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Key Documents

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D5816

Sigma-Aldrich

(−)-Depudecin

>95% (HPLC), from microbial

Sinónimos:

4,5:8,9-Dianhydro-1,2,6,7,11-pentadeoxy-D-threo-D-ido-undeca-1,6-dienitol

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About This Item

Fórmula empírica (notación de Hill):
C11H16O4
Número de CAS:
139508-73-9
Peso molecular:
212.24
MDL number:
MFCD04039998
UNSPSC Code:
12352200
PubChem Substance ID:
24893973

biological source

microbial

assay

>95% (HPLC)

form

liquid

shipped in

dry ice

storage temp.

−20°C

SMILES string

C[C@@H](O)[C@@H]1O[C@H]1\C=C\[C@@H]2O[C@H]2[C@H](O)C=C

InChI

1S/C11H16O4/c1-3-7(13)11-9(15-11)5-4-8-10(14-8)6(2)12/h3-13H,1H2,2H3/b5-4+/t6-,7-,8+,9+,10+,11+/m1/s1

InChI key

DLVJMFOLJOOWFS-INMLLLKOSA-N

Biochem/physiol Actions

Inhibitor of histone deacetylase (HDAC) both in vivo and in vitro. Alters the spindle shaped morphology of v-Ha-ras-transformed NIH3T3 cells to a flattened shape and induces an intricate actin stress fiber network in these cells and in MG63 osteosarcoma cells. Also exhibits anti-angiogenic activity.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

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K Sugita et al.
Biochemical and biophysical research communications, 182(1), 379-387 (1992-01-15)
A novel compound, depudecin, induced production of the flat phenotype of Ki-ras-transformed NIH3T3 cells at the low concentration of 1 microgram/ml. This effect was reversible. Actin stress fiber was detected in these cells after depudecin treatment. Almost complete reversion to
Wanessa D Wight et al.
Molecular plant-microbe interactions : MPMI, 22(10), 1258-1267 (2009-09-10)
Depudecin, an eleven-carbon linear polyketide made by the pathogenic fungus Alternaria brassicicola, is an inhibitor of histone deacetylase (HDAC). A chemically unrelated HDAC inhibitor, HC toxin, was earlier shown to be a major virulence factor in the interaction between Cochliobolus
M Matsumoto et al.
The Journal of antibiotics, 45(6), 879-885 (1992-06-01)
A novel compound depudecin inducing the flat phenotype of ras- and src- transformed NIH3T3 cells at a concentration of 1 microgram/ml was isolated from the culture broth of Alternaria brassicicola. Based on its spectroscopic characteristics and X-ray crystallographic analysis of
Ho Jeong Kwon et al.
Veterinary parasitology, 112(4), 269-276 (2003-03-08)
Neospora caninum is an apicomplexan parasite associated with abortion in cattle worldwide. Apicidin, histone deacetylase (HDAC) inhibitor, has shown a broad spectrum of anti-protozoal activity against apicomplexan parasites. Cultured vero cells infected with N. caninum tachyzoites were treated with 0.5
M Isaka et al.
Planta medica, 66(5), 473-475 (2000-07-26)
Bioassay-guided fractionation of the extract from the wood-decayed fungus Xylaria sp. BCC 1067 led to the isolation of five antiplasmodial compounds, (-)-depudecin, (+)-phaseolinone, (+)-phomenone, 19,20-epoxycytochalasin Q, and (E)-methyl 3-(4-methoxyphenoxy)propenoate. These structures were elucidated using spectroscopic methods, especially NMR analysis.
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