Ailanthone | CAS# 981-15-7 | Anti-tumor agent

MedKoo Cat#: 574498 | Name: Ailanthone

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ailanthone is a quassinoid that has been found to be active against the P. falciparum strains HB-3 and Dd-2 in vitro. Ailanthone is phytotoxic and inhibits dihydrotestosterone-induced androgen receptor transcriptional activity as well as the growth and colony formation of LNCaP and 22RV1 androgen receptor-expressing cells. Ailanthone reduces tumor volume in 22Rv1, LNCaP, and VCaP castration-resistant prostate cancer (CRPC) mouse xenograft models.

Chemical Structure

Ailanthone

CAS#981-15-7

Theoretical Analysis

MedKoo Cat#: 574498

Name: Ailanthone

CAS#: 981-15-7

Chemical Formula: C20H24O7

Exact Mass: 376.1522

Molecular Weight: 376.40

Elemental Analysis: C, 63.82; H, 6.43; O, 29.75

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 615.00	2 Weeks

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Related CAS #

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Synonym

Δ13-Dehydrochaparrinone, Ailanthone

IUPAC/Chemical Name

(1R,2R,3aS,3a1S,6aR,7aS,11S,11aS,11bR)-1,2,11-trihydroxy-8,11a-dimethyl-3-methylene-1,2,3,3a,4,7,7a,11,11a,11b-decahydro-5H-1,3a1-(epoxymethano)dibenzo[de,g]chromene-5,10(6aH)-dione

InChi Key

WBBVXGHSWZIJST-RLQYZCPESA-N

InChi Code

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

SMILES Code

C=C1[C@]([C@@]2([C@]3([H])[C@@](O)(OC2)[C@@H]1O)[C@@](O4)([H])C[C@@]([C@]3(C)[C@@H]5O)([H])C(C)=CC5=O)([H])CC4=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ailanthone (Δ13-Dehydrochaparrinone) is an inhibitor of both full-length androgen receptor (AR) (IC50=69 nM) and constitutively active truncated AR splice variants (AR1-651 IC50=309 nM).

In vitro activity:

The sensitivity or the resistance of ovarian cancer cells to CDDP was tested by exposing cells to increasing concentration of CDDP. MTT analysis confirmed the CDDP resistance of A2780/CP70 cells (S1 supplementary data). To evaluate the effect of Aila (Ailanthone) in ovarian cancer cell lines, this study exposed these cells to increasing concentrations of Aila and evaluated cell growth through MTT and colony forming assays. Aila was more effective than CDDP in inhibiting the growth of both sensitive and resistant cells (Fig. 1A). Colony forming assays, performed in A2780 and in A2780/CP70 cells (Fig. 1B and C, D), also confirmed the Aila ability in inhibiting cell growth, and, in particular, the higher effectiveness of Aila, with respect to CDDP, was most pronounced in A2780/CP70 cells. Reference: Free Radic Biol Med. 2020 Apr;150:125-135. https://pubmed.ncbi.nlm.nih.gov/32101771/

In vivo activity:

Results showed that Aila (Ailanthone) significantly inhibited H1975 cell tumour growth (Figure 2A), the body weight of mice was not changed (Supplementary Figure S1A) and the median survival time for 0, 1 and 2 mg kg−1 of Aila treatment groups was 30, 40.5 and 48 days, respectively (Figure 2B). Mice with A549 cell subcutaneous xenograft tumour were then treated with 2 mg kg−1 of Aila to determine the effect of Aila on other NSCLC cells, and similar results were obtained (Supplementary Figure S1B). Mice treated with 2 mg kg−1 of Aila were killed, and the tumours of Aila-treated mice were much smaller (Supplementary Figure S2C and D) and lighter (Supplementary Figure S2E and F) compared with vehicle-treated mice. This study further investigated the efficacy of Aila in an orthotopic eGFP-FFLuc+ A549 cell tumour model by bioluminescent imaging. Results showed that Aila clearly inhibited orthotopic lung tumour growth (Figure 2C and D), and the median survival time for vehicle- and Aila-treated mice was 35 and 55 days (Figure 2E), respectively. Taken together, these results demonstrated that Aila could significantly inhibit NSCLC cell growth in vitro and tumour growth in vivo with low toxicity, leading to prolonged survival of tumour-bearing mice. Reference: Br J Cancer. 2017 Nov 21; 117(11): 1621–1630. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5729430/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	100.0	265.67

