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SML2021

Sigma-Aldrich

MIND4-17

≥98% (HPLC)

Synonym(s):

5-Nitro-2-{[5-(phenoxymethyl)-4-phenyl-4H-1,2,4-triazol-3-yl]thio}pyridine

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About This Item

Empirical Formula (Hill Notation):
C20H15N5O3S
CAS Number:
345989-24-4
Molecular Weight:
405.43
MDL number:
MFCD01899657
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to brown

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

O=[N+]([O-])C(C=C1)=CN=C1SC2=NN=C(COC3=CC=CC=C3)N2C4=CC=CC=C4

Biochem/physiol Actions

MIND4-17 is a potent NRF2 (nuclear factor erythroid 2-related factor 2) activator that covalently modifies a critical stress-sensor cysteine (C151) in the BTB domain of the E3 ligase substrate adaptor protein Kelch-like ECH-associated protein 1 (KEAP1), the primary negative regulator of NRF2. MIND4-17 induces NRF2 activation responses in neuronal and non-neuronal cultures (effective conc. 0.1-10 μM) of human, mouse, and rat origins. In addition, MIND4-17 effectively reduces endotoxin-induced IL-6 release from WT as well as YAC128 HD mutant mice-derived primary microglia and astrocytes, however, NRF2 induction by MIND4-17 is shown to be compromised in human Huntington′s diseased (HD) relative to non-disesed neural stem cells due to suppressive influence of the expanded CAG repeat mutation on pathway activation.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Luisa Quinti et al.
Cell chemical biology, 23(7), 849-861 (2016-07-19)
There are currently no disease-modifying therapies for the neurodegenerative disorder Huntington's disease (HD). This study identified novel thiazole-containing inhibitors of the deacetylase sirtuin-2 (SIRT2) with neuroprotective activity in ex vivo brain slice and Drosophila models of HD. A systems biology approach
Luisa Quinti et al.
Proceedings of the National Academy of Sciences of the United States of America, 114(23), E4676-E4685 (2017-05-24)
The activity of the transcription factor nuclear factor-erythroid 2 p45-derived factor 2 (NRF2) is orchestrated and amplified through enhanced transcription of antioxidant and antiinflammatory target genes. The present study has characterized a triazole-containing inducer of NRF2 and elucidated the mechanism

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