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Dorsomorphin dihydrochloride

Catalog #: 3093
66 Citations Datasheet / COA / SDS
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Dorsomorphin dihydrochloride | CAS No. 1219168-18-9 | AMPK Inhibitors
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Description: Potent AMPK inhibitor; also BMP type I receptor 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%

Product Details
Citations (66)
Supplemental Products
Reviews
Biological Activity Technical Data Background Product Datasheets Calculators

Biological Activity

Dorsomorphin dihydrochloride is a 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). Dorsomorphin dihydrochloride also inhibits bone morphogenetic protein (BMP) type I receptors (ALK2, ALK3 and ALK6), promotes cardiomyogenesis in mouse embryonic stem cells (ESCs) in vitro and promotes neural differentiation of hPSCs as part of a chemical cocktail. The compound can also be used in protocols for the chemical reprogramming of somatic cells to iPSCs.Shown to induce autophagy in cancer cell lines via a mechanism independent of AMPK inhibition. Also used in a protocol to generate brain organoids from human iPSCs.

Technical Data

M.Wt:
472.41
Formula:
C24H25N5O.2HCl
Solubility:
Soluble to 100 mM in water and to 20 mM in DMSO with gentle warming
Purity:
≥98%
Storage:
Desiccate at RT
CAS No:
1219168-18-9

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.

Background References

  1. Sensory neurons do not induce motor neuron loss in a human stem cell model of spinal muscular atrophy.
    Schwab, Andrew J, Ebert, Allison
    PLoS ONE, 2014;9(7):e103112.
  2. Direct Reprogramming of Fibroblasts via a Chemically Induced XEN-like State
    X Li, D Liu, Y Ma, X Du, J Jing, L Wang, B Xie, D Sun, S Sun, X Jin, X Zhang, T Zhao, J Guan, Z Yi, W Lai, P Zheng, Z Huang, Y Chang, Z Chai, J Xu, H Deng
    Cell Stem Cell, 2017;0(0):.
  3. Bone morphogenetic protein 2 increases lysyl oxidase activity via up-regulation of snail in human granulosa-lutein cells
    L Bai, HM Chang, YM Zhu, PCK Leung
    Cell. Signal., 2018;53(0):201-211.
  4. A transient wave of BMP signaling in the retina is necessary for Muller glial differentiation.
    Ueki Y, Wilken M, Cox K, Chipman L, Bermingham-McDonogh O, Reh T
    Development, 2015;142(3):533-43.
  5. Deterministic HOX patterning in human pluripotent stem cell-derived neuroectoderm

    Stem Cell Reports, 2015;4(4):632-44.
  6. Generation of nephron progenitor cells and kidney organoids from human pluripotent stem cells

