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330175-M

Millipore

Echinomycin Streptomyces sp.

A cell-permeable Streptomyces-derived antibiotic that contains two bicyclic peptide-linked quinoxalines and acts as a sequence-specific DNA bisintercalator.

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Synonym(s):
Echinomycin Streptomyces sp., NSC-13502, Quinomycin A
Empirical Formula (Hill Notation):
C51H64N12O12S2
CAS Number:
512-64-1
Molecular Weight:
1101.26

Assay

≥98% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

white

solubility

DMSO: 5 mg/mL

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

General description

A cell-permeable Streptomyces-derived antibiotic that contains two bicyclic peptide-linked quinoxalines and acts as a sequence-specific DNA bisintercalator. Echinomycin at 10 µM is shown to inhibit HIF-1 and Myc/Max DNA binding activities in U251 and MCF-7 nuclear extracts by >90%, while exhibiting little effect against the binding of AP-1 or NF-κB to their respective DNA targets that lack the 5′-ACGTG-3′ core structure in cell-free EMSA assays. Reversibly inhibits hypoxia-induced HIF-1 transcription activity in an HRE promoter-based reporter assay in U215 cells (EC50 = 1.2 nM) and is of no effect against SV40 promoter-driven transcription activity. Despite echinomycin′s in vitro apoptosis-inducing activity and the initial report of its in vivo antitumor effect in mice, clinical trials have not yet resulted in promising data regarding its therapeutic efficacy in cancer treatment.

Warning

Toxicity: Toxic (F)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C.) Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Park, J.Y., et al. 2008. Cell. Biol. Int.32, 1207.
Kong, D., et al. 2005. Cancer Res.65, 9047.
Chang, A.Y., et al. 1998. Cancer82, 292.
Wadler, S., et al. 1994. Cancer Chemother. Pharmacol.34, 266.
Muss, H.B., et al. 1993. Am. J. Clin. Oncol.16, 492.
Foster, B.J., et al. 1985. Invest. New Drugs3, 403.
Van Dyke, N.M., et al. 1984. Science225, 1122.
Ward, D.C., et al. 1965. Science149, 1259.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

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(C)

Not applicable

Regulatory Information

监管及禁止进口产品

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