8-(1H-IMIDAZOL-4-YLMETHYLENE)-6,8-DIHYDRO-THIAZOLO[5,4-E]INDOL-7-ONE Struktur

8-(1H-IMIDAZOL-4-YLMETHYLENE)-6,8-DIHYDRO-THIAZOLO[5,4-E]INDOL-7-ONE

Bezeichnung:8-(1H-IMIDAZOL-4-YLMETHYLENE)-6,8-DIHYDRO-THIAZOLO[5,4-E]INDOL-7-ONE

CAS-Nr608512-97-6

Englisch Name:8-(1H-IMIDAZOL-4-YLMETHYLENE)-6,8-DIHYDRO-THIAZOLO[5,4-E]INDOL-7-ONE

CBNumberCB3160831

SummenformelC13H8N4OS

Molgewicht268.29

MOL-Datei608512-97-6.mol

8-(1H-IMIDAZOL-4-YLMETHYLENE)-6,8-DIHYDRO-THIAZOLO[5,4-E]INDOL-7-ONE physikalisch-chemischer Eigenschaften

Siedepunkt	674.6±55.0 °C(Predicted)
Dichte	1.604±0.06 g/cm3(Predicted)
storage temp.	-20°C
Löslichkeit	DMSO: soluble12mg/mL
pka	10.20±0.20(Predicted)
Aggregatzustand	Orange to orange brown solid
Farbe	yellow to orange-brown
Stabilität	Stable for 2 years from date of purchsae as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26
WGK Germany	3

Gefahreninformationscode (GHS)

Bildanzeige (GHS)
Alarmwort

Warnung
Gefahrenhinweise

H302：Gesundheitsschädlich bei Verschlucken.

H315：Verursacht Hautreizungen.

H319：Verursacht schwere Augenreizung.

H335：Kann die Atemwege reizen.
Sicherheit

P261：Einatmen von Staub vermeiden.

P264：Nach Gebrauch gründlich waschen.

P264：Nach Gebrauch gründlich waschen.

P270：Bei Gebrauch nicht essen, trinken oder rauchen.

P271：Nur im Freien oder in gut belüfteten Räumen verwenden.

P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

P301+P312：BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.

P302+P352：BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.

P304+P340：BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.

P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

P330：Mund ausspülen.

P332+P313：Bei Hautreizung: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

P337+P313：Bei anhaltender Augenreizung: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

P362：Kontaminierte Kleidung ausziehen und vor erneutem Tragen waschen.

P403+P233：An einem gut belüfteten Ort aufbewahren. Behälter dicht verschlossen halten.

P405：Unter Verschluss aufbewahren.

P501：Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

8-(1H-IMIDAZOL-4-YLMETHYLENE)-6,8-DIHYDRO-THIAZOLO[5,4-E]INDOL-7-ONE Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
The activity of double-stranded RNA-activated protein kinase (PKR) is altered by viral infection as well as by various neuropathologies. A primary phosphorylation target of PKR is eukaryotic initiation factor 2 subunit α (eIF2α), blocking translation and driving apoptosis. PKR Inhibitor is an oxindole/imidazole derivative that binds the ATP-binding site of PKR and blocks autophosphorylation with an IC₅₀ value of 186-210 nM. PKR Inhibitor protects human neuroblastoma cells against cell damage triggered by tunicamycin-mediated endoplasmic reticulum stress. It also prevents phosphorylation of Fas-associated protein with a death domain (FADD) in neuroblastoma cells, preventing FADD-dependent activation of caspases and apoptosis. Intraperitoneal administration of PKR inhibitor in rats reduces phosphorylation of PKR and eIF2α in the brain. Similar administration in mice enhances long-term memory storage, including contextual and auditory long-term fear memories.
Verwenden
PKR Inhibitor is a drug which acts as a selective inhibitor of the enzyme double-stranded RNA-dependent protein kinase (PKR). It has been shown to effectively inhibit PKR function in vivo and has neuroprotective and nootropic effects in animal studies.
Biochem/physiol Actions
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.
in vitro
pkr inhibitor was identified as a small molecule able to inhibit the autophosphorylation of pkr and to rescue the translation blockade induced by pkr. it was found that pkr inhibitor prevented not only pkr phosphorylation but also the activation of caspase 3 induced by ab in sh-sy5y cells. in addition, the protective effect of pkr inhibitor on the neuronal cell death induced by endoplasmic reticulum-stress in sh-sy5y cells has been reported [1].
in vivo
a previous animal study used an in-vivo model of 7-day-old rat exhibiting a high activation of brain pkr to investigate the effects of pkr inhibitor. results showed for the first time that acute systemic injection of pkr inhibitor could specifically inhibit the apoptotic pkr/eif2a signaling pathway without stimulating the proliferative mtor/p70s6k signaling mechanism [1].
IC 50
186-210 nm
Lager
Store at -20°C
Einzelnachweise
1) Jammi et al. (2003), Small molecule inhibitors of the RNA-dependent protein kinase; Biochem. Biophys. Res. Commun., 308 50 2) Shimazawa et al. (2007), Involvement of double-stranded RNA-dependent protein kinase in ER stress-induced retinal neuron damage; Ophthalmol. Vis. Sci., 48 3729 3) Ingrand et al. (2007), The oxindole/imidazole derivative C16 reduces in vivo brain PKR activation; FEBS Lett. 581 4473 4) Tronel et al. (2014), The specific PKR inhibitor C16 prevents apoptosis and IL-1β production in an acute excitotoxic rat model with a neuroinflammatory component; Neurochem. Int. 64 73 5) Couturier et al. (2011) Prevention of the β-amyloid peptide-induced inflammatory process by inhibition of double-stranded RNA-dependent protein kinase in primary murine mixed co-cultures; Neuroinflammation, 8 72

8-(1H-IMIDAZOL-4-YLMETHYLENE)-6,8-DIHYDRO-THIAZOLO[5,4-E]INDOL-7-ONE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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