Purmorphamine
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MedKoo CAT#: 406133

CAS#: 483367-10-8

Description: Purmorphamine is a Hedgehog agonist, which activates the Hedgehog pathway by targeting Smoothened. Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway. Purmorphamine increases DARPP-32 differentiation in human striatal neural stem cells through the Hedgehog pathway. Purmorphamine enhances osteogenic activity of human osteoblasts derived from bone marrow mesenchymal cells. Hedgehog (Hh) signaling is an important regulator of embryonic patterning, tissue regeneration, stem cell renewal and cancer growth.


Chemical Structure

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Purmorphamine
CAS# 483367-10-8

Theoretical Analysis

MedKoo Cat#: 406133
Name: Purmorphamine
CAS#: 483367-10-8
Chemical Formula: C31H32N6O2
Exact Mass: 520.25867
Molecular Weight: 520.62
Elemental Analysis: C, 71.52; H, 6.20; N, 16.14; O, 6.15

Price and Availability

Size Price Availability Quantity
10.0mg USD 90.0 Ready to ship
25.0mg USD 150.0 Ready to ship
50.0mg USD 250.0 Ready to ship
100.0mg USD 450.0 Ready to ship
200.0mg USD 750.0 Ready to ship
500.0mg USD 1650.0 Ready to ship
1.0g USD 2950.0 2 Weeks
2.0g USD 5250.0 2 Weeks
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Synonym: Purmorphamine

IUPAC/Chemical Name: 9-cyclohexyl-N-(4-morpholinophenyl)-2-(naphthalen-1-yloxy)-9H-purin-6-amine

InChi Key: FYBHCRQFSFYWPY-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: N1(C2CCCCC2)C=NC3=C(NC4=CC=C(N5CCOCC5)C=C4)N=C(OC6=C7C=CC=CC7=CC=C6)N=C13

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not soluble in water.

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Purmorphamine (Shh Signaling Antagonist VI) is a smoothened/Smo receptor agonist with an EC50 of 1 μM.
In vitro activity: The Müller glial cells were cultured for 2 days in the presence of different concentrations of SHH-N or purmorphamine, with or without cyclopamine. Compared with the untreated control cells, the percentage of PCNA-positive Müller glia increased significantly following treatment with the two SHH-N concentrations and the 0.5 mM purmorphamine treatment, whereas cyclopamine inhibited the production of PCNA-positive Müller glial cells compared with treatment with purmorphamine alone (representative immunostaining image are presented in Fig. 1B. These data indicated that the proliferation of Müller glial cells was promoted by purmorphamine treatment as well as SHH-N. Reference: Mol Med Rep. 2017 Dec; 16(6): 7993–8002. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5779882/
In vivo activity: In the preliminary pilot study, this study tested the effects of PUR (Purmorphamine) at 1, 5, and 10 mg/kg upon infarct volumes and edema. PUR treatment at 5 and 10 mg/kg reduced infarct volumes (p < 0.05, p < 0.001, respectively), PUR treatment at 10 mg/kg reduced edema (p < 0.001), compared with those in the HI group at 72 h post-HI. From these studies, it was established that the 10 mg/kg dose exerted remarkable beneficial effects in the absence of any toxicity (data not shown). As shown in Figure 1A, HI insult led to a remarkable edematous condition and significantly increased the water content within the ipsilateral side at 72 h following HI. PUR treatment markedly reduced this HI-induced brain edema (p < 0.001) as compared with vehicle-HI mouse group. Reference: Front Pharmacol. 2020; 11: 204. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7064623/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 10.0 19.2

Preparing Stock Solutions

The following data is based on the product molecular weight 520.62 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Gu D, Wang S, Zhang S, Zhang P, Zhou G. Directed transdifferentiation of Müller glial cells to photoreceptors using the sonic hedgehog signaling pathway agonist purmorphamine. Mol Med Rep. 2017 Dec;16(6):7993-8002. doi: 10.3892/mmr.2017.7652. Epub 2017 Sep 28. PMID: 28983586; PMCID: PMC5779882. 2. Bahrami N, Malekolkottab F, Ebrahimi-Barough S, Alizadeh Tabari Z, Hamisi J, Kamyab A, Mohamadnia A, Ai A, Bayat F, Bahrami N, Ai J. The effect of purmorphamine on differentiation of endometrial stem cells into osteoblast-like cells on collagen/hydroxyapatite scaffolds. Artif Cells Nanomed Biotechnol. 2017 Nov;45(7):1343-1349. doi: 10.1080/21691401.2016.1236804. Epub 2016 Sep 30. PMID: 27686538. 3. Rahi S, Gupta R, Sharma A, Mehan S. Smo-Shh signaling activator purmorphamine ameliorates neurobehavioral, molecular, and morphological alterations in an intracerebroventricular propionic acid-induced experimental model of autism. Hum Exp Toxicol. 2021 Apr 28:9603271211013456. doi: 10.1177/09603271211013456. Epub ahead of print. PMID: 33906504. 4. Liu D, Bai X, Ma W, Xin D, Chu X, Yuan H, Qiu J, Ke H, Yin S, Chen W, Wang Z. Purmorphamine Attenuates Neuro-Inflammation and Synaptic Impairments After Hypoxic-Ischemic Injury in Neonatal Mice via Shh Signaling. Front Pharmacol. 2020 Mar 4;11:204. doi: 10.3389/fphar.2020.00204. PMID: 32194421; PMCID: PMC7064623.
In vitro protocol: 1. Gu D, Wang S, Zhang S, Zhang P, Zhou G. Directed transdifferentiation of Müller glial cells to photoreceptors using the sonic hedgehog signaling pathway agonist purmorphamine. Mol Med Rep. 2017 Dec;16(6):7993-8002. doi: 10.3892/mmr.2017.7652. Epub 2017 Sep 28. PMID: 28983586; PMCID: PMC5779882. 2. Bahrami N, Malekolkottab F, Ebrahimi-Barough S, Alizadeh Tabari Z, Hamisi J, Kamyab A, Mohamadnia A, Ai A, Bayat F, Bahrami N, Ai J. The effect of purmorphamine on differentiation of endometrial stem cells into osteoblast-like cells on collagen/hydroxyapatite scaffolds. Artif Cells Nanomed Biotechnol. 2017 Nov;45(7):1343-1349. doi: 10.1080/21691401.2016.1236804. Epub 2016 Sep 30. PMID: 27686538.
In vivo protocol: 1. Rahi S, Gupta R, Sharma A, Mehan S. Smo-Shh signaling activator purmorphamine ameliorates neurobehavioral, molecular, and morphological alterations in an intracerebroventricular propionic acid-induced experimental model of autism. Hum Exp Toxicol. 2021 Apr 28:9603271211013456. doi: 10.1177/09603271211013456. Epub ahead of print. PMID: 33906504. 2. Liu D, Bai X, Ma W, Xin D, Chu X, Yuan H, Qiu J, Ke H, Yin S, Chen W, Wang Z. Purmorphamine Attenuates Neuro-Inflammation and Synaptic Impairments After Hypoxic-Ischemic Injury in Neonatal Mice via Shh Signaling. Front Pharmacol. 2020 Mar 4;11:204. doi: 10.3389/fphar.2020.00204. PMID: 32194421; PMCID: PMC7064623.

