α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile
Synonym(s):a,a-diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile; 2,2-diphenyl-5-(4-[[(1 E)-pyridin-3-yl-methylidene]amino]piperazin-1-yl)pentanenitrile;SC-26196
- CAS NO.：218136-59-5
- Empirical Formula: C27H29N5
- Molecular Weight: 423.55
- MDL number: MFCD11226148
- Update Date: 2023-06-30 15:45:59
![α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile Structural](https://img.chemicalbook.in/CAS/20181012/GIF/218136-59-5.gif)
What is α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile?
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.
The Uses of α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile
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.
The Uses of α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile
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
What are the applications of Application
SC 26196 is a selective Δ6 desaturase inhibitor that displays selectivity over Δ5 and Δ9 desaturases
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
Properties of α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile
| storage temp. | 2-8°C |
| solubility | DMSO: ≥10mg/mL |
| form | powder |
| color | white to tan |
Safety information for α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile
| Signal word | Warning |
| Pictogram(s) |
 Exclamation Mark Irritant GHS07 |
| GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
| Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for α,α-Diphenyl-4-[(3-pyridinylmethylene)amino]-1-piperazinepentanenitrile
New Products
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![4-ThiazolecarboxaMide, N-(6-benzoyl-1H-benziMidazol-2-yl)-2-(1-thieno[3,2-d]pyriMidin-4-yl-4-piperidinyl)-](https://img.chemicalbook.in/CAS/GIF/913822-46-5.gif)
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