Ailanthone (δ13-Dehydrochaparrinone)
(Synonyms: 臭椿酮,Δ13-Dehydrochaparrinone) 目录号 : GC31742
Ailanthone (δ13-Dehydrochaparrinone)是一种源自传统中药植物臭椿（Ailanthus altissima）的苦木素类化合物，是全长雄激素受体（AR）（IC50=69nM）及其组成型活性截短剪接变体（AR-Vs）（IC50=309nM）的强效抑制剂。
Cas No.:981-15-7
Sample solution is provided at 25 µL, 10mM.
Ailanthone (δ13-Dehydrochaparrinone), a quassinoid extract from the traditional Chinese medicine plant Ailanthus altissima, is a potent inhibitor of both full-length androgen receptor (AR) (IC50=69nM) and constitutively active truncated AR splice variants (AR-Vs IC50=309nM)[1]. The androgen receptor (AR) is a ligand-dependent nuclear receptor that, upon stimulation by testosterone or dihydrotestosterone, transcriptionally regulates genes essential for prostate development and function,while AR-Vs lack the ligand-binding domain and sustain AR signaling even in the absence of androgens, thereby driving cancer progression[2]. Ailanthone (δ13-Dehydrochaparrinone) is widely used in various cancer researches[3].
In vitro, treatment of human Huh7 hepatocellular carcinoma cells with Ailanthone (δ13-Dehydrochaparrinone) (0, 0.2, 0.4 or 0.8μM for 0, 36h, 48h, or 60h)inhibits cell proliferation in a concentration- and time-dependent manner, induces G0/G1 cell-cycle arrest and DNA damage, triggers activation of the ATM/ATR pathway, and elicits caspase-dependent mitochondrial apoptosis[4]. Ailanthone (δ13-Dehydrochaparrinone) (0.1–0.8μM; 48h) dose-dependently inhibits the proliferation of human melanoma cell lines SK-MEL-5, SK-MEL-28, A375 and WM35, induces c-Jun degradation, and suppresses PD-L1 transcription[5].
In vivo, Ailanthone (δ13-Dehydrochaparrinone) (5mg/kg; i.p. qod; 20 days) reversed bleomycin-induced pulmonary fibrosis in mice, reduced collagen deposition and lung hydroxyproline content, and restored the lung function parameter Penh to normal levels[6]. Ailanthone (δ13-Dehydrochaparrinone) (2mg/kg; i.p.; every 3 days for 30 days) reduced the number of lung metastatic nodules in Saos-2 osteosarcoma mice from 31 to 8 and markedly down-regulated KMT2A, MEN1, PHGDH, PSAT1 and PSPH proteins in metastatic lung tissues[7].
References:
[1] He Y, Peng S, Wang J, et al. Ailanthone targets p23 to overcome MDV3100 resistance in castration-resistant prostate cancer. Nat Commun. 2016;7:13122.
[2] Kato M, Banuelos CA, Imamura Y, et al. Cotargeting Androgen Receptor Splice Variants and mTOR Signaling Pathway for the Treatment of Castration-Resistant Prostate Cancer. Clin Cancer Res. 2016;22(11):2744-2754.
[3] Ding H, Yu X, Hang C, et al. Ailanthone: A novel potential drug for treating human cancer. Oncol Lett. 2020;20(2):1489-1503.
[4] Zhuo Z, Hu J, Yang X, et al. Ailanthone Inhibits Huh7 Cancer Cell Growth via Cell Cycle Arrest and Apoptosis In Vitro and In Vivo. Sci Rep. 2015;5:16185.
[5] Yu P, Wei H, Li K, et al. The traditional chinese medicine monomer Ailanthone improves the therapeutic efficacy of anti-PD-L1 in melanoma cells by targeting c-Jun. J Exp Clin Cancer Res. 2022;41(1):346.
[6] Zhao L, Zhu Y, Tao H, et al. Ailanthone ameliorates pulmonary fibrosis by suppressing JUN-dependent MEOX1 activation. Acta Pharm Sin B. 2024;14(8):3543-3560.
[7] Liang J, Qiao G, Zhang Y, et al. Ailanthone targets the KMT2A-MEN1 complex to suppress lung metastasis of osteosarcoma. Phytomedicine. 2025;136:156258.
