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483367-10-8

483367-10-8 structure
483367-10-8 structure

Name Purmorphamine
Synonyms Purmorphamine
9H-Purin-6-amine, 9-cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-
9-Cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)
9-cyclohexyl-N-(4-morpholin-4-ylphenyl)-2-naphthalen-1-yloxypurin-6-amine
9-Cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthyloxy)-9H-purin-6-amine
2-(1-Naphthoxy)-6-(4-morpholinoanilino)-9-cyclohexylpurine
9H-Purin-6-amine (9-cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)
Description Purmorphamine is a smoothened receptor agonist with an EC50 of 1 μM.
Related Catalog
Target

IC50: 1.5 μM (Smoothened)

In Vitro Purmorphamine (10, 20 μM) in combination with sirolimus significantly decreases cell numbers according to the MTT assay. Purmorphamine induces up-regulation of alkaline phosphatase activity and expression of RUNX-2 at day 14. Up-regulation of osteocalcin is detected at the 3 and 5 μM doses of purmorphamine on day 14 post-induction. Matrix mineralization remains unchanged in the presence or absence of purmorphamine[1]. Purmorphamine induces STAT3 phosphorylation in mouse ES cell line ES14 and mesenchymal stem cell line C3H10T1/2[2]. Purmorphamine up-regulates the expressionof markers of the osteoblast phenotype-ALP activity and bone-like nodule formationd-in human bonemarrow mesenchymal cells[3].
Cell Assay To determine non-toxic doses of the small molecules, 5×105 passaged-3 human MSCs are seeded in each well of a six-well culture plate and incubated in expansion medium (as mentioned above) at 37°Cand 5% CO2. Two days later, the medium is exchanged with osteogenic medium (OM) that consisted of α-MEM supplemented with 10% FBS, 10 nM dexamethasone, 50 μg/mL ascorbic acid 2-phosphate, and 10 mM beta-glycerol phosphate. This OM is supplemented with different concentrations of purmorphamine (1, 3, 5, 10, and 20 μM) and sirolimus (0.1, 1, 10, 100, and 200 nM). The cultures are maintained for an additional two days and then assessed for the presence of viable cells with the MTT assay, by the addition of MTT solution (5 mg/mL in PBS) to the medium at a ratio of 1:5. Cells are then incubated at 37°C and 5% CO2. Two hours later, the medium is removed and 500 μL of DMSO is added to the treated cells in order to dissolve the formazone precipitate. The optical absorption rate is read at 570 nm. Cell viability is calculated as percent value relative to the control group which is only treated with OM.
References

[1]. F. Faghihia, et al. The effect of purmorphamine and sirolimus on osteogenic differentiation of human bone marrow-derived mesenchymal stem cells. Biomedicine & Pharmacotherapy. 2013, 67(1): 31-38.

[2]. Gu D, et al. A role for transcription factor STAT3 signaling in oncogene smoothened-driven carcinogenesis. J Biol Chem. 2012 Nov 2;287(45):38356-66.

[3]. Beloti MM, et al. Purmorphamine enhances osteogenic activity of human osteoblasts derived from bone marrow mesenchymal cells. Cell Biol Int. 2005 Jul;29(7):537-41.

Density 1.4±0.1 g/cm3
Boiling Point 790.3±70.0 °C at 760 mmHg
Melting Point 210-212ºC
Molecular Formula C31H32N6O2
Molecular Weight 520.625
Flash Point 431.8±35.7 °C
Exact Mass 520.258667
PSA 77.33000
LogP 4.52
Appearance white to beige
Vapour Pressure 0.0±2.8 mmHg at 25°C
Index of Refraction 1.711
Storage condition -20°C Freezer
Water Solubility DMSO: soluble5mg/mL, clear (warmed)
RIDADR NONH for all modes of transport