Artemisitene | CAS# 101020-89-7 | Anti-malarial

MedKoo Cat#: 573279 | Name: Artemisitene

Description:

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

Artemisitene, also known as ATT, is an antimalarial agent and the oxidized form of Artemisinin. Artemisitene suppresses tumorigenesis by inducing DNA damage through deregulating c-Myc-topoisomerase pathway. Artemisitene (ATT) is a natural derivative of the antimalarial drug artemisinin, selectively induces DNA double-stranded breaks (DSBs) and apoptosis in various human cancer cells by suppressing the expression of topoisomerases in human cancer cells. ATT effectively kills human cancer cells without apparent cytotoxicity on normal human cells or mouse liver and kidney. Artemisitene selectively destabilizes c-Myc in human cancer cells by promoting the ubiquitination of c-Myc through the specific induction of the c-Myc E3 ligase NEDD4.

Chemical Structure

Artemisitene

CAS#101020-89-7

Theoretical Analysis

MedKoo Cat#: 573279

Name: Artemisitene

CAS#: 101020-89-7

Chemical Formula: C15H20O5

Exact Mass: 280.1311

Molecular Weight: 280.32

Elemental Analysis: C, 64.27; H, 7.19; O, 28.54

Price and Availability

Size	Price	Availability
25mg	USD 750.00	2 Weeks
50mg	USD 1,350.00	2 Weeks
100mg	USD 1,950.00	2 Weeks
200mg	USD 2,950.00	2 Weeks
500mg	USD 4,650.00	2 Weeks

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Synonym

(+)-Artemisitene; Artemisitene; Dehydroqinghaosu; Methenyl-artemisinin; ATT.

IUPAC/Chemical Name

3,12-Epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one, octahydro-3,6-dimethyl-9-methylene-, (3R-(3alpha,5abeta,6beta,8abeta,12beta,12aR*))-

InChi Key

IGEBZMMCKFUABB-MHVOBNHCSA-N

InChi Code

1S/C15H20O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8,10-11,13H,2,4-7H2,1,3H3/t8-,10+,11?,13-,14-,15-/m1/s1

SMILES Code

C[C@@H]1CC[C@@H]2C(=C)C(=O)O[C@H]3[C@@]42OO[C@@](O3)(CC[C@@H]14)C

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Artemisitene suppresses tumorigenesis by inducing DNA damage through deregulating c-Myc-topoisomerase pathway.

In vitro activity:

To further verify activation of Nrf2-dependent antioxidant effects by artemisitene, MDA-MB-231 cells were pretreated with 2 μM artemisitene (AT) for 8 h, and challenged with 0.2 mM H2O2 for an additional 8 h. Then cellular ROS levels were examined by dichlorofluorescein staining. AT-pretreated cells had reduced ROS levels compared with control cells at 0.2 mM H2O2 challenge. Next, cellular survival rates were compared between the control and AT-pretreated cells when challenged with 1 mM H2O2. The results indicated that AT pretreatment significantly promoted cellular viability in response to high concentration of H2O2 compared with the control (survival rate 0.965 vs. 0.499). All these data strongly demonstrated that artemisitene can effectively protect cells from oxidative stress by activation of the Nrf2 pathway. Reference: FASEB J. 2016 Jul;30(7):2500-10. https://pubmed.ncbi.nlm.nih.gov/27006451/

In vivo activity:

To further explore the potential cytoprotective activity of artemisitene (AT) in vivo, artemisitene was tested in a BLM-induced lung injury mouse model. It was demonstrated that systemic delivery of artemisitene (10 mg/kg, i.p.) is effective in activating the Nrf2-dependent response in lung tissue of B6 mice. At 48 h after intraperitoneal injection of artemisitene, pulmonary protein levels of Nrf2 were up-regulated. Consistent with this, mRNA levels of Nrf2 downstream genes NQO1 and HO-1 also increased. Next, it was tested whether artemisitene can effectively protect against BLM-induced lung injury. B6 Mice were injected intraperitoneally with 2 mg BLM once every week for 3 wk. At 48 h before BLM injection, mice received systemic treatment with PBS or 10 mg/kg AT. At 7 d after the third injection of BLM, lung tissues were isolated and subjected to HE staining. HE staining revealed that BLM induced pulmonary pathologic alteration, and artemisitene pretreatment significantly reduced BLM-induced pulmonary pathologic alteration. In addition, artemisitene itself cannot induce any pathologic alteration in lung and other organs, including liver and kidney, indicating that artemisitene shows no toxicity at a 10 mg/kg dose. Artemisitene can effectively protect mice from BLM-induced lung injury by inducing activation of the Nrf2-dependent pathway. Reference: FASEB J. 2016 Jul;30(7):2500-10. https://pubmed.ncbi.nlm.nih.gov/27006451/

