260010-M

Demethylasterriquinone B1

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

• Sinônimo(s): 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 (Notação de Hill): C₃₂H₃₀N₂O₄
• Número CAS: 78860-34-1
• Peso molecular: 506.59
• Código UNSPSC: 12352200

Propriedades

• Ensaio: ≥95% (HPLC)
• Formulário: solid
• fabricante/nome comercial: Calbiochem^®
• condição de armazenamento: OK to freeze; protect from light
• cor: blue-black
• solubilidade: DMSO: 50 mg/mL
• temperatura de armazenamento: −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
• chave InChI: XMGNJVXBPZAETK-UHFFFAOYSA-N

Descrição

Descrição geral

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.

Ações bioquímicas/fisiológicas

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

Primary Target
Insulin receptor (IR) tyrosine kinase activity

Advertência

Toxicity: Irritant (B)

Reconstituição

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

Outras 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.

Informações legais

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

Informações de segurança

• Código de classe de armazenamento: 11 - Combustible Solids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable