Dorsomorphin dihydrochloride

Pricing Availability Delivery Time Qty
Cat.No. 3093 - Dorsomorphin dihydrochloride | C24H25N5O.2HCl | CAS No. 1219168-18-9
Description: Potent AMPK inhibitor
Alternative Names: Compound C, BML-275
Chemical Name: 6-[4-[2-(1-Piperidinyl)ethoxy]phenyl]-3-(4-pyridinyl)-pyrazolo[1,5-a]pyrimidine dihydrochloride
Purity: ≥98% (HPLC)
Datasheet
Citations (33)
Literature
Pathways

Biological Activity

Potent inhibitor of AMP-activated protein kinase (AMPK) (Ki = 109 nM). Displays no significant activity on several structurally related kinases including ZAPK, SYK, PKCθ, PKA and JAK3. Inhibits AMPK activation induced by AICAR (Cat. No. 2840) and metformin (Cat. No. 2864). Also inhibits bone morphogenetic protein (BMP) type I receptors (ALK2, ALK3 and ALK6). Promotes cardiomyogenesis in mouse embryonic stem cells (ESCs) in vitro. Shown to induce autophagy in cancer cell lines via a mechanism independent of AMPK inhibition.

Compound Libraries

Dorsomorphin dihydrochloride is also offered as part of the Tocriscreen Plus and Tocriscreen Stem Cell Toolbox. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 472.41
Formula C24H25N5O.2HCl
Storage Desiccate at RT
Purity ≥98% (HPLC)
CAS Number 1219168-18-9
PubChem ID 49761481
InChI Key RJDVIJJQKMGPMV-UHFFFAOYSA-N
Smiles C(C=N2)(C4=CC=C(OCCN5CCCCC5)C=C4)=CN1C2=C(C3=CC=NC=C3)C=N1.Cl.Cl

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

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 9.45 20mM with gentle warming
water 47.24 100

Preparing Stock Solutions

The following data is based on the product molecular weight 472.41. Batch specific molecular weights may vary from batch to batch due to solvent 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
1 mM 2.12 mL 10.58 mL 21.17 mL
5 mM 0.42 mL 2.12 mL 4.23 mL
10 mM 0.21 mL 1.06 mL 2.12 mL
50 mM 0.04 mL 0.21 mL 0.42 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Zhou et al (2001) Role of AMP-activated protein kinase in mechanism of metformin action. J.Clin.Invest. 108 1167 PMID: 11602624

Yu et al (2008) Dorsomorphin inhibits BMP signals required for embryogenesis and iron metabolism. Nat.Chem.Biol. 4 33 PMID: 18026094

Vucicevic et al (2011) Compound C induces protective autophagy in cancer cells through AMPK inhibition-independent blockade of Akt/mTOR pathway. Autophagy 7 40 PMID: 20980833

Hao et al (2008) Dorsomorphin, a selective small molecule inhibitor of BMP signaling, promotes cardiomyogenesis in embryonic stem cells. PLoS ONE 3 2904 PMID: 18682835

Diekmann et al (2015) A reliable and efficient protocol for human pluripotent stem cell differentiation into the definitive endoderm based on dispersed single cells. Stem Cells Dev. 24 190 PMID: 25137387


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33 Citations for Dorsomorphin dihydrochloride

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

Al-Bayati et al (2016) Effects of thrombin on insulin signalling and glucose uptake in cultured human myotubes. J Diabetes Complications 30 1209 PMID: 27396242

Kapeli et al (2016) Distinct and shared functions of ALS-associated proteins TDP-43, FUS and TAF15 revealed by multisystem analyses Nature Communications 7 12143 PMID: 27378374

Mou et al (2016) Dual SMAD Signaling Inhibition Enables Long-Term Expansion of Diverse Epithelial Basal Cells Cell: Stem Cell 19 217 PMID: 27320041

Ahmed (2016) Effects of novel muscarinic M3 receptor ligand C1213 in pulmonary arterial hypertension models. Physiological Reports 4  e13069 PMID: 28039410

Obba et al (2015) The PRKAA1/AMPKα1 pathway triggers autophagy during CSF1-induced human monocyte differentiation and is a potential target in CMML. Nat Protoc 11 1114 PMID: 26029847

Huang et al (2015) The in vitro generation of lung and airway progenitor cells from human pluripotent stem cells. Nat Genet 10 413 PMID: 25654758

Liao et al (2015) Targeted disruption of DNMT1, DNMT3A and DNMT3B in human embryonic stem cells. Exp Ther Med 47 469 PMID: 25822089

Zhu et al (2015) Adenosine monophosphate-activated protein kinase activation mediates the leptin-induced attenuation of cognitive impairment in a streptozotocin-induced rat model. Nature 9 1998 PMID: 26136928

Tsankov et al (2015) Transcription factor binding dynamics during human ES cell differentiation. Biomed Res Int 518 344 PMID: 25693565

