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Merck

SML0477

Sigma-Aldrich

棘霉素

≥98% (HPLC)

别名:

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

经验公式(希尔记法):
C51H64N12O12S2
CAS号:
分子量:
1101.26
分類程式碼代碼:
12352200
NACRES:
NA.77

化驗

≥98% (HPLC)

形狀

powder

儲存條件

desiccated

顏色

white to beige

運輸包裝

dry ice

儲存溫度

−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 密鑰

AUJXLBOHYWTPFV-UHFFFAOYSA-N

應用

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

生化/生理作用

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.

象形圖

Skull and crossbonesHealth hazard

訊號詞

Danger

危險分類

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

儲存類別代碼

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

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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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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