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SML0552

Sigma-Aldrich

Tirapazamine

≥98% (HPLC)

Sinónimos:

4-Hydroxy-1-oxido-1,2,4-benzotriazin-1-ium-3-imine, SR 259075, SR 4233, Tirazone, Win 59075

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About This Item

Fórmula empírica (notación de Hill):
C7H6N4O2
Número de CAS:
27314-97-2
Peso molecular:
178.15
MDL number:
MFCD00132954
UNSPSC Code:
12352116
PubChem Substance ID:
329825548
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

, orange to dark orange-red

solubility

DMSO: 10 mg/mL, clear

shipped in

wet ice

storage temp.

−20°C

SMILES string

Nc1n[n+]([O-])c2ccccc2[n+]1[O-]

InChI

1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9)

InChI key

ORYDPOVDJJZGHQ-UHFFFAOYSA-N

Application

Tirapazamine has been used to evaluate its cytotoxic effect on U-251 MG (glioblastoma cell line) cell viability.

Biochem/physiol Actions

Under hypoxic conditions, tirapazamine is a potent cytotoxic agent that induces apoptosis by inducing breaks in single and double stranded DNA, as well as chromosomal breaks. The compound sensitizes cells to other ionizing radiation and other cytotoxic agents like cisplatin.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Yunzhou Shi et al.
Neoplasia (New York, N.Y.), 19(11), 950-959 (2017-10-11)
The effect of anti-angiogenic agents on tumor oxygenation has been in question for a number of years, where both increases and decreases in tumor pO
K M Govaert et al.
The British journal of surgery, 99(4), 567-575 (2012-02-15)
Radiofrequency ablation (RFA) is a common procedure for the management of colorectal liver metastases. RFA-generated lesions are surrounded by a rim of hypoxia that is associated with aggressive outgrowth of intrahepatic micrometastases. Hypoxia-activated prodrugs such as tirapazamine are designed selectively
Yung-Ann Chen et al.
Lab on a chip, 11(21), 3626-3633 (2011-09-15)
This paper reports a microfluidic device capable of generating oxygen gradients for cell culture using spatially confined chemical reactions with minimal chemical consumption. The microfluidic cell culture device is constructed by single-layer polydimethylsiloxane (PDMS) microfluidic channels, in which the cells
Quynh-Thu Le et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 18(6), 1798-1807 (2012-03-03)
Hepatocyte growth factor (HGF) is a hypoxia-induced secreted protein that binds to cMet and regulates interleukin (IL)-8 expression. We evaluated the role of circulating HGF and IL-8 as prognostic and predictive factors for efficacy of tirapazamine (TPZ), a hypoxic cell
Yao Tang et al.
Theranostics, 10(19), 8691-8704 (2020-08-06)
Rationale: Nanoscale vehicles responsive to abnormal variation in tumor environment are promising for use in targeted delivery of therapeutic drugs specifically to tumor sites. Herein, we report the design and fabrication of self-accelerating H2O2-responsive plasmonic gold nanovesicles (GVs) encapsulated with
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