    Nat Protoc, 2017;12(1):195-207.
  7. Identification of bone morphogenetic protein 7 (BMP7) as an instructive factor for human epidermal Langerhans cell differentiation.
    Yasmin N, Bauer T, Modak M, Wagner K, Schuster C, Koffel R, Seyerl M, Stockl J, Elbe-Burger A, Graf D, Strobl H
    J Exp Med, 2013;210(12):2597-610.
  8. Adenosine inhibits tumor cell invasion via receptor-independent mechanisms.
    Virtanen S, Kukkonen-Macchi A, Vainio M, Elima K, Harkonen P, Jalkanen S, Yegutkin G
    Mol Cancer Res, 2014;12(12):1863-74.
  9. Small molecules dorsomorphin and LDN-193189 inhibit myostatin/GDF8 signaling and promote functional myoblast differentiation.
    Horbelt D, Boergermann J, Chaikuad A, Alfano I, Williams E, Lukonin I, Timmel T, Bullock A, Knaus P
    J Biol Chem, 2015;290(6):3390-404.
  10. Activation of BMP-Smad1/5/8 signaling promotes survival of retinal ganglion cells after damage in vivo.
    Ueki Y, Reh TA,
    PLoS ONE, 2012;7(6):e38690.
  11. BMP and TGF-beta pathway mediators are critical upstream regulators of Wnt signaling during midbrain dopamine differentiation in human pluripotent stem cells.
    Cai J, Schleidt S, Pelta-Heller J, Hutchings D, Cannarsa G, Iacovitti L
    Dev Biol, 2013;376(1):62-73.
  12. SMAD1/5 mediates bone morphogenetic protein 2-induced up-regulation of BAMBI expression in human granulosa-lutein cells
    L Bai, HM Chang, JC Cheng, C Klausen, G Chu, PCK Leung, G Yang
    Cell. Signal., 2017;37(0):52-61.
  13. BMP15 suppresses progesterone production by down-regulating StAR via ALK3 in human granulosa cells.
    Chang H, Cheng J, Klausen C, Leung P
    Mol Endocrinol, 2013;27(12):2093-104.
  14. Efficient generation of lung and airway epithelial cells from human pluripotent stem cells.
    Huang, Sarah X, Islam, Mohammad, O'Neill, John, Hu, Zheng, Yang, Yong-Gua, Chen, Ya-Wen, Mumau, Melanie, Green, Michael, Vunjak-Novakovic, Gordana, Bhattacharya, Jahar, Snoeck, Hans-Wil
    Nat Biotechnol, 2014;32(1):84-91.
  15. Bone morphogenetic protein 2 regulates cell-cell communication by down-regulating connexin43 expression in luteinized human granulosa cells
    Yan-Ting Wu
    Mol. Hum. Reprod, 2016;0(0):.
  16. Glucose Alters Per2 Rhythmicity Independent of AMPK, Whereas AMPK Inhibitor Compound C Causes Profound Repression of Clock Genes and AgRP in mHypoE-37 Hypothalamic Neurons.
    Oosterman J, Belsham D
    PLoS ONE, 2016;11(1):e0146969.
  17. Transcription factor binding dynamics during human ES cell differentiation.
    Tsankov, Alexande, Gu, Hongcang, Akopian, Veronika, Ziller, Michael, Donaghey, Julie, Amit, Ido, Gnirke, Andreas, Meissner, Alexande
    Nature, 2015;518(7539):344-9.
  18. Regulation of endodermal differentiation of human embryonic stem cells through integrin-ECM interactions.
    Brafman D, Phung C, Kumar N, Willert K
    Cell Death Differ, 2013;20(3):369-81.
  19. Deterministic HOX Patterning in Human Pluripotent Stem Cell-Derived Neuroectoderm.
    Lippmann E, Williams C, Ruhl D, Estevez-Silva M, Chapman E, Coon J, Ashton R
    Stem Cell Reports, 2015;4(4):632-44.
  20. Macrophage Migration Inhibitor Factor Upregulates MCP-1 Expression in an Autocrine Manner in Hepatocytes during Acute Mouse Liver Injury
    Jieshi Xie
    Sci Rep, 2016;6(0):27665.
  21. Analysis of SOX2-expressing cell populations derived from human pluripotent stem cells.
    Brafman D, Moya N, Allen-Soltero S, Fellner T, Robinson M, McMillen Z, Gaasterland T, Willert K
