U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C20H18N2O2
Molecular Weight 318.3691
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NILE RED

SMILES

CCN(CC)C1=CC2=C(C=C1)N=C3C(O2)=CC(=O)C4=CC=CC=C34

InChI

InChIKey=VOFUROIFQGPCGE-UHFFFAOYSA-N
InChI=1S/C20H18N2O2/c1-3-22(4-2)13-9-10-16-18(11-13)24-19-12-17(23)14-7-5-6-8-15(14)20(19)21-16/h5-12H,3-4H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C20H18N2O2
Molecular Weight 318.3691
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Nile red (9-diethylamino-5H-benzo[alpha]phenoxazine-5-one) is an excellent vital stain for the detection of intracellular lipid droplets by fluorescence microscopy and flow cytofluorometry. It has environment-sensitive fluorescence. Nile red is intensely fluorescent in a lipid-rich environment while it has minimal fluorescence in aqueous media. Better selectivity for cytoplasmic lipid droplets can be obtained when the cells are viewed with yellow-gold fluorescence (450-500 nm excitation; >528 nm emission) rather than red fluorescence (515-560 nm excitation; >590 nm emission). Nile red is strongly fluorescent, but only in a hydrophobic environment.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Mice were used to quantify brain uptake of fluorescently-labeled nanoparticles. Nile red-loaded nanoparticles were resuspended in PBS and administered at 200 mg/kg via the tail vein.
Route of Administration: Intravenous
In Vitro Use Guide
Prepare cells with test compounds. Add 200 to 1000 nM Nile Red working solution. Incubate at room temperature or 37C for 5 to 10 min. Remove the Nile Red working solution. Read fluorescence intensity at Ex/Em = 552/636 nm
Substance Class Chemical
Record UNII
P476F1L81G
Record Status Validated (UNII)
Record Version