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Merck

SML0477

Echinomycin

≥98% (HPLC), HIF-1α inhibitor, powder

Sinónimos:

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 L-valine (81)-lactone cyclic (37)-thioester, Quinomycin A

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Fórmula empírica (notación de Hill):
C51H64N12O12S2
Número CAS:
512-64-1
Peso molecular:
1101.26
UNSPSC Code:
12352200
NACRES:
NA.77

Documentos clave

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Nombre del producto

Echinomycin, ≥98% (HPLC)

SMILES string

S1C(C2N(C(=O)C(NC(=O)C(COC(=O)C(N(C(=O)C(N(C(=O)C(NC(=O)C(COC(=O)C(N(C2=O)C)C(C)C)NC(=O)c5nc6c(nc5)cccc6)C)C)C1)C)C(C)C)NC(=O)c3nc4c(nc3)cccc4)C)C)SC

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)24-77-51(40)76-11/h12-21,25-28,35-40,51H,22-24H2,1-11H3,(H,54,66)(H,55,67)(H,58,64)(H,59,65)

InChI key

AUJXLBOHYWTPFV-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

shipped in

dry ice

storage temp.

−20°C

Quality Level

100

Categorías relacionadas

Application

Echinomycin has been used for inhibition of hypoxia-inducible factor 1.

Biochem/physiol Actions

Echinomycin is an antitumor antibiotic and potent hypoxia inducible factor 1α (HIF-1α) inhibitor.
Echinomycin is an antitumor antibiotic and potent hypoxia inducible factor 1α (HIF-1α) inhibitor. It binds to DNA via bifunctional intercalation, blocking the binding of HIF-1α, a transcription factor important in tumor growth. Echinomycin selectively eliminated cancer stem cells in a study with mouse lymphoma and human AML xenogeneic models, eradicating the lymphomas. Recently, echinomycin was also found to act as an antibiotic adjuvant having synergistic effects with novobiocin in gram negative bacteria.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Repr. 2

Clase de almacenamiento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000482804
0000482806
0000482806
0000482804
0000437257

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Rationally engineered total biosynthesis of a synthetic analogue of a natural quinomycin depsipeptide in Escherichia coli.
Kenji Watanabe et al.
Chembiochem : a European journal of chemical biology, 10(12), 1965-1968 (2009-07-10)
Jianqiu Zou et al.
Cell reports, 42(1), 112018-112018 (2023-01-21)
Cardiac maturation is crucial for postnatal cardiac development and is increasingly known to be regulated by a series of transcription factors. However, post-translational mechanisms regulating this process remain unclear. Here we report the indispensable role of neddylation in cardiac maturation.
Kenji Watanabe et al.
Journal of the American Chemical Society, 131(26), 9347-9353 (2009-06-12)
Natural products display impressive activities against a wide range of targets, including viruses, microbes, and tumors. However, their clinical use is hampered frequently by their scarcity and undesirable toxicity. Not only can engineering Escherichia coli for plasmid-based pharmacophore biosynthesis offer
S M Zimmermann et al.
Injury, 44(4), 570-575 (2013-02-13)
Heterotopic ossification (HO) frequently causes complications following orthopaedic and trauma surgery and may drastically reduce the postoperative outcome due to pain and joint contracture. Current therapeutic options include NSAID's and local radiation. However, both options of prevention show disadvantages such
Dilip V Jarikote et al.
Bioorganic & medicinal chemistry, 19(2), 826-835 (2011-01-05)
Echinomycin is a natural depsipeptide, which is a bisintercalator, inserting quinoxaline units preferentially adjacent to CG base pairs of DNA. Herein the design and synthesis of echinomycin mimetics based on grafting of two quinoxaline residues onto a macrocyclic scaffold (glycophane)
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