An inhibitor of HIF-1-mediated gene transcription
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Echinomycin

Item No. 11049

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal 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
CAS Number
512-64-1
Synonyms
  • Antibiotic A 654I
  • NSC 13502
  • NSC 526417
  • Quinomycin A
  • SK 302B
Molecular Formula
C51H64N12O12S2
Formula Weight
1101.3
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: Soluble
λmax
244 nm
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
InChi Code
InChI=1S/C51H64N12O12S2/c1-25(2)38-49(72)74-22-36(59-42(65)34-21-53-30-17-13-15-19-32(30)57-34)44(67)55-28(6)46(69)63(10)40-48(71)62(9)39(26(3)4)50(73)75-23-35(58-41(64)33-20-52-29-16-12-14-18-31(29)56-33)43(66)54-27(5)45(68)60(7)37(47(70)61(38)8)24-
InChi Key
AUJXLBOHYWTPFV-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    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.1 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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 Res. 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 Chem. Biol. 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).