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Merck

SML2143

Sigma-Aldrich

Ailanthone

≥98% (HPLC)

Sinónimos:

Δ13-Dehydrochaparrinone, (1β,11β,12α)-11,20-Epoxy-1,11,12-trihydroxypicrasa-3,13(21)-diene-2,16-dione, 13,21-Didehydrochaparrinone

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About This Item

Fórmula empírica (notación de Hill):
C20H24O7
Número de CAS:
Peso molecular:
376.40
EC Number:
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

O[C@@H]1C([C@]([C@@]2([C@]3([H])[C@@]1(O)OC2)[C@@](O4)([H])C[C@@]([C@]3(C)[C@@H]5O)([H])C(C)=CC5=O)([H])CC4=O)=C

InChI

1S/C20H24O7/c1-8-4-12(21)16(24)18(3)10(8)5-13-19-7-26-20(25,17(18)19)15(23)9(2)11(19)6-14(22)27-13/h4,10-11,13,15-17,23-25H,2,5-7H2,1,3H3/t10-,11-,13+,15+,16+,17+,18+,19+,20-/m0/s1

InChI key

WBBVXGHSWZIJST-RLQYZCPESA-N

Biochem/physiol Actions

Ailanthone, natural compound isolated from Ailanthus altissima (Simaroubaceae), is a potent inhibitor of androgen receptor (AR) that blocks activities of full-length AR and AR splice variants. It overcomes MDV3100 (Enzalutamide)-resistance in castration-resistant prostate cancer cell lines. Ailanthone disrupts the interaction between AR and the chaperones HSP90, HSP70, and HSP40, which leads to AR ubiquitination and degradation.

pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificados de análisis (COA)

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Ailanthone: a new potential drug for castration-resistant prostate cancer.
Shihong Peng et al.
Chinese journal of cancer, 36(1), 25-25 (2017-03-05)
Yundong He et al.
Nature communications, 7, 13122-13122 (2016-12-14)
Androgen receptor (AR) antagonist MDV3100 is the first therapeutic approach in treating castration-resistant prostate cancer (CRPC), but tumours frequently become drug resistant via multiple mechanisms including AR amplification and mutation. Here we identify the small molecule Ailanthone (AIL) as a
Zhenjian Zhuo et al.
Scientific reports, 5, 16185-16185 (2015-11-04)
While searching for natural anti-hepatocellular carcinoma (HCC) components in Ailanthus altissima, we discovered that ailanthone had potent antineoplastic activity against HCC. However, the molecular mechanisms underlying the antitumor effect of ailanthone on HCC have not been examined. In this study

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