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P5499

Dorsomorphin

Name: Dorsomorphin
Brand: SIGMA

≥98% (HPLC), powder, AMPK inhibitor

Synonym(s):

6-[4-(2-Piperidin-1-ylethoxy)phenyl]-3-pyridin-4-ylpyrazolo[1,5-a]pyrimidine, AMPK Inhibitor, Compound C

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About This Item

Empirical Formula (Hill Notation):

C₂₄H₂₅N₅O

CAS Number:

866405-64-3

Molecular Weight:

399.49

UNSPSC Code:

51111800

PubChem Substance ID:

24898658

NACRES:

NA.77

MDL number:

MFCD08705402

Assay:

≥98% (HPLC)

Form:

powder

Quality level:

300

Storage condition:

protect from light

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Properties

Product Name

Dorsomorphin, ≥98% (HPLC)

Quality Level

300

assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white to beige

solubility

DMSO: >2 mg/mL (warmed)

storage temp.

2-8°C

SMILES string

C1CCN(CC1)CCOc2ccc(cc2)-c3cnc4c(cnn4c3)-c5ccncc5

InChI

1S/C24H25N5O/c1-2-12-28(13-3-1)14-15-30-22-6-4-19(5-7-22)21-16-26-24-23(17-27-29(24)18-21)20-8-10-25-11-9-20/h4-11,16-18H,1-3,12-15H2

InChI key

XHBVYDAKJHETMP-UHFFFAOYSA-N

Description

General description

Dorsomorphin got its name due to its ability to induce dorsoventral patterning abnormalities in zebrafish, a characteristic trait of BMP-pathway mutant embryos. Structurally, dorsomorphin is identical to compound C. Dorsomorphin induces stem cell differentiation, suggesting potential therapeutic implications for fibrodysplasia ossificans progressiva (FOP), a progressive muscle and bone disease. Besides its BMP signaling inhibition, dorsomorphin also hinders the vascular endothelial growth factor (VEGF) type 2 receptor (FLK1/KDR) and disrupts angiogenesis during zebrafish development.

Application

Dorsomorphin has been used:

as an inhibitor of adenosine monophosphate-activated protein kinase (AMPK) to find the effects of trans-resveratrol on lipid mobilization in 3T3-L1 (a murine cell line of adipocytes) cells
as an AMPK inhibitor, to indicate the involvement of AMPK/mTOR (mammalian target of rapamycin) pathway in LRG (liraglutide) -induced autophagy
in the induction step, employed in in vitro differentiation of Friedreich′s ataxia (FRDA) and induced pluripotent stem cells (iPSCs) to neurospheres and neurons using ES (embryonic stem cell) media

Biochem/physiol Actions

BMP Inhibitor; Cell-permeable pyrrazolopyrimidine compound that acts as a potent, selective, reversible, and ATP-competitive inhibitor of AMPK (AMP-activated protein kinase; Ki = 109 nM in the presence of 5 μM ATP and the absence of AMP).

Dorsomorphin is a selective inhibitor of Bone morphogenetic protein (BMP) signaling. It has been found to inhibit BMP signals required for embryogenesis and promoted significant neural differentiation from human pluripotent stem cell (hPSC) lines. Dorsomorphin also acts as a potent, selective, reversible, and ATP-competitive inhibitor of AMPK (AMP-activated protein kinase); Ki = 109 nM in the presence of 5 μM ATP and the absence of AMP).

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the AMPKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

0000541030

0000524253

0000513984

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Articles

Naive Pluripotent Stem Cell Culture in Serum-Free Media

Naive pluripotent stem cells cultured in vitro using specialized media and inhibitors mimic "ground-state" cells from blastocysts.

AMPKs

The AMP-activated protein kinase (AMPK) acts as a sensor of cellular energy status. AMPK exists as heterotrimeric complexes comprising a catalytic α subunit and regulatory β and γ subunits.

Discover Bioactive Small Molecules for Kinase Phosphatase Biology

GLP-1 analogue improves hepatic lipid accumulation by inducing autophagy via AMPK/mTOR pathway

He Qin, et al.

Biochemical and Biophysical Research Communications, 476(4), 196-203 (2016)

Compound C/dorsomorphin: its use and misuse as an AMPK inhibitor

Dasgupta B and Seibel W

The Journal of biological chemistry, 195-202 (2018)

Role of mismatch repair enzymes in GAA-TTC triplet-repeat expansion in Friedreich's ataxia induced pluripotent stem cells (iPSCs)

Du J, et al.

Test, jbc-M112 (2012)

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