BioViotica

Echinomycin

CHF 110.00
In stock
BVT-0267-M0011 mgCHF 110.00
BVT-0267-M0055 mgCHF 385.00
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Product Details
Synonyms Quinomycin A
Product Type Chemical
Properties
Formula

C51H64N12O12S2

MW 1101.3
Merck Index 14: 3497
CAS 512-64-1
RTECS JW5250000
Source/Host Chemicals Isolated from Streptomyces echinatus.
Purity Chemicals ≥98% (HPLC)
Appearance White to off-white solid.
Solubility Soluble in acetone, DMSO (5mg/ml), methanol, dichloromethane or ethyl acetate.
Identity Determined by 1H-NMR.
Declaration Manufactured by BioViotica.
Other Product Data

Contains traces of water.

InChi Key AUJXLBOHYWTPFV-UHFFFAOYSA-N
Smiles CSC1SCC2N(C)C(=O)C(C)NC(=O)C(COC(=O)C(C(C)C)N(C)C(=O)C1N(C)C(=O)C(C)NC(=O)C(COC(=O)C(C(C)C)N(C)C2=O)NC(=O)C1=NC2=C(C=CC=C2)N=C1)NC(=O)C1=NC2=CC=CC=C2N=C1
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Hygroscopic.
Use/Stability Stable for at least 1 year after receipt when stored at -20°C.
After reconstitution protect from light at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description
  • Antibiotic.
  • Antitumor compound.
  • Powerful, selective inhibitor of nucleic acid synthesis in vitro.
  • Potent hypoxia-inducible factor 1 (HIF-1) DNA binding activity inhibitor.
  • Apoptosis inducer.
  • Antibacterial, antifungal and antiviral.
  • Shown to inhibit the type I IFN−MHC class I pathway in muscle precursor cells (myoblasts).
Product References
  1. A "quinoxaline antibiotic" similar to the triostins, q.v.: I. Kuroya, et al.; J. Antibiot. 14A, 324 (1961)
  2. The mode of action of quinoxaline antibiotics. Interaction of quinomycin A with deoxyribonucleic acid: K. Sato, et al.; J. Antibiot. 20, 270 (1967)
  3. Echinomycin binding sites on DNA: M.M. Van Dyke & P.B. Dervan; Science 225, 1122 (1984)
  4. Kinetic evidence that echinomycin migrates between potential DNA binding sites: K.R. Fox & M.J. Waring; Nucl. Acids Res. 13, 595 (1985)
  5. Effect of echinomycin on DNA methylation: R.L. Adams & A. Rinaldi; FEBS Lett. 215, 266 (1987)
  6. Echinomycin and a novel analogue induce apoptosis of HT-29 cells via the activation of MAP kinases pathway: J.Y. Park, et al.; Pharmacol. Res. 50, 201 (2004)
  7. Echinomycin, a small-molecule inhibitor of hypoxia-inducible factor-1 DNA-binding activity: D. Kong, et al.; Cancer Res. 65, 9047 (2005)
  8. Molecular signaling cascade in DNA bisintercalator, echinomycin-induced apoptosis of HT-29 cells: evidence of the apoptotic process via activation of the cytochrome c-ERK-caspase-3 pathway: J.Y. Park, et al.; Int. J. Biochem. Cell Biol. 38, 244 (2006)
  9. Effects of the HIF1 inhibitor, echinomycin, on growth and NOTCH signalling in leukaemia cells: S. Yonekura, et al.; Anticancer Res. 33, 3099 (2013)
  10. Echinomycin, a potential binder of FKBP12, shows minor effect on calcineurin activity: V. Singh, et al.; J. Biomol. Screen. 19, 1275 (2014)
  11. Effects of the hypoxia-inducible factor-1 inhibitor echinomycin on vascular endothelial growth factor production and apoptosis in human ectopic endometriotic stromal cells: T. Tsuzuki, et al.; Gynecol. Endocrinol. 32, 323 (2016)
  12. miRNA profile of neuroprotection mechanism of echinomycin in parkinson's disease: D. Kwon & H. Liew; Mol. Cell. Toxicol. 13, 229 (2017)
  13. Molecular and cellular toxicological profiling of DNA bis-intercalator, quinoxaline compounds: echinomycin as the versatile lead: Y.-S. Park, et al.; Mol. Cell. Toxicol. 14, 9 (2018)
  14. Encapsulation of echinomycin in cyclodextrin inclusion complexes into liposomes: in vitro anti-proliferative and anti-invasive activity in glioblastoma: W. Alshaer, et al.; RSC Adv. 9, 30976 (2019)
  15. Design, synthesis, and conformation-activity study of unnatural bridged bicyclic depsipeptides as highly potent hypoxia inducible Factor-1 inhibitors and antitumor agents: K. Koike, et al.; J. Med. Chem. 63, 4022 (2020)
  16. Therapeutic targeting of TP53-mutated acute myeloid leukemia by inhibiting HIF-1a with echinomycin: Y. Wang, et al.; Oncogene 39, 3015 (2020)
  17. High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle: T.B. Kinder, et al.; ACS Chem. Biol. 15, 1974 (2020)
  18. HIF-1a is involved in blood-brain barrier dysfunction and paracellular migration of bacteria in pneumococcal meningitis: G. Devraj, et al.; Acta Neuropathol. 140, 183 (2020)
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