    Stem Cell Reports, 213;1(5):464-78.
  22. Modeling of TREX1-Dependent Autoimmune Disease using Human Stem Cells Highlights L1 Accumulation as a Source of Neuroinflammation
    CA Thomas, L Tejwani, CA Trujillo, PD Negraes, RH Herai, P Mesci, A Macia, YJ Crow, AR Muotri
    Cell Stem Cell, 2017;0(0):.
  23. Modeling anorexia nervosa: transcriptional insights from human iPSC-derived neurons
    PD Negraes, FR Cugola, RH Herai, CA Trujillo, AS Cristino, T Chailangka, AR Muotri, V Duvvuri
    Transl Psychiatry, 2017;7(3):e1060.
  24. Optimal effector functions in human natural killer cells rely upon autocrine bone morphogenetic protein signaling.
    Robson N, Hidalgo L, McAlpine T, Wei H, Martinez V, Entrena A, Melen G, MacDonald A, Phythian-Adams A, Sacedon R, Maraskovsky E, Cebon J, Ramirez M, Vicente A, Varas A
    Cancer Res, 2014;74(18):5019-31.
  25. Open Chromatin Profiling in hiPSC-Derived Neurons Prioritizes Functional Noncoding Psychiatric Risk Variants and Highlights Neurodevelopmental Loci
    MP Forrest, H Zhang, W Moy, H McGowan, C Leites, LE Dionisio, Z Xu, J Shi, AR Sanders, WJ Greenleaf, CA Cowan, ZP Pang, PV Gejman, P Penzes, J Duan
    Cell Stem Cell, 2017;0(0):.
  26. COH-SR4 reduces body weight, improves glycemic control and prevents hepatic steatosis in high fat diet-induced obese mice.
    Figarola J, Singhal P, Rahbar S, Gugiu B, Awasthi S, Singhal S
    PLoS ONE, 2013;8(12):e83801.
  27. Multi-level characterization of balanced inhibitory-excitatory cortical neuron network derived from human pluripotent stem cells
    AG Nadadhur, J Emperador, M Meijer, D Schut, G Jacobs, KW Li, JJJ Hjorth, RM Meredith, RF Toonen, RE Van Kester, AB Smit, M Verhage, VM Heine
    PLoS ONE, 2017;12(6):e0178533.
  28. Role of AMP-activated protein kinase in mechanism of MetF. action.
    Zhou et al.
    J.Clin.Invest., 2001;108:1167
  29. Dorsomorphin inhibits BMP signals required for embryogenesis and iron metabolism.
    Yu et al.
    Nat.Chem.Biol., 2008;4:33
  30. Compound C induces protective autophagy in cancer cells through AMPK inhibition-independent blockade of Akt/mTOR pathway.
    Vucicevic et al.
    Autophagy, 2011;7:40
  31. Dorsomorphin, a selective small molecule inhibitor of BMP signaling, promotes cardiomyogenesis in embryonic stem cells.
    Hao et al.
    PLoS ONE, 2008;3:2904
  32. A reliable and efficient protocol for human pluripotent stem cell differentiation into the definitive endoderm based on dispersed single cells.
    Diekmann et al.
    Stem Cells Dev., 2015;24:190
  33. Chemically defined neural conversion of human pluripotent stem cells.
    Chen et al.
    Methods Mol.Biol., 2019;1919:59
  34. Modeling COVID-19 with Human Pluripotent Stem Cell-Derived Cells Reveals Synergistic Effects of Anti-inflammatory Macrophages with ACE2 Inhibition Against SARS-CoV-2
    F Duan, L Guo, L Yang, Y Han, A Thakur, BE Nilsson-Pa, P Wang, Z Zhang, CY Ma, X Zhou, T Han, T Zhang, X Wang, D Xu, X Duan, J Xiang, HF Tse, C Liao, W Luo, FP Huang, YW Chen, T Evans, RE Schwartz, B tenOever, DD Ho, S Chen, Q Lian, HJ Chen
    Res Sq, 2020;0(0):.
  35. Pharmacological reversal of synaptic and network pathology in human MECP2-KO neurons and cortical organoids
    CA Trujillo, JW Adams, PD Negraes, C Carromeu, L Tejwani, A Acab, B Tsuda, CA Thomas, N Sodhi, KM Fichter, S Romero, F Zanella, TJ Sejnowski, H Ulrich, AR Muotri
    Embo Molecular Medicine, 2021;13(1):e12523.

