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72964

Sigma-Aldrich

6-(7-Nitrobenzofurazan-4-ylamino)hexanoic acid

suitable for fluorescence

Synonym(s):

6-(7-Nitro-2,1,3-benzoxadiazol-4-ylamino)hexanoic acid

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About This Item

Empirical Formula (Hill Notation):
C12H14N4O5
CAS Number:
88235-25-0
Molecular Weight:
294.26
Beilstein:
6936249
MDL number:
MFCD00057884
UNSPSC Code:
12352116
PubChem Substance ID:
329764495
NACRES:
NA.32

Assay

≥96.0% (HPLC)

form

powder

fluorescence

λex 466 nm; λem 535 nm in methanol

suitability

suitable for fluorescence

SMILES string

OC(=O)CCCCCNc1ccc([N+]([O-])=O)c2nonc12

InChI

1S/C12H14N4O5/c17-10(18)4-2-1-3-7-13-8-5-6-9(16(19)20)12-11(8)14-21-15-12/h5-6,13H,1-4,7H2,(H,17,18)

InChI key

DJFNQJJTTPMBIL-UHFFFAOYSA-N

Other Notes

Probing of the binding sites of fatty acid and sterol carrier proteins

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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S Lin et al.
Photochemistry and photobiology, 54(3), 361-365 (1991-09-01)
The fluorescence kinetics of the nitrobenzoxadiazole (NBD) chromophore were studied at low concentrations in solvents with varying polarity and hydrogen-bonding donor strength. The emission decay was essentially single exponential in all solvents studied. While the absorption and fluorescence solvatochromism is
J C McIntyre et al.
Chemistry and physics of lipids, 66(3), 171-180 (1993-12-01)
The synthesis, identification and characterization of neutral lipid analogs containing N-(7-nitro-2,1,3-benzoxadiazoi-4-yl)-aminocaproic acid are reported. The acyl-imidazole derivative of the fluorescent fatty acid was used to esterify L-alpha-glycerophosphorylcholine. Fluorescent phosphatidylcholines were converted to the corresponding diacylglycerols by phospholipase C digestion. Triacylglycerols
A Sofer et al.
Journal of cell science, 109 ( Pt 8), 2111-2119 (1996-08-01)
In order to study the endocytosis of membrane lipids during the development of neuronal polarity, we examined the internalization of a short acyl chain fluorescent derivative of ganglioside GM1, N-(6-(4-nitrobenz-2-oxa-1,3-diazole-7-yl)-aminohexanoyl)-GM1 (C6-NBD-GM1), in hippocampal neurons cultured at low density. C6-NBD-GM1 was
S J Slater et al.
Biochemistry, 32(14), 3714-3721 (1993-04-13)
It is proposed that increased phospholipid unsaturation in membranes and perturbation by agents such as ethanol weaken interlipid hydrogen bonding involving water and that the process is independent of effects on lipid order. To investigate this, the rates of phospholipid
D W Dekkers et al.
The Biochemical journal, 350 Pt 2, 531-535 (2000-08-19)
The role of multidrug resistance protein 1 (MRP1) in the maintenance of transbilayer lipid asymmetry in the erythrocyte membrane was investigated. The transbilayer distribution of endogenous phospholipids and [(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]hexanoyl (NBD)-labelled lipid analogues was compared in the absence and the presence
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