SC 26196CAS# 218136-59-5 |
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Quality Control & MSDS
3D structure
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| Cas No. | 218136-59-5 | SDF | Download SDF |
| PubChem ID | 9845201 | Appearance | Powder |
| Formula | C27H29N5 | M.Wt | 423.55 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : 5 mg/mL (11.80 mM; Need ultrasonic) | ||
| Chemical Name | 2,2-diphenyl-5-[4-[(E)-pyridin-3-ylmethylideneamino]piperazin-1-yl]pentanenitrile | ||
| SMILES | C1CN(CCN1CCCC(C#N)(C2=CC=CC=C2)C3=CC=CC=C3)N=CC4=CN=CC=C4 | ||
| Standard InChIKey | QFYKXKMYVYOUNJ-JBASAIQMSA-N | ||
| Standard InChI | 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+ | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Selective Δ6 desaturase inhibitor (IC50 = 0.2 μM in vitro). Displays selectivity over Δ5 and Δ9 desaturases (IC50 values are >200 μM in vitro). Exhibits anti-inflammatory properties in a mouse edema model. |
SC 26196 Dilution Calculator
SC 26196 Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.361 mL | 11.805 mL | 23.61 mL | 47.2199 mL | 59.0249 mL |
| 5 mM | 0.4722 mL | 2.361 mL | 4.722 mL | 9.444 mL | 11.805 mL |
| 10 mM | 0.2361 mL | 1.1805 mL | 2.361 mL | 4.722 mL | 5.9025 mL |
| 50 mM | 0.0472 mL | 0.2361 mL | 0.4722 mL | 0.9444 mL | 1.1805 mL |
| 100 mM | 0.0236 mL | 0.118 mL | 0.2361 mL | 0.4722 mL | 0.5902 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Effect of the delta6-desaturase inhibitor SC-26196 on PUFA metabolism in human cells.[Pubmed:12848296]
Lipids. 2003 Apr;38(4):469-76.
The objective of this study was to determine the effect of 2,2-diphenyl-5-(4-[[(1 E)-pyridin-3-yl-methylidene]amino]piperazin-1-yl)pentanenitrile (SC-26196), a delta6-desaturase inhibitor, on PUFA metabolism in human cells. SC-26196 inhibited the desaturation of 2 microM [1-14C] 18:2n-6 by 87-95% in cultured human skin fibroblasts, coronary artery smooth muscle cells, and astrocytes. By contrast, SC-26196 did not affect the conversion of [1-14C]20:3n-6 to 20:4 in the fibroblasts, demonstrating that it is selective for delta6-desaturase. The IC50 values for inhibition of the desaturation of 2 microM [1-14C] 18:3n-3 and [3-14C]24:5n-3 in the fibroblasts, 0.2-0.4 microM, were similar to those for the inhibition of [1-14C 18:2n-6 desaturation, and the rates of recovery of [1-14C]18:2n-6 and [3-14C]24:5n-3 desaturation after removal of SC-26196 from the culture medium also were similar. SC-26196 reduced the conversion of [3-14C]22:5n-3 and [3-14C]24:5n-3 to DHA by 75 and 84%, respectively, but it had no effect on the retroconversion of [3-14C]24:6n-3 to DHA. These results demonstrate that SC-26196 effectively inhibits the desaturation of 18- and 24-carbon PUFA and, therefore, decreases the synthesis of arachidonic acid, EPA, and DHA in human cells. Furthermore, they provide additional evidence that the conversion of 22:5n-3 to DHA involves delta6-desaturation.
A multiplexed cell assay in HepG2 cells for the identification of delta-5, delta-6, and delta-9 desaturase and elongase inhibitors.[Pubmed:20086206]
J Biomol Screen. 2010 Feb;15(2):169-76.
