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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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5 MG
MXP 2,212.00
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MXP 8,743.00

MXP 2,212.00

Estimated to ship onApril 15, 2025

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5 MG
MXP 2,212.00
25 MG
MXP 8,743.00

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

MXP 2,212.00

Estimated to ship onApril 15, 2025

Request a Bulk Order

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[1]
  • to inhibit the strong induction of interferon stimulated genes (ISGs) after plasmid transfection in HeLa-S3 cells[2]
  • to augment eukaryotic translation initiation factor 2 (eIF2) activity[3]

Biochem/physiol Actions

C16 exhibits a neuroprotective role in adult brain injuries.[4]
Imidazolo-oxindole PKR inhibitor C16 is a selectiv inhibitor of RNA-dependent protein kinases (PKR, Eif2ak2).
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

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Certificates of Analysis (COA)

Lot/Batch Number
0000332292
0000332279
0000329197
0000332292
0000332279

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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)
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)
Mohamad A Zaini et al.
Scientific reports, 7, 42603-42603 (2017-02-16)
An important part of the beneficial effects of calorie restriction (CR) on healthspan and lifespan is mediated through regulation of protein synthesis that is under control of the mechanistic target of rapamycin complex 1 (mTORC1). As one of its activities
Jiahui Tang et al.
Antioxidants (Basel, Switzerland), 11(10) (2022-10-28)
Retinal ganglion cells (RGCs), the projection neurons of the eye, are irreversibly lost once the optic nerve is injured, which is a critical mechanism of glaucoma. Mobile zinc (Zn2+) levels rapidly increase in retinal interneuron amacrine cells and Zn2+ is
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