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287194-41-6

287194-41-6 structure
287194-41-6 structure
  • Name: (+)-DHMEQ
  • Chemical Name: (+)-DHMEQ
  • CAS Number: 287194-41-6
  • Molecular Formula: C13H11NO5
  • Molecular Weight: 261.230
  • Catalog: Signaling Pathways NF-κB Keap1-Nrf2
  • Create Date: 2018-06-26 17:55:14
  • Modify Date: 2024-01-08 16:34:05
  • (+)-DHMEQ is an activator of antioxidant transcription factor Nrf2. (+)-DHMEQ is the enantiomer of (-)-DHMEQ. (-)-DHMEQ inhibits NF-kB than its enantiomer (+)-DHMEQ.

Name (+)-DHMEQ
Synonyms 2-Hydroxy-N-[(1R,2R,6R)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]benzamide
Benzamide, 2-hydroxy-N-[(1R,2R,6R)-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-
Description (+)-DHMEQ is an activator of antioxidant transcription factor Nrf2. (+)-DHMEQ is the enantiomer of (-)-DHMEQ. (-)-DHMEQ inhibits NF-kB than its enantiomer (+)-DHMEQ.
Related Catalog
Target

Nrf2[1]

In Vitro (+)-DHMEQ ((2R,3R,4R)-DHMEQ) activates Nrf2, which is a transcription factor that induces the expression of multiple antioxidant enzymes. (+)-DHMEQ activates Nrf2 in a promoter reporter assay. (+)-DHMEQ also increases the expression of target antioxidant proteins and cancelled reactive oxygen species (ROS)-induced cell death in a neuronal cell line. ROS generating 6-hydroxydopamine hydrochloride (6-OHDA) induces the death of SK-N-SH cells, and (+)-DHMEQ decreases the cytotoxic effect of 6-OHDA, whereas its effect is weaker in Nrf2-knockdown cells prepared with siRNA. Thus, enhancement of the neural cell viability by (+)-DHMEQ is due to the activation of Nrf2[1].
Cell Assay SK-N-SH cells are seeded at 1.75×104 cells/well in a 24-well plate and cultured overnight. The cells are treated with various concentrations of (+)-DHMEQ (1, 3, and 10 μg/mL) for 24 h and subsequently treated with 300 μM 6-OHDA for 24 h. Then, cells are stained with Trypan blue, and the number of stained cells is counted[1].
References

[1]. Niitsu Y, et al. Chemoenzymatic synthesis of (2R,3R,4R)-dehydroxymethylepoxyquinomicin (DHMEQ), a newactivator of antioxidant transcription factor Nrf2. Org Biomol Chem. 2011 Jun 21;9(12):4635-41.

Density 1.6±0.1 g/cm3
Boiling Point 617.2±55.0 °C at 760 mmHg
Molecular Formula C13H11NO5
Molecular Weight 261.230
Flash Point 327.1±31.5 °C
Exact Mass 261.063721
LogP 0.39
Vapour Pressure 0.0±1.9 mmHg at 25°C
Index of Refraction 1.694