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Citations for Dorsomorphin dihydrochloride

The citations listed below are publications that use Tocris products. Selected citations for Dorsomorphin dihydrochloride include:

66 Citations: Showing 1 - 10

  1. An in vivo neuroimmune organoid model to study human microglia phenotypes.
    Authors: Schafer Et al.
    Cell  2023;186:2111
  2. A Human Pluripotent Stem Cell-based Platform to Study SARS-CoV-2 Tropism and Model Virus Infection in Human Cells and Organoids
    Authors: Yang Et al.
    Cell Stem Cell  2020;27:125
  3. Neurons Derived from Human Induced Pluripotent Stem Cells Integrate into Rat Brain Circuits and Maintain Both Excitatory and Inhibitory Synaptic Activities.
    Authors: Yin Et al.
    Eneuro  2019;6
  4. Microtubules Deform the Nuclear Membrane and Disrupt Nucleocytoplasmic Transport in Tau-Mediated Frontotemporal Dementia.
    Authors: Paonessa Et al.
    Cell Rep  2019;26:582
  5. FMR1 Reactivating Treatments in Fragile X iPSC-Derived Neural Progenitors In Vitro and In Vivo.
    Authors: Vershkov Et al.
    Cell Rep  2019;26:2531
  6. Chemically Defined Neural Conversion of Human Pluripotent Stem Cells
    Authors: Chen Et al.
    Methods Mol Biol  2019;1919:59
  7. Inhibition of proliferation and migration of melanoma cells by ketoconazole and Ganoderma immunomodulatory proteins.
    Authors: Lu Et al.
    Oncol Lett  2019;18:891
  8. mTORC1/AMPK responses define a core gene set for developmental cell fate switching.
    Authors: Jaiswal and Kimmel
    BMC Biol  2019;17:58
  9. An isogenic neurovascular unit model comprised of human induced pluripotent stem cell-derived brain microvascular endothelial cells, pericytes, astrocytes, and neurons.
    Authors: Canfield Et al.
    Fluids Barriers CNS  2019;16:25
  10. Exosomes regulate neurogenesis and circuit assembly.
    Authors: Sharma Et al.
    Proc Natl Acad Sci U S A  2019;116:16086
  11. A stably self-renewing adult blood-derived induced neural stem cell exhibiting patternability and epigenetic rejuvenation.
    Authors: Sheng Et al.
    Nat Commun  2018;9:4047
  12. Discordant congenital Zika syndrome twins show differential in vitro viral susceptibility of neural progenitor cells.
    Authors: Caires-J?nior
    Nat Commun  2018;9(1):475
  13. Combined Experimental and System-Level Analyses Reveal the Complex Regulatory Network of miR-124 during Human Neurogenesis.
    Authors: Kutsche Et al.
    Cell Syst  2018;7:438
  14. Rab5 and Alsin regulate stress-activated cytoprotective signaling on mitochondria.
    Authors: Hsu Et al.
    Elife  2018;7
  15. Hey2 regulates the size of the cardiac progenitor pool during vertebrate heart development.
    Authors: Gibb Et al.
    Development  2018;145
  16. Self-patterning of rostral-caudal neuroectoderm requires dual role of Fgf signaling for localized Wnt antagonism.
    Authors: Takata Et al.
    Nat Commun  2017;8:1339
  17. Lactate-activated macrophages induced aerobic glycolysis and epithelial-mesenchymal transition in breast cancer by regulation of CCL5-CCR5 axis: a positive metabolic feedback loop.
    Authors: Lin Et al.
    Oncotarget  2017;8:110426
  18. Single-Cell Alternative Splicing Analysis with Expedition Reveals Splicing Dynamics during Neuron Differentiation.
    Authors: Song Et al.
    Mol Cell  2017;67:148
  19. DGAT1-Dependent Lipid Droplet Biogenesis Protects Mitochondrial Function during Starvation-Induced Autophagy.
    Authors: Nguyen Et al.
    Dev Cell  2017;42:9
  20. Methyl-β-cyclodextrin restores impaired autophagy flux in Niemann-Pick C1-deficient cells through activation of AMPK.
    Authors: Dai Et al.
    Autophagy  2017;13:1435
