260010-M

Demethylasterriquinone B1

A cell-permeable unsymmetrical bis-indolylquinone insulin mimic with anti-diabetic activity in animal models.

• Sinónimos: Demethylasterriquinone B1, L-783,281, DMAQ-B1, DAQ B1, 2-[2-(1,1-Dimethylallyl)-1H-indol-3-yl]-3,6-dihydroxy-5-[7-(3-methylbut-2-enyl)-1H-indol-3-yl][1,4]benzoquinone, 2,5-Dihydroxy-3-[7-(3-methyl-but-2-enyl)-1H-indol-3-yl]-6-[2-(1,1-dimethyl-allyl)-1H-indol-3-yl]-[1,4]benzoquinon
• Fórmula empírica (notación de Hill): C₃₂H₃₀N₂O₄
• Número de CAS: 78860-34-1
• Peso molecular: 506.59
• Código UNSPSC: 12352200

Propiedades

• Análisis: ≥95% (HPLC)
• formulario: solid
• fabricante / nombre comercial: Calbiochem^®
• condiciones de almacenamiento: OK to freeze; protect from light
• color: blue-black
• solubilidad: DMSO: 50 mg/mL
• temp. de almacenamiento: −20°C
• InChI: 1S/C32H30N2O4/c1-6-32(4,5)31-23(20-11-7-8-13-22(20)34-31)25-29(37)27(35)24(28(36)30(25)38)21-16-33-26-18(15-14-17(2)3)10-9-12-19(21)26/h6-14,16,33-35,38H,1,15H2,2-5H3
• Clave InChI: XMGNJVXBPZAETK-UHFFFAOYSA-N

Descripción

Descripción general

A cell-permeable unsymmetrical bis-indolylquinone insulin mimic with anti-diabetic activity in animal models. Selectively stimulates insulin receptor (IR) tyrosine kinase activity (EC₅₀ ~ 6 µM in CHO•IR cells), while showing little effect towards IGF-1R, EGFR, or PDGFR. Also acts as an agonist for the neurotrophin receptors TrkA, B, and C in both cortical neurons and dorsal root ganglion neurons (~ 20 µM). DMAQ-B1 and insulin show differential effects on cellular gene expression profiles and DMAQ-B1 is a more selective agonist than insulin for the IR-mediated activation of PI-3 kinase/Akt pathway.

A cell-permeable unsymmetrical bis-indolylquinone insulin mimic with anti-diabetic activity in animal models. Selectively stimulates insulin receptor (IR) tyrosine kinase activity (EC₅₀ ~6 µM in CHO•IR cells), while showing little effect towards IGF-1R, EGFR, or PDGFR. Also acts as an agonist for the neurotrophin receptors TrkA, B, and C in both cortical neurons and dorsal root ganglion neurons (~20 µM). DMAQ-B1 and insulin show differential effects on cellular gene expression profiles and DMAQ-B1 is a more selective agonist than insulin for the IR-mediated activation of PI-3 kinase/Akt pathway.

Acciones bioquímicas o fisiológicas

EC50 ~ 6 µM stimulating insulin receptor (IR) tyrosine kinase activity in CHO•IR cells

Primary Target
Insulin receptor (IR) tyrosine kinase activity

Advertencia

Toxicity: Irritant (B)

Reconstitución

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Otras notas

Webster, N.J., et al. 2003. Chembiochem4, 379.
Pirrung, M.C., et al. 2002. J. Org. Chem.6, 23.
Westerlund, J., et al. 2002. Diabetes51, S50.
Roper, M.G., et al. 2002. Diabetes51, S43.
Air, E.L., et al. 2002. Nat. Med.8, 179.
Wilkie, N., et al. 2001. J. Neurochem.78, 1135.
Salituro, G.M., et al. 2001. Recent Prog. Horm. Res.56, 107.
Liu, K., et al. 2000. J. Med. Chem.43, 3487.
Zhang, B., et al. 1999. Science284, 974.

Información legal

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable