Harringtonine
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MedKoo CAT#: 540191

CAS#: 26833-85-2

Description: Harringtonine is found in Cephalotaxuts. It immobilizes initiated ribtosomes, inhibiting protein translation by blocking the ribosomal A site. It suppresses viral replication and protein expression in chikungunya virus infection, inhibits cell growth in actue promyelocytic leukemia cells, and induces apoptosis in leukemia cells.


Price and Availability

Size
Price

10mg
USD 250
100mg
USD 950
Size
Price

25mg
USD 450
Size
Price

50mg
USD 650

Harringtonine, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 540191
Name: Harringtonine
CAS#: 26833-85-2
Chemical Formula: C28H37NO9
Exact Mass: 531.2468
Molecular Weight: 531.6
Elemental Analysis: C, 63.26; H, 7.02; N, 2.63; O, 27.09


Synonym: 2'R-Harringtonine; Harringtonine; Alkaloid C from cephalotaxus; NSC 124147; NSC-124147; NSC124147.

IUPAC/Chemical Name: 1-((1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-1-yl) 4-methyl (R)-2-hydroxy-2-(3-hydroxy-3-methylbutyl)succinate

InChi Key: HAVJATCHLFRDHY-KSZYUSJVSA-N

InChi Code: InChI=1S/C28H37NO9/c1-26(2,32)8-9-28(33,15-22(30)35-4)25(31)38-24-21(34-3)14-27-7-5-10-29(27)11-6-17-12-19-20(37-16-36-19)13-18(17)23(24)27/h12-14,23-24,32-33H,5-11,15-16H2,1-4H3/t23-,24-,27+,28-/m1/s1

SMILES Code: O=C(O[C@@H]1C(OC)=C[C@]2(CCC3)N3CCC4=CC5=C(OCO5)C=C4[C@@]21[H])[C@](CCC(C)(O)C)(O)CC(OC)=O


Technical Data

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:
>2 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).

Harmonized System Code:
293490


References

1: Kaur P, Thiruchelvan M, Lee RC, Chen H, Chen KC, Ng ML, Chu JJ. Inhibition of chikungunya virus replication by harringtonine, a novel antiviral that suppresses viral protein expression. Antimicrob Agents Chemother. 2013 Jan;57(1):155-67. doi: 10.1128/AAC.01467-12. Epub 2012 Oct 22. PubMed PMID: 23275491; PubMed Central PMCID: PMC3535938.

2: Moirangthem DS, Borah JC, Laishram S, Kalita MC, Talukdar NC. HPLC analysis of harringtonine and homoharringtonine in the needles of Cephalotaxus griffithii alkaloid fraction and cytotoxic activity on chronic myelogenous leukaemia K562 cell. Nat Prod Res. 2014;28(18):1503-6. doi: 10.1080/14786419.2014.913241. Epub 2014 Apr 30. PubMed PMID: 24787645.

3: Yang H, Sun M, Zhao S, Zhu M, Xie Y, Niu C, Li C. Construction of chiral tertiary alcohol stereocenters via the [2,3]-Meisenheimer rearrangement: enantioselective synthesis of the side-chain acids of homoharringtonine and harringtonine. J Org Chem. 2013 Jan 18;78(2):339-46. doi: 10.1021/jo302203g. Epub 2012 Dec 18. PubMed PMID: 23214949.

4: 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. Chinese. PubMed PMID: 24022932.

5: Ingolia NT, Brar GA, Rouskin S, McGeachy AM, Weissman JS. 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. doi: 10.1038/nprot.2012.086. PubMed PMID: 22836135; PubMed Central PMCID: PMC3535016.

6: Cao W, Liu Y, Zhang R, Zhang B, Wang T, Zhu X, Mei L, Chen H, Zhang H, Ming P, Huang L. Homoharringtonine induces apoptosis and inhibits STAT3 via IL-6/JAK1/STAT3 signal pathway in Gefitinib-resistant lung cancer cells. Sci Rep. 2015 Jul 13;5:8477. doi: 10.1038/srep08477. PubMed PMID: 26166037; PubMed Central PMCID: PMC4499885.

7: Zheng C, Cai X, Wu S, Liu Z, Shi Y, Zhou W. Enhancing effect of β-elemene emulsion on chemotherapy with harringtonine, aclacinomycin, and Ara-c in treatment of refractory/relapsed acute myeloid leukemia. Pak J Med Sci. 2014 Nov-Dec;30(6):1270-2. doi: 10.12669/pjms.306.5207. PubMed PMID: 25674121; PubMed Central PMCID: PMC4320713.

