Demethylasterriquinone B1A cell-permeable insulin mimic that does not affect IGF-1R, EGFR, or PDGFR

Demethylasterriquinone B1 (CAS 78860-34-1)

Demethylasterriquinone B1 | CAS 78860-34-1 is rated 5.0 out of 5 by 1.
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Synonym: DMAQ-B1
Application: A cell-permeable insulin mimic that does not affect IGF-1R, EGFR, or PDGFR
CAS Number: 78860-34-1
Purity: >95%
Molecular Weight: 506.59
Molecular Formula: C32H30N2O4
* Refer to Certificate of Analysis for lot specific data (including water content).
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Demethylasterriquinone B1 is a cell-permeable asymmetrical 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. Demethylasterriquinone B1 also acts as an agonist for Trk A, Trk B and Trk C (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. Demethylasterriquinone B1 is an activator of insulin R.


References

1. Zhang, B. et al. 1999. Science. 284(5416): 974-977. PMID: 10320380
2. Liu, K. et al. 2000. J. Med. Chem. 43(19): 3487-3494. PMID: 11000003
3. Wilkie, N. et al. 2001. J. Neurochem. 78(5): 1135-1145. PMID: 11553687
4. Salituro, G.M. et al. 2001. Recent Prog. Horm. Res. 56 : 107-126. PMID: 11237209
5. Roper, M.G. et al. 2002. Diabetes. 51Suppl1 : S43-S49. PMID: 11815457
6. Westerlund, J. et al. 2002. Diabetes. 51Suppl1 : S50-S52. PMID: 11815458
7. Pirrung, M.C. et al. 2002. J. Org. Chem. 67(23): 7919-7926. PMID: 12423119
8. Air, E.L. et al. 2002. Nat. Med. 8(2): 179-183. PMID: 11821903
9. Webster, N.J. et al. 2003. Chembiochem. 4(5): 379-385. PMID: 12740809

Physical State :
Solid
Solubility :
Soluble in DMSO (100 mM).
Storage :
Store at -20° C
Boiling Point :
780.16° C at 760 mmHg (Predicted)
Density :
1.34 g/cm3 (Predicted)
Refractive Index :
n20D 1.72 (Predicted)
IC50 :
Glyceraldehyde-3-phosphate dehydrogenase: IC50 = 15 µM (Oryctolagus cuniculus); IRTK: EC5050 = 3 - 6 µM; HIV-1(WT): IC50 = ~57 µM; IGF1R: EC5050 = 100 µM
pK Values :
pKa: 2.82 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
RTECS :
GU5308000
PubChem CID :
3013166
MDL Number :
MFCD06410990
SMILES :
CC(=CCC1=CC=CC2=C1NC=C2C3=C(C(=O)C(=C(C3=O)O)C4=C(NC5=CC=CC=C54)C(C)(C)C=C)O)C

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Certificate of Analysis

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Demethylasterriquinone B1  Product Citations

See how others have used Demethylasterriquinone B1. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 17687071  Lin, B. et al. 2007. J. Pharmacol. Exp. Ther. 323: 579-585.

PMID: # 12740809  Webster, NJ. et al. 2003. Chembiochem. 4: 379-385.

Citations 1 to 2 of 2 total
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Rated 5 out of 5 by from Lin et al Lin et al. (PubMed ID 17687071) used Demethylasterriquinone B1 (DAQ-B1), a cell-permeable insulin mimic that selectively interacts with the intracellular tyrosine kinase domain of the insulin receptor, to increase glucose uptake. -SCBT Publication Review
Date published: 2015-03-26
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