Harringtonine

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

Cat No.:V20830 Purity: ≥98%

COA Product Data Instructions for use SDS

Harringtonine is anatural Cephalotaxus alkaloid found in Cephalotaxuts.

Harringtonine Chemical Structure CAS No.: 26833-85-2
Product category: Influenza Virus

This product is for research use only, not for human use. We do not sell to patients.

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Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Biological Data

Product Description

Harringtonine is a natural Cephalotaxus alkaloid 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.

Biological Activity I Assay Protocols (From Reference)

ln Vitro	By blocking substrate binding to the acceptor site on the 60-S ribosome subunit, harringtonine inhibits the elongation phase of translation by preventing aminoacyl-tRNA binding and the formation of peptide bonds[1]. With an EC50 of 0.24 μM, harringtonine exhibits strong inhibition of Chikungunya virus infection. Other alphaviruses may be inhibited by harringtonine[2]. At low concentrations, haltrine inhibits the growth of human myeloid leukemia cells in vitro. The breakdown of polysomes into monosomes is thought to be the hallmark of harringtonine's antitumor action mechanism, which is thought to be based on an impact on protein synthesis[3].
References	[1]. Inhibition of translation in eukaryotic systems by harringtonine. Eur J Biochem. 1977 Jan;72(2):323-30. [2]. 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]. Growth inhibition of human myeloid leukemia cells in vitro by harringtonine. Gan To Kagaku Ryoho. 1990 Feb;17(2):281-5.

ln Vitro

By blocking substrate binding to the acceptor site on the 60-S ribosome subunit, harringtonine inhibits the elongation phase of translation by preventing aminoacyl-tRNA binding and the formation of peptide bonds[1]. With an EC50 of 0.24 μM, harringtonine exhibits strong inhibition of Chikungunya virus infection. Other alphaviruses may be inhibited by harringtonine[2]. At low concentrations, haltrine inhibits the growth of human myeloid leukemia cells in vitro. The breakdown of polysomes into monosomes is thought to be the hallmark of harringtonine's antitumor action mechanism, which is thought to be based on an impact on protein synthesis[3].

References

[1]. Inhibition of translation in eukaryotic systems by harringtonine. Eur J Biochem. 1977 Jan;72(2):323-30.

[2]. 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]. Growth inhibition of human myeloid leukemia cells in vitro by harringtonine. Gan To Kagaku Ryoho. 1990 Feb;17(2):281-5.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula	C28H37NO9
Molecular Weight	531.5947
Exact Mass	531.25
Elemental Analysis	C, 63.26; H, 7.02; N, 2.63; O, 27.09
CAS #	26833-85-2
Appearance	Solid powder
SMILES	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
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
Chemical Name	1-((1S,3aR,14bS)-2-methoxy-1,5,6,8,9,14b-hexahydro-4H-[1,3]dioxolo[4',5'
Synonyms	2'R-Harringtonine; Harringtonine; Alkaloid C from cephalotaxus; NSC 124147; NSC-124147; NSC124147.
HS Tariff Code	2934.99.9001
Storage	Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)	DMSO : ~100 mg/mL ( ~188.11 mM ) Ethanol : ~100 mg/mL
Solubility (In Vivo)	Solubility in Formulation 1: ≥ 2.5 mg/mL (4.70 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (4.70 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More Solubility in Formulation 3: ≥ 2.5 mg/mL (4.70 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (4.70 mM) (Please use freshly prepared in vivo formulations for optimal results.)

Solubility (In Vitro)

DMSO : ~100 mg/mL ( ~188.11 mM )
Ethanol : ~100 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (4.70 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (4.70 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

View More

Solubility in Formulation 3: ≥ 2.5 mg/mL (4.70 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (4.70 mM)

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.8811 mL	9.4057 mL	18.8115 mL
	5 mM	0.3762 mL	1.8811 mL	3.7623 mL
	10 mM	0.1881 mL	0.9406 mL	1.8811 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Mass

Concentration

Volume

Molecular Weight*

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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Concentration (End)

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

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g/mol

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Biological Data

Dose-dependent inhibition of ribavirin on CHIKV infectivity shown using immunofluorescence assay. [2].Antimicrob Agents Chemother. 2013 Jan;57(1):155-67.
Dose-dependent study of anti-CHIKV activities of selected compounds from a primary high-throughput screen as observed via plaque assay. [2].Antimicrob Agents Chemother. 2013 Jan;57(1):155-67.
Dose-dependent studies of antiviral activities of harringtonine and homoharringtonine against both CHIKV strains.[2].Antimicrob Agents Chemother. 2013 Jan;57(1):155-67.
Antiviral effect of harringtonine on CHIKV infection of HSMM (primary human skeletal myoblasts), an in vivo target of CHIKV infection. [2].Antimicrob Agents Chemother. 2013 Jan;57(1):155-67.
(a) BHK21 cells were treated with harringtonine at different time points before and after infection in time-of addition studies. [2].Antimicrob Agents Chemother. 2013 Jan;57(1):155-67.
Western blot analyses were performed to determine the effect of harringtonine on production of CHIKV nsP3 and E2 proteins. [2].Antimicrob Agents Chemother. 2013 Jan;57(1):155-67.