8: Jiang X, Wang Z, Ding B, Yin C, Zhong Q, Carter BZ, Yu G, Jiang L, Ye J, Dai M, Zhang Y, Liang S, Zhao Q, Liu Q, Meng F. The hypomethylating agent decitabine prior to chemotherapy improves the therapy efficacy in refractory/relapsed acute myeloid leukemia patients. Oncotarget. 2015 Oct 20;6(32):33612-22. doi: 10.18632/oncotarget.5600. PubMed PMID: 26384351; PubMed Central PMCID: PMC4741789.

9: Trendowski M. Recent Advances in the Development of Antineoplastic Agents Derived from Natural Products. Drugs. 2015 Nov;75(17):1993-2016. doi: 10.1007/s40265-015-0489-4. Review. PubMed PMID: 26501980; PubMed Central PMCID: PMC4642600.

10: Ingolia NT, Lareau LF, Weissman JS. Ribosome profiling of mouse embryonic stem cells reveals the complexity and dynamics of mammalian proteomes. Cell. 2011 Nov 11;147(4):789-802. doi: 10.1016/j.cell.2011.10.002. Epub 2011 Nov 3. PubMed PMID: 22056041; PubMed Central PMCID: PMC3225288.

11: Omacetaxine (Synribo) for CML. Med Lett Drugs Ther. 2015 May 25;57(1469):e80-1. PubMed PMID: 26039555.

12: Fresno M, Jiménez A, Vázquez D. Inhibition of translation in eukaryotic systems by harringtonine. Eur J Biochem. 1977 Jan;72(2):323-30. PubMed PMID: 319998.

13: Biever A, Puighermanal E, Nishi A, David A, Panciatici C, Longueville S, Xirodimas D, Gangarossa G, Meyuhas O, Hervé D, Girault JA, Valjent E. PKA-dependent phosphorylation of ribosomal protein S6 does not correlate with translation efficiency in striatonigral and striatopallidal medium-sized spiny neurons. J Neurosci. 2015 Mar 11;35(10):4113-30. doi: 10.1523/JNEUROSCI.3288-14.2015. PubMed PMID: 25762659.

14: Yamamoto S, Hui PZ, Fukuda Y, Tatsumi K, Mino M. Potentiation of harringtonine cytotoxicity by calcium antagonist diltiazem and biscoclaurine alkaloid cepharanthine in adriamycin-resistant P388 murine leukemia and K562 human leukemia cells. Biochem Int. 1989 Jun;18(6):1077-83. PubMed PMID: 2751676.

15: Liu H, Yu J, Li X, Yan R, Xiao JC, Hong R. Stereoselectivity in N-Iminium Ion Cyclization: Development of an Efficient Synthesis of (±)-Cephalotaxine. Org Lett. 2015 Sep 18;17(18):4444-7. doi: 10.1021/acs.orglett.5b02106. Epub 2015 Sep 2. PubMed PMID: 26332648.

16: Jiang TL, Liu RH, Salmon SE. Comparative in vitro antitumor activity of homoharringtonine and harringtonine against clonogenic human tumor cells. Invest New Drugs. 1983;1(1):21-5. PubMed PMID: 6678854.

17: Damlaj M, Assouline S. Is there a role for omacetaxine in the management of chronic myelogenous leukemia in the era of the tyrosine kinase inhibitors? Leuk Lymphoma. 2015 Jan;56(1):6-7. doi: 10.3109/10428194.2014.918972. Epub 2014 Jun 25. PubMed PMID: 24898667.

18: Geng S, Yao H, Weng J, Tong J, Huang X, Wu P, Deng C, Li M, Lu Z, Du X. Effects of the combination of decitabine and homoharringtonine in SKM-1 and Kg-1a cells. Leuk Res. 2016 May;44:17-24. doi: 10.1016/j.leukres.2016.02.002. Epub 2016 Feb 16. PubMed PMID: 26991610.

19: Al Ustwani O, Griffiths EA, Wang ES, Wetzler M. Omacetaxine mepesuccinate in chronic myeloid leukemia. Expert Opin Pharmacother. 2014 Nov;15(16):2397-405. doi: 10.1517/14656566.2014.964642. Review. PubMed PMID: 25301179.

20: Piao YF, Okabe T, Zhang LJ. [Growth inhibition of human myeloid leukemia cells in vitro by harringtonine]. Gan To Kagaku Ryoho. 1990 Feb;17(2):281-5. Japanese. PubMed PMID: 2301953.