Teniposide (VM-26)

Alias: VM26; NSC-122819; VM-26; HSDB 6546; NSC 122819; VM 26; HSDB-6546; NSC122819; HSDB6546; CCRIS 2058. Trade name: Vumon; Vehem. Abbreviations: EPT; PTG

Cat No.:V1406 Purity: ≥98%

COA Product Data Instructions for use SDS

Teniposide (VM-26) Chemical Structure CAS No.: 29767-20-2
Product category: Topoisomerase

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

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Citations by Top Journals: Nature, Cell, Science, etc.

Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

Cell Reports 2023,42(4):112313

Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Teniposide (VM-26; HSDB-6546; NSC-122819; CCRIS-2058; Vumon; Vehem; EPT; PTG) is a semisynthetic podophyllotoxin derivative and chemotherapeutic agent mainly used in the treatment of childhood acute lymphocytic leukemia (ALL). It functions by combining with DNA and the enzyme topoisomerase II to form a ternary complex. This complex causes dose-dependent breaks in DNA, both single and double stranded, as well as protein cross-links, inhibition of DNA strand religation, and cytotoxicity. Teniposide acts during the cell cycle's late S or early G phases.

Biological Activity I Assay Protocols (From Reference)

Targets	Topoisomerase II
ln Vitro	Teniposide is a topoisomerase II inhibitor. Teniposide (VM-26, 0.15–45 mg/L) has an IC50 of 0.35 mg/L and inhibits Tca8113 cell proliferation in a dose-dependent manner. Tca8113 cells undergo apoptosis when exposed to 5 mg/L of Teniposide. Cells in Tca8113 cells are arrested at the G2/M phase by Teniposide (5.0 mg/L)[2]. With an IC50 of 1.3?±?0.34 μg/mL, Teniposide is active on patient-derived primary cultured glioma cells when the cells have a high level of miR-181b. In comparison to control cells, Teniposide-treated cells exhibit reduced viability, and when MDM2 is suppressed, the IC50 drops from 5.86?±?0.36 μg/mL to 2.90?±?0.35 μg/mL. Via the mediation of MDM2, Teniposide also reduces the viability of glioma cells expressing high levels of miR-181b[3].
ln Vivo	Teniposide (0.5 mg/kg, i.p.) profoundly raises the frequencies of micronucleated polychromatic erythrocytes (MNPCEs), a finding that is directly linked to bone marrow toxicity due to the significant suppression of bone marrow. The frequencies of BrdU-labeled sperm are significantly reduced by Teniposide (24 mg/kg, i.p.). Additionally, Teniposide (12, 24 mg/kg, i.p.) significantly induces disomic sperm in male mouse germ cells[1].
References	[1]. Molecular cytogenetic evaluation of the aneugenic effects of teniposide in somatic and germinal cells of male mice. Mutagenesis. 2012 Jan;27(1):31-9. [2]. Topoisomerase II trapping agent teniposide induces apoptosis and G2/M or S phase arrest of oral squamous cell carcinoma. World J Surg Oncol. 2006 Jul 6;4:41. [3]. MiR-181b sensitizes glioma cells to teniposide by targeting MDM2. BMC Cancer. 2014 Aug 25;14:611.

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

Physicochemical Properties

Molecular Formula

C32H32O13S

Molecular Weight

656.65

Exact Mass

656.16

Elemental Analysis

C, 58.53; H, 4.91; O, 31.67; S, 4.88

CAS #

29767-20-2

Related CAS #

29767-20-2

Appearance

Solid powder

SMILES

COC1=CC(=CC(=C1O)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@@H](C4=CC5=C(C=C24)OCO5)O[C@H]6[C@@H]([C@H]([C@H]7[C@H](O6)CO[C@H](O7)C8=CC=CS8)O)O

InChi Key

NRUKOCRGYNPUPR-QBPJDGROSA-N

InChi Code

InChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31+,32-/m0/s1

Chemical Name

(5S,5aR,8aR,9R)-5-[[(2R,4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one

Synonyms

VM26; NSC-122819; VM-26; HSDB 6546; NSC 122819; VM 26; HSDB-6546; NSC122819; HSDB6546; CCRIS 2058. Trade name: Vumon; Vehem. Abbreviations: EPT; PTG

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: ~40 mg/mL (~60.9 mM)

Water: <1 mg/mL

Ethanol: <1 mg/mL

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.5229 mL	7.6144 mL	15.2288 mL
	5 mM	0.3046 mL	1.5229 mL	3.0458 mL
	10 mM	0.1523 mL	0.7614 mL	1.5229 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.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (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

Total molecular weight

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.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

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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.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
Recruiting	Completed	Drug: Teniposide	HLH	Beijing Friendship Hospital	October 22, 2023	Not Applicable
NCT00004916	Completed	Drug: teniposide Drug: paclitaxel	Lymphoma	Northwestern University	February 1999	Phase 1 Phase 2
NCT00186875	Completed	Drug: methotrexate, teniposide, PEG-asparaginase Drug: L-asparaginase, erwinia asparaginase	Acute Lymphoblastic Leukemia Lymphoma, Lymphoblastic	St. Jude Children's Research Hospital	November 2003	Phase 2
NCT00184041	Completed	Drug: Daunorubicin, Vincristine, Prednisone, Methotrexate, PEG- Asparaginase, 6-Mercaptopurine, Cytoxan, Cytosine Arabinoside, VM-26 and 6-Thioguanine	Acute Lymphoblastic Leukemia	St. Jude Children's Research Hospital	July 2004	Phase 2

Biological Data

MiR-181b level is positively related to glioma cell sensitivity to teniposide. BMC Cancer . 2014 Aug 25:14:611.
Downregulation of MDM2 promotes cell sensitivity to teniposide. BMC Cancer . 2014 Aug 25:14:611.
Upregulation of miR-181b enhances cell sensitivity to teniposide through mediation of MDM2. BMC Cancer. 2014 Aug 25:14:611.

Illustration of the contribution of clastogenicity and aneugenicity to the induced MN frequencies in animals treated with colchicine (2 mg/kg), mitomycin C (2 mg/kg) and teniposide (0.5 mg/kg). Mutagenesis . 2012 Jan;27(1):31-9.

Time course of appearance of BrdU-labelled sperm in the epididymis after treatment with 24 mg/kg teniposide. *P < 0.05, **P < 0.01 compared with the concurrent control (Mann–Whitney U-test). Mutagenesis . 2012 Jan;27(1):31-9.

Dose–response curves of the frequencies of abnormal sperm from mice after treatment with teniposide. *P < 0.05, **P < 0.01 compared with the concurrent control (Mann–Whitney U-test). Mutagenesis . 2012 Jan;27(1):31-9.

Dose–response curves of the frequencies of abnormal sperm from mice 23 days after the last treatment with teniposide (daily exposure for 12 consecutive days). Mutagenesis . 2012 Jan;27(1):31-9.