Skip to Content
Merck
CN

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

Sign In to View Organizational & Contract Pricing.

Select a Size

About This Item

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

InChI key

XMGNJVXBPZAETK-UHFFFAOYSA-N

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

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

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.

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

Preparation Note

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

Disclaimer

Toxicity: Irritant (B)

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service