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Merck
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Documentos clave

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:
143621-35-6
Peso molecular:
195.24
Código UNSPSC:
12352200
NACRES:
NA.77

Ensayo

≥98% (HPLC)

Formulario

powder

color

white to light brown

solubilidad

DMSO: 10 meq/mL, clear

temp. de almacenamiento

2-8°C

cadena SMILES

S=C(N\N=C\c1ncccc1N)N

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+

Clave InChI

XMYKNCNAZKMVQN-NYYWCZLTSA-N

Acciones bioquímicas o fisiológicas

3-Aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) is a ribonucleotide reductase inhibitor and iron chelator with anti-tumor activity.
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.

Pictogramas

Skull and crossbones
GHS06

Palabra de señalización

Danger

Frases de peligro

H301,H315,H319,H335

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

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
124M4736V
023M4713V

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Sigma-Aldrich

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Sigma-Aldrich

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Molecular cell, 71(4), 498-509 (2018-07-24)
Chromosomal rearrangements including large DNA-fragment inversions, deletions, and duplications by Cas9 with paired sgRNAs are important to investigate genome structural variations and developmental gene regulation, but little is known about the underlying mechanisms. Here, we report that disrupting CtIP or
J Li et al.
Current medicinal chemistry, 8(2), 121-133 (2001-02-15)
The reductive conversion of ribonucleotides to deoxyribonucleotides by ribonucleotide reductase (RR) is a crucial and rate-controlling step in the pathway leading to the biosynthesis of DNA, since deoxyribonucleotides are present in extremely low levels in mammalian cells. Mammalian ribonucleotide reductase
Christian R Kowol et al.
Dalton transactions (Cambridge, England : 2003), 39(3), 704-706 (2010-01-13)
Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone), which entered several phase I and II clinical trials as an antitumor chemotherapeutic agent, was found to possess intrinsic fluorescence properties (lambda(ex) = 360 nm), which enabled us to monitor the uptake and intracellular distribution in living
Charles A Kunos et al.
Radiation research, 172(6), 666-676 (2009-11-26)
Therapeutic ionizing radiation damages DNA, increasing p53-regulated ribonucleotide reductase (RNR) activity required for de novo synthesis of the deoxyribonucleotide triphosphates used during DNA repair. This study investigated the pharmacological inhibition of RNR in cells of virally or mutationally silenced p53
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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