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 376.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Cucci MA, Grattarola M, Dianzani C, Damia G, Ricci F, Roetto A, Trotta F, Barrera G, Pizzimenti S. Ailanthone increases oxidative stress in CDDP-resistant ovarian and bladder cancer cells by inhibiting of Nrf2 and YAP expression through a post-translational mechanism. Free Radic Biol Med. 2020 Apr;150:125-135. doi: 10.1016/j.freeradbiomed.2020.02.021. Epub 2020 Feb 23. PMID: 32101771. 2. Zhang Y, Zhang C, Min D. Ailanthone up-regulates miR-449a to restrain acute myeloid leukemia cells growth, migration and invasion. Exp Mol Pathol. 2019 Jun;108:114-120. doi: 10.1016/j.yexmp.2019.04.011. Epub 2019 Apr 17. PMID: 31002772. 3. Ni Z, Yao C, Zhu X, Gong C, Xu Z, Wang L, Li S, Zou C, Zhu S. Ailanthone inhibits non-small cell lung cancer cell growth through repressing DNA replication via downregulating RPA1. Br J Cancer. 2017 Nov 21;117(11):1621-1630. doi: 10.1038/bjc.2017.319. Epub 2017 Oct 12. PMID: 29024939; PMCID: PMC5729430. 4. He Y, Peng S, Wang J, Chen H, Cong X, Chen A, Hu M, Qin M, Wu H, Gao S, Wang L, Wang X, Yi Z, Liu M. Ailanthone targets p23 to overcome MDV3100 resistance in castration-resistant prostate cancer. Nat Commun. 2016 Dec 13;7:13122. doi: 10.1038/ncomms13122. PMID: 27959342; PMCID: PMC5159881.

In vitro protocol:

In vivo protocol:

1. Ni Z, Yao C, Zhu X, Gong C, Xu Z, Wang L, Li S, Zou C, Zhu S. Ailanthone inhibits non-small cell lung cancer cell growth through repressing DNA replication via downregulating RPA1. Br J Cancer. 2017 Nov 21;117(11):1621-1630. doi: 10.1038/bjc.2017.319. Epub 2017 Oct 12. PMID: 29024939; PMCID: PMC5729430. 2. He Y, Peng S, Wang J, Chen H, Cong X, Chen A, Hu M, Qin M, Wu H, Gao S, Wang L, Wang X, Yi Z, Liu M. Ailanthone targets p23 to overcome MDV3100 resistance in castration-resistant prostate cancer. Nat Commun. 2016 Dec 13;7:13122. doi: 10.1038/ncomms13122. PMID: 27959342; PMCID: PMC5159881.

