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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

Signal Word

Danger

Hazard Statements

H350

Hazard Classifications

Carc. 1B

Storage Class Code

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

WGK

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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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
Baohong Wang et al.
Hematological oncology, 31(1), 29-33 (2012-04-11)
There are two different international standards for the treatment of follicular lymphoma (FL): intensified therapy followed by autologous stem-cell transplantation (ASCT) and conventional therapy in the first-line setting. However, their role remains unclear. Our aim was to define the treatment
Mauro Pagani
The Medical clinics of North America, 94(4), 835-852 (2010-07-09)
The number of drugs used for the treatment of different types of cancers is constantly increasing and actually exceeds 100 distinct chemical formulations. The use of most cytotoxic agents is associated with potential hypersensitivity reactions, and the constant increase of
Ludovic Reveiz et al.
The Cochrane database of systematic reviews, 6(6), CD007464-CD007464 (2012-06-15)
Small cell lung cancer (SCLC) accounts for approximately 20% of all cases of lung cancer. It tends to disseminate early in the course of its natural history and to grow quickly. Approximately 10% to 18% of patients present with brain
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
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