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PZ0176

Sigma-Aldrich

SC-26196

≥98% (HPLC)

Synonyme(s) :

SC-26196, 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

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About This Item

Formule empirique (notation de Hill):
C27H29N5
Numéro CAS:
218136-59-5
Poids moléculaire :
423.55
Numéro MDL:
MFCD11226148
Code UNSPSC :
41121801
ID de substance PubChem :
329823750
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to tan

Solubilité

DMSO: ≥10 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

N#CC(CCCN1CCN(CC1)\N=C\c2cccnc2)(c3ccccc3)c4ccccc4

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+

Clé InChI

QFYKXKMYVYOUNJ-JBASAIQMSA-N

Application

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

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Wan-Hsin Chang et al.
Lipids in health and disease, 17(1), 201-201 (2018-08-30)
The macrophage plays an important role in innate immunity to induce immune responses. Lipid replacement therapy has been shown to change the lipid compositions of mitochondria and potentially becomes an alternative to reduce the inflammatory response. We examined the effects
Wondong Kim et al.
Cell metabolism, 29(4), 856-870 (2019-01-29)
The reactions catalyzed by the delta-5 and delta-6 desaturases (D5D/D6D), key enzymes responsible for highly unsaturated fatty acid (HUFA) synthesis, regenerate NAD+ from NADH. Here, we show that D5D/D6D provide a mechanism for glycolytic NAD+ recycling that permits ongoing glycolysis
Jie Wang et al.
Cancer management and research, 10, 6779-6790 (2018-12-26)
It has been reported that cell inflammation pathways contribute to the development of prostaglandin E2 (PGE2)-inhibitor of DNA-binding protein-1 (ID1)-dependent radio-resistance in glioblastoma. Here, we proposed that inhibiting delta-6-desaturase (D6D) could block arachidonic acid synthesis and PGE2 production, thereby reversing
Jiajun Du et al.
Nature communications, 11(1), 4830-4830 (2020-09-26)
Non-invasively probing metabolites within single live cells is highly desired but challenging. Here we utilize Raman spectro-microscopy for spatial mapping of metabolites within single cells, with the specific goal of identifying druggable metabolic susceptibilities from a series of patient-derived melanoma
Shuxian Dong et al.
Nature, 591(7848), 117-123 (2021-01-15)
The activation of mostly quiescent haematopoietic stem cells (HSCs) is a prerequisite for life-long production of blood cells1. This process requires major molecular adaptations to allow HSCs to meet the regulatory and metabolic requirements for cell division2-4. The mechanisms that

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