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Purmorphamine

Hedgehog agonist CAS# 483367-10-8

Purmorphamine

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Chemical structure

Purmorphamine

3D structure

Chemical Properties of Purmorphamine

Cas No. 483367-10-8 SDF Download SDF
PubChem ID 5284329 Appearance Powder
Formula C31H32N6O2 M.Wt 520.62
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : 50 mg/mL (96.04 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name 9-cyclohexyl-N-(4-morpholin-4-ylphenyl)-2-naphthalen-1-yloxypurin-6-amine
SMILES C1CCC(CC1)N2C=NC3=C2N=C(N=C3NC4=CC=C(C=C4)N5CCOCC5)OC6=CC=CC7=CC=CC=C76
Standard InChIKey FYBHCRQFSFYWPY-UHFFFAOYSA-N
Standard InChI InChI=1S/C31H32N6O2/c1-2-9-25(10-3-1)37-21-32-28-29(33-23-13-15-24(16-14-23)36-17-19-38-20-18-36)34-31(35-30(28)37)39-27-12-6-8-22-7-4-5-11-26(22)27/h4-8,11-16,21,25H,1-3,9-10,17-20H2,(H,33,34,35)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Purmorphamine

DescriptionSmoothened (Smo) receptor agonist (EC50 ~ 1 μM). Induces osteogenesis in mouse mesenchymal progenitor cells (C3H10T1/2). When combined with BMP-4, can transdifferentiate pre-adipocytes (3T3-L1) and myoblasts (C2C12) into osteoblasts. Induces differentiation of multipotent mesenchymal progenitor cells into osteoblasts.

Purmorphamine Dilution Calculator

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Purmorphamine Molarity Calculator

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Preparing Stock Solutions of Purmorphamine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.9208 mL 9.6039 mL 19.2079 mL 38.4157 mL 48.0197 mL
5 mM 0.3842 mL 1.9208 mL 3.8416 mL 7.6831 mL 9.6039 mL
10 mM 0.1921 mL 0.9604 mL 1.9208 mL 3.8416 mL 4.802 mL
50 mM 0.0384 mL 0.1921 mL 0.3842 mL 0.7683 mL 0.9604 mL
100 mM 0.0192 mL 0.096 mL 0.1921 mL 0.3842 mL 0.4802 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Purmorphamine

Purmorphamine, a purine derivative, is a Hedgehog agonist. Purmorphamine directly binds to and activates the 7-transmembrane Smo receptor of the Hedgehog signaling pathway. Hedgehog agonist Purmorphamine most significantly increased the neuronal differentiation of a human striatal NSC line (STROC05). Purmorphamine up-regulated gene expression of the mediators of Hh pathway, SMO, PTCH1, GLI1, and GLI2. The activation of Hh pathway by Purmorphamine increased the expression of several genes. Purmorphamine triggers Hh signaling pathway in hMSCs, inducing an increase in the expression of a set of genes involved in the osteoblast differentiation program. The EC50 value for differentiation of C3H10T1/2 cells based on alkaline phosphatase expression is 1 μM.

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References on Purmorphamine

The effect of purmorphamine on differentiation of endometrial stem cells into osteoblast-like cells on collagen/hydroxyapatite scaffolds.[Pubmed:27686538]

Artif Cells Nanomed Biotechnol. 2017 Nov;45(7):1343-1349.

We assessed the effect of Purmorphamine along with collagen/hydroxyapatite scaffold in inducing osteogenesis of human endometrial stem cells (hEnSCs). The adhesion, viability, proliferation, and differentiation of cells on scaffold were assayed with SEM, MTT, real time-PCR, and ALP assay, respectively. The results were shown good integration of cells with scaffold. Also, qRT-PCR of differentiated cells shows that osteoblast cell markers are expressed after 21d in 2D and scaffold groups while in the scaffold group the expression of these markers were higher than the 2D group. Based on our findings, collagen/hydroxyapatite scaffold with PMA has the potential role in osteogenic differentiation of hEnSCs.

Purmorphamine increased adhesion, proliferation and expression of osteoblast phenotype markers of human dental pulp stem cells cultured on beta-tricalcium phosphate.[Pubmed:27470382]

Biomed Pharmacother. 2016 Aug;82:432-8.

OBJECTIVES: Growth factors play a significant role in cell proliferation and differentiation during different stages of the bone repair. However, several limitations have been brought researchers attention to an osteoinductive small molecule including Purmorphamine. In this study, we aimed to evaluate the effect of Purmorphamine on adhesion, proliferation and differentiation of human dental pulp stem cells (hDPSCs) seaded on beta-tricalcium phosphate (beta-TCP) granules. METHODS: hDPSCs were established from extracted wisdom teeth of healthy volenteers. Cells at passage 3 were seeded on beta-TCP in the presence or absence of Purmorphamine. Cell adhesion and proliferation were assessed using scanning electeron microscopy (SEM) and DNA counting assay, respectively, after 1, 3 and 5days. Then, hDPSCs seeded on beta-TCP were subjected to osteogenic medium with or without Purmorphamine. After 7 and 14days osteogenic diffrentiation capability of hDPSCs were determined using real-time RT-PCR and alkaline phosphatase (ALP) activity assay. RESULTS: The significant increase in amount of DNA was observed at day 3 and 5 in the presence of Purmorphamine. SEM imaging also was confirmed the DNA counting assay; in all given time points, hDPSC attachment and growth was significantly higher in the presence of Purmorphamine. ALP activity was increased by Purmorphamine at both 7 and 14days of induction. Purmorphamine showed to effect on osteopontin expression at earlier stage of osteogenic differentiation, whereas for osteocalcin expression, this effect was more evident at later stage of differentiation. CONCLUSION: Purmorphamine had a promotive effect on adhesion, proliferation and osteogenic differentiation of hDPSCs cultured on beta-TCP. The outcome of the current study would help in development of in vitro culture conditions for better osteogenic differentiation of hDPSCs prior to transplantation.

