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Dorsomorphin (Compound C)

In stock
Catalog No.
B3252
AMPK inhibitor
Grouped product items
SizePriceStock Qty
5mg
$50.00
In stock
10mg
$75.00
In stock
50mg
$250.00
In stock

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Background

Dorsomorphin is a cell-permeable and reversible ATP-competitive inhibitor of AMP-activated protein kinase (AMPK) with Ki value of 109nM [1].

Dorsomorphin is highly selective against AMPK over other structure related kinases such as protein kinase A, protein kinase C and Janus kinase 3. As an AMPK inhibitor, dorsomorphin is found to reverse the anti-proliferation induced by AMPK signaling in glucose-deprived mouse neural stem cells. It also shows inhibition of adipogenic differentiation in mouse 3T3-L1 fibroblasts [2].

Dorsomorphin is also reported to be an inhibitor of BMP signaling. It inhibits the phosphorylation of Smad 1/5/8, resulting in a reduction of heterotopic ossification. It also decreases the gene transcription of hepatic hepcidin and leads to increased iron levels subsequently. Moreover, the inhibition of BMP caused by dorsomorphin promotes self-renewal and neural induction of human ESC [2]

References:
[1] Lu Y, Akinwumi BC, Shao Z, Anderson HD. Ligand Activation of Cannabinoid Receptors Attenuates Hypertrophy of Neonatal Rat Cardiomyocytes. J Cardiovasc Pharmacol. 2014 Jun 26.
[2] Kudo T, Kanetaka H, Mizuno K, et al. Effects of the Small Molecule Dorsomorphin on Intracellular Signaling. Interface Oral Health Science 2011. Springer Japan, 2012: 131-133.

Product Citation

Chemical Properties

Physical AppearanceA solid
StorageStore at -20°C
M.Wt399.49
Cas No.866405-64-3
FormulaC24H25N5O
SynonymsCompound C
Solubility≥8.49 mg/mL in DMSO with ultrasonic and warming, <1.96 mg/mL in H2O
Chemical Name6-[4-(2-piperidin-1-ylethoxy)phenyl]-3-pyridin-4-ylpyrazolo[1,5-a]pyrimidine
SDFDownload SDF
Canonical SMILESC1CCN(CC1)CCOC2=CC=C(C=C2)C3=CN4C(=C(C=N4)C5=CC=NC=C5)N=C3
Shipping ConditionEvaluation sample solution : ship with blue ice.All other available size: ship with RT , or blue ice upon request
General tipsFor 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.

Protocol

Cell experiment [1]:

Cell lines

HT-29 human colon cancer cells and HeLa cells, zebrafish embryos

Preparation method

This compound is soluble in DMSO. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.

Reacting condition

40 μM, 4-10 μM, 30 min

Applications

Dorsomorphin could inhibit AMPK activity in intact hepatocytes. Dorsomorphin inhibited autophagic proteolysis. Dorsomorphin inhibited ACC phosphorylation by 80%. Dorsomorphin inhibited proteolysis in HT-29 cells. Dorsomorphin inhibited AMPK activity in HeLa cells expressing LKB1 and STRAD and in control HeLa cells. Dorsomorphin induced dorsalization in zebrafish embryos. Dorsomorphin inhibited BMP4-induced phosphorylation of BMP-responsive SMADs with the IC50 of 0.47 μM.

Animal experiment [2]:

Animal models

C57BL/6 mice injected via the tail vein with 0.2 g/kg of dextran or 0.2 g/kg of iron-dextran USP, zebrafish

Dosage form

Intraperitoneal injection, 10 mg/kg

Application

Dorsomorphin reduced hepatic hepcidin mRNA levels to one-third of that of vehicle-injected mice. Administration of dorsomorphin over 24 h led to a 60% increase in total serum iron concentrations. Injection of dorsomorphin in mice abolished the iron-mediated increase in hepatic SMAD1/5/8 phosphorylation. Intraperitoneal injection of iron-dextran in adult zebrafish led to a nearly three-fold increase in SMAD1/5/8 phosphorylation in liver extracts within 1 h. Coinjected with iron-dextran and dorsomorphin decreased SMAD1/5/8 phosphorylation by nearly three-fold relative to fish injected with iron-dextran and vehicle.

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.

References:

[1]. Meley D, Bauvy C, Houben-Weerts J H P M, et al. AMP-activated protein kinase and the regulation of autophagic proteolysis[J]. Journal of biological chemistry, 2006, 281(46): 34870-34879.

[2]. Paul B Y, Hong C C, Sachidanandan C, et al. Dorsomorphin inhibits BMP signals required for embryogenesis and iron metabolism[J]. Nature chemical biology, 2008, 4(1): 33-41.

Quality Control

Chemical structure

Dorsomorphin

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Dorsomorphin

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Dorsomorphin

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Dorsomorphin

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Dorsomorphin

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Dorsomorphin