2-HBA

Names

[ Name ]:
2-HBA

[Synonym ]:
1,4-Pentadien-3-one, 1,5-bis(2-hydroxyphenyl)-, (1E,4E)-
(1E,4E)-1,5-Bis(2-hydroxyphenyl)penta-1,4-dien-3-one
QR B1U1V1U1R BQ &&(E,E)- Form
(1E,4E)-1,5-Bis(2-hydroxyphenyl)-1,4-pentadien-3-one

Biological Activity

[Description]:

2-HBA is a potent inducer of NAD(P)H:quinone acceptor oxidoreductase 1 (NQO1) which can also activate caspase-3 and caspase-10.

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Caspase

Research Areas >> Cancer

[Target]

Caspase-3

Caspase-10

[In Vitro]

When L1210 cells are exposed to 0.6 μM 2-HBA (bis(2-hydroxy-benzylidene)acetone), the specific activities of NQO1 and glutathione reductase increase by 6- and 1.5-fold, respectively. The total cellular glutathione content is also coordinately induced by 2.4-fold. In a more detailed study it is found that NQO1 is induced by 2-HBA in a concentration-dependent manner. Treatments with 2-HBA cause cell cycle arrest and apoptosis in both L1210 wild type cells and their Y8 drug-resistant counterparts in a concentration-dependent manner. 2-HBA can also activate caspase-3 and caspase-10[1].

[Kinase Assay]

Cells (20,000 per well) are grown for 24 h in 96-well plates, then exposed to 2-HBA (bis(2-hydroxybenzylidene)acetone) for either 24 h (for glutathione determination) or 48 h (for determination of enzyme activities). At the end of the exposure period, cells are collected by centrifugation (1500×g for 15 min at 4°C), washed with DPBS, and finally lysed in 0.08% digitonin. An aliquot (25 μL) is used for protein analysis. Activity of NQO1 is determined by the Prochaska test[1].

[Cell Assay]

After exposure to 2-HBA (bis(2-hydroxybenzylidene)acetone) for 24 h, duplicate aliquots of cells (1×106) are collected by centrifugation and washed with cold DPBS. Apoptosis is determined using the Annexin-V-FLUOS assay with simultaneous determination of the necrotic fraction by the uptake of propidium iodide[1].

[References]

[1]. Dinkova-Kostova AT, et al. Bis(2-hydroxybenzylidene)acetone, a potent inducer of the phase 2 response, causes apoptosis in mouse leukemia cells through a p53-independent, caspase-mediated pathway. Cancer Lett. 2007 Jan 8;245(1-2):341-9.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
495.5±40.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₇H₁₄O₃

[ Molecular Weight ]:
266.291

[ Flash Point ]:
267.6±23.8 °C

[ Exact Mass ]:
266.094299

[ PSA ]:
57.53000

[ LogP ]:
4.91

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.704

[ Storage condition ]:
2-8℃

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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