	Solvent	mg/mL	mM
Solubility
	DMSO	0.0	0.00

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 280.32 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. Chen W, Li S, Li J, Zhou W, Wu S, Xu S, Cui K, Zhang DD, Liu B. Artemisitene activates the Nrf2-dependent antioxidant response and protects against bleomycin-induced lung injury. FASEB J. 2016 Jul;30(7):2500-10. doi: 10.1096/fj.201500109R. Epub 2016 Mar 22. PMID: 27006451. 2. Chen J, Li W, Cui K, Ji K, Xu S, Xu Y. Artemisitene suppresses tumorigenesis by inducing DNA damage through deregulating c-Myc-topoisomerase pathway. Oncogene. 2018 Sep;37(37):5079-5087. doi: 10.1038/s41388-018-0331-z. Epub 2018 May 24. PMID: 29795406.

In vitro protocol:

In vivo protocol:

1: Cheong DHJ, Tan DWS, Wong FWS, Tran T. Anti-malarial drug, artemisinin and its derivatives for the treatment of respiratory diseases. Pharmacol Res. 2020 Aug;158:104901. doi: 10.1016/j.phrs.2020.104901. Epub 2020 May 13. PMID: 32405226; PMCID: PMC7217791. 2: Liu S, Xu S, Wei R, Cui Z, Wu X, Wei R, Xie L, Zhou Y, Li W, Chen W. Keap1 Cystenine 151 as a Potential Target for Artemisitene-Induced Nrf2 Activation. Biomed Res Int. 2019 Oct 15;2019:5198138. doi: 10.1155/2019/5198138. PMID: 31737667; PMCID: PMC6815614. 3: Pratap S, Naaz F, Reddy S, Jha KK, Sharma K, Sahal D, Akhter M, Nayakanti D, Kumar HMS, Kumari V, Pandey K, Shafi S. Anti-proliferative and anti-malarial activities of spiroisoxazoline analogues of artemisinin. Arch Pharm (Weinheim). 2018 Dec 10:e1800192. doi: 10.1002/ardp.201800192. Epub ahead of print. PMID: 30537298. 4: Czechowski T, Larson TR, Catania TM, Harvey D, Wei C, Essome M, Brown GD, Graham IA. Detailed Phytochemical Analysis of High- and Low Artemisinin- Producing Chemotypes of Artemisia annua. Front Plant Sci. 2018 May 18;9:641. doi: 10.3389/fpls.2018.00641. PMID: 29868094; PMCID: PMC5968107. 5: Chen J, Li W, Cui K, Ji K, Xu S, Xu Y. Artemisitene suppresses tumorigenesis by inducing DNA damage through deregulating c-Myc-topoisomerase pathway. Oncogene. 2018 Sep;37(37):5079-5087. doi: 10.1038/s41388-018-0331-z. Epub 2018 May 24. PMID: 29795406. 6: Wu LL, Wu YS, Chen WY, Zhou W, Tang L, Li B, Liu B. Determination of artemisitene in rat plasma by ultra-performance liquid chromatography/tandem mass spectrometry and its application in pharmacokinetics. Rapid Commun Mass Spectrom. 2017 Jul 15;31(13):1121-1128. doi: 10.1002/rcm.7881. PMID: 28403574. 7: Chen W, Li S, Li J, Zhou W, Wu S, Xu S, Cui K, Zhang DD, Liu B. Artemisitene activates the Nrf2-dependent antioxidant response and protects against bleomycin-induced lung injury. FASEB J. 2016 Jul;30(7):2500-10. doi: 10.1096/fj.201500109R. Epub 2016 Mar 22. PMID: 27006451. 8: Ooko E, Saeed ME, Kadioglu O, Sarvi S, Colak M, Elmasaoudi K, Janah R, Greten HJ, Efferth T. Artemisinin derivatives induce iron-dependent cell death (ferroptosis) in tumor cells. Phytomedicine. 2015 Oct 15;22(11):1045-54. doi: 10.1016/j.phymed.2015.08.002. Epub 2015 Aug 18. PMID: 26407947. 9: Liu G, Song S, Shu S, Miao Z, Zhang A, Ding C. Novel spirobicyclic artemisinin analogues (artemalogues): Synthesis and antitumor activities. Eur J Med Chem. 2015 Oct 20;103:17-28. doi: 10.1016/j.ejmech.2015.08.035. Epub 2015 Aug 18. PMID: 26318055. 