CAS 981-15-7|Ailanthone

Introduction：Basic information about CAS 981-15-7|Ailanthone, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Ailanthone BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Synonyms

Common Name	Ailanthone
CAS Number	981-15-7	Molecular Weight	376.400
Density	1.5±0.1 g/cm3	Boiling Point	641.0±55.0 °C at 760 mmHg
Molecular Formula	C₂₀H₂₄O₇	Melting Point	/
MSDS	/	Flash Point	231.6±25.0 °C

Names

Name	ailanthone
Synonym	More Synonyms

Ailanthone BiologicalActivity

Description	Ailanthone (Δ13-Dehydrochaparrinone) is a potent inhibitor of both full-length androgen receptor (AR) (IC50=69 nM) and constitutively active truncated AR splice variants (AR1-651 IC50=309 nM).
Related Catalog	Signaling Pathways >>Others >>Androgen ReceptorResearch Areas >>CancerResearch Areas >>Inflammation/ImmunologyNatural Products >>Others
Target	IC50: 69 nM (Full-length androgen receptor), 309 nM (AR1-651)[1]
In Vitro	Ailanthone is a potent inhibitor of both full-length AR (AR-FL) and constitutively active truncated AR splice variants (AR-Vs). Ailanthone binds to the co-chaperone protein p23 and prevents AR's interaction with HSP90, thus resulting in the disruption of the AR-chaperone complex followed by ubiquitin/proteasome-mediated degradation of AR as well as other p23 clients including AKT and Cdk4, and downregulates AR and its target genes in PCa cell lines and orthotopic animal tumours. In addition, Ailanthone blocks tumour growth and metastasis of CRPC[1]. Ailanthone has been shown to possess an growth-inhibitory effect against several cancer cell lines including HepG2, Hep3B, R-HepG2, Jurkat, HeLa, MCF-7, MDA-MB-231 and A549 cells. Ailanthone inhibits Huh7 cell growth through the induction of mitochondrion-mediated cell apoptosis and G0/G1 cell cycle arrest. Ailanthone-induced apoptosis is mitochondrion-mediated and involved the PI3K/AKT signaling pathway in Huh7 cells[2].
In Vivo	Not only i.p. administration but also p.o. administration of Ailanthone has excellent efficiency for blocking the growth of CRPC xenografts. In pharmacokinetic studies, Ailanthone exhibits good solubility in water and good bioavailability (>20%). In addition, Ailanthone effectively suppresses CRPC tumour growth, despite not reaching a steady state of plasma drug concentration during the course of treatment[1].
Cell Assay	For SRB assay, cells are cultured in complete RPMI 1640 and incubated with indicated concentrations of Ailanthone or cells are maintained in fresh phenol red-free RPMI 1640 medium with 5% charcoal-stripped FBS, 1 nM DHT and indicated compounds. After 48 or 72 h, the cells are then fixed and the cell growth is detected with the SRB assay. For colony formation assay, prostate cancer cells are incubated with indicated concentrations of Ailanthone in complete RPMI 1640 for 2 weeks and then cells are fixed with 4% paraformaldehyde and stained with crystal violet. Colonies are visualized under a microscope, and all of the fields are imaged and counted. Colony formation as a percentage of vehicle control for each cell line is presented[1].
Animal Admin	Mice[1] In orthotopic castration-resistant prostate cancer xenografts model, mice are intraperitoneally injected with Ailanthone (2 mg/kg), MDV (10 mg/kg) or DMSO (as controls). Prostate tumour growth and local metastasis are monitored weekly using the IVIS Imaging System. Images and measurements of bioluminescent signals are acquired and analysed using Living Image and Xenogen software[1].
References	[1]. He Y, et al. Ailanthone targets p23 to overcome MDV3100 resistance in castration-resistant prostate cancer. Nat Commun. 2016 Dec 13;7:13122. [2]. Zhuo Z, et al. Ailanthone Inhibits Huh7 Cancer Cell Growth via Cell Cycle Arrest and Apoptosis In Vitro and In Vivo. Sci Rep. 2015 Nov 3;5:16185.

Chemical & Physical Properties

Density	1.5±0.1 g/cm3
Boiling Point	641.0±55.0 °C at 760 mmHg
Molecular Formula	C₂₀H₂₄O₇
Molecular Weight	376.400
Flash Point	231.6±25.0 °C
Exact Mass	376.152191
PSA	113.29000
LogP	-0.76
Vapour Pressure	0.0±4.3 mmHg at 25°C
Index of Refraction	1.640
InChIKey	WBBVXGHSWZIJST-HORRRRDZSA-N
SMILES	C=C1C(O)C2(O)OCC34C(CC5C(C)=CC(=O)C(O)C5(C)C23)OC(=O)CC14
Storage condition	2-8C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KT0930000

CHEMICAL NAME :: 2H-1,11c-(Epoxymethano)phenanthro(10,1-bc)pyran-5,10( 3H,6ah)-dione, 1,3a,4,7,7a,11,11a,11b- octahydro-8,11a-beta-dimethyl-3-methylene-1-alpha,2-b eta,11-beta-trihydrox y-

CAS REGISTRY NUMBER :: 981-15-7

LAST UPDATED :: 199303

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C20-H24-O7

MOLECULAR WEIGHT :: 376.44

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 9800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PSSGAR Parassitologia. (Parassitologia, E. Biocca, A. Corradetta, Leonardo, via Baglivi 5, 00161 Roma, Italy) V.1- 1959- Volume(issue)/page/year: 10,215,1968

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 31400 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EJMCA5 European Journal of Medicinal Chemistry--Chimie Therapeutique. (Editions Scientifiques Elsevier, 29 rue Buffon, F-75005, Paris, France) V.9- 1974- Volume(issue)/page/year: 26,345,1991

Synonyms

Picrasa-3,13(21)-diene-2,16-dione, 11,20-epoxy-1,11,12-trihydroxy-, (1β,11β,12α)-

13,21-Didehydrochaparrinone

Ailanthone

Picrasa-3,13(21)-diene-2,16-dione, 11,20-epoxy-1,11,12-trihydroxy-, (1β,11β,12α,14ξ)-

(1β,11β,12α,14ξ)-1,11,12-Trihydroxy-11,20-epoxypicrasa-3,13(21)-diene-2,16-dione

(1β,11β,12α)-1,11,12-Trihydroxy-11,20-epoxypicrasa-3,13(21)-diene-2,16-dione

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