I9785

Imidazolo-oxindole PKR inhibitor C16

Name: Imidazolo-oxindole PKR inhibitor C16
Brand: SIGMA

≥98% (HPLC), RNA-dependent protein kinases (PKR, Eif2ak2) inhibitor

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

Key Documents

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Product Name

Imidazolo-oxindole PKR inhibitor C16, ≥98% (HPLC)

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

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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This Item	SML1728	SML0651	S8442
Sigma-Aldrich I9785 Imidazolo-oxindole PKR inhibitor C16	Sigma-Aldrich SML1728 STK16-IN-1	Sigma-Aldrich SML0651 OAC1	Sigma-Aldrich S8442 SU 5416
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. −20°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. −20°C
solubility DMSO: 12 mg/mL	solubility DMSO: 10 mg/mL, clear (warmed)	solubility DMSO: 20 mg/mL, clear	solubility DMSO: 20 mg/mL, clear (warmed), H₂O: insoluble
shipped in wet ice	shipped in -	shipped in -	shipped in -
color yellow to orange-brown	color white to beige	color white to beige	color yellow to yellow-orange

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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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)

AIM2 inflammasome mediates Arsenic-induced secretion of IL-1 beta and IL-18

Zhang MF, et al.

Oncoimmunology, 5(6), e1160182-e1160182 (2016)

PKR-a Kinase to Remember

Gal-Ben-Ari S, et al.

Frontiers in Molecular Neuroscience, 11, 480-480 (2018)

African Swine Fever Virus MGF110-7L Induces Host Cell Translation Suppression and Stress Granule Formation by Activating the PERK/PKR-eIF2α Pathway.

Han Zhong et al.

Microbiology spectrum, 10(6), e0328222-e0328222 (2022-11-16)

African swine fever (ASF) is a highly contagious and often lethal disease of pigs caused by ASF virus (ASFV) and recognized as the biggest killer in global swine industry. Despite exhibiting incredible self-sufficiency, ASFV remains unconditionally dependent on the host

Increased Mobile Zinc Regulates Retinal Ganglion Cell Survival via Activating Mitochondrial OMA1 and Integrated Stress Response.

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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