10: Suberu JO, Gorka AP, Jacobs L, Roepe PD, Sullivan N, Barker GC, Lapkin AA. Anti-plasmodial polyvalent interactions in Artemisia annua L. aqueous extract-- possible synergistic and resistance mechanisms. PLoS One. 2013 Nov 14;8(11):e80790. doi: 10.1371/journal.pone.0080790. Erratum in: PLoS One. 2013;8(11). doi:10.1371/annotation/57ae25b0-d2c8-444b-ab62-f047c5f3e01e. PMID: 24244716; PMCID: PMC3828274. 11: Suberu J, Song L, Slade S, Sullivan N, Barker G, Lapkin AA. A rapid method for the determination of artemisinin and its biosynthetic precursors in Artemisia annua L. crude extracts. J Pharm Biomed Anal. 2013 Oct;84:269-77. doi: 10.1016/j.jpba.2013.06.025. Epub 2013 Jun 28. PMID: 23867088. 12: Efferth T, Herrmann F, Tahrani A, Wink M. Cytotoxic activity of secondary metabolites derived from Artemisia annua L. towards cancer cells in comparison to its designated active constituent artemisinin. Phytomedicine. 2011 Aug 15;18(11):959-69. doi: 10.1016/j.phymed.2011.06.008. Epub 2011 Aug 9. PMID: 21831619. 13: Kawamoto H, Sekine H, Furuya T. Production of Artemisinin and Related Sesquiterpenes in Japanese Artemisia annua During a Vegetation Period. Planta Med. 1999 Feb;65(1):88-9. doi: 10.1055/s-2006-960449. PMID: 17260242. 14: Haynes RK. From artemisinin to new artemisinin antimalarials: biosynthesis, extraction, old and new derivatives, stereochemistry and medicinal chemistry requirements. Curr Top Med Chem. 2006;6(5):509-37. doi: 10.2174/156802606776743129. PMID: 16719805. 15: Van Nieuwerburgh FC, Vande Casteele SR, Maes L, Goossens A, Inzé D, Van Bocxlaer J, Deforce DL. Quantitation of artemisinin and its biosynthetic precursors in Artemisia annua L. by high performance liquid chromatography- electrospray quadrupole time-of-flight tandem mass spectrometry. J Chromatogr A. 2006 Jun 23;1118(2):180-7. doi: 10.1016/j.chroma.2006.03.121. Epub 2006 May 2. PMID: 16650427. 16: Efferth T, Oesch F. Oxidative stress response of tumor cells: microarray- based comparison between artemisinins and anthracyclines. Biochem Pharmacol. 2004 Jul 1;68(1):3-10. doi: 10.1016/j.bcp.2004.03.003. PMID: 15183112. 17: Jung M, Lee K, Kim H, Park M. Recent advances in artemisinin and its derivatives as antimalarial and antitumor agents. Curr Med Chem. 2004 May;11(10):1265-84. doi: 10.2174/0929867043365233. PMID: 15134519. 18: Avery MA, Muraleedharan KM, Desai PV, Bandyopadhyaya AK, Furtado MM, Tekwani BL. Structure-activity relationships of the antimalarial agent artemisinin. 8. design, synthesis, and CoMFA studies toward the development of artemisinin-based drugs against leishmaniasis and malaria. J Med Chem. 2003 Sep 25;46(20):4244-58. doi: 10.1021/jm030181q. PMID: 13678403. 19: Avery MA, Alvim-Gaston M, Vroman JA, Wu B, Ager A, Peters W, Robinson BL, Charman W. Structure-activity relationships of the antimalarial agent artemisinin. 7. Direct modification of (+)-artemisinin and in vivo antimalarial screening of new, potential preclinical antimalarial candidates. J Med Chem. 2002 Sep 12;45(19):4321-35. doi: 10.1021/jm020142z. PMID: 12213073. 20: Ekthawatchai S, Kamchonwongpaisan S, Kongsaeree P, Tarnchompoo B, Thebtaranonth Y, Yuthavong Y. C-16 artemisinin derivatives and their antimalarial and cytotoxic activities: syntheses of artemisinin monomers, dimers, trimers, and tetramers by nucleophilic additions to artemisitene. J Med Chem. 2001 Dec 20;44(26):4688-95. doi: 10.1021/jm0103007. PMID: 11741486.