A Long-Wavelength, Fluorogenic Probe for Epoxide Hydrolase: 7-(2-(Oxiran-2-yl)ethoxy) Resorufin

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  • Shen Wei
    Department of General Surgery, Jinhua Central Hospital
  • Zhang Jiaming
    Department of General Surgery, Jinhua Central Hospital
  • Mao Genjun
