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Merck
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Key Documents

SML0568

Sigma-Aldrich

3-AP

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C7H9N5S
Numéro CAS:
143621-35-6
Poids moléculaire :
195.24
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to light brown

Solubilité

DMSO: 10 meq/mL, clear

Température de stockage

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+

Clé InChI

XMYKNCNAZKMVQN-NYYWCZLTSA-N

Actions biochimiques/physiologiques

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.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301,H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Sigma-Aldrich

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Sigma-Aldrich

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Patricia Quach et al.
Molecular pharmacology, 82(1), 105-114 (2012-04-18)
Thiosemicarbazones are a group of compounds that have received comprehensive investigation as anticancer agents. The antitumor activity of the thiosemicarbazone, 3-amino-2-pyridinecarboxaldehyde thiosemicarbazone (3-AP; triapine), has been extensively assessed in more than 20 phase I and II clinical trials. These studies
Charles A Kunos et al.
Radiation research, 174(5), 574-581 (2010-10-20)
For repair of damaged DNA, cells increase de novo synthesis of deoxyribonucleotide triphosphates through the rate-limiting, p53-regulated ribonucleotide reductase (RNR) enzyme. In this study we investigated whether pharmacological inhibition of RNR by 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, NSC #663249) enhanced chemoradiation sensitivity
Charles Kunos et al.
Journal of translational medicine, 10, 79-79 (2012-05-01)
The potent ribonucleotide reductase (RNR) inhibitor 3-aminopyridine-2-carboxyaldehyde-thiosemicarbazone (3-AP) was tested as a chemosensitizer for restored cisplatin-mediated cytotoxicity in platinum-resistant ovarian cancer. Preclinical in vitro platinum-resistant ovarian cancer cell survival, RNR activity, and DNA damage assays were done after cisplatin or
Charles A Kunos et al.
Gynecologic oncology, 130(1), 75-80 (2013-04-23)
Cervical and vaginal cancers have virally-mediated or mutated defects in DNA damage repair responses, making these cancers sensible targets for ribonucleotide reductase inhibition during radiochemotherapy. We conducted a phase II study evaluating 3× weekly 2-hour intravenous 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, 25
C M Nutting et al.
Annals of oncology : official journal of the European Society for Medical Oncology, 20(7), 1275-1279 (2009-02-28)
Treatment options for recurrent or metastatic head and neck squamous cell carcinoma (HNSCC) are limited with response rates to cytotoxic chemotherapy of approximately 30% and median survival of 6 months. In a multicentre phase II study, 32 patients with recurrent
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