Matsuda et al (2015) Comparative Study on the Cytoprotective Effects of Activated Protein C Treatment in Nonsteatotic and Steatotic Livers under Ischemia-Reperfusion Injury. BMC Neurosci 2015 635041 PMID: 26539519

Khan et al (2015) Blocking a vicious cycle nNOS/peroxynitrite/AMPK by S-nitrosoglutathione: implication for stroke therapy. J Pharmacol Exp Ther 16 42 PMID: 26174015

Sposito et al (2015) Developmental regulation of tau splicing is disrupted in stem cell-derived neurons from frontotemporal dementia patients with the 10 + 16 splice-site mutation in MAPT. Sci Rep 24 5260 PMID: 26136155

Palm et al (2015) Rapid and robust generation of long-term self-renewing human neural stem cells with the ability to generate mature astroglia. Int J Mol Sci 5 16321 PMID: 26541394

Chen et al (2015) Chemical constituents analysis and antidiabetic activity validation of four fern species from Taiwan. Exp Neurol 16 2497 PMID: 25622260

Holtzhausen et al (2014) Novel bone morphogenetic protein signaling through Smad2 and Smad3 to regulate cancer progression and development. FASEB J 28 1248 PMID: 24308972

Huang et al (2014) Efficient generation of lung and airway epithelial cells from human pluripotent stem cells. Nat Biotechnol 32 84 PMID: 24291815

Mourabit et al (2014) Bmp suppression in mangrove killifish embryos causes a split in the body axis. PLoS One 9 e84786 PMID: 24497921

Graham et al (2014) BMP signalling regulates the pre-implantation development of extra-embryonic cell lineages in the mouse embryo. Nat Neurosci 5 5667 PMID: 25514175

Fong et al (2013) Moderate excess of pyruvate augments osteoclastogenesis. Biol Open 2 387 PMID: 23616923

Reinhardt et al (2013) Derivation and expansion using only small molecules of human neural progenitors for neurodegenerative disease modeling. PLoS One 8 e59252 PMID: 23533608

Ueki and Reh (2013) EGF stimulates Müller glial proliferation via a BMP-dependent mechanism. Glia 61 778 PMID: 23362023

Sheehan-Rooney et al (2013) Bmp and Shh signaling mediate the expression of satb2 in the pharyngeal arches. PLoS One 8 e59533 PMID: 23555697

Knelson et al (2013) Type III TGF-β receptor promotes FGF2-mediated neuronal differentiation in neuroblastoma. J Clin Invest 123 4786 PMID: 24216509

Kim et al (2013) Epigallocatechin gallate (EGCG) stimulates autophagy in vascular endothelial cells: a potential role for reducing lipid accumulation. J Biol Chem 288 22693 PMID: 23754277

Taub et al (2013) Distinct energy requirements for human memory CD4 T-cell homeostatic functions. Stem Cells Dev 27 342 PMID: 22972918

Brafman et al (2013) Regulation of endodermal differentiation of human embryonic stem cells through integrin-ECM interactions. Cell Metab 20 369 PMID: 23154389

Pol et al (2013) Sox10-MCS5 enhancer dynamically tracks human oligodendrocyte progenitor fate. Lab Chip 247 694 PMID: 23507034

Li et al (2013) Flow-based pipeline for systematic modulation and analysis of 3D tumor microenvironments. Nat Commun 13 1969 PMID: 23563587

Hou et al (2012) Liraglutide, a long-acting GLP-1 mimetic, and its metabolite attenuate inflammation after intracerebral hemorrhage. J Cereb Blood Flow Metab 32 2201 PMID: 22968320

Petersen et al (2012) Engineering artificial signaling centers to polarize embryoid body differentiation. Br J Pharmacol 21 647 PMID: 21958075

Shi et al (2012) Human cerebral cortex development from pluripotent stem cells to functional excitatory synapses. FASEB J 15 477 PMID: 22306606

Sellayah et al (2011) Orexin is required for brown adipose tissue development, differentiation, and function. Autophagy 14 478 PMID: 21982708

Bumpus and Johnson (2011) 5-Aminoimidazole-4-carboxyamide-ribonucleoside (AICAR)-stimulated hepatic expression of Cyp4a10, Cyp4a14, Cyp4a31, and other peroxisome proliferator-activated receptor α-responsive mouse genes is AICAR 5'-monophosphate-dependent and AMP-activated Hum Mol Genet 339 886 PMID: 21896918


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Literature in this Area

Kinases

Kinases Product Listing

A collection of over 400 products for kinase research, the listing includes inhibitors of:

  • Receptor Tyrosine Kinases
  • Protein Kinases A, C, D and G
  • PI-3 Kinase, Akt and mTOR
  • MAPK Signaling
  • Receptor Serine/Threonine Kinases

Pathways for Dorsomorphin dihydrochloride

AMPK

AMPK Signaling Pathway

AMPK signaling pathway plays an important role in the cellular reponse to low levels of available ATP, often caused by stresses such as heat shock, ischemia or hypoxia.

Protocols

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