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1: Wöltje M, Böbel M, Heiland M, Beck-Broichsitter B, Al-Dam A, Gröbe A, Friedrich RE, Hanken H, Smeets R. Purmorphamine and oxysterols accelerate and promote osteogenic differentiation of mesenchymal stem cells in vitro. In Vivo. 2015 Mar-Apr;29(2):247-54. PubMed PMID: 25792653.

2: Faghihi F, Baghaban Eslaminejad M, Nekookar A, Najar M, Salekdeh GH. The effect of purmorphamine and sirolimus on osteogenic differentiation of human bone marrow-derived mesenchymal stem cells. Biomed Pharmacother. 2013 Feb;67(1):31-8. doi: 10.1016/j.biopha.2012.10.004. Epub 2012 Nov 16. PubMed PMID: 23228449.

3: Granéli C, Karlsson C, Lindahl A, Thomsen P. Virtual ligand-based screening reveals purmorphamine analogs with the capacity to induce the osteogenic differentiation of human mesenchymal stem cells. Cells Tissues Organs. 2013;197(2):89-102. doi: 10.1159/000342796. Epub 2012 Nov 10. PubMed PMID: 23147751.

4: Oliveira FS, Bellesini LS, Defino HL, da Silva Herrero CF, Beloti MM, Rosa AL. Hedgehog signaling and osteoblast gene expression are regulated by purmorphamine in human mesenchymal stem cells. J Cell Biochem. 2012 Jan;113(1):204-8. doi: 10.1002/jcb.23345. PubMed PMID: 21898541.

5: Gellynck K, Neel EA, Li H, Mardas N, Donos N, Buxton P, Young AM. Cell attachment and response to photocured, degradable bone adhesives containing tricalcium phosphate and purmorphamine. Acta Biomater. 2011 Jun;7(6):2672-7. doi: 10.1016/j.actbio.2011.02.033. Epub 2011 Feb 25. PubMed PMID: 21354477.

6: El-Akabawy G, Medina LM, Jeffries A, Price J, Modo M. Purmorphamine increases DARPP-32 differentiation in human striatal neural stem cells through the Hedgehog pathway. Stem Cells Dev. 2011 Nov;20(11):1873-87. doi: 10.1089/scd.2010.0282. Epub 2011 Apr 5. PubMed PMID: 21345011.

7: Lee SJ, Lee HK, Cho SY, Choi JK, Shin HK, Kwak EJ, Cho MR, Kim HR, Kim SR, Kim YM, Park KJ, Choi JK. Identification of osteogenic purmorphamine derivatives. Mol Cells. 2008 Oct 31;26(4):380-6. Epub 2008 Aug 12. PubMed PMID: 18695357.

8: Sinha S, Chen JK. Purmorphamine activates the Hedgehog pathway by targeting Smoothened. Nat Chem Biol. 2006 Jan;2(1):29-30. Epub 2005 Nov 20. PubMed PMID: 16408088.

9: Beloti MM, Bellesini LS, Rosa AL. Purmorphamine enhances osteogenic activity of human osteoblasts derived from bone marrow mesenchymal cells. Cell Biol Int. 2005 Jul;29(7):537-41. PubMed PMID: 15979909.

10: Beloti MM, Bellesini LS, Rosa AL. The effect of purmorphamine on osteoblast phenotype expression of human bone marrow mesenchymal cells cultured on titanium. Biomaterials. 2005 Jul;26(20):4245-8. PubMed PMID: 15683647.

11: Wu X, Walker J, Zhang J, Ding S, Schultz PG. Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway. Chem Biol. 2004 Sep;11(9):1229-38. PubMed PMID: 15380183.



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