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Merck
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Key Documents

SML0568

Sigma-Aldrich

3-AP

≥98% (HPLC)

Sinónimos:

3-AP, 3-Aminopyridine-2-carboxaldehyde thiosemicarbazone, PAN-811

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About This Item

Fórmula empírica (notación de Hill):
C7H9N5S
Número de CAS:
Peso molecular:
195.24
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to light brown

solubility

DMSO: 10 meq/mL, clear

storage temp.

2-8°C

InChI

1S/C7H9N5S/c8-5-2-1-3-10-6(5)4-11-12-7(9)13/h1-4H,8H2,(H3,9,12,13)/b11-4+

InChI key

XMYKNCNAZKMVQN-NYYWCZLTSA-N

Biochem/physiol Actions

3-Aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) is a ribonucleotide reductase inhibitor and iron chelator with anti-tumor activity.
3-aminopyridine carboxaldehyde thiosemicarbazone (3-AP) has a IC50 value of 0.3μM. It exhibits anti-proliferative activity in preclinical models of cancer, such as lung cancer. It also has an ability to increase the cytotoxicity, intracellular uptake and DNA incorporation of gemcitabine in vitro.

pictograms

Skull and crossbones

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

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


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Los clientes también vieron

Charles A Kunos et al.
Radiation research, 176(4), 425-433 (2011-07-16)
Cells generate 2'-deoxyribonucleoside triphosphates (dNTPs) for both replication and repair of damaged DNA predominantly through de novo reduction of intracellular ribonucleotides by ribonucleotide reductase (RNR). Cells can also salvage deoxynucleosides by deoxycytidine kinase/thymidine kinase 1 in the cytosol or by
Éva A Enyedy et al.
Dalton transactions (Cambridge, England : 2003), 40(22), 5895-5905 (2011-04-28)
Stoichiometry and stability of Ga(III), Fe(III), Fe(II) complexes of Triapine and five related α-N heterocyclic thiosemicarbazones with potential antitumor activity have been determined by pH-potentiometry, UV-vis spectrophotometry, (1)H NMR spectroscopy, and spectrofluorimetry in aqueous solution (with 30% DMSO), together with
Christian R Kowol et al.
Journal of medicinal chemistry, 52(16), 5032-5043 (2009-07-30)
The first metal complexes of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (Triapine) were synthesized. Triapine was prepared by a novel three-step procedure in 64% overall yield. In addition, a series of related ligands, namely, 2-formylpyridine thiosemicarbazone, 2-acetylpyridine thiosemicarbazone, 2-pyridineformamide thiosemicarbazone, and their N(4)-dimethylated derivatives
Charles A Kunos et al.
International journal of radiation oncology, biology, physics, 80(4), 1198-1204 (2011-04-08)
To test whether pharmacologic inhibition of ribonucleotide reductase (RNR) by 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, NSC #663249) enhances radiation sensitivity during low-dose-rate ionizing radiation provided by a novel purpose-built iridium-192 cell irradiator. The cells were exposed to low-dose-rate radiation (11, 23, 37
R A Finch et al.
Advances in enzyme regulation, 39, 3-12 (1999-09-02)
The enzyme RR catalyzes the conversion of ribonucleoside diphosphates to their deoxyribonucleotide counterparts. RR is critical for the generation of the cytosine, adenine, and guanine deoxyribonucleotide 5'-triphosphate building blocks of DNA, which are present in cells as exceedingly small intracellular

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