Artemisitene

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.

Product information

CAS Number: 101020-89-7

Molecular Weight: 280.32

Formula: C15H20O5

Synonym:

(+)-Artemisitene

Artemisitene

Dehydroqinghaosu

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*))-

Smiles: C[C@@]12CC[C@H]3[C@H](C)CC[C@@H]4C(=C)C(=O)O[C@H](O1)[C@]43OO2

InChiKey: IGEBZMMCKFUABB-WJYBAWFFSA-N

InChi: InChI=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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: To be determined

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

References:

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.

Products are for research use only. Not for human use.