Purmorphamine as a Shh Signaling Activator Small Molecule Promotes Motor Neuron Differentiation of Mesenchymal Stem Cells Cultured on Nanofibrous PCL Scaffold.[Pubmed:27629890]

Mol Neurobiol. 2017 Sep;54(7):5668-5675.

There is variety of stem cell sources but problems in ethical issues, contamination, and normal karyotype cause many limitations in obtaining and using these cells. The cells in Wharton's jelly region of umbilical cord are abundant and available stem cells with low immunological incompatibility, which could be considered for cell replacement therapy. Small molecules have been presented as less expensive biologically active compounds that can regulate different developmental process. Purmorphamine (PMA) is a small molecule that, according to some studies, possesses certain differentiation effects. In this study, we investigated the effect of the PMA on Wharton's jelly mesenchymal stem cell (WJ-MSC) differentiation into motor neuronal lineages instead of sonic hedgehog (Shh) on PCL scaffold. After exposing to induction media for 15 days, the cells were characterized for expression of motor neuron markers including PAX6, NF-H, Islet1, HB9, and choline acetyl transferase (ChAT) by quantitative reverse transcription (PCR) and immunocytochemistry. Our results demonstrated that induced WJ-MSCs with PMA could significantly express motor neuron markers in RNA and protein levels 15 days post induction. These results suggested that WJ-MSCs can differentiate to motor neuron-like cells with PMA on PCL scaffold and might provide a potential source in cell therapy for nervous system.

Purmorphamine and oxysterols accelerate and promote osteogenic differentiation of mesenchymal stem cells in vitro.[Pubmed:25792653]

In Vivo. 2015 Mar-Apr;29(2):247-54.

AIM: The purpose of the present study was to find inexpensive and non-toxic additives enhancing and accelerating the osteogenesis of mesenchymal stem cells in vitro, which can be used for tissue engineering of bone material. MATERIALS AND METHODS: Osteogenic differentiation of rat mesenchymal stem cells was carried-out using classic differentiation medium containing or lacking Purmorphamine, statins or oxysterols, respectively. Cell proliferation, alkaline phosphatase activity, calcium sedimentation and expression of bone matrix protein genes were measured to monitor differentiation. RESULTS: Purmorphamine substantially suppressed proliferation, enhanced and accelerated alkaline phosphatase activity and calcium sedimentation and increased the expression of osteopontin and osteocalcin in rat mesenchymal stem cells in vitro. A similar osteogenesis-promoting effect was observed for oxysterols but not for the two statins. CONCLUSION: Purmorphamine and oxysterols promote and accelerate osteogenesis of mesenchymal stem cells in vitro suggesting their potential application for tissue engineering of bone material.

Purmorphamine activates the Hedgehog pathway by targeting Smoothened.[Pubmed:16408088]

Nat Chem Biol. 2006 Jan;2(1):29-30.

Hedgehog (Hh) signaling is an important regulator of embryonic patterning, tissue regeneration, stem cell renewal and cancer growth. A purine derivative named Purmorphamine was previously found to activate the Hh pathway and affect osteoblast differentiation through an unknown mechanism. We demonstrate here that Purmorphamine directly targets Smoothened, a critical component of the Hh signaling pathway.

Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway.[Pubmed:15380183]

Chem Biol. 2004 Sep;11(9):1229-38.

Previously, a small molecule, Purmorphamine, was identified that selectively induces osteogenesis in multipotent mesenchymal progenitor cells. In order to gain insights into the mechanism of action of Purmorphamine, high-density oligonucleotide microarrays were used to profile gene expression in multipotent mesenchymal progenitor cells treated with either Purmorphamine or bone morphogenetic protein-4 (BMP-4). In contrast to BMP-4 treatment, Purmorphamine activates the Hedgehog (Hh) signaling pathway, resulting in the up- and downregulation of its downstream target genes, including Gli1 and Patched. Moreover, the known Hh signaling antagonists, cyclopamine and forskolin, completely block the osteogenesis and Glimediated transcription induced by Purmorphamine. These results demonstrate that Purmorphamine is a small molecule agonist of Hedgehog signaling, and it may ultimately be useful in the treatment of bone-related disease and neurodegenerative disease.

A small molecule with osteogenesis-inducing activity in multipotent mesenchymal progenitor cells.[Pubmed:12465946]

J Am Chem Soc. 2002 Dec 11;124(49):14520-1.

Purmorphamine, which is a 2,6,9-trisubstituted purine compound, was discovered through cell-based high-throughput screening from a heterocycle combinatorial library. It differentiates multipotent mesenchymal progenitor cells into an osteoblast lineage. It will serve as a unique chemical tool to study the molecular mechanisms of osteogenesis of stem cells and bone development.

Description

Purmorphamine (Shh Signaling Antagonist VI) is a smoothened receptor agonist with an EC50 of 1 μM.

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