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SML1055

Sigma-Aldrich

3-AP-Me

≥98% (HPLC)

Synonym(s):

2-[(3-Amino-2-pyridinyl)methylene]-N,N-dimethyl-hydrazinecarbothioamide

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About This Item

Empirical Formula (Hill Notation):
C9H13N5S
CAS Number:
Molecular Weight:
223.30
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

CN(C)C(N/N=C/C1=C(N)C=CC=N1)=S

InChI

1S/C9H13N5S/c1-14(2)9(15)13-12-6-8-7(10)4-3-5-11-8/h3-6H,10H2,1-2H3,(H,13,15)/b12-6+

InChI key

DQVSEUUIXQTWRB-WUXMJOGZSA-N

Biochem/physiol Actions

3-AP-Me is a dimethyl derivative of the ribonucleotide reductase inhibitor 3-AP (SML0568). 3-AP-Me is a potent inducer of ER stress and the unfolded protein response in cancer cell lines, incuding IRE1, PERK and ATF6 activity. Treatment with 3-AP-Me induces CHOP expression, phosphorylation of eIF2α, up-regulation of ATF4 and Bim, and causes mitochondrial membrane depolarization and apoptosis.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Related Content

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.

n proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during the synthesis (S) phase, which is followed by a second gap phase (G2) during which growth and preparation for cell division occurs. Together, these three stages comprise the interphase phase of the cell cycle. Interphase is followed by the mitotic (M) phase.

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