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SML0146

Sigma-Aldrich

ZL006

≥98% (HPLC)

Synonym(s):

4-((3,5-Dichloro-2-hydroxybenzyl)amino)-2-hydroxybenzoic acid

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About This Item

Empirical Formula (Hill Notation):
C14H11Cl2NO4
CAS Number:
1181226-02-7
Molecular Weight:
328.15
MDL number:
MFCD20527326
UNSPSC Code:
12352200
PubChem Substance ID:
329825194
NACRES:
NA.25

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥5 mg/mL (warmed to 60° C)

storage temp.

2-8°C

SMILES string

OC1=C(Cl)C=C(Cl)C=C1CNC(C=C2)=CC(O)=C2C(O)=O

InChI

1S/C14H11Cl2NO4/c15-8-3-7(13(19)11(16)4-8)6-17-9-1-2-10(14(20)21)12(18)5-9/h1-5,17-19H,6H2,(H,20,21)

InChI key

RTEYSQSXRFVKTJ-UHFFFAOYSA-N

Biochem/physiol Actions

ZL006 inhibits the ischemia-induced interaction of nNOS with postsynaptic density protein-95 (PSD-95), preventing glutamate-induced excitotoxicity and cerebral ischemic damage. It does not inhibit nNOS itself. ZL006 is brain penetrant, and has been tested in both rat and mouse models of stroke.
ZL006, a novel neuroprotectant, is also called as 5-(3, 5-dichloro-2-hydroxybenzylamino)-2-hydroxybenzoic acid. It has the ability to block the interaction of neuronal nitric oxide synthase (nNOS)/postsynaptic density protein-95 (PSD-95) in co-immunoprecipitation assays of extracts from glutamate or cultured neurons and cortical brain, stimulated by ischemia.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

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Wenrui Qu et al.
Cerebral cortex (New York, N.Y. : 1991), 30(7), 3859-3871 (2020-01-29)
Excessive activation of N-methyl-D-aspartate receptors (NMDARs) and the resulting neuronal nitric oxide synthase (nNOS) activation plays a crucial role in the pathogenesis of traumatic brain injury (TBI). However, directly inhibiting NMDARs or nNOS produces adverse side effects because they play
Sandra Tillmann et al.
PloS one, 12(8), e0182698-e0182698 (2017-08-05)
N-methyl-D-aspartate receptor (NMDA-R) antagonists and nitric oxide inhibitors have shown promising efficacy in depression but commonly induce adverse events. To circumvent these, a more indirect disruption of the nitric oxide synthase/postsynaptic density protein 95 kDa complex at the NMDA-R has
Xiaoli Gu et al.
Journal of separation science, 40(17), 3522-3534 (2017-07-14)
In the scope of stroke treatment, new neuronal nitric oxide synthase-postsynaptic density protein-95 uncouplers from herbal medicines were discovered and captured. To do so, highly selective magnetic molecularly imprinted polymers with a core-shell structure were prepared as artificial antibodies. According
Sukwoon Song et al.
Biochemical and biophysical research communications, 523(1), 86-90 (2019-12-14)
Fear renewal is defined as return of the conditioned fear responses after extinction when a conditioned stimulus (CS) is given outside of the extinction context. Previously, we have suggested that extinction induces S-nitrosylation of GluA1 in the lateral amygdala (LA)
Satoshi Deyama et al.
Neuropharmacology, 118, 59-68 (2017-03-13)
Pain consists of sensory and affective components. Although the neuronal mechanisms underlying the sensory component of pain have been studied extensively, those underlying its affective component are only beginning to be elucidated. Previously, we showed the pivotal role of the
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