # NL001) and Northernlights™ 493-conjugated Donkey anti-Mouse Secondary Antibody (R&D Systems, Catalog # NL009 NL009) and counterstained with DAPI (blue, Catalog # 5748, Tocris).

Licensing Information

Sold for research purposes under exclusive agreement from The Brigham and Women's Hospital Inc. US patents 8,507,501 and 9,045,484

Compound Libraries for LDN 193189 dihydrochloride

LDN 193189 dihydrochloride is also offered as part of the Tocriscreen 2.0 Max and Tocriscreen Stem Cell Library. Find out more about compound libraries available from Tocris.

Technical Data for LDN 193189 dihydrochloride

M. Wt 479.4
Formula C25H22N6.2HCl
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 1435934-00-1
PubChem ID 91900717
Smiles N1(C2=CC=C(C3=CN4N=CC(C5=CC=NC6=C5C=CC=C6)=C4N=C3)C=C2)CCNCC1.Cl.Cl

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for LDN 193189 dihydrochloride

Solvent Max Conc. mg/mL Max Conc. mM
water 23.97 50
DMSO 4.79 10

Preparing Stock Solutions for LDN 193189 dihydrochloride

The following data is based on the product molecular weight 479.4. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
0.5 mM 4.17 mL 20.86 mL 41.72 mL
2.5 mM 0.83 mL 4.17 mL 8.34 mL
5 mM 0.42 mL 2.09 mL 4.17 mL
25 mM 0.08 mL 0.42 mL 0.83 mL

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Product Datasheets for LDN 193189 dihydrochloride

Certificate of Analysis / Product Datasheet
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References for LDN 193189 dihydrochloride

References are publications that support the biological activity of the product.

Yu et al (2008) BMP type I receptor inhibition reduces heterotopic ossification. Nat.Med. 14 1363 PMID: 19029982

Chambers et al (2012) Combined small-molecule inhibition accelerates developmental timing and converts human pluripotent stem cells into nociceptors. Nat.Biotechnol. 30 715 PMID: 22750882

Cuny et al (2008) Structure-activity relationship study of bone morphogenetic protein (BMP) signaling inhibitors. Bioorg.Med.Chem.Lett. 18 4388 PMID: 18621530

Li et al (2013) Chemical approaches to stem cell biology and therapeutics. Cell Stem Cell 13 270 PMID: 24012368

Lancaster et al (2015) Generation of Cerebral Organoids from Human Pluripotent Stem Cells Nat. Protoc. 9 2329 PMID: 25188634

Kadoshima et al (2013) Self-organization of axial polarity, inside-out layer pattern, and species-specific progenitor dynamics in human ES cell-derived neocortex. Proc.Natl.Acad.Sci.USA. 110 20284 PMID: 24277810

Dye et al (2015) In vitro generation of human pluripotent stem cell derived lung organoids. Elife 4 PMID: 25803487

Wimmer et al (2019) Human blood vessel organoids as a model of diabetic vasculopathy. Nature 565 505 PMID: 30651639

If you know of a relevant reference for LDN 193189 dihydrochloride, please let us know.

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Keywords: LDN 193189 dihydrochloride, LDN 193189 dihydrochloride supplier, LDN193189, dihydrochloride, BMP, signaling, ALK2, ALK3, activin, bone, morphogenetic, proteins, stem, cells, neural, differentiation, neurons, and, Other, Activin, Receptors, ESCs, iPSC, Neural, Stem, Cells, Organoids, 6053, Tocris Bioscience

37 Citations for LDN 193189 dihydrochloride

Citations are publications that use Tocris products. Selected citations for LDN 193189 dihydrochloride include:

Sommer et al (2018) Th17 lymphocytes induce neuronal cell death in a human iPSC-based model of Parkinson's disease. Cell Stem Cell 23 123 PMID: 29979986

Beraldo et al (2018) Mechanisms of neuroprotection against ischemic insult by stress-inducible phosphoprotein-1/prion protein complex. J Neurochem 145 68 PMID: 29265373

Sara et al (2023) Expansion of ventral foregut is linked to changes in the enhancer landscape for organ-specific differentiation. Nat Cell Biol 25 481-492 PMID: 36690849

