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Echinomycin Catalog No.GC18236

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1mg
$95.00
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5mg
$427.00
In stock

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Sample solution is provided at 25 µL, 10mM.

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Chemical Properties

Cas No. 512-64-1 SDF Download SDF
Synonyms Antibiotic A 654I; NSC 13502; NSC 526417; Quinomycin A; SK 302B
Chemical Name N-(2-quinoxalinylcarbonyl)-O-[N-(2-quinoxalinylcarbonyl)-D-seryl-L-alanyl-3-mercapto-N,S-dimethylcysteinyl-N-methyl-L-valyl]-D-seryl-L-alanyl-N-methylcysteinyl-N-methyl-(8→1)-lactone, cyclic (3→7)-thioether-L-valine
Canonical SMILES O=C(NC(COC(C(C(C)C)N(C)C(C1CS2)=O)=O)C(NC(C)C(N(C(C2SC)C(N(C)C(C(OCC(NC(C3=NC(C=CC=C4)=C4N=C3)=O)C(NC(C(N1C)=O)C)=O)=O)C(C)C)=O)C)=O)=O)C5=NC6=C(N=C5)C=CC=C6
Formula C51H64N12O12S2 M.Wt 1101.3
Solubility Soluble in DMSO & methanol Storage Store at -20°C
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request

Background

Hypoxia-inducible factor-1 (HIF-1) is a transcription factor that controls genes involved in glycolysis, angiogenesis, migration, and invasion. Echinomycin is a cell-permeable inhibitor of HIF-1-mediated gene transcription.[1][2] It acts by intercalating into DNA in a sequence-specific manner, blocking the binding of either HIF-1α or HIF-1β to the hypoxia-responsive element.[1][2][3] Echinomycin reversibly inhibits hypoxia-induced HIF-1 transcription activity in U215 cells with an EC50 value of 1.2 nM. It inhibits hypoxia-induced expression of vascular endothelial growth factor, blocking angiogenesis and altering excitatory synaptic transmission in hippocampal neurons.[2][4] Echinomycin also impairs expression of survivin, enhancing the sensitivity of multiple myeloma cells to melphalan.[5]

Reference:

[1]. Kong, D., Park, E.J., Stephen, A.G., et al. Echinomycin, a small-molecule inhibitor of hypoxia-inducible factor-1 DNA-binding activity Cancer Research 65(19), 9047-9055 (2005).
[2]. Nickols, N.G., Jacobs, C.S., Farkas, M.E., et al. Modulating hypoxia-inducible transcription by disrupting the HIF-1-DNA interface ACS Chemical Biology 2(8), 561-571 (2007).
[3]. Ward, D.C., Reich, E., and Goldberg, I.H. Base specificity in the interaction of polynucleotides with antibiotic drugs Science 149(3689), 1259-1263 (1965).
[4]. Huang, Y.F., Yang, C.H., Huang, C.C., et al. Pharmacological and genetic accumulation of hypoxia-inducible factor-1α enhances excitatory synaptic transmission in hippocampal neurons through the production of vascular endothelial growth factor J. Neurosci. 30(17), 6080-6093 (2010).
[5]. Hu, Y., Kirito, K., Yoshida, K., et al. Inhibition of hypoxia-inducible factor-1 function enhances the sensitivity of multiple myeloma cells to melphalan Mol. Cancer Ther. 8(8), 2329-2338 (2009).