Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

SML2381

Sigma-Aldrich

APY29

≥97% (HPLC)

Synonym(s):

APY 29, APY-29, APY29 (type I kinase inhibitor), N2-(1H-Benzo[d]imidazol-6-yl)-N4-(3-cyclopropyl-1H-pyrazol-5-yl)pyrimidine-2,4-diamine, N2-1H-Benzimidazol-6-yl-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-2,4-pyrimidinediamine

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C17H16N8
CAS Number:
1216665-49-4
Molecular Weight:
332.36
MDL number:
MFCD27991280
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥97% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

C1(NC2=CC(C3CC3)=NN2)=CC=NC(NC4=CC=C(N=CN5)C5=C4)=N1

InChI

1S/C17H16N8/c1-2-10(1)13-8-16(25-24-13)22-15-5-6-18-17(23-15)21-11-3-4-12-14(7-11)20-9-19-12/h3-10H,1-2H2,(H,19,20)(H3,18,21,22,23,24,25)

InChI key

WJNBSTLIALIIEW-UHFFFAOYSA-N

General description

APY29 is considered as a type I kinase inhibitor of inositol requiring kinase enzyme 1 α (IRE1α).

Biochem/physiol Actions

APY29 has the ability to enhance inositol requiring kinase enzyme 1 α (IRE1α) (P830L)′s oligomeric state to rescue RNase activity.
APY29 is a small molecule that inhibits the kinase activity of IRE1α (in vitro autophosphorylation IC50 = 280 nM) by targeting its active site ATP-binding pocket, while simultaneously acting as an allosteric activator of IRE1α RNase activity (EC50 = 460 nM) by keeping the active site in an open conformation. When applied 1 hr prior to stress induction by 4-hr 6 nM thapsigargin treatment, APY29 significantly potentiates stress-induced unfolded protein response (UPR) in rat insulinoma INS-1 cultures (XBP1 mRNA processing induction = 54% without vs. 78% with 1-hr 3 μM APY29 pretreatment).

Storage Class Code

11 - Combustible Solids

WGK

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Alexei V Korennykh et al.
BMC biology, 9, 48-48 (2011-07-07)
Ire1 is a signal transduction protein in the endoplasmic reticulum (ER) membrane that serves to adjust the protein-folding capacity of the ER according to the needs of the cell. Ire1 signals, in a transcriptional program, the unfolded protein response (UPR)
Airong Su et al.
Viruses, 9(9) (2017-08-24)
In response to the endoplasmic reticulum (ER) stress induced by herpes simplex virus type 1 (HSV-1) infection, host cells activate the unfolded protein response (UPR) to reduce the protein-folding burden in the ER. The regulation of UPR upon HSV-1 infection
Megan M Robblee et al.
Cell reports, 14(11), 2611-2623 (2016-03-15)
Diets rich in saturated fatty acids (SFAs) produce a form of tissue inflammation driven by "metabolically activated" macrophages. We show that SFAs, when in excess, induce a unique transcriptional signature in both mouse and human macrophages that is enriched by
Likun Wang et al.
Nature chemical biology, 8(12), 982-989 (2012-10-23)
Under endoplasmic reticulum stress, unfolded protein accumulation leads to activation of the endoplasmic reticulum transmembrane kinase/endoRNase (RNase) IRE1α. IRE1α oligomerizes, autophosphorylates and initiates splicing of XBP1 mRNA, thus triggering the unfolded protein response (UPR). Here we show that IRE1α's kinase-controlled
Alexei V Korennykh et al.
Nature, 457(7230), 687-693 (2008-12-17)
Aberrant folding of proteins in the endoplasmic reticulum activates the bifunctional transmembrane kinase/endoribonuclease Ire1. Ire1 excises an intron from HAC1 messenger RNA in yeasts and Xbp1 messenger RNA in metozoans encoding homologous transcription factors. This non-conventional mRNA splicing event initiates
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service