330175-M

Echinomycin Streptomyces sp.

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

• Synonym(s): Echinomycin Streptomyces sp., NSC-13502, Quinomycin A
• Empirical Formula (Hill Notation): C₅₁H₆₄N₁₂O₁₂S₂
• CAS Number: 512-64-1
• Molecular Weight: 1101.26
• UNSPSC Code: 12352200

Properties

• 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

Description

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

Safety Information

• Pictograms: GHS06,GHS08
• Signal Word: Danger
• Hazard Statements: H301 + H311 + H331,H361
• Precautionary Statements: P202 - P261 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311
• 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