Tricyclic bis(cyanoenone), TBE-31, one of the most potent activators of the Keap1/Nrf2/antioxidant response element pathway, has been developed as a new anti-inflammatory and cytoprotective agent. 13C215N2-labeled TBE-31 ([13C215N2]-TBE-31), which has two 13C and two 15N atoms in two cyano groups, was designed to develop a method for quantification of cell, tissue, and plasma levels of TBE-31 that involves chromatography/mass spectrometry coupled with the use of a stable isotope-labeled internal standard. [13C215N2]-TBE-31 was successfully synthesized in four steps from a previously reported intermediate, which is prepared in 11 steps from cyclohexanone, by introduction of two 13C atoms with ethyl [13C]formate and two 15N atoms with hydroxyl[15N]amine. The stable isotope dilution liquid chromatography–mass spectrometry method for quantification of TBE-31 was successfully developed using [13C215N2]-TBE-31 to compensate for any variables encountered during sample processing and analysis.
|Number of pages||5|
|Journal||Journal of Labelled Compounds & Radiopharmaceuticals|
|Publication status||Published - Aug 2014|
- Isotopically labeled synthesis
- Keap1/Nrf2/ARE activator
- Stable isotope dilution LC-MS method
Zheng, S., Huang, J. T. -J., Knatko, E. V., Sharp, S., Higgins, M., Ojima, I., Dinkova-Kostova, A. T., & Honda, T. (2014). Synthesis of 13C215N2-labeled anti-inflammatory and cytoprotective tricyclic bis(cyanoenone) ([13C215N2]-TBE-31) as an internal standard for quantification by stable isotope dilution LC-MS method. Journal of Labelled Compounds & Radiopharmaceuticals, 57(10), 606-610. https://doi.org/10.1002/jlcr.3230