Mustafa et al (2023) A Robust Pipeline for the Multi-Stage Accelerated Differentiation of Functional 3D Cortical Organoids from Human Pluripotent Stem Cells. Curr Protoc 3 e641 PMID: 36633423

Wei et al (2023) Generation and characterization of NGLY1 patient-derived midbrain organoids. Front Cell Dev Biol 11 1039182 PMID: 36875753

Emmanouil et al (2022) Derivation of nociceptive sensory neurons from hiPSCs with early patterning and temporally controlled NEUROG2 overexpression. Cell Rep Methods 2 100341 PMID: 36452863

Shinong et al (2022) CRISPRi screens in human iPSC-derived astrocytes elucidate regulators of distinct inflammatory reactive states. Nat Neurosci 25 1528-1542 PMID: 36303069

Jessica et al (2022) Uncovering specificity of endogenous TAU aggregation in a human iPSC-neuron TAU seeding model. iScience 25 103658 PMID: 35072001

Richard et al (2022) Substantial somatic genomic variation and selection for BCOR mutations in human induced pluripotent stem cells. Nat Genet 54 1406-1416 PMID: 35953586

Jop et al (2022) A pendulum of induction between the epiblast and extra-embryonic endoderm supports post-implantation progression. Development 149 PMID: 35993866

Mark J et al (2022) Multidimensional analysis and therapeutic development using patient iPSC-derived disease models of Wolfram syndrome. JCI Insight 7 PMID: 36134655

Kyung-Sun et al (2022) Wnt-activating human skin organoid model of atopic dermatitis induced by Staphylococcus aureus and its protective effects by Cutibacterium acnes. iScience 25 105150 PMID: 36193049

Jia et al (2022) Selective activation and down-regulation of Trk receptors by neurotrophins in human neurons co-expressing TrkB and TrkC. J Neurochem 161 463-477 PMID: 35536742

Timothy et al (2022) Classical Complement Pathway Inhibition in a Human-On-A-Chip" Model of Autoimmune Demyelinating Neuropathies." Adv Ther (Weinh) 5 PMID: 36211621

Mustafa et al (2022) Dynamic 3D Combinatorial Generation of hPSC-Derived Neuromesodermal Organoids With Diverse Regional and Cellular Identities. Curr Protoc 2 e568 PMID: 36264199

Surendran et al (2022) An improved protocol for generation and characterization of human-induced pluripotent stem cell-derived retinal pigment epithelium cells. STAR Protoc 3 101803 PMID: 36386870

Katja et al (2020) A Human Skeletal Muscle Atlas Identifies the Trajectories of Stem and Progenitor Cells across Development and from Human Pluripotent Stem Cells. Cell Stem Cell 27 158-176.e10 PMID: 32396864

Bo et al (2020) Cellular and molecular characterization of multiplex autism in human induced pluripotent stem cell-derived neurons. Mol Autism 10 51 PMID: 31893020

Frédéric H-T et al (2020) Aberrant interaction of FUS with the U1 snRNA provides a molecular mechanism of FUS induced amyotrophic lateral sclerosis. Nat Commun 11 6341 PMID: 33311468

April D et al (2020) Generation of PAX7 Reporter Cells to Investigate Skeletal Myogenesis from Human Pluripotent Stem Cells. STAR Protoc 1 100158 PMID: 33377052

Steven et al (2020) Optogenetic Control of the BMP Signaling Pathway. ACS Synth Biol 9 3067-3078 PMID: 33084303

Tristan et al (2021) Robotic high-throughput biomanufacturing and functional differentiation of human pluripotent stem cells. Stem Cell Reports 16 3076 PMID: 34861164

Thomas S et al (2021) Altered temporal sequence of transcriptional regulators in the generation of human cerebellar granule cells. Elife 10 PMID: 34842137

Stefan et al (2021) Distinct properties of Ca2+ efflux from brain, heart and liver mitochondria: The effects of Na+, Li+ and the mitochondrial Na+/Ca2+ exchange inhibitor CGP37157. Cell Calcium 96 102382 PMID: 33684833

Beth A et al (2021) Resolving cell state in iPSC-derived human neural samples with multiplexed fluorescence imaging. Commun Biol 4 786 PMID: 34168275

Christof et al (2021) RSPO2 inhibits BMP signaling to promote self-renewal in acute myeloid leukemia. Cell Rep 36 109559 PMID: 34407399

