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SML0568

Sigma-Aldrich

3-AP

≥98% (HPLC)

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C7H9N5S
CAS-Nummer:
143621-35-6
Molekulargewicht:
195.24
UNSPSC-Code:
12352200
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Farbe

white to light brown

Löslichkeit

DMSO: 10 meq/mL, clear

Lagertemp.

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+

InChIKey

XMYKNCNAZKMVQN-NYYWCZLTSA-N

Biochem./physiol. Wirkung

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.

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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Sigma-Aldrich

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Sigma-Aldrich

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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
Jia Shou et al.
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
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
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
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
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