α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile Chemical Properties

storage temp. 

2-8°C

solubility 

DMSO: ≥10mg/mL

form 

powder

color 

white to tan

Safety Information

WGK Germany 

3

α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile Usage And Synthesis

Description

The enzyme Δ⁶ desaturase mediates the conversion of linoleic acid to γ-linolenic acid (GLA), which can then be elongated to dihomo-γ-linolenic acid (DGLA). DGLA can then be used as a substrate for Δ⁵ desaturase to produce arachidonic acid (AA), the fatty acid that is used to generate eicosanoids. SC 26196 is an inhibitor of Δ⁶ desaturase (IC₅₀ = 0.2 μM in a rat liver microsomal assay) that completely blocks the conversion of linoleic acid to arachidonic acid (AA). It is selective for Δ⁶ desaturase, as IC₅₀ values for Δ⁵ and Δ⁹ desaturases exceed 200 μM and it has no effect on the conversion of dihomo-γ-linolenic acid to AA. SC 26196 is orally active in vivo, decreasing edema in the carrageenan paw edema model in mice. It also blocks aging-related increases in AA in myocardial cardiolipin in mice, attenuating contractile dysfunction without impacting mitochondrial oxidative stress.

Uses

SC-26196 has been used as an inhibitor of delta6 (Δ6) fatty acid desaturase:

• in mouse inner medullary?collecting duct?(IMCD3) and human (female) embryonic kidney (HEK) 293 cell culture as Dulbecco′s modified eagle′s medium (DMEM) component
• in hepatic HepG2 cells
• in glioblastoma cell lines to test its effect post-radiation treatments

Uses

A selective Δ6 desaturase inhibitor (IC50 = 0.2 μM in vitro). Displays selectivity over Δ5 and Δ9 desaturases (IC50 values are >200 μM in vitro). It exhibits anti-inflammatory properties in a mouse edema model.

Biochem/physiol Actions

SC-26196 is a Delta6 fatty acid desaturase (Delta6D) inhibitor. It specifically inhibited Delta6D activity with an IC(50) value of 100 nM. The rate-limiting step in arachidonic acid synthesis is the desaturation of dietary linoleic acid by Delta6D. SC-26196 completely prevented this conversion of linoleic acid to arachidonic acid.

storage

Store at -20°C

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