Purmorphamine

Alias: Purmorphamine; Shh Signaling Antagonist VI
Cat No.:V1335 Purity: ≥98%
Purmorphamine (also called Shh Signaling Antagonist VI) is a potentpurine-based agonist ofthe hedgehog signaling pathway-smoothened receptor with an EC50of 1 μM.
Purmorphamine Chemical Structure CAS No.: 483367-10-8
Product category: Hedgehog(Smoothened) ROCK
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Purmorphamine (also called Shh Signaling Antagonist VI) is a potent purine-based agonist of the hedgehog signaling pathway-smoothened receptor with an EC50 of 1 μM. Given the significance of the Hedgehog (Hh) signaling pathway in regulating embryonic patterning, tissue regeneration, stem cell renewal, and cancer growth, it may find application as a therapeutic agent for bone diseases such as osteoporosis.

Biological Activity I Assay Protocols (From Reference)
Targets
Smoothened ( IC50 = 1.5 μM )
ln Vitro
Purmorphamine directly binds to and activates Smoothened, competing with cyclopamine, an antagonist of Smo, to activate the Hedgehog pathway with an IC50 of approximately 1.5 μM.[1]
Purmorphamine stimulates osteogenesis in multipotent C3H10T1/2 cells in a powerful way. In C3H10T1/2 cells, the EC50 for purmorphamine is 1 μM, as determined by ALP expression. In 3T3-L1 cells, the combination of purmorphamine (1 μM) and BMP-4 (100 ng/mL) increases ALP activity by over 90 times.[2]
Purmorphamine, as opposed to BMP-4, causes osteogenesis in multipotent mesenchymal progenitor cells by triggering Hedgehog signaling.[3]
ln Vivo
Purmorphamine increases the expression of ALP in rat constructs made of human mesenchymal stem cells. [4]
Enzyme Assay
Smo binding assays are carried out using BODIPY-cyclopamine and Smo-overexpressing cells as previously described4,5. Expression constructs for Smo-Myc3, Smo⁄CRD (deletion of amino acids 68 to 182), and SmoCT (deletion of amino acids 556 to 793) are based on the CMV promoter and contain the SV40 origin. According to the manufacturer, HEK 293T cells are cultured on poly-D-lysine-treated glass coverslips in 12-well plates until 70% confluency. After that, they are transfected using FuGene 6 with the appropriate expression construct (0.5 g/well).
Cell Assay
In T175 flasks, C3H10T1/2 cells are cultivated; at the thirteenth passage, the cells are separated using trypsin/EDTA and then diluted in the cultures. A Multi-dropTM liquid delivery system is then used to plate the resultant cell suspension into black clear bottom 384-well plates with 2500 cells/well in 100 µL growth medium. Cells adhered to the bottom of the wells following an overnight incubation. A Mini TrakTM multiposition dispenser system is used to transfer a 500 nL stock solution of each Purmorphamine in DMSO into the corresponding well, resulting in a final concentration of 5μM Purmorphamine. After that, the cells are incubated in an air atmosphere at 37 °C with 5% CO2. After four days, each well receives 10 μL of passive lysis buffer after the medium is removed. Ten microliters of alkaline phosphatase substrate solution are added to each well after five minutes. The plates are read using an Acquest high-throughput plate reader in accordance with the manufacturer's instructions after being incubated for 15 minutes at room temperature.
Animal Protocol
Male C57BL/6J mouse pups
10 mg/kg
i.p.
References

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

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

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

[4]. Biomed Pharmacother . 2013 Feb;67(1):31-8.

[5]. Front Pharmacol . 2020 Mar 4:11:204.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C31H32N6O2
Molecular Weight
520.62
Exact Mass
520.26
Elemental Analysis
C, 71.52; H, 6.20; N, 16.14; O, 6.15
CAS #
483367-10-8
Appearance
Solid powder
SMILES
C1CCC(CC1)N2C=NC3=C(N=C(N=C32)OC4=CC=CC5=CC=CC=C54)NC6=CC=C(C=C6)N7CCOCC7
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)
Chemical Name
9-cyclohexyl-N-(4-morpholin-4-ylphenyl)-2-naphthalen-1-yloxypurin-6-amine
Synonyms
Purmorphamine; Shh Signaling Antagonist VI
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 4~33.3 mg/mL (7.7~64.0 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Solubility (In Vivo)
2% DMSO+30% PEG 300+5% Tween 80+ddH2O: 1 mg/mL
 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.9208 mL 9.6039 mL 19.2079 mL
5 mM 0.3842 mL 1.9208 mL 3.8416 mL
10 mM 0.1921 mL 0.9604 mL 1.9208 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

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Biological Data
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