Purmorphamine
Purmorphamine (CAS 483367-10-8) is a synthetic small molecule agonist targeting the Smoothened (Smo) protein, a critical component of the Hedgehog (Hh) signaling pathway. By binding and activating Smo, Purmorphamine induces downstream modulation of key pathway targets, such as Gli1 and Patched. In vitro studies demonstrated activation with an IC50 value of approximately 1.5 μM during competitive assays with the antagonist cyclopamine, and an EC50 of about 1 μM for alkaline phosphatase (ALP) expression in C3H10T1/2 multipotent cells. This agent has been applied in research contexts for inducing osteogenic differentiation, with implications for studying bone regeneration and neural degeneration processes.
References:
[1]. Sinha S, Chen J K. Purmorphamine activates the Hedgehog pathway by targeting Smoothened[J]. Nature chemical biology, 2006, 2(1): 29.
[2]. Wu X, Walker J, Zhang J, et al. Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway[J]. Chemistry & biology, 2004, 11(9): 1229-1238.
[3]. Wu X, Ding S, Ding Q, et al. A small molecule with osteogenesis-inducing activity in multipotent mesenchymal progenitor cells[J]. Journal of the American Chemical Society, 2002, 124(49): 14520-14521.
[4]. Faghihi F, Eslaminejad M B, Nekookar A, et al. The effect of purmorphamine and sirolimus on osteogenic differentiation of human bone marrow-derived mesenchymal stem cells[J]. Biomedicine & Pharmacotherapy, 2013, 67(1): 31-38.
| Physical Appearance | A solid |
| Storage | Store at -20°C |
| M.Wt | 520.62 |
| Cas No. | 483367-10-8 |
| Formula | C31H32N6O2 |
| Solubility | insoluble in H2O; ≥1.82 mg/mL in EtOH with ultrasonic; ≥8.68 mg/mL in DMSO |
| Chemical Name | 9-cyclohexyl-N-(4-morpholin-4-ylphenyl)-2-naphthalen-1-yloxypurin-6-amine |
| SDF | Download SDF |
| Canonical SMILES | C1CCC(CC1)N2C=NC3=C2N=C(N=C3NC4=CC=C(C=C4)N5CCOCC5)OC6=CC=CC7=CC=CC=C76 |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment [1]: | |
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Cell lines |
Mesenchymal stem cells (MSCs) |
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Preparation method |
The solubility of this compound in DMSO is |
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Reaction Conditions |
14 d; 2 μM |
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Applications |
Modulation of Hh signaling by purmorphamine in hMSCs was evaluated at 7 and 14 days through the gene expression of the membrane receptors SMO and PTCH1, and the transcriptional factors GLI1 and GLI2. Gene expression of SMO was up-regulated at 7 days (P≤0.05) and down-regulated at 14 days (P≤0.05) by purmorphamine. PTCH1 expression was increased by purmorphamine at 7 days (P≤0.05) and not affected at 14 days (P≤0.05). Purmorphamine up-regulated the expression of GLI1 and GLI2 at 7 (P≤ 0.05) and 14 days (P≤0.05). |
| Animal experiment [2]: | |
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Animal models |
Normal male Wistar rats |
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Dosage form |
5 μM; s.c. |
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Applications |
Subcutaneous transplantation of human mesenchymal stem cell-based constructs into rats. According to the histology sections, labeled cells were present inside the scaffolds. Based on real-time PCR results, it has been shown the up-regulation of human osteoblast genes, ALP, osteocalcin, Runx-2, and collagen I in transplanted cell constructs. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: [1] Oliveira F S, Bellesini L S, Defino H L A, et al. Hedgehog signaling and osteoblast gene expression are regulated by purmorphamine in human mesenchymal stem cells[J]. Journal of cellular biochemistry, 2012, 113(1): 204-208. [2]Faghihi F, Baghaban Eslaminejad M, Nekookar A, et al. The effect of purmorphamine and sirolimus on osteogenic differentiation of human bone marrow-derived mesenchymal stem cells[J]. Biomedicine & Pharmacotherapy, 2013, 67(1): 31-38. |
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| Description | Purmorphamine is a blocker of BODIPY-cyclopamine binding to Smo with IC50 of ~ 1.5 μM and also is an inducer of osteoblast differentiation with EC50 of 1 μM. | |||||
| Targets | Smoothened | |||||
| IC50 | ~ 1.5 μM | |||||
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