Philip J et al (2021) Transplantable human motor networks as a neuron-directed strategy for spinal cord injury. iScience 24 102827 PMID: 34381965

Anestis et al (2021) In Vitro Generation of Posterior Motor Neurons from Human Pluripotent Stem Cells. Curr Protoc 1 e244 PMID: 34547185

Ling et al (2021) Commitment and oncogene-induced plasticity of human stem cell-derived pancreatic acinar and ductal organoids. Cell Stem Cell 28 1090-1104.e6 PMID: 33915081

Schahram et al (2021) Publicly Available hiPSC Lines with Extreme Polygenic Risk Scores for Modeling Schizophrenia. Complex Psychiatry 6 68-82 PMID: 34883504

Ruili et al (2021) Human Pluripotent Stem Cells for High-Throughput Drug Screening and Characterization of Small Molecules. Methods Mol Biol 2454 811-827 PMID: 34128205

Xiang et al (2019) Long-term functional maintenance of primary human hepatocytes in vitro. Science 364 399 PMID: 31023926

Alsanie (2017) Specification of murine ground state pluripotent stem cells to regional neuronal populations. Sci Rep 7 16001 PMID: 29167563

Young (2017) The doublesex-related Dmrta2 safeguards neural progenitor maintenance involving transcriptional regulation of Hes1. Proc Natl Acad Sci U S A. 114 E5599 PMID: 28655839

Kenneth R et al (2017) Generation of Induced Pluripotent Stem Cells from Patients with COL3A1 Mutations and Differentiation to Smooth Muscle Cells for ECM-Surfaceome Analyses. Methods Mol Biol 1722 261-302 PMID: 29264811

Eva et al (2019) Axon-seq for in Depth Analysis of the RNA Content of Neuronal Processes. Bio Protoc 9 e3312 PMID: 33654821

Genga et al (2019) Single-Cell RNA-Sequencing-Based CRISPRi Screening Resolves Molecular Drivers of Early Human Endoderm Development. Cell Rep 27 708 PMID: 30995470

Do you know of a great paper that uses LDN 193189 dihydrochloride from Tocris? Please let us know.

Reviews for LDN 193189 dihydrochloride

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Efficient and effective inhibitor of BMP-like receptors.
By Paul Humphreys on 12/11/2020
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: TC28a2

To perform inhibition of BMP-like receptors during various interrogations. Performed blanket inhibition of BMP-like receptor kinase activity with 50nM (working) and selective inhibition of ALK3/BMPR1A with 5nM (working) leaving ALK6/BMPR1B active. Non-toxic at concentrations used.

Be wary of storage as activity will degrade over time.

PMID: 33084303
review image

Differentiation to cortical neurons.
By Julieta O'Flaherty on 12/11/2020
Species: Human
Cell Line/Tissue: Induced pluripotent stem cells

I used the product for 10 days to differentiate ipscs into a neuroepithelium

***Bio-Techne Response: Thank you for reviewing our product. We are sorry to hear that this compound did not perform as expected. We have been in touch with the customer to resolve this issue according to our Product Guarantee and to the customer’s satisfaction.***

review image

Protocols for LDN 193189 dihydrochloride

The following protocols feature additional information for the use of LDN 193189 dihydrochloride (Cat. No. 6053).

Literature in this Area

Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!

*Please note that Tocris will only send literature to established scientific business / institute addresses.

Stem Cell Research Product Guide

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Stem Cells Scientific Review

Stem Cells Scientific Review

Written by Kirsty E. Clarke, Victoria B. Christie, Andy Whiting and Stefan A. Przyborski, this review provides an overview of the use of small molecules in the control of stem cell growth and differentiation. Key signaling pathways are highlighted, and the regulation of ES cell self-renewal and somatic cell reprogramming is discussed. Compounds available from Tocris are listed.

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Stem Cells Poster

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Written by Rebecca Quelch and Stefan Przyborski from Durham University (UK), this poster describes the isolation of pluripotent stem cells, their maintenance in culture, differentiation, and the generation and potential uses of organoids.

Pathways for LDN 193189 dihydrochloride

TGF-β Signaling Pathway

TGF-β Signaling Pathway

The TGF-β signaling pathway is involved in the regulation of growth and proliferation of cells along with migration, differentiation and apoptosis.