  21. Generation of nephron progenitor cells and kidney organoids from human pluripotent stem cells.
    Authors: Morizane and Bonventre
    Nat Protoc  2017;12:195
  22. Distinct and shared functions of ALS-associated proteins TDP-43, FUS and TAF15 revealed by multisystem analyses
    Authors: Kapeli Et al.
    Nature Communications  2016;7:12143
  23. LKB1 loss links serine metabolism to DNA methylation and tumorigenesis.
    Authors: Kottakis Et al.
    Nature  2016;539:390
  24. Effects of novel muscarinic M3 receptor ligand C1213 in pulmonary arterial hypertension models.
    Authors: Ahmed
    Physiological Reports  2016;4:e13069
  25. Ethanol extract of Kalopanax septemlobus leaf induces caspase-dependent apoptosis associated with activation of AMPK in human hepatocellular carcinoma cells.
    Authors: Park Et al.
    Int J Oncol  2016;48:261
  26. Effects of thrombin on Ins signalling and glucose uptake in cultured human myotubes.
    Authors: Al-Bayati Et al.
    J Diabetes Complications  2016;30:1209
  27. Nutrient-regulated Phosphorylation of ATG13 Inhibits Starvation-induced Autophagy.
    Authors: Puente Et al.
    J Biol Chem  2016;291:6026
  28. Cockayne syndrome-derived neurons display reduced synapse density and altered neural network synchrony.
    Authors: Vessoni Et al.
    Hum Mol Genet  2016;25:1271
  29. Dual SMAD Signaling Inhibition Enables Long-Term Expansion of Diverse Epithelial Basal Cells
    Authors: Mou Et al.
    Cell: Stem Cell  2016;19:217
  30. Histone deacetylase 3 associates with MeCP2 to regulate FOXO and social behavior.
    Authors: Nott Et al.
    Nat Neurosci  2016;19:1497
  31. Adenosine monophosphate-activated protein kinase activation mediates the leptin-induced attenuation of cognitive impairment in a streptozotocin-induced rat model.
    Authors: Zhu Et al.
    Nature  2015;9:1998
  32. A transcriptome-based classifier to identify developmental toxicants by stem cell testing: design, validation and optimization for histone deacetylase inhibitors.
    Authors: Rempel Et al.
    Arch Toxicol  2015;89:1599
  33. Rapid and robust generation of long-term self-renewing human neural stem cells with the ability to generate mature astroglia.
    Authors: Palm Et al.
    Int J Mol Sci  2015;5:16321
  34. Transcription factor binding dynamics during human ES cell differentiation.
    Authors: Tsankov Et al.
    Biomed Res Int  2015;518:344
  35. Targeted disruption of DNMT1, DNMT3A and DNMT3B in human embryonic stem cells.
    Authors: Liao Et al.
    Exp Ther Med  2015;47:469
  36. 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.
    Authors: Sposito Et al.
    Sci Rep  2015;24:5260
  37. Comparative Study on the Cytoprotective Effects of Activated Protein C Treatment in Nonsteatotic and Steatotic Livers under Ischemia-Reperfusion Injury.
    Authors: Matsuda Et al.
    BMC Neurosci  2015;2015:635041
  38. Blocking a vicious cycle nNOS/peroxynitrite/AMPK by S-nitrosoglutathione: implication for stroke therapy.
    Authors: Khan Et al.
    J Pharmacol Exp Ther  2015;16:42
  39. Chemical constituents analysis and antidiabetic activity validation of four fern species from Taiwan.
    Authors: Chen Et al.
    Exp Neurol  2015;16:2497
  40. A transient wave of BMP signaling in the retina is necessary for Müller glial differentiation.
    Authors: Ueki Et al.
    Development  2015;142:533
  41. The PRKAA1/AMPKα1 pathway triggers autophagy during CSF1-induced human monocyte differentiation and is a potential target in CMML.
    Authors: Obba Et al.
    Nat Protoc  2015;11:1114
  42. The in vitro generation of lung and airway progenitor cells from human pluripotent stem cells.
    Authors: Huang Et al.
    Nat Genet  2015;10:413
  43. Bmp suppression in mangrove killifish embryos causes a split in the body axis.
