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Submit ReviewPurmorphamine
Description: Smo receptor agonist
Chemical Name: 9-Cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-9H-purin-6-amine
Purity: ≥98% (HPLC)
Biological Activity for Purmorphamine
Purmorphamine is a smoothened (Smo) receptor agonist (EC50 ~ 1 μM) and activates the Hedgehog pathway. Purmorphamine induces osteogenesis in mouse mesenchymal progenitor cells (C3H10T1/2). When combined with BMP-4, Purmorphamine can transdifferentiate pre-adipocytes (3T3-L1) and myoblasts (C2C12) into osteoblasts. Purmorphamine induces differentiation of multipotent mesenchymal progenitor cells into osteoblasts, and of spinal motor neurons from pluripotent human stem cells, and protects dopaminergic neurons in a mouse model of Parkinson's disease.
Scientific Data
Applications of Purmorphamine in Neurons Derived from hiPSCs Dopaminergic neurons derived from human induced pluripotent stem cells (hiPSC) using SB 431542 (Catalog # 1614, Tocris), CHIR 99021 (Catalog # 4423, Tocris), DAPT (Catalog # 2634, Tocris) and Purmorphamine. Cells cultured in Neuronal Media supplemented with TGF-3 (Catalog # 8420-B3, R&D Systems), cAMP, GDNF (Catalog # 212-GD, R&D Systems), BDNF (Catalog # 248-BDB, R&D Systems), N21-MAX (Catalog # AR008, R&D Systems). Differentiation shown at days 55 (left) and 62 (right). Images courtesy of Kevin Flynn, Bio-Techne.
Compound Libraries for Purmorphamine
Purmorphamine 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 Purmorphamine
| M. Wt | 520.62 |
| Formula | C31H32N6O2 |
| Storage | Store at -20°C |
| Purity | ≥98% (HPLC) |
| CAS Number | 483367-10-8 |
| PubChem ID | 5284329 |
| InChI Key | FYBHCRQFSFYWPY-UHFFFAOYSA-N |
| Smiles | C1(OC4=CC=CC5=C4C=CC=C5)=NC(NC3=CC=C(N6CCOCC6)C=C3)=C2C(N(C7CCCCC7)C=N2)=N1 |
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 Purmorphamine
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 52.06 | 100 |
Preparing Stock Solutions for Purmorphamine
The following data is based on the product molecular weight 520.62. 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.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.92 mL | 9.6 mL | 19.21 mL |
| 5 mM | 0.38 mL | 1.92 mL | 3.84 mL |
| 10 mM | 0.19 mL | 0.96 mL | 1.92 mL |
| 50 mM | 0.04 mL | 0.19 mL | 0.38 mL |
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Product Datasheets for Purmorphamine
References for Purmorphamine
References are publications that support the biological activity of the product.
Wu et al (2004) Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway. Chem.Biol. 11 1229 PMID: 15380183
Sinha et al (2006) Purmorphamine activates the Hedgehog pathway by targeting Smoothened. Nat.Chem.Biol. 2 29 PMID: 16408088
Wu et al (2002) A small molecule with osteogenesis-inducing activity in multipotent mesenchymal progenitor cells. J.Am.Chem.Soc. 124 14520 PMID: 12465946
Sinha and Chen et al (2006) Purmorphamine activates the Hedgehog pathway by targeting Smoothened. Nat.Chem.Biol. 2 29 PMID: 16408088
If you know of a relevant reference for Purmorphamine, please let us know.
