Harringtonine
Harringtonine is a cephalotaxine alkaloid originally found in Cephalotaxus hainanensis Li; it exhibits antiviral and anticancer activities. Harringtonine immobilizes initiated ribosomes, inhibiting protein translation by binding the A site of the 60 S ribosomal subunit and preventing aminoacyl-tRNA binding. Harringtonine inhibits chikungunya virus infection, suppressing replication, RNA production, and viral protein expression. Alone, harringtonine downregulates production of Mcl-1, increases cleavage of PARP, and inhibits cell growth in acute promyelocytic leukemia (APL) cells. Additionally, this compound improves the efficacy of co-administered chemotherapeutic compounds, further inhibiting proliferation and inducing apoptosis in leukemia cells.
References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18930133
Cas No. |
26833-85-2 |
---|---|
Purity |
≥97% |
Formula |
C28H37NO9 |
Formula Wt. |
531.59 |
Synonym |
Cephalotaxine, 4-methyl (2R)-2-hydroxy-2-(3-hydroxy-3-methylbutyl)butanedioate (ester) (9CI) |
Melting Point |
73-75°C |
Solubility |
Does not mix well with water. Soluble in DMSO to 100 mM and in ethanol to 50 mM. |
Appearance |
White to off white powder |
Wu C, Shen H, Xia D. Harringtonine induces apoptosis in NB4 cells through down-regulation of Mcl-1. Zhejiang Da Xue Xue Bao Yi Xue Ban. 2013 Jul;42(4):431-6. PMID: 24022932.
Kaur P, Thiruchelvan M, Lee RC, et al. Inhibition of chikungunya virus replication by harringtonine, a novel antiviral that suppresses viral protein expression. Antimicrob Agents Chemother. 2013 Jan;57(1):155-67. PMID: 23275491.
Ingolia NT, Brar GA, Rouskin S, et al. The ribosome profiling strategy for monitoring translation in vivo by deep sequencing of ribosome-protected mRNA fragments. Nat Protoc. 2012 Jul 26;7(8):1534-50. PMID: 22836135.
Zhang C, Li Y, Ma H, et al. Simultaneous multi-parameter observation of Harringtonine-treating HL-60 cells with both two-photon and confocal laser scanning microscopy. Sci China C Life Sci. 2001 Aug;44(4):383-91. PMID: 18726419.
Fresno M, Jiménez A, Vázquez D. Inhibition of translation in eukaryotic systems by harringtonine. Eur J Biochem. 1977 Jan;72(2):323-30. PMID: 319998.