    Authors: Mourabit Et al.
    PLoS One  2014;9:e84786
  44. BMP signalling regulates the pre-implantation development of extra-embryonic cell lineages in the mouse embryo.
    Authors: Graham Et al.
    Nat Neurosci  2014;5:5667
  45. Co-operative Bmp- and Fgf-signaling inputs convert skin wound healing to limb formation in urodele amphibians.
    Authors: Makanae Et al.
    Dev Biol  2014;396:57
  46. Efficient generation of lung and airway epithelial cells from human pluripotent stem cells.
    Authors: Huang Et al.
    Nat Biotechnol  2014;32:84
  47. Novel bone morphogenetic protein signaling through Smad2 and Smad3 to regulate cancer progression and development.
    Authors: Holtzhausen Et al.
    FASEB J  2014;28:1248
  48. Adenosine inhibits tumor cell invasion via receptor-independent mechanisms.
    Authors: Virtanen Et al.
    Mol Cancer Res  2014;12:1863
  49. Bmp and Shh signaling mediate the expression of satb2 in the pharyngeal arches.
    Authors: Sheehan-Rooney Et al.
    PLoS One  2013;8:e59533
  50. Derivation and expansion using only small molecules of human neural progenitors for neurodegenerative disease modeling.
    Authors: Reinhardt Et al.
    PLoS One  2013;8:e59252
  51. EGF stimulates Müller glial proliferation via a BMP-dependent mechanism.
    Authors: Ueki and Reh
    Glia  2013;61:778
  52. Moderate excess of pyruvate augments osteoclastogenesis.
    Authors: Fong Et al.
    Biol Open  2013;2:387
  53. Epigallocatechin gallate (EGCG) stimulates autophagy in vascular endothelial cells: a potential role for reducing lipid accumulation.
    Authors: Kim Et al.
    J Biol Chem  2013;288:22693
  54. Distinct energy requirements for human memory CD4 T-cell homeostatic functions.
    Authors: Taub Et al.
    Stem Cells Dev  2013;27:342
  55. Sox10-MCS5 enhancer dynamically tracks human oligodendrocyte progenitor fate.
    Authors: Pol Et al.
    Lab Chip  2013;247:694
  56. Regulation of endodermal differentiation of human embryonic stem cells through integrin-ECM interactions.
    Authors: Brafman Et al.
    Cell Metab  2013;20:369
  57. Flow-based pipeline for systematic modulation and analysis of 3D tumor microenvironments.
    Authors: Li Et al.
    Nat Commun  2013;13:1969
  58. Type III TGF-β receptor promotes FGF2-mediated neuronal differentiation in neuroblastoma.
    Authors: Knelson Et al.
    J Clin Invest  2013;123:4786
  59. BML-275, an AMPK inhibitor, induces DNA damage, G2/M arrest and apoptosis in human pancreatic cancer cells.
    Authors: Duong Et al.
    Int J Oncol  2012;41:2227
  60. LirGlu., a long-acting GLP-1 mimetic, and its metabolite attenuate inflammation after intracerebral hemorrhage.
    Authors: Hou Et al.
    J Cereb Blood Flow Metab  2012;32:2201
  61. Engineering artificial signaling centers to polarize embryoid body differentiation.
    Authors: Petersen Et al.
    Br J Pharmacol  2012;21:647
  62. Human cerebral cortex development from pluripotent stem cells to functional excitatory synapses.
    Authors: Shi Et al.
    FASEB J  2012;15:477
  63. Estrogen inhibits NPY secretion through membrane-associated estrogen receptor (ER)-α in clonal, immortalized hypothalamic neurons.
    Authors: Dhillon and Belsham
    Int J Obes (Lond)  2011;35:198
  64. 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
    Authors: Bumpus and Johnson
    Hum Mol Genet  2011;339:886
  65. Orexin is required for brown adipose tissue development, differentiation, and function.
    Authors: Sellayah Et al.
    Autophagy  2011;14:478
  66. Smarcd3b and Gata5 promote a cardiac progenitor fate in the zebrafish embryo.
    Authors: Lou Et al.
    Development  2011;138:3113

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