1: Liu W, Liu X, Pan Z, Wang D, Li M, Chen X, Zhou L, Xu M, Li D, Zheng Q. Ailanthone Induces Cell Cycle Arrest and Apoptosis in Melanoma B16 and A375 Cells. Biomolecules. 2019 Jul 11;9(7):275. doi: 10.3390/biom9070275. Retraction in: Biomolecules. 2020 Apr 17;10(4): PMID: 31336757; PMCID: PMC6681521. 2: Ding H, Yu X, Hang C, Gao K, Lao X, Jia Y, Yan Z. Ailanthone: A novel potential drug for treating human cancer. Oncol Lett. 2020 Aug;20(2):1489-1503. doi: 10.3892/ol.2020.11710. Epub 2020 Jun 9. PMID: 32724391; PMCID: PMC7377054. 3: Yu P, Wei H, Li K, Zhu S, Li J, Chen C, Zhang D, Li Y, Zhu L, Yi X, Liu N, Liu P, Zhao S, Chen X, Peng C. 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 Dec 15;41(1):346. doi: 10.1186/s13046-022-02559-z. PMID: 36522774; PMCID: PMC9753288. 4: Bailly C. Anticancer properties and mechanism of action of the quassinoid ailanthone. Phytother Res. 2020 Sep;34(9):2203-2213. doi: 10.1002/ptr.6681. Epub 2020 Apr 1. PMID: 32239572. 5: Gao W, Ge S, Sun J. Retraction notice to "Ailanthone exerts anticancer effect by up-regulating miR-148a expression in MDA-MB-231 breast cancer cells and inhibiting proliferation, migration and invasion" [Biomed. Pharmacother. 109 (2019) 1062-1069]. Biomed Pharmacother. 2022 Jun;150:112854. doi: 10.1016/j.biopha.2022.112854. Epub 2022 Mar 24. PMID: 35341636. 6: Zhang Y, Zhang C, Min D. Retraction notice to "Ailanthone up-regulates miR-449a to restrain acute myeloid leukemia cells growth, migration and invasion" [Experimental and Molecular Pathology 108 (2019) 114-120]. Exp Mol Pathol. 2022 Jun;126:104776. doi: 10.1016/j.yexmp.2022.104776. Epub 2022 May 23. PMID: 35618520. 7: Wang S, Cui Q, Chen X, Zhu X, Lin K, Zheng Q, Wang Y, Li D. Ailanthone Inhibits Cell Proliferation in Tongue Squamous Cell Carcinoma via PI3K/AKT Pathway. Evid Based Complement Alternat Med. 2022 Nov 1;2022:3859489. doi: 10.1155/2022/3859489. PMID: 36387351; PMCID: PMC9643058. 8: Retraction. J Cell Biochem. 2021 Apr;122(3-4):489. doi: 10.1002/jcb.29880. Epub 2021 Jan 5. PMID: 33590513. 9: Wei C, Chen C, Cheng Y, Zhu L, Wang Y, Luo C, He Y, Yang Z, Ji Z. Ailanthone induces autophagic and apoptotic cell death in human promyelocytic leukemia HL-60 cells. Oncol Lett. 2018 Sep;16(3):3569-3576. doi: 10.3892/ol.2018.9101. Epub 2018 Jul 6. PMID: 30127963; PMCID: PMC6096173. 10: Zhang Y, Gong R, Liu Y, Sun X, Liang J, Zhou Y, Wang Y, Yu W, Wang Y, Tang L, He A, Shen Z, Yao Y, Hu H, Liu X, Zhang J. Ailanthone Inhibits Proliferation, Migration and Invasion of Osteosarcoma Cells by Downregulating the Serine Biosynthetic Pathway. Front Oncol. 2022 Feb 3;12:842406. doi: 10.3389/fonc.2022.842406. PMID: 35186770; PMCID: PMC8850634. 11: Ding H, Yu X, Yan Z. Ailanthone suppresses the activity of human colorectal cancer cells through the STAT3 signaling pathway. Int J Mol Med. 2022 Feb;49(2):21. doi: 10.3892/ijmm.2021.5076. Epub 2021 Dec 27. PMID: 34958109; PMCID: PMC8722763. 12: Hou S, Cheng Z, Wang W, Wang X, Wu Y. Ailanthone exerts an antitumor function on the development of human lung cancer by upregulating microRNA-195. J Cell Biochem. 2019 Jun;120(6):10444-10451. doi: 10.1002/jcb.28329. Epub 2018 Dec 19. Retraction in: J Cell Biochem. 2021 Apr;122(3-4):489. PMID: 30565729. 13: Chen Y, Zhu L, Yang X, Wei C, Chen C, He Y, Ji Z. Ailanthone induces G2/M cell cycle arrest and apoptosis of SGC‑7901 human gastric cancer cells. Mol Med Rep. 2017 Nov;16(5):6821-6827. doi: 10.3892/mmr.2017.7491. Epub 2017 Sep 13. PMID: 28901518; PMCID: PMC5865840. 14: Zhuo Z, Hu J, Yang X, Chen M, Lei X, Deng L, Yao N, Peng Q, Chen Z, Ye W, Zhang D. Ailanthone Inhibits Huh7 Cancer Cell Growth via Cell Cycle Arrest and Apoptosis In Vitro and In Vivo. Sci Rep. 2015 Nov 3;5:16185. doi: 10.1038/srep16185. PMID: 26525771; PMCID: PMC4630794. 15: Hopson CA, Natarajan P, Shinde S, Kshetry AO, Challa KR, Valenciana AP, Nimmakayala P, Reddy UK. Physiological and Transcriptomic Analysis of Arabidopsis thaliana Responses to Ailanthone, a Potential Bio-Herbicide. Int J Mol Sci. 2022 Oct 6;23(19):11854. doi: 10.3390/ijms231911854. PMID: 36233154; PMCID: PMC9570483. 16: Peng S, Yi Z, Liu M. Ailanthone: a new potential drug for castration- resistant prostate cancer. Chin J Cancer. 2017 Mar 3;36(1):25. doi: 10.1186/s40880-017-0194-7. PMID: 28257652; PMCID: PMC5336637. 17: Biomolecules Editorial Office. Retraction: Liu, W., et al. Ailanthone Induces Cell Cycle Arrest and Apoptosis in Melanoma B16 and A375 Cells. Biomolecules 2019, 9, 275. Biomolecules. 2020 Apr 17;10(4):627. doi: 10.3390/biom10040627. PMID: 32316691; PMCID: PMC7226567. 18: Cucci MA, Grattarola M, Dianzani C, Damia G, Ricci F, Roetto A, Trotta F, Barrera G, Pizzimenti S. Ailanthone increases oxidative stress in CDDP-resistant ovarian and bladder cancer cells by inhibiting of Nrf2 and YAP expression through a post-translational mechanism. Free Radic Biol Med. 2020 Apr;150:125-135. doi: 10.1016/j.freeradbiomed.2020.02.021. Epub 2020 Feb 23. PMID: 32101771. 19: Demasi S, Caser M, Fogliatto S, Vidotto F, Trotta F, Scariot V. Ailanthone inhibition data on seed germination and seedling growth of Lepidium sativum L. and Raphanus sativus L. Data Brief. 2019 Sep 23;26:104550. doi: 10.1016/j.dib.2019.104550. PMID: 31667308; PMCID: PMC6811969. 20: Hu P, Guo D, Xie J, Chen H, Hu S, Bian A, Xu S, Yi Z, Peng S, Liu M. Determining the Drug-Like Properties of Ailanthone, a Novel Chinese Medicine Monomer with Anti-CRPC Activity. Planta Med. 2020 May;86(7):482-488. doi: 10.1055/a-1125-0385. Epub 2020 Mar 13. PMID: 32168548.