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I9785

Sigma-Aldrich

Imidazolo-oxindole PKR inhibitor C16

≥98% (HPLC)

Synonym(s):

6,8-Dihydro-8-(1H-imidazol-5-ylmethylene)-7H-pyrrolo[2,3-g]benzothiazol-7-one

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About This Item

Empirical Formula (Hill Notation):
C13H8N4OS
CAS Number:
608512-97-6
Molecular Weight:
268.29
MDL number:
MFCD06735404
UNSPSC Code:
12352200
PubChem Substance ID:
329815469
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

color

yellow to orange-brown

solubility

DMSO: 12 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

O=C1NC2=CC=C3C(SC=N3)=C2/C1=C/C4=CNC=N4

InChI

1S/C13H8N4OS/c18-13-8(3-7-4-14-5-15-7)11-9(17-13)1-2-10-12(11)19-6-16-10/h1-6H,(H,14,15)(H,17,18)/b8-3-

InChI key

VFBGXTUGODTSPK-BAQGIRSFSA-N

Application

Imidazolo-oxindole PKR inhibitor C16 has been used:
  • to rescue fear memory deficits and restore long-term potentiation (LTP) impairment in mice
  • to inhibit the strong induction of interferon stimulated genes (ISGs) after plasmid transfection in HeLa-S3 cells
  • to augment eukaryotic translation initiation factor 2 (eIF2) activity

Biochem/physiol Actions

C16 exhibits a neuroprotective role in adult brain injuries.
Imidazolo-oxindole PKR inhibitor C16 is a selective inhibitor of RNA-dependent protein kinases (PKR, Eif2ak2). C16 is a first reported, potent and selective PKR inhibitor. Its inhibition effect on PKR is ATP-binding site directed. C16 specifically inhibits the apoptotic PKR/eIF2a signaling pathway without stimulating the proliferative mTOR/p70S6K signaling mechanism.

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’.

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The specific protein kinase R (PKR) inhibitor C16 protects neonatal hypoxia-ischemia brain damages by inhibiting neuroinflammation in a neonatal rat model
Xiao J, et al.
Medical Science Monitor : International Medical Journal of Experimental and Clinical Research, 22, 5074-5074 (2016)
PKR-a Kinase to Remember
Gal-Ben-Ari S, et al.
Frontiers in Molecular Neuroscience, 11, 480-480 (2018)
AIM2 inflammasome mediates Arsenic-induced secretion of IL-1 beta and IL-18
Zhang MF, et al.
Oncoimmunology, 5(6), e1160182-e1160182 (2016)
Che C Colpitts et al.
eLife, 9 (2020-06-17)
Counteracting innate immunity is essential for successful viral replication. Host cyclophilins (Cyps) have been implicated in viral evasion of host antiviral responses, although the mechanisms are still unclear. Here, we show that hepatitis C virus (HCV) co-opts the host protein
Fabian Borghese et al.
Journal of virology, 93(19) (2019-07-12)
Leader (L) proteins encoded by cardioviruses are multifunctional proteins that contribute to innate immunity evasion. L proteins of Theiler's murine encephalomyelitis virus (TMEV), Saffold virus (SAFV), and encephalomyocarditis virus (EMCV) were reported to inhibit stress granule assembly in infected cells.
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