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Merck
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Documentos clave

SML0609

Sigma-Aldrich

Teniposide

≥97% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C32H32O13S
Número de CAS:
29767-20-2
Peso molecular:
656.65
Número CE:
249-831-2
Código UNSPSC:
12352200
NACRES:
NA.77
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Nivel de calidad

100

Ensayo

≥97% (HPLC)

Formulario

powder

actividad óptica

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

color

white to beige

solubilidad

DMSO: 10 mg/mL, clear

Condiciones de envío

wet ice

temp. de almacenamiento

−20°C

cadena SMILES

[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

Clave InChI

NRUKOCRGYNPUPR-QBPJDGROSA-N

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Aplicación

Teniposide has been used as a topoisomerase II inhibitor to study its effects on the flagellum length in Trypanosoma brucei.[1][2] It has also been used as a chemotherapeutic agent to study its interactions with piperazine(B87).[3]

Acciones bioquímicas o fisiológicas

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 Topoisomerase II inhibitor with antitumor activity.
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.[4]

Pictogramas

Health hazard
GHS08

Palabra de señalización

Danger

Frases de peligro

H350

Clasificaciones de peligro

Carc. 1B

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000391467
0000391466
0000391467
0000391466
0000225567

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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
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
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
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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