Molecular structure of Demethylasterriquinone B1, CAS Number: 78860-34-1
Demethylasterriquinone B1 (CAS 78860-34-1)
See product citations (2)
Alternate Names:
DMAQ-B1
Application:
Demethylasterriquinone B1 is 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
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
QUICK LINKS
Ordering Information
Product Citations
Description
Technical Information
Safety Information
SDS & Certificate of Analysis
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 muM 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 muM). 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.
Demethylasterriquinone B1 (CAS 78860-34-1) References
- Discovery of a small molecule insulin mimetic with antidiabetic activity in mice. | Zhang, B., et al. 1999. Science. 284: 974-7. PMID: 10320380
- Discovery of a potent, highly selective, and orally efficacious small-molecule activator of the insulin receptor. | Liu, K., et al. 2000. J Med Chem. 43: 3487-94. PMID: 11000003
- Discovery of a small molecule insulin receptor activator. | Salituro, GM., et al. 2001. Recent Prog Horm Res. 56: 107-26. PMID: 11237209
- The non-peptidyl fungal metabolite L-783,281 activates TRK neurotrophin receptors. | Wilkie, N., et al. 2001. J Neurochem. 78: 1135-45. PMID: 11553687
- Effect of the insulin mimetic L-783,281 on intracellular Ca2+ and insulin secretion from pancreatic beta-cells. | Roper, MG., et al. 2002. Diabetes. 51 Suppl 1: S43-9. PMID: 11815457
- Glucose-dependent promotion of insulin release from mouse pancreatic islets by the insulin-mimetic compound L-783,281. | Westerlund, J., et al. 2002. Diabetes. 51 Suppl 1: S50-2. PMID: 11815458
- Small molecule insulin mimetics reduce food intake and body weight and prevent development of obesity. | Air, EL., et al. 2002. Nat Med. 8: 179-83. PMID: 11821903
- Total syntheses of demethylasterriquinone B1, an orally active insulin mimetic, and demethylasterriquinone A1. | Pirrung, MC., et al. 2002. J Org Chem. 67: 7919-26. PMID: 12423119
- Signaling effects of demethylasterriquinone B1, a selective insulin receptor modulator. | Webster, NJ., et al. 2003. Chembiochem. 4: 379-85. PMID: 12740809
- Methyl scanning: total synthesis of demethylasterriquinone B1 and derivatives for identification of sites of interaction with and isolation of its receptor(s). | Pirrung, MC., et al. 2005. J Am Chem Soc. 127: 4609-24. PMID: 15796526
- Glyceraldehyde 3-phosphate dehydrogenase is a cellular target of the insulin mimic demethylasterriquinone B1. | Kim, H., et al. 2007. J Med Chem. 50: 3423-6. PMID: 17595071
- Quinone replacements for small molecule insulin mimics. | Pirrung, MC., et al. 2008. Chembiochem. 9: 360-2. PMID: 18232038
- Synthesis of heteroaryl/aryl kojic acid conjugates as stimulators of glucose uptake by GLUT4 translocation. | Sharma, DK., et al. 2014. Eur J Med Chem. 85: 727-36. PMID: 25129867
- Novel therapeutics for type 2 diabetes: insulin resistance. | Altaf, QA., et al. 2015. Diabetes Obes Metab. 17: 319-34. PMID: 25308775
Activator of:
insulin R, Trk A, Trk B, and Trk C.Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
Demethylasterriquinone B1, 5 mg | sc-203025 | 5 mg | $510.00 |