| Identification | Back Directory | [Name]
5-nitro-2-[[5-(phenoxymethyl)-4-phenyl-1,2,4-triazol-3-yl]sulfanyl]pyridine | [CAS]
345989-24-4 | [Synonyms]
MIND4-17
MIND4-17 >=98% (HPLC)
5-nitro-2-[[5-(phenoxymethyl)-4-phenyl-1,2,4-triazol-3-yl]sulfanyl]pyridine
Pyridine, 5-nitro-2-[[5-(phenoxymethyl)-4-phenyl-4H-1,2,4-triazol-3-yl]thio]- | [Molecular Formula]
C20H15N5O3S | [MDL Number]
MFCD01899657 | [MOL File]
345989-24-4.mol | [Molecular Weight]
405.43 |
| Chemical Properties | Back Directory | [Boiling point ]
667.5±65.0 °C(Predicted) | [density ]
1.39±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: 2mg/mL, clear (warmed) | [form ]
Solid | [pka]
-0.38±0.10(Predicted) | [color ]
Off-white to light yellow | [InChI]
1S/C20H15N5O3S/c26-25(27)16-11-12-19(21-13-16)29-20-23-22-18(14-28-17-9-5-2-6-10-17)24(20)15-7-3-1-4-8-15/h1-13H,14H2 | [InChIKey]
OZUBDKIROJPQGE-UHFFFAOYSA-N | [SMILES]
O=[N+]([O-])C(C=C1)=CN=C1SC2=NN=C(COC3=CC=CC=C3)N2C4=CC=CC=C4 |
| Safety Data | Back Directory | [WGK Germany ]
WGK 3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
MIND4-17 is a potent NRF2 activator that covalently modifies a C151 residue of Keap1. MIND4-17 disrupts Keap1-Nrf2 association, leading to Nrf2 protein stabilization and nuclear translocation. MIND4‐17 exerts potent antioxidant activity[1][2]. | [Biological Activity]
MIND4-17 is a potent NRF2 (nuclear factor erythroid 2-related factor 2) activator th at 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 humanmouseand r at origins. In additionMIND4-17 effectively reduces endotoxin-induced IL-6 release from WT as well as YAC128 HD mutant mice-derived primary microglia and astrocyteshoweverNRF2 induction by MIND4-17 is shown to be compromised in human Huntingtonμs diseased (HD) relative to non-disesed neural stem cells due to suppressive influence of the expanded CAG repe at mutation on pathway activation. | [in vivo]
MIND4‐17 (2 mg/kg; intravitreal injection; once) activates Nrf2 signaling and attenuates retinal dysfunction by light damage in mice[2]. | Animal Model: | BALB/c mice bearing white fluorescent light exposure[2] | | Dosage: | 2 mg/kg | | Administration: | Intravitreal injection; once | | Result: | Activated Nrf2 signaling and attenuated retinal dysfunction by light damage in mice. |
| [References]
[1] Luisa Quinti, et al. SIRT2- and NRF2-Targeting Thiazole-Containing Compound with Therapeutic Activity in Huntington's Disease Models. Cell Chem Biol. 2016 Jul 21;23(7):849-861. DOI:10.1016/j.chembiol.2016.05.015
[2] Nan Chen, et al. The Nrf2 activator MIND4-17 protects retinal ganglion cells from high glucose-induced oxidative injury. J Cell Physiol. 2020 Oct;235(10):7204-7213. DOI:10.1002/jcp.29619 |
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| Company Name: |
Energy Chemical
|
| Tel: |
021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
| Company Name: |
Merck KGaA
|
| Tel: |
21-20338288 |
| Website: |
www.sigmaaldrich.cn |
|