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Keywords: Purmorphamine, Purmorphamine supplier, Smoothened, Smo, receptors, agonists, differentiation, multipotent, mesenchymal, progenitor, cells, osteoblasts, osteogenic, Receptors, Mesenchymal, Stem, Cells, Osteogenic, 4551, Tocris Bioscience
22 Citations for Purmorphamine
Citations are publications that use Tocris products. Selected citations for Purmorphamine include:
Sheng et al (2018) A stably self-renewing adult blood-derived induced neural stem cell exhibiting patternability and epigenetic rejuvenation. Nat Commun 9 4047 PMID: 30279449
Kaindl et al (2018) Zooming in on Cryopreservation of hiPSCs and Neural Derivatives: A Dual-Center Study Using Adherent Vitrification. Stem Cells Transl Med PMID: 30456912
Yuan et al (2019) IFT80 is required for stem cell proliferation, differentiation, and odontoblast polarization during tooth development. Cell Death Dis 10 63 PMID: 30683845
Lang et al (2019) Single-Cell Sequencing of iPSC-DA Neurons Reconstructs Disease Progression and Identifies HDAC4 as a Regulator of Parkinson Cell Phenotypes. Cell Stem Cell 24 93 PMID: 30503143
Willeke F et al (2021) Growth factor mimetics for skin regeneration: In vitro profiling of primary human fibroblasts and keratinocytes. Arch Pharm (Weinheim) 354 e2100082 PMID: 33963608
Jason G et al (2021) Robust single-cell discovery of RNA targets of RNA-binding proteins and ribosomes. Nat Methods 18 507-519 PMID: 33963355
Fanny et al (2021) ARP-T1-associated Bazex-Dupré-Christol syndrome is an inherited basal cell cancer with ciliary defects characteristic of ciliopathies. Commun Biol 4 544 PMID: 33972689
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
Hackland et al (2019) FGF Modulates the Axial Identity of Trunk hPSC-Derived Neural Crest but Not the Cranial-Trunk Decision. Stem Cell Reports 12 920 PMID: 31091435
Shinn-Zong et al (2010) Characterization of axon formation in the embryonic stem cell-derived motoneuron. Cell Transplant 20 493-502 PMID: 21054941
Yuan et al (2016) Ciliary IFT80 balances canonical versus non-canonical hedgehog signalling for osteoblast differentiation. J Immunol 7 11024 PMID: 26996322
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
Cheng et al (2022) Genome-wide identification of the genetic basis of amyotrophic lateral sclerosis. Neuron 110 992-1008.e11 PMID: 35045337
Beate et al (2022) Primary cilia and SHH signaling impairments in human and mouse models of Parkinson's disease. Nat Commun 13 4819 PMID: 35974013
Lu et al (2022) Directed differentiation of human pluripotent stem cells into diverse organ-specific mesenchyme of the digestive and respiratory systems. Nat Protoc 17 2699-2719 PMID: 35978039
Georg C et al (2019) Generating Human iPSC-Derived Astrocytes with Chemically Defined Medium for In Vitro Disease Modeling. Methods Mol Biol 1994 31-39 PMID: 31124102
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
Rajamani et al (2018) Super-Obese Patient-Derived iPSC Hypothalamic Neurons Exhibit Obesogenic Signatures and Hormone Responses. Cell Stem Cell 22 698 PMID: 29681516
Ying et al (2020) Transcriptomic and epigenomic dynamics associated with development of human iPSC-derived GABAergic interneurons. Hum Mol Genet 29 2579-2595 PMID: 32794569
Frederick J et al (2020) Variable Outcomes in Neural Differentiation of Human PSCs Arise from Intrinsic Differences in Developmental Signaling Pathways. Cell Rep 31 107732 PMID: 32521257
Kristel et al (2020) IPSC-Derived Neuronal Cultures Carrying the Alzheimer's Disease Associated TREM2 R47H Variant Enables the Construction of an Aβ-Induced Gene Regulatory Network. Int J Mol Sci 21 PMID: 32630447
Wei et al (2023) Generation and characterization of NGLY1 patient-derived midbrain organoids. Front Cell Dev Biol 11 1039182 PMID: 36875753
Do you know of a great paper that uses Purmorphamine from Tocris? Please let us know.
Reviews for Purmorphamine
Average Rating: 5 (Based on 3 Reviews.)
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Usage Information.
By
Anonymous on 07/04/2020
Assay Type: In Vitro
Species: Mouse
Cell Line/Tissue: iPSC
iPSC-derived hypothalamic neuron differentiation activation by Smoothened agonist SAG 1 μM and purmorphamine 1 μM.
From Day 2 to day 9 to direct the cells toward ventral diencephalon with regular media change every 2 days.
For differentiation of DaNs.
By
Phi Anh Phan on 02/04/2020
Species: Human
Cell Line/Tissue: iPSC
Used for the differentiation of human iPSCs into dopaminergic neurons (Kriks et al.,2011).
Great for differentiation of huiPSCs into DaNs!.
By
Phi Anh Phan on 01/31/2020
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: iPSC
Purmorphamine was used to differentiate human iPSCs into dopaminergic neurons with above 60% TH positive cells.
Literature in this Area
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