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SML1104

Sigma-Aldrich

NQTrp

≥98% (HPLC)

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Synonym(s):
1,4-Naphthoquinon-2-yl-l-tryptophan, N-(1,4-Dihydro-1,4-dioxo-2-naphthalenyl)-L-tryptophan
Empirical Formula (Hill Notation):
C21H16N2O4
CAS Number:
185351-19-3
Molecular Weight:
360.36
MDL number:
MFCD21496345
UNSPSC Code:
12352200
PubChem Substance ID:
329825479
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

, orange to dark orange-red

solubility

DMSO: 20 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C1C(N[C@H](C(O)=O)CC2=CNC3=C2C=CC=C3)=CC(C4=C1C=CC=C4)=O

InChI

1S/C21H16N2O4/c24-19-10-17(20(25)15-7-2-1-6-14(15)19)23-18(21(26)27)9-12-11-22-16-8-4-3-5-13(12)16/h1-8,10-11,18,22-23H,9H2,(H,26,27)/t18-/m0/s1

InChI key

DZZUYZXINNHEGM-SFHVURJKSA-N

Biochem/physiol Actions

NQTrp is a potent inhibitor of amyloid aggregation (AD). NQTrp completely inhibits Ab oligomerization and fibrillization, and the cytotoxic effect of Ab oligomers in cultured neuronal cell line.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Moran Frenkel-Pinter et al.
Journal of Alzheimer's disease : JAD, 51(1), 165-178 (2016-02-03)
Tauopathies, such as Alzheimer's disease (AD), are a group of disorders characterized neuropathologically by intracellular toxic accumulations of abnormal protein aggregates formed by misfolding of the microtubule-associated protein tau. Since protein self-assembly appears to be an initial key step in
Olivia Berthoumieu et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 21(36), 12657-12666 (2015-07-17)
Inhibition of the aggregation of the monomeric peptide β-amyloid (Aβ) into oligomers is a widely studied therapeutic approach in Alzheimer's disease (AD). Many small molecules have been reported to work in this way, including 1,4-naphthoquinon-2-yl-L-tryptophan (NQ-Trp). NQ-Trp has been reported

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