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Key Documents

SML0609

Sigma-Aldrich

Teniposide

≥97% (HPLC)

Synonym(s):

4′-Dimethyl-9-(4,6-O-2-thenyid)-epipodophyllotoxin, Tenoposide, VM-26

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About This Item

Empirical Formula (Hill Notation):
C32H32O13S
CAS Number:
29767-20-2
Molecular Weight:
656.65
EC Number:
249-831-2
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥97% (HPLC)

form

powder

optical activity

[α]/D -100 to -115°, c = 1 in chloroform/methanol (9:1)

color

white to beige

solubility

DMSO: 10 mg/mL, clear

shipped in

wet ice

storage temp.

−20°C

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

InChI key

NRUKOCRGYNPUPR-QBPJDGROSA-N

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Application

Teniposide has been used as a topoisomerase II inhibitor to study its effects on the flagellum length in Trypanosoma brucei. It has also been used as a chemotherapeutic agent to study its interactions with piperazine(B87).

Biochem/physiol Actions

Teniposide (VM-26) is a Topoisomerase II inhibitor with antitumor activity. Teniposide inhibits DNA synthesis by forming a complex with topoisomerase II and DNA, inducing breaks in double stranded DNA and preventing repair.
Teniposide is a derivative of podophyllotoxin and has been studied to treat several cancers. It acts during the late S phase or the early G2 phase of the cell cycle.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H350

Hazard Classifications

Carc. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Madison Atkins et al.
The Journal of cell biology, 220(1) (2020-11-10)
Cilia and flagella are required for cell motility and sensing the external environment and can vary in both length and stability. Stable flagella maintain their length without shortening and lengthening and are proposed to "lock" at the end of growth
Zhiwen Zhang et al.
Journal of controlled release : official journal of the Controlled Release Society, 166(1), 30-37 (2012-12-26)
We attempted to improve the oral delivery of lipophilic teniposide to achieve higher drug concentration in tumor by self-assembled nanocarrier for further oral chemotherapy. The teniposide loaded self-assembled nanocarrier (TSN) was spherical nanometric particles with narrow size distribution. The intestinal
S A Bakheet et al.
Mutagenesis, 26(4), 533-543 (2011-03-25)
The intention of the present study was to answer the question whether the catalytic topoisomerase-II inhibitor, dexrazoxane, can be used as a modulator of teniposide-induced DNA damage and programmed cell death (apoptosis) in the bone marrow cells in vivo. The
Eloïse Bertiaux et al.
Current biology : CB, 28(23), 3802-3814 (2018-11-20)
Several models have been proposed to explain how eukaryotic cells control the length of their cilia and flagella. Here, we investigated this process in the protist Trypanosoma brucei, an excellent model system for cells with stable cilia like photoreceptors or
M Lv et al.
Mini reviews in medicinal chemistry, 11(10), 901-909 (2011-07-26)
Podophyllotoxin, one of the well-known naturally occurring aryltetralin lignans, has been used as the lead-compound for the preparation of potent anticancer agents, such as etoposide, teniposide, and etopophos. In our previous review, we described the advances of podophyllotoxin derivatives from
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