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

Product Nameα,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile
CAS218136-59-5
MFC27H29N5
MW423.55
EINECS
MOL File218136-59-5.mol

Chemical Properties

storage temp.	2-8°C
solubility	DMSO: ≥10mg/mL
form	powder
color	white to tan
InChI	1S/C27H29N5/c28-23-27(25-10-3-1-4-11-25,26-12-5-2-6-13-26)14-8-16-31-17-19-32(20-18-31)30-22-24-9-7-15-29-21-24/h1-7,9-13,15,21-22H,8,14,16-20H2/b30-22+
InChIKey	QFYKXKMYVYOUNJ-JBASAIQMSA-N
SMILES	N#CC(CCCN1CCN(CC1)\N=C\c2cccnc2)(c3ccccc3)c4ccccc4

Safety Information

WGK Germany	3
Storage Class	11 - Combustible Solids

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

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.

Uses

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

in mouse inner medullarycollecting 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

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.

in vivo

SC-26196 ( included in the diet at 0, 0.07, 0.21, or 0.7 mg/kg diet to achieve dosages of 0, 10, 30, and 100 mg/kg per day) causes a decrease in the calculated Δ6-desaturase index in both adipose tissue and liver. Feeding 100 mg SC-26196 per kg BW per day inhibits the Δ6-desaturase enzyme^[3].

Animal Model:	Male mice (12- or 15-week-old)^[3]
Dosage:	0, 10, 30, and 100 mg/kg per day
Administration:	Included in the diet at 0, 0.07, 0.21, or 0.7mg/kg diet to achieve dosages of 0, 10, 30, and 100mg/kg per day.
Result:	Caused a decrease in the calculated Δ6-desaturase index in both adipose tissue and liver.

storage

Store at -20°C

References

[1] M. OBUKOWICZ. Novel, selective Δ6 or Δ5 fatty acid desaturase inhibitors as antiinflammatory agents in mice[J]. Lipids, 1999, 34 S1Part2: S149. DOI: 10.1007/bf02562269
[2] SHAWN D. HARMON. Effect of the Δ6-desaturase inhibitor SC-26196 on PUFA metabolism in human cellsinhibitor SC-26196 on PUFA metabolism in human cells[J]. Lipids, 2003, 38 4: 469-476. DOI: 10.1007/s11745-003-1086-9
[3] CHRISTOPHER M MULLIGAN. Inhibition of delta-6 desaturase reverses cardiolipin remodeling and prevents contractile dysfunction in the aged mouse heart without altering mitochondrial respiratory function.[J]. Journals of Gerontology Series A-Biological Sciences and Medical Sciences, 2014, 69 7: 799-809. DOI: 10.1093/gerona/glt209
[4] T. LAVAL. De novo synthesized polyunsaturated fatty acids operate as both host immunomodulators and nutrients for Mycobacterium tuberculosis[J]. eLife, 2021. DOI: 10.1101/2021.07.08.451715

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