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253359

Sigma-Aldrich

4-Maleimido-TEMPO

for ESR-spectroscopy

Synonym(s):

4-Maleimido-2,2,6,6-tetramethyl-1-piperidinyloxy, free radical

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About This Item

Empirical Formula (Hill Notation):
C13H19N2O3
CAS Number:
15178-63-9
Molecular Weight:
251.30
MDL number:
MFCD00010110
UNSPSC Code:
12352005
PubChem Substance ID:
24855307
NACRES:
NA.22

grade

for ESR-spectroscopy

description

free radical

form

solid

mp

91-94 °C (lit.)

functional group

imide
maleimide

storage temp.

2-8°C

SMILES string

CC1(C)CC(CC(C)(C)N1[O])N2C(=O)C=CC2=O

InChI

1S/C13H19N2O3/c1-12(2)7-9(8-13(3,4)15(12)18)14-10(16)5-6-11(14)17/h5-6,9H,7-8H2,1-4H3

InChI key

CMNDHIFMYRPBGH-UHFFFAOYSA-N

General description

4-Maleimido-TEMPO, a water-soluble nitroxide radical, is commonly employed as spin probe. It has been reported to inhibit the survival of CHO cells at 1mM concentrations.[1] It is widely employed maleimide spin label for EPR studies.[2]

application

4-Maleimido-TEMPO (4-Maleimido-2,2,6,6,-tetramethylpiperidinooxyl) was employed as spin label to investigate the influence of bile salts on the intact rat mitochondrial membranes by electron paramagnetic resonance spectroscopy (EPR).[2] It may be employed as spin label for the labeling of erythrocyte membranes to investigate the interaction of quercetin with erythrocyte proteins by EPR spectra.[3]

Biochem/physiol Actions

Spin label used to study fluidity of brain synaptosomal membranes, internal microviscosity of erythrocytes, and human high density lipoproteins.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000101882
0000091917
BGBB2584V
11916BU
06917KZ

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Sigma-Aldrich

371343

4-Hydroxy-TEMPO benzoate, free radical

4-Oxo-TEMPO

Sigma-Aldrich

179485

4-Oxo-TEMPO

T Koppal et al.
Journal of neurochemistry, 72(1), 310-317 (1999-01-14)
Peroxynitrite (ONOO ) is a highly reactive, oxidizing anion with a half-life of <1 s that is formed by reaction of superoxide radical anion with nitric oxide. Several reports of ONOO--induced oxidation of lipids, proteins, DNA, sulfhydryls, and inactivation of
R Subramaniam et al.
Journal of neurochemistry, 69(3), 1161-1169 (1997-09-01)
Alzheimer's disease (AD) is widely held to be a disorder associated with oxidative stress due, in part, to the membrane action of amyloid beta-peptide (A beta). A beta-associated free radicals cause lipid peroxidation, a major product of which is 4-hydroxy-2-trans-nonenal
S Güldütuna et al.
Biochimica et biophysica acta, 1453(3), 396-406 (1999-04-02)
Intact mitochondria were incubated with and without calcium in solutions of chenodeoxycholate, ursodeoxycholate, or their conjugates. Glutamate dehydrogenase, protein and phospholipid release were measured. Alterations in membrane and organelle structure were investigated by electron paramagnetic resonance spectroscopy. Chenodeoxycholate enhanced enzyme
I N Gorshkova et al.
Biochimica et biophysica acta, 1300(2), 103-113 (1996-04-19)
Human low and high density lipoproteins (LDL and HDL, respectively) were treated with porcine pancreatic phospholipase A2 (PLA2) in the presence of albumin resulting in hydrolysis of 40-84% of the lipoproteins phospholipids. The resulting PLA2-treated LDL and HDL and concurrent
D A Butterfield et al.
Methods in enzymology, 309, 746-768 (1999-10-03)
Given the increasing evidence of oxidative stress in AD brain and studies from different perspectives that appear to show a converging, central role for A beta in the pathogenesis and etiology of AD, insight into A beta-associated free radical oxidative
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