A multiplexed cell assay has been optimized to measure the activities of fatty acyl-CoA elongase, delta-5 desaturase (Delta5D), delta-6 desaturase (Delta6D), and delta-9 desaturase (Delta9D) together using (14)C-labeled tracers in HepG2 cells, which express the human stearoyl-CoA desaturase-1 isoform (SCD1) exclusively. The Delta5 and Delta9 desaturase activities are indexed by the efficient conversion of [1-(14)C]-eicosatrienoic acid (C20:3, cis-8,11,14) to (14)C-arachidonic acid (C20:4, cis-5,8,11,14) and the conversion of [1-(14)C]-stearic acid to (14)C-oleic acid (C18:1, cis-9), respectively. CP-74006 potently blocks the Delta5D activity with an IC(50) value of 20 nM and simplifies the metabolism of [1-(14)C]-alpha-linolenate (C18:3, cis-9,12,15) by accumulating (14)C-eicosatetraenoic acid (C20:4, cis-8,11,14,17) as the major (14)C-eicosatrienoic acid (C20:3, cis-11,14,17) and (14)C-docosatetraenoic acid (C22:4, cis-10,13,16,19) as the minor metabolites through Delta6 desaturation and elongation. This simplified metabolite spectrum enables the delineation of the Delta6D activity by comparing the combined Delta6D/elongase activity index of the (14)C-(C20:4/C18:3) ratio with the corresponding elongation index of the (14)C-(C20:3/C18:3) ratio following compound treatment. SC-26196 and sterculic acid specifically inhibit the Delta6D and Delta9D activities with an IC(50) value of 0.1 microM and 0.9 microM, respectively. This medium-throughput cell assay provides an efficient tool in the identification of specific desaturase and elongase inhibitors.
Selective inhibition of Delta-6 desaturase impedes intestinal tumorigenesis.[Pubmed:11741743]
Cancer Lett. 2002 Jan 25;175(2):157-63.
Arachidonic acid is an important polyunsaturated fatty acid involved in cell signaling. It is derived primarily from dietary linoleic acid, and the rate-limiting step in its biosynthesis is the initial desaturation of linoleic acid via Delta-6 desaturase. Evidence suggests that downstream metabolic products of arachidonic acid, e.g. prostaglandins, are involved in colorectal cancer, but involvement of the biosynthetic pathway of arachidonic acid has not been previously investigated. In the present study, we report the effects of a novel selective Delta-6 desaturase inhibitor, SC-26196, on tumorigenesis in two in vivo models of intestinal cancer. SC-26196 treatment resulted in 36-37% fewer tumors in Apc(Min/+) mice and 35% decrease in primary tumor size in nude mice bearing HT-29 human colon cancer cell xenografts (P<0.05). As expected, SC-26196 treatment resulted in significantly higher linoleic acid levels in tissue phospholipids and lower levels of arachidonic acid. The effects on both tissue fatty acid composition and tumorigenesis in Apc(Min/+) mice were abrogated by concomitant treatment with dietary arachidonic acid, indicating that the observed effects were due to interference with the biosynthetic pathway of arachidonic acid.
Novel, selective delta6 or delta5 fatty acid desaturase inhibitors as antiinflammatory agents in mice.[Pubmed:9765335]
J Pharmacol Exp Ther. 1998 Oct;287(1):157-66.
Decreased synthesis of arachidonic acid by inhibition of the Delta6 or Delta5 desaturase was evaluated as a means to mitigate inflammation. Using quantitative in vitro and in vivo radioassays, novel compounds representing five classes of Delta5 desaturase inhibitors and one class of Delta6 desaturase inhibitor were identified. The Delta6 desaturase inhibitor, SC-26196, had pharmacokinetic and pharmacodynamic profiles in mice that allowed for the evaluation of the pharmacological effects of chronic inhibition of desaturase activity. SC-26196 decreased edema to the same extent as indomethacin or essential fatty acid deficiency in the carrageenan paw edema model in the mouse. The antiinflammatory properties of SC-26196 were consistent with its mechanism of action as a Delta6 desaturase inhibitor: 1) A correlation existed between inhibition of liver Delta6 desaturase activity and decreases in edema. 2) The onset of the decrease in edema was time dependent. 3) Selective reduction of arachidonic acid occurred dose dependently in liver, plasma and peritoneal cells. 4) In the presence of SC-26196, controlled refeeding of arachidonic acid, but not oleic acid, reversed the changes resulting from desaturase inhibition. The Delta6 desaturase may be a target for development of antiinflammatory drugs whose mechanism of action is unique.
