Purmorphamine
Synonym(s):2-(1-Naphthoxy)-6-(4-morpholinoanilino)-9-cyclohexylpurine; 9-Cyclohexyl-N-[4-(4-morpholinyl)phenyl]-2-(1-naphthalenyloxy)-
- CAS NO.:483367-10-8
- Empirical Formula: C31H32N6O2
- Molecular Weight: 520.62
- MDL number: MFCD09037557
- EINECS: 200-256-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-06-30 15:45:59
What is Purmorphamine?
Description
Small molecules that promote osteoblast differentiation might be useful as therapeutic agents for bone diseases such as osteoporosis. Purmorphamine is a 2,6,9-
Chemical properties
Light Tan Solid
The Uses of Purmorphamine
Purmorphamine has been used to study the consequences of upregulation of Hedgehog signalling pathway in Tupfel long fin strain Zebrafish.
The Uses of Purmorphamine
Activates the Hedgehog pathway by targeting Smoothened
The Uses of Purmorphamine
An activator of the hedgehog (Hh) signaling pathway.
What are the applications of Application
Purmorphamine is An activator of the hedgehog (Hh) signaling pathway
Definition
ChEBI: 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 Actions
Purmorphamine 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 vitro
purmorphamine 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 vivo
in 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
References
1) 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
Properties of Purmorphamine
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) |
pka | 5.44±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. |
Safety information for Purmorphamine
Signal word | Warning |
Pictogram(s) |
Health Hazard GHS08 |
GHS Hazard Statements |
H341:Germ cell mutagenicity |
Precautionary Statement Codes |
P201:Obtain special instructions before use. P202:Do not handle until all safety precautions have been read and understood. P280:Wear protective gloves/protective clothing/eye protection/face protection. P308+P313:IF exposed or concerned: Get medical advice/attention. P405:Store locked up. P501:Dispose of contents/container to..… |
Computed Descriptors for Purmorphamine
InChIKey | FYBHCRQFSFYWPY-UHFFFAOYSA-N |
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