Shelf life (days): 1460.0
Formulation: A crystalline solid
Formal Name: (1E,4E)-1,5-bis(2-hydroxyphenyl)-1,4-pentadien-3-one
Purity: ≥98%
Formula Markup: C17H14O3
Formula Weight: 266.3
CAS Number: 131359-24-5
Notes: Nrf2 activation of the antioxidant response element (ARE) is central to cytoprotective gene expression against oxidative and/or electrophilic stress.{17702} Unless activated by inflammatory, environmental, or oxidative stressors, Nrf2 is sequestered in the cytoplasm by its repressor, Keap1.{16386} Because of its protective capabilities, small molecules that activate Nrf2 signaling are being examined as potential anti-cancer or anti-inflammatory agents.{20661} 2-HBA, a synthetic analog of curcumin, is an indirect inducer of enzymes that catalyze detoxification reactions through the Keap1-Nrf2-ARE pathway. As a double Michael reaction acceptor, 2-HBA can directly modify cysteine sulfhydryl groups in Keap1 and consequently suppress Nrf2 ubiquitination, which leads to enhanced expression of antioxidative and cytoprotective enzymes.{21471} 2-HBA doubles the specific activity of NAD(P)H:quinone acceptor oxidoreductase 1 (NQO1) in Hepa1c1c7 cells at 0.15 μM.{21472} In rapidly dividing mouse leukemia L1210 cells, 0.6 μM 2-HBA increases the activities of NQO1, glutathione reductase, and the levels of total glutathione.{21472,21473} At 5-15 μM, 2-HBA causes G2/M cell cycle arrest and p53-independent, caspase 3-mediated apoptosis.{21472}
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