2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester Chemical Properties

Boiling point:

524.8±50.0 °C(Predicted)

Density 

1.340±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

DMSO: soluble20mg/mL, clear

form 

powder

pka

3.03±0.40(Predicted)

color 

white to beige

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.

Safety Information

WGK Germany 

3

HS Code 

2932990090

2-AMino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester Usage And Synthesis

Description

SC-79 is an activator of Akt that blocks its membrane translocation while allowing its phosphorylation, in the cytosol, by upstream kinases. For example, both Thr³⁰⁸ and Ser⁴⁷³ on Akt are phosphorylated in serum starved HeLa cells treated for 1 hour with insulin growth factor and SC-79 (4 μg/ml). SC-79 permits phosphorylation and activation of all isoforms of Akt, it is active in multiple cell types, and works in both receptor tyrosine kinase- and G protein-coupled receptor-mediated signaling. SC-79 has been used to elucidate the role of Akt signaling in neuronal survival, glucose-mediated apoptosis in podocytes, and miR-221-regulated cancer cell proliferation.

Uses

2-Amino-6-chloro-α-cyano-3-(ethoxycarbonyl)-4H-1-benzopyran-4-acetic Acid Ethyl Ester is a useful synthetic intermediate.

Uses

SC79 has been used in western blot analysis as a positive control to measure the extent of phosphorylation of Akt and also to activate Akt that has been suppressed by nitidine chloride, a natural bioactive alkaloid.

General Description

A cell-permeable and blood-brain barrier permeant bromo-to-chloro substituted HA14-1 (Cat. No. 371971) analog that renders Akt in a conformation susceptible to phosphorylation by upstream kinases via specific interaction with Akt pleckstrin homology (PH) domain PtdIns(3,4,5)P3- (PIP3) binding pocket. Shown to enhance both basal and receptor-mediated Akt phosphorylation (Thr308 and Ser473) in a time- and dose-dependent manner (2 to 4 μg/ml) with concomitant inhibition Akt membrane translocation in various cell cultures. Efficiently reduces glutamate-induced neurotoxicity both in primary neuron cultures (EC₅₀ = 4 μg/ml) in vitro and in a murine MCAO (middle cerebral artery occlusion) model (40 mg/kg, i.p.) in vivo.

Biochem/physiol Actions

Cell permeable: yes

in vitro

sc79 was identified by a cell-based high-throughput chemical genetic screening, and inhibits akt membrane translocation. however, akt was paradoxically activated by sc79in the cytosol, specifically binding to the ph domain of akt. the conformation of sc79-bound akt is favorable for phosphorylation by upstream protein kinases. in a mouse model and a hippocampal neuronal culture system for ischemic stroke, the result of augmented neuronal survival is attained, based on the cytosolic activation of akt by sc79, which is sufficient to recapitulate the primary cellular function of akt signaling. thus, sc79, a unique specific akt activator, may be applied to enhance akt activity in various physiological and pathological conditions.

in vivo

in aqueous environment, sc79 is relatively unstable. intriguingly, however, the sustained level of phosphorylated akt was observed both in cell culture and in vivo after the removal of sc79, indicating that sc79 may act irreversibly. the chemical moieties of sc79 (i.e., nitrile group) could be modified and/or reacts with amino acids. nevertheless, sc79, a relatively safe drug, was revealed by following fact. assignment of sc79 treatment much high dose (0.4 mg/g of body weight) did not accelerate any detectable changes in body weight (survival rate, appearance, and behavior) in mice. achievement of neuronal protective effect by i.p. injection suggests that sc79 also has a good penetration of blood–brain barrier. sc79 can be applied as a chemical platform to develop novel drugs for neurological and other complications

storage

Store at -20°C

References

1) Jo?et al. (2012),?Small-molecule-induced cytosolic activation of protein kinase Akt rescues ischemia-elicited neuronal death; Proc. Natl. Acad. Sci. USA,?109?10581 2) Yang?et al.?(2016),?MiR-221 Promotes Capan-2 Pancreatic Ductal Adenocarcinoma Cells Proliferation by Targeting PTEN-Akt; Cell. Physiol. Biochem.?38?2366 3) Chen?et al.?(2017),?Novel Akt activator SC-79 is a potential treatment for alcohol-induced osteonecrosis of the femoral head; Oncotarget,?8?31065

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