Ailanthone (δ13-Dehydrochaparrinone)是一种源自传统中药植物臭椿（Ailanthus altissima）的苦木素类化合物，是全长雄激素受体（AR）（IC50=69nM）及其组成型活性截短剪接变体（AR-Vs）（IC50=309nM）的强效抑制剂[1]。雄激素受体（AR）是一种依赖配体的核受体，在睾酮或二氢睾酮刺激下，通过转录调控前列腺发育与功能相关基因；而AR-Vs缺乏配体结合结构域，可在无雄激素条件下持续激活AR信号通路，从而驱动癌症进展[2]。Ailanthone (δ13-Dehydrochaparrinone)被广泛应用于多种癌症研究[3]。
体外实验中，Ailanthone (δ13-Dehydrochaparrinone)（0.2、0.4或0.8μM，作用0、36、48或60小时）可浓度-和时间依赖性地抑制人Huh7肝细胞癌细胞的增殖，诱导G0/G1期细胞周期阻滞和DNA损伤，激活ATM/ATR通路，并触发半胱天冬酶依赖性线粒体凋亡[4]。Ailanthone (δ13-Dehydrochaparrinone)(0.1–0.8μM; 48小时) 剂量依赖性地抑制人黑色素瘤细胞系SK-MEL-5、SK-MEL-28、A375及WM35的增殖，诱导c-Jun降解并抑制PD-L1转录[5]。
体内实验中，Ailanthone (δ13-Dehydrochaparrinone)（5mg/kg；隔日腹腔注射；持续20天）逆转了博来霉素诱导的小鼠肺纤维化，减少胶原沉积及肺羟脯氨酸含量，并将肺功能参数Penh恢复至正常水平[6]。Ailanthone (δ13-Dehydrochaparrinone)（2mg/kg；腹腔注射；每3天一次，共30天）使Saos-2骨肉瘤小鼠肺转移结节数由31个降至8个，并显著下调转移肺组织中的KMT2A、MEN1、PHGDH、PSAT1和PSPH蛋白表达[7]。
| Cell experiment [1]: | |
Cell lines | human HCC cell line Huh7 |
Preparation Method | The human HCC cell line Huh7 cells were maintained in a 95% air and 5% CO2 humidified atmosphere at 37°C. DMEM medium supplemented with 10% FBS and 1% PS was used for routine subculturing and for all experiments. Cells (5×103/well) were seeded into 96-well plates and cultured overnight. Different concentrations of Ailanthone (δ13-Dehydrochaparrinone) (0, 0.2, 0.4 or 0.8μM) were added to each well for different times (0, 36h, 48h, or 60h). Next, an MTT solution (5mg/mL) was added to each well for an additional 4h. The resulting formazan crystals were dissolved in DMSO, and the optical density was measured at 595nm using a DTX 880 Multimode Detector. |
Reaction Conditions | 0, 0.2, 0.4 or 0.8μM for 0, 36h, 48h, or 60h |
Applications | Ailanthone (δ13-Dehydrochaparrinone) inhibits cell proliferation in a concentration- and time-dependent manner. |
| Animal experiment [2]: | |
Animal models | NSG mice |
Preparation Method | The inhibitory effect of Ailanthone (δ13-Dehydrochaparrinone) on OS lung metastasis was evaluated in a mouse model. Briefly, 5×106 Saos-2 cells were suspended in 75ml of serum-free DMEM and combined with 75ml of Matrigel. Then, the mixture was injected orthotopically into the medullar cavity of the tibia of 6- to 8-week-old NSG mice. Cell line-derived xenografts were allowed to grow to an average volume of 100mm3 ; then, mice were randomly assigned to groups and treated with Ailanthone (δ13-Dehydrochaparrinone) (2mg/kg) or PBS solution containing 1% DMSO intraperitoneally every 3 days. The length and width of resulting tumors were measured every 5 days. Mice were sacrificed and tumors were harvested 30 days after treatment initiation. Whole lungs and livers were resected and photographed. |
Dosage form | 2mg/kg; i.p.; every 3 days for 30 days |
Applications | Ailanthone (δ13-dehydrochaparrinone) reduced the number of lung metastatic nodules in Saos-2 osteosarcoma mice from 31 to 8 and markedly down-regulated KMT2A, MEN1, PHGDH, PSAT1 and PSPH proteins in metastatic lung tissues. |
References: | |
| Cas No. | 981-15-7 | SDF | |
| 别名 | 臭椿酮,Δ13-Dehydrochaparrinone | ||
| Canonical SMILES | C[C@@]1([C@@H]2O)[C@]([C@@]3([C@@H]4O)O)([H])[C@@]([C@](C5)([H])C4=C)(CO3)[C@@](OC5=O)([H])C[C@@]1([H])C(C)=CC2=O | ||
| 分子式 | C20H24O7 | 分子量 | 376.4 |
| 溶解度 | DMSO : 83.3 mg/mL (221.31 mM) | 储存条件 | Store at 4°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.6567 mL | 13.2837 mL | 26.5675 mL |
| 5 mM | 0.5313 mL | 2.6567 mL | 5.3135 mL |
| 10 mM | 0.2657 mL | 1.3284 mL | 2.6567 mL |
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| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
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2.
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