Harringtonine

CAS# 26833-85-2

Harringtonine

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Quality Control of Harringtonine

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Chemical structure

Harringtonine

3D structure

Chemical Properties of Harringtonine

Cas No. 26833-85-2 SDF Download SDF
PubChem ID 276389 Appearance Powder
Formula C28H37NO9 M.Wt 531.6
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility DMSO : ≥ 100 mg/mL (188.11 mM)
*"≥" means soluble, but saturation unknown.
SMILES CC(C)(CCC(CC(=O)OC)(C(=O)OC1C2C3=CC4=C(C=C3CCN5C2(CCC5)C=C1OC)OCO4)O)O
Standard InChIKey HAVJATCHLFRDHY-KSZYUSJVSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Harringtonine

The branch of Cephalotaxus fortunei Hook.f.

Biological Activity of Harringtonine

DescriptionHarringtonine , an anticancer drug with high chemotherapeutic efficiency to human chronic granulocytic/myelomonocytic leukemia, has been reported to rapidly induce apoptosis in HL-60 cells in a wide scope/range of dosage by investigators from our lab and others. Harringtonine exerts its antiviral effects by inhibiting Chikungunya virus (CHIKV) viral protein synthesis.
TargetsCalcium Channel | Antifection
In vitro

Intracellular calcium distribution in apoptosis of HL-60 cells induced by harringtonine: intranuclear accumulation and regionalization.[Pubmed: 9619866]

Cancer Lett. 1998 May 15;127(1-2):113-21.

Harringtonine (HT), an anticancer drug with high chemotherapeutic efficiency to human chronic granulocytic/myelomonocytic leukemia, has been reported to rapidly induce apoptosis in HL-60 cells in a wide scope/range of dosage by investigators from our lab and others.
METHODS AND RESULTS:
In the present studies, by using video enhancement contrast (VEC) microscopy, we dynamically analyzed changes in intracellular calcium distribution in a single HL-60 cell over the period from the initiation of apoptosis to the obvious appearance of chromatin condensation. The results from this paper demonstrated the striking distinction of intracellular calcium distribution at different time points after treatment with HT. Before treatment in normal HL-60 cells the highest [Ca2+]i accumulation was observed in the peri-nuclear area and the lowest was observed in the nucleus; after treatment with 1 microg/ml HT for 30 min intracellular calcium diffused all over the cell compartments, while intranuclear calcium increased comparatively and significantly. The phenomenon of intranuclear calcium accumulation was further confirmed by using laser scanning confocal microscopy (LSCM). In addition, co-localization of the highest calcium region with condensed chromatin in apoptotic HL-60 cells was also observed by LSCM.
CONCLUSIONS:
Our results suggest that two sequential alterations of intracellular calcium distribution occurred in apoptotic HL-60 cells induced by HT, i.e. (a) accumulation of calcium in the nucleus and (b) regionalization in a specific nuclear region.

Inhibition of Chikungunya Virus Replication by Harringtonine, a Novel Antiviral That Suppresses Viral Protein Expression[Reference: WebLink]

Antimicrob. Agents Chemother., 2013, 57(1): 155-67.

Chikungunya virus (CHIKV) is a mosquito-transmitted virus that has reemerged as a significant public health threat in the last decade.
METHODS AND RESULTS:
Harringtonine, a cephalotaxine alkaloid, displayed potent inhibition of CHIKV infection (50% effective concentration [EC50] = 0.24 μM) with minimal cytotoxicity and was selected for elucidation of its antiviral mechanism. Time-of-addition studies, cotreatment assays, and direct transfection of viral genomic RNA indicated that Harringtonine inhibited an early stage of the CHIKV replication cycle which occurred after viral entry into cells. In addition, quantitative reverse transcription-PCR (qRT-PCR) and Western blot analyses indicated that Harringtonine affects CHIKV RNA production as well as viral protein expression.
CONCLUSIONS:
Treatment of Harringtonine against Sindbis virus, a related alphavirus, suggested that Harringtonine could inhibit other alphaviruses. This study suggests for the first time that Harringtonine exerts its antiviral effects by inhibiting CHIKV viral protein synthesis.

Harringtonine Dilution Calculator

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Preparing Stock Solutions of Harringtonine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.8811 mL 9.4056 mL 18.8111 mL 37.6223 mL 47.0278 mL
5 mM 0.3762 mL 1.8811 mL 3.7622 mL 7.5245 mL 9.4056 mL
10 mM 0.1881 mL 0.9406 mL 1.8811 mL 3.7622 mL 4.7028 mL
50 mM 0.0376 mL 0.1881 mL 0.3762 mL 0.7524 mL 0.9406 mL
100 mM 0.0188 mL 0.0941 mL 0.1881 mL 0.3762 mL 0.4703 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Harringtonine

Harringtonine, a natural Cephalotaxus alkaloid, is an inhibitor of protein synthesis.

In Vitro:Harringtonine inhibits the elongation phase of translation by preventing substrate binding to the acceptor site on the 60-S ribosome subunit and therefore block aminoacyl-tRNA binding and peptide bond formation[1]. Harringtonine displays potent inhibition of Chikungunya virus infection with an EC50 of 0.24 μM. Harringtonine could inhibit other alphaviruses[2]. Harringtonine inhibits the growth of human myeloid leukemia cells in vitro at low concentrations. The mechanism of the antitumor action of harringtonine is considered to be an effect on protein synthesis and is characterized by breakdown of polysomes to monosomes[3].

References:
[1]. Fresno M, et al. Inhibition of translation in eukaryotic systems by harringtonine. Eur J Biochem. 1977 Jan;72(2):323-30. [2]. Kaur P, 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. [3]. Piao YF, et al. Growth inhibition of human myeloid leukemia cells in vitro by harringtonine. Gan To Kagaku Ryoho. 1990 Feb;17(2):281-5.

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References on Harringtonine

Intracellular calcium distribution in apoptosis of HL-60 cells induced by harringtonine: intranuclear accumulation and regionalization.[Pubmed:9619866]

Cancer Lett. 1998 May 15;127(1-2):113-21.

Harringtonine (HT), an anticancer drug with high chemotherapeutic efficiency to human chronic granulocytic/myelomonocytic leukemia, has been reported to rapidly induce apoptosis in HL-60 cells in a wide scope/range of dosage by investigators from our lab and others. In the present studies, by using video enhancement contrast (VEC) microscopy, we dynamically analyzed changes in intracellular calcium distribution in a single HL-60 cell over the period from the initiation of apoptosis to the obvious appearance of chromatin condensation. The results from this paper demonstrated the striking distinction of intracellular calcium distribution at different time points after treatment with HT. Before treatment in normal HL-60 cells the highest [Ca2+]i accumulation was observed in the peri-nuclear area and the lowest was observed in the nucleus; after treatment with 1 microg/ml HT for 30 min intracellular calcium diffused all over the cell compartments, while intranuclear calcium increased comparatively and significantly. The phenomenon of intranuclear calcium accumulation was further confirmed by using laser scanning confocal microscopy (LSCM). In addition, co-localization of the highest calcium region with condensed chromatin in apoptotic HL-60 cells was also observed by LSCM. Our results suggest that two sequential alterations of intracellular calcium distribution occurred in apoptotic HL-60 cells induced by HT, i.e. (a) accumulation of calcium in the nucleus and (b) regionalization in a specific nuclear region.

Description

Harringtonine is a natural Cephalotaxus alkaloid that inhibits protein synthesis. Harringtonine has anti-chikungunya virus (CHIKV) activities with an EC50 of 0.24 μM.

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