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P5499

Sigma-Aldrich

Dorsomorphin

≥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
MDL number:
MFCD08705402
UNSPSC Code:
51111800
PubChem Substance ID:
24898658
NACRES:
NA.77

product name

Dorsomorphin, ≥98% (HPLC)

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

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

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
Yan-Ting Wu et al.
Molecular human reproduction, 23(3), 155-165 (2016-12-18)
Does bone morphogenetic protein 2 (BMP2) regulate connexin43 (Cx43) and modulate cell-cell communication in luteinized human granulosa cells? BMP2 decreases gap junction intercellular communication (GJIC) of luteinized human granulosa cells by down-regulating Cx43 expression through an activin receptor-like kinase (ALK)2/ALK3-mediated
Qingjie Wang et al.
Molecular medicine reports, 13(2), 1577-1585 (2016-01-01)
Hypoxia induces pulmonary vasoconstriction and reconstruction in the pulmonary arteries and pulmonary veins (PVs), and elevation of intracellular calcium concentration ([Ca2+]i) is a primary factor of these processes. In the present study, the role of transient receptor potential cation channels
Morgane Dolez et al.
Development (Cambridge, England), 138(1), 97-106 (2010-12-01)
In zebrafish, Hedgehog-induced Engrailed expression defines a muscle fibre population that includes both slow and fast fibre types and exhibits an organisational role on myotome and surrounding tissues, such as motoneurons and lateral line. This Engrailed-positive population is restricted in
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