P5499

Dorsomorphin

≥98% (HPLC), powder, AMPK inhibitor

• Synonyme(s) : Dorsomorphin
• Formule empirique (notation de Hill): C₂₄H₂₅N₅O
• Numéro CAS: 866405-64-3
• Poids moléculaire : 399.49
• Numéro MDL: MFCD08705402
• Code UNSPSC : 51111800
• ID de substance PubChem : 24898658
• Nomenclature NACRES : NA.77

Propriétés

• Nom du produit: Dorsomorphin, ≥98% (HPLC)
• Niveau de qualité: 100
• Essai: ≥98% (HPLC)
• Forme: powder
• Conditions de stockage: protect from light
• Couleur: white to beige
• Solubilité: DMSO: >2 mg/mL (warmed)
• Température de stockage: 2-8°C
• Chaîne SMILES: 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
• Clé InChI: XHBVYDAKJHETMP-UHFFFAOYSA-N

Description

Description générale

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

Actions biochimiques/physiologiques

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).

Caractéristiques et avantages

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.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Équipement de protection individuelle: dust mask type N95 (US), Eyeshields, Gloves