260010-M

Demethylasterriquinone B1

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

• Synonim(y): 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
• Wzór empiryczny (zapis Hilla): C₃₂H₃₀N₂O₄
• Numer CAS: 78860-34-1
• Masa cząsteczkowa: 506.59
• Kod UNSPSC: 12352200

Właściwości

• Próba: ≥95% (HPLC)
• Postać: solid
• producent / nazwa handlowa: Calbiochem^®
• warunki przechowywania: OK to freeze; protect from light
• kolor: blue-black
• rozpuszczalność: DMSO: 50 mg/mL
• temp. przechowywania: −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
• Klucz InChI: XMGNJVXBPZAETK-UHFFFAOYSA-N

Opis

Opis ogólny

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.

Działania biochem./fizjol.

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

Primary Target
Insulin receptor (IR) tyrosine kinase activity

Ostrzeżenie

Toxicity: Irritant (B)

Rekonstytucja

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

Inne uwagi

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.

Informacje prawne

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

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Informacja o środkach bezpieczeństwa

• Kod klasy składowania: 11 - Combustible Solids
• Klasa zagrożenia wodnego (WGK): WGK 3
• Temperatura zapłonu (°F): Not applicable
• Temperatura zapłonu (°C): Not applicable