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Merck
CN

810110C

Avanti

12-NBD Stearate

Avanti Research™ - A Croda Brand

Synonym(s):

12-N-methyl-(7-nitrobenz-2-oxa-1,3-diazo)aminostearic acid

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About This Item

Empirical Formula (Hill Notation):
C25H40N4O5
CAS Number:
117056-67-4
Molecular Weight:
476.61
UNSPSC Code:
12352211
NACRES:
NA.25

Key Documents

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Product Name

12-NBD Stearate, Avanti Research™ - A Croda Brand 810110C

InChI

1S/C25H40N4O5/c1-3-4-5-12-15-20(16-13-10-8-6-7-9-11-14-17-23(30)31)28(2)21-18-19-22(29(32)33)25-24(21)26-34-27-25/h18-20H,3-17H2,1-2H3,(H,30,31)

InChI key

SAAVELCIPHKGJE-UHFFFAOYSA-N

assay

>99% (TLC)

form

liquid

packaging

pkg of 1 × 1 mL (810110C-1mg)

manufacturer/tradename

Avanti Research™ - A Croda Brand 810110C

concentration

1 mg/mL (810110C-1mg)

shipped in

dry ice

storage temp.

−20°C

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General description

12-NBD Stearate is a fluorescent long-chain fatty acid (LCFA) derivative. It is amphipathic and a non-esterifiable fatty acid probe for incorporation into lipid droplets.

Application

12-NBD Stearate may be used:
  • as a ligand for fatty-acid binding protein 5 (FABP5) in competitive binding based high throughput fluorescence displacement assay
  • as a ligand for FABPs in spectrofluorometric measurements
  • as an inhibitor for FABP3, FABP5 and FABP7

Biochem/physiol Actions

12-NBD Stearate is unmetabolizable in HepG2 cells and colocalizes with α-caveolin-1 and its uptake is inhibited by filipin III. The sterol carrier protein-2 (SCP-2) 15-kDa isoform favors NBD Stearate transport compared to its 13.2-kDa isoform. The fatty-acid binding protein (FABP) expression in differentiating embryonic stem cells (ES) regulates the uptake of NBD Stearate. NBD Stearate is used majorly in fluorescence displacement binding assays of fatty-acid binding proteins.

Packaging

5 mL Amber Glass Screw Cap Vial (810110C-1mg)

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 1 - STOT SE 3

target_organs

Central nervous system

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

wgk

WGK 3

flash_point_f

does not flash

flash_point_c

does not flash

Regulatory Information

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Inhibition of fatty acid binding proteins elevates brain anandamide levels and produces analgesia
Kaczocha M, et al.
Testing, 9(4) (2014)
Targeting fatty acid binding protein (FABP) anandamide transporters-a novel strategy for development of anti-inflammatory and anti-nociceptive drugs
Berger WT, et al.
PLoS ONE, 7(12) (2012)
Fatty acid-binding proteins transport N-acylethanolamines to nuclear receptors and are targets of endocannabinoid transport inhibitors
Kaczocha M, et al.
The Journal of Biological Chemistry, 287(5), 3415-3424 (2012)
Targeting fatty acid binding protein (FABP) anandamide transporters-a novel strategy for development of anti-inflammatory and anti-nociceptive drugs
Berger WT, et al.
Testing, 7(12) (2012)
B P Atshaves et al.
The Journal of biological chemistry, 276(27), 25324-25335 (2001-05-03)
Despite the critical role lipid droplets play in maintaining energy reserves and lipid stores for the cell, little is known about the regulation of the lipid or protein components within the lipid droplet. Although immunofluorescence of intact cells as well
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