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Key Documents

Safety Information

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

SMILES string

[s]1c(ccc1)[C@H]2O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O)O[C@H]4[C@@H]5[C@@H]([C@@H](c7c4cc8c(c7)OCO8)c6cc(c(c(c6)OC)O)OC)C(=O)OC5)CO2

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

Regulatory Information

监管及禁止进口产品

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Certificates of Analysis (COA)

Lot/Batch Number
0000391466
0000391467
0000391467
0000391466
0000228249

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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
Xiaoming Zhai et al.
Nan fang yi ke da xue xue bao = Journal of Southern Medical University, 32(2), 255-257 (2012-03-03)
To compare the therapeutic efficacy of two regimens of postoperative radiotherapy with concurrent chemotherapy using temozolomide (TMZ) and teniposide (VM-26) plus semustine (Me-CCNU) in adult patients with grade III-IV cerebral gliomas. Ninety-six adult postoperative patients with grade III-IV cerebral gliomas
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
Liqian Mo et al.
International journal of pharmaceutics, 436(1-2), 815-824 (2012-08-01)
Many studies have demonstrated the uptake mechanisms of various nanoparticle delivery systems with different physicochemical properties in different cells. In this study, we report for the first time the preparation and characterization of teniposide (VM-26) poly(D,L-lactide-co-glycolide) (PLGA) nanoparticles (NPs) and
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
View All Related Papers

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