Purmorphamine

Purmorphamine Basic information
Product Name:Purmorphamine
Synonyms:2-(1-NAPHTHOXY)-6-(4-MORPHOLINOANILINO)-9-CYCLOHEXYLPURINE;PURMORPHAMINE;9-Cyclohexyl-N-[(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-9H-purin-6-amine;9-Cyclohexyl-N-[4-(Morpholin-4-yl)phenyl]-2-(naphthalen-1-yloxy)-9H-purin-6-aMine;9-Cyclohexyl-N-[4-(4-Morpholinyl)phenyl]-2-(1-naphthalenyloxy)-;9-Cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-9H-purin-6-amine;9H-Purin-6-amine, 9-cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-;9-Cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-9H-purin-6-amine Purmorphamine
CAS:483367-10-8
MF:C31H32N6O2
MW:520.62
EINECS:200-256-5
Product Categories:Inhibitors;Bases & Related Reagents;Heterocycles;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Heterocyclic Compounds;Lipid signaling
Mol File:483367-10-8.mol
Purmorphamine Structure
Purmorphamine Chemical Properties
Melting point 210-212°C
Boiling point 790.3±70.0 °C(Predicted)
density 1.35±0.1 g/cm3(Predicted)
storage temp. -20°C
solubility DMSO: soluble5mg/mL, clear (warmed)
pka5.44±0.40(Predicted)
form powder
color white to beige
Stability:Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChIKeyFYBHCRQFSFYWPY-UHFFFAOYSA-N
Safety Information
WGK Germany 3
MSDS Information
Purmorphamine Usage And Synthesis
DescriptionSmall molecules that promote osteoblast differentiation might be useful as therapeutic agents for bone diseases such as osteoporosis. Purmorphamine is a 2,6,9-trisubstituted purine that promotes the differentiation of both human and mouse mesenchymal progenitor cells into osteoblasts. The EC50 value for differentiation of C3H10T1/2 cells based on alkaline phosphatase expression is 1 μM. Investigation into purmorphamine’s mechanism of action indicates that it directly binds to and activates the 7-transmembrane Smo receptor of the Hedgehog signaling pathway.
Chemical PropertiesLight Tan Solid
UsesAn activator of the hedgehog (Hh) signaling pathway.
UsesPurmorphamine has been used to study the consequences of upregulation of Hedgehog signalling pathway in Tupfel long fin strain Zebrafish.
UsesActivates the Hedgehog pathway by targeting Smoothened
DefinitionChEBI: A member of the class of purines that is purine substituted at C-2 by a 1-naphthyloxy group, at C-4 by a 4-morpholinophenylamino group, and at N-9 by a cyclohexyl group.
Biochem/physiol ActionsPurmorphamine activates the Hedgehog (Hh) signaling pathway, directly binding to the Smoothened (Smo) receptor. In various studies, purmorphamine has been shown to induce osteoblast differentiation, generate cardiomyocytes from human embryonic stem cells, increase the neuronal differentiation of a human striatal neural stem cell line, and to differentiate human umbilical cord mesenchymal stem cells (hUCMSCs) into motoneurons.
in vitropurmorphamine activated the hedgehog pathway by directly bound and activated smoothened with the ic50value of ~ 1.5 μm in competing with cyclopamine, a smo antagonist [1]. in multi-potent c3h10t1/2 cells, purmorphamine was a potent inducer of osteogenesis. in c3h10t1/2 cells, the ec50 values assessed based on alp expression for purmorphamine was 1 μm. purmorphamine (1 μm) in combination with bmp-4 (100 ng/ml) increased alp activity more than 90-fold in 3t3-l1 cells [3].administration of purmorphamine at 3 and 5 μm up-regulated the level of osteocalcin on day 14 (p ≤ 0.05)[4].
in vivoin rats transplanted with stem cell-based constructs subcutaneously, treatment with purmorphamine tended to up-regulate alp transcripts when compared with those injected by either dexamethasone or injection water (p ≤ 0.05) [4].
storage-20°C
References1) Wu et al. (2002), A small molecule with osteogenesis-inducing activity in multipotent mesenchymal progenitor cells; J. Am. Chem. Soc., 124 14520 2) Wu et al. (2004), Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway; Chem. Biol. 11 1229 3) Sinha and Chen (2006), Purmorphamine activates the Hedgehog pathway by targeting Smoothened; Nat. Chem. Biol., 2 29 4) Kang et al. (2015), Reprogramming of mouse somatic cells into pluripotent stem-like cells using a combination of small molecules; Biomaterials, 35 7336 5) Zhang et al. (2015), Small Molecules Efficiently Reprogram Human Astroglial Cells into Functional Neurons; Cell Stem Cell 17 735
Purmorphamine Preparation Products And Raw materials
LDN-193189 HCl Rapamycin DNA, SINGLE STRANDED, IMM. ON CELLULOSE, FROM CALF THYMUS* Palmitoylethanolamide NS-398 Ginkgolide B N-[3-(1H-Benzimidazol-2-yl)-4-chlorophenyl]-3,4,5-triethoxybenzamide LDE-225 Diphosphate Vismodegib (GDC-0449) Hh-Ag 1.3 CYCLOPAMINE Varenicline tartrate Everolimus 6-Amino-3,7-dihydro-2H-purin-2-one 6-ANILINOPURINE Purmorphamine 2-HYDROXYPURINE 9-cyclohexyladenine

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