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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 Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Peng Luo et al.
Cell death & disease, 10(7), 496-496 (2019-06-27)
Traumatic brain injury (TBI) has become a major health concern worldwide, and the poor outcome of TBI increases the need for therapeutic improvement. Secondary injuries following TBI, including excitotoxicity, lead to synaptic dysfunction and provide potential targets for intervention. Postsynaptic
Wen-Yuan Tao et al.
Neural regeneration research, 15(12), 2296-2305 (2020-07-01)
Amyloid beta (Aβ)-induced neurotoxicity and oxidative stress plays an important role in the pathogenesis of Alzheimer's disease (AD). ZL006 is shown to reduce over-produced nitric oxide and oxidative stress in ischemic stroke by interrupting the interaction of neuronal nitric oxide
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