SML0172
Cercosporamide from Cercosporidium henningsii
≥98% (HPLC)
Synonym(s):
4-Dibenzofurancarboxamide
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About This Item
Empirical Formula (Hill Notation):
C16H13NO7
CAS Number:
Molecular Weight:
331.28
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (HPLC)
Quality Segment
assay
≥98% (HPLC)
solubility
chloroform: 1 mg/mL, ethyl acetate: 1 mg/mL, DMSO: 5 mg/mL (Solution in DMSO is unstable and thus should be freshly prepared.)
storage temp.
−20°C
InChI
1S/C16H13NO7/c1-5(18)10-7(20)4-9-16(2,14(10)22)12-8(21)3-6(19)11(15(17)23)13(12)24-9/h3-4,19-21H,1-2H3,(H2,17,23)/t16-/m1/s1
InChI key
GEWLYFZWVLXQME-MRXNPFEDSA-N
Application
Cercosporamide from Cercosporidium henningsii has been used as a mitogen-activated protein (MAP) kinase-interacting kinase (MNK) inhibitor in glioblastoma (GBM)-derived BS287 spheres. It has also been used as an inhibitor of bone morphogenetic protein receptor (BMPR) type I kinase in HepG2 cells and zebrafish embryos in particular to test its rescue potential against developmental defects.
Biochem/physiol Actions
Cercosporamide was initially identified as a phytotoxin with broad-spectrum anti-fungal activity. Studies have shown that cercosporamide is a specific, highly potent fungal inhibitor of the cell wall integrity-signaling pathway mediator, protein kinase (Pkc1) inhibitor. Semisynthetic cercosporamide analogues demonstrated hypoglycemic activity and therefore, serve as candidates for potential new anti diabetic drugs. Cercosporamide was found to block eIF4E (Eukaryotic Initiation Factor) phosphorylation in cultured cancer cells, inducing apoptosis, suppressing proliferation, and reducing soft agar colonization. Its eIF4E phosphorylation inhibitory effect was also shown when administrated orally on xenograft human tissue and mouse liver tissue. Cercosporamide is a potent and selective Mnk inhibitor. It reduces tumor growth in xenografted HCT116 tumor and suppresses the outgrowth of B16 melanoma lung metastases. Hence, blocking Mnk function and eIF4E phosphorylation may be an attractive anticancer strategy.
Phytotoxin with broad-spectrum anti-fungal activity.
Preparation Note
DMSO solution (1 mg/ml), kept at -20 °C, is stable for at least three months.
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