260010-M

Demethylasterriquinone B1

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

• Synonym(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
• Empirical Formula (Hill Notation): C₃₂H₃₀N₂O₄
• CAS Number: 78860-34-1
• Molecular Weight: 506.59
• UNSPSC Code: 12352200

Properties

• assay: ≥95% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: blue-black
• solubility: DMSO: 50 mg/mL
• storage temp.: −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
• InChI key: XMGNJVXBPZAETK-UHFFFAOYSA-N

Description

General description

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.

Biochem/physiol Actions

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

Primary Target
Insulin receptor (IR) tyrosine kinase activity

Warning

Toxicity: Irritant (B)

Reconstitution

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

Other Notes

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.

Legal Information

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable