SC 26196 (Synonyms: α,αDiphenyl4(3pyridinylmethylene)amino1piperazinepentanenitrile) |
Catalog No.GC13772
One-Click Copy Product Info
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SC 26196 is an orally active Delta6 desaturase (D6D, FADS2) inhibitor that regulates lipid metabolism by inhibiting the conversion of linoleic acid and α-linolenic acid into long-chain unsaturated fatty acids.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 218136-59-5
Sample solution is provided at 25 µL, 10mM.
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SC 26196 is an orally active Delta6 desaturase (D6D, FADS2) inhibitor that regulates lipid metabolism by inhibiting the conversion of linoleic acid and α-linolenic acid into long-chain unsaturated fatty acids[1-2]. SC 26196 is applicable for research related to inflammatory diseases and lipid metabolism disorders[3-4].
In vitro, in skin fibroblasts, coronary artery smooth muscle cells, and astrocytes, SC 26196 (2μM; 24 hours) inhibited the desaturation of 2μM [1-14C]18:2n-6 and significantly reduced the synthesis of arachidonic acid, EPA, and DHA[5]. During the differentiation of 3T3-L1 adipocytes, SC 26196 (5μM; 8 days) blocked the conversion of α-linolenic acid (ALA) to eicosapentaenoic acid (EPA) and docosapentaenoic acid (DPAn-3), and reduced triacylglycerol accumulation in adipocytes. SC 26196 treatment increased the release of non-esterified fatty acids and glycerol into the culture medium and decreased the expression of the fatty acid re-esterification markers PEPCK and CD36[6].
In vivo, in athymic mice bearing U-87 MG cell xenografts, SC 26196 (30mg/kg) administered via intraperitoneal injection (every three days for four weeks). SC 26196 synergistically inhibited the growth of U-87 MG xenograft tumors when combined with radiation therapy (5Gy local X-ray irradiation, every three days)[7]. In ApcMin/+ mice bearing HT-29 colon cancer cell xenografts, dietary administration of SC 26196 (100mg/kg) for seven weeks. SC 26196 reduced number of intestinal tumors and a significant decrease in tumor size[8].
References:
[1] Sibbons CM, Irvine NA, Pérez-Mojica JE, et al. Polyunsaturated Fatty Acid Biosynthesis Involving Δ8 Desaturation and Differential DNA Methylation of FADS2 Regulates Proliferation of Human Peripheral Blood Mononuclear Cells. Front Immunol. 2018 Mar 5;9:432.
[2] Hargrave-Barnes KM, Azain MJ, Miner JL. Conjugated linoleic acid-induced fat loss dependence on Delta6-desaturase or cyclooxygenase. Obesity (Silver Spring). 2008 Oct;16(10):2245-52.
[3] Duffin KL, Obukowicz MG, Salsgiver WJ, et al. Lipid remodeling in mouse liver and plasma resulting from delta6 fatty acid desaturase inhibition. Lipids. 2001 Nov;36(11):1203-8.
[4] Obukowicz MG, Welsch DJ, Salsgiver WJ, et al. Novel, selective delta6 or delta5 fatty acid desaturase inhibitors as antiinflammatory agents in mice. J Pharmacol Exp Ther. 1998 Oct;287(1):157-66.
[5] Harmon SD, Kaduce TL, Manuel TD, et al. Effect of the delta6-desaturase inhibitor SC-26196 on PUFA metabolism in human cells. Lipids. 2003 Apr;38(4):469-76.
[6] Wang C, MacIntyre B, Mutch DM. Inhibition of Δ-6 desaturase reduces fatty acid re-esterification in 3T3-L1 adipocytes independent of changes in n3-PUFA cellular content. Biochim Biophys Acta Mol Cell Biol Lipids. 2022 Jul;1867(7):159160.
[7] Wang J, Liang H, Sun M, et al. Delta-6-desaturase inhibitor enhances radiation therapy in glioblastoma in vitro and in vivo. Cancer Manag Res. 2018 Dec 7;10:6779-6790.
[8] Hansen-Petrik MB, McEntee MF, Johnson BT, et al. Selective inhibition of Delta-6 desaturase impedes intestinal tumorigenesis. Cancer Lett. 2002 Jan 25;175(2):157-63.
| Cell experiment [1]: | |
Cell lines | 3T3-L1 adipocytes (murine preadipocyte cell line) |
Preparation Method | 3T3-L1 pre-adipocytes were differentiated in high-glucose DMEM supplemented with 10% FBS, a standard differentiation cocktail (IBMX, DEX, insulin), and treated with the Δ-6 desaturase (D6D) inhibitor SC 26196 (5μM) throughout the 8-day differentiation process, either in the presence or absence of α-linolenic acid (ALA, 50μM) or eicosapentaenoic acid (EPA, 50μM). |
Reaction Conditions | 5μM; treatment throughout differentiation (8 days). |
Applications | SC 26196 treatment significantly reduced triacylglycerol (TAG) accumulation in differentiated 3T3-L1 adipocytes. SC 26196 inhibited the conversion of ALA to EPA and docosapentaenoic acid (DPAn-3). SC 26196 increased the release of non-esterified fatty acids (NEFA) and glycerol into the medium, elevated the NEFA/glycerol ratio, and decreased the expression of fatty acid re-esterification markers PEPCK and CD36 at both mRNA and protein levels. These effects on TAG accumulation and fatty acid re-esterification were observed independently of changes in cellular n-3 polyunsaturated fatty acid (PUFA) content. |
| Animal experiment [2]: | |
Animal models | ApcMin/+ mice (intestinal tumorigenesis model) and nude mice bearing HT-29 human colon cancer cell xenografts. |
Preparation Method | ApcMin/+ mice were fed SC 26196 mixed into their diet (AIN-93G diet or US17 diet) at a dosage of 100mg/kg/day for 7 weeks. In a separate xenograft study, nude mice were inoculated with HT-29 cells, maintained on the US17 diet, and then fed SC 26196 mixed into the same diet (100mg/kg/day) starting 5 days after tumor cell implantation. Primary tumor growth in the xenograft model was monitored. |
Dosage form | 100mg/kg/day; Administered in the diet; Daily for 7 weeks (ApcMin/+ mice) and for the study duration post-implantation (xenograft mice). |
Applications | SC 26196 treatment resulted fewer intestinal tumors in ApcMin/+ mice and reduced average primary tumor size. In nude mice bearing HT-29 xenografts, SC 26196 treatment inhibited tumor growth at 4 weeks. The anti-tumorigenic effects on ApcMin/+ mice were nullified by concomitant dietary supplementation of arachidonic acid (AA), which bypassed the SC 26196-mediated inhibition of Δ-6 desaturase. |
References: | |
| Cas No. | 218136-59-5 | SDF | |
| Synonyms | α,αDiphenyl4(3pyridinylmethylene)amino1piperazinepentanenitrile | ||
| Chemical Name | (E)-2,2-diphenyl-5-(4-((pyridin-3-ylmethylene)amino)piperazin-1-yl)pentanenitrile | ||
| Canonical SMILES | N#CC(C1=CC=CC=C1)(C2=CC=CC=C2)CCCN(CC3)CCN3/N=C/C4=CC=CN=C4 | ||
| Formula | C27H29N5 | M.Wt | 423.55 |
| Solubility | DMF: 12 mg/mL,DMF:PBS (pH 7.2) (1:4): 0.2 mg/mL,DMSO: 5 mg/mL | Storage | Store at -20°C |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
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| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
| Prepare stock solution | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.361 mL | 11.805 mL | 23.61 mL |
| 5 mM | 472.2 μL | 2.361 mL | 4.722 mL |
| 10 mM | 236.1 μL | 1.1805 mL | 2.361 mL |
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Note: 1. Please make sure the liquid is clear before adding the next solvent.
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Quality Control & SDS
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- Purity: >98.00% Appearance: A solid
- COA (Certificate of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 8 reference(s) in Google Scholar.)