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SML0477

Sigma-Aldrich

Echinomycin

≥98% (HPLC)

Synonym(s):

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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About This Item

Empirical Formula (Hill Notation):
C51H64N12O12S2
CAS Number:
512-64-1
Molecular Weight:
1101.26
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

shipped in

dry ice

storage temp.

−20°C

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

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. 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

Signal Word

Danger

Hazard Statements

H301 + H311 + H331,H361

Hazard Classifications

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

Storage Class Code

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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Certificates of Analysis (COA)

Lot/Batch Number
037M4717V
016M4748V
033M4711V

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Actinomycin D from Streptomyces sp., ~98% (HPLC)

Sigma-Aldrich

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Kenji Watanabe et al.
Current opinion in chemical biology, 13(2), 189-196 (2009-03-13)
Echinomycin, a bis-intercalator antitumor cyclic peptide, is biosynthesized by a unique nonribosomal peptide synthetase (NRPS). Successful heterologous expression of the whole gene cluster of echinomycin in Escherichia coli let us to investigate a further application of echinomycin NRPS. To construct
Michio Sato et al.
Current opinion in chemical biology, 17(4), 537-545 (2013-07-17)
Echinomycin is an antitumor antibiotic secondary metabolite isolated from streptomycetes, whose core structure is biosynthesized by nonribosomal peptide synthetase (NRPS). The echinomycin biosynthetic pathway was successfully reconstituted in Escherichia coli. NRPS often contains a thioesterase domain at its C terminus
Hypoxia-inducible factor 1 mediates hypoxia-enhanced synthesis of progesterone during luteinization of granulosa cells
Yoshioka S, et al.
Journal of Reproduction and Development, 63, 75-85 (2017)
Antitumour drug-DNA interactions: NMR studies of echinomycin and chromomycin complexes.
X L Gao et al.
Quarterly reviews of biophysics, 22(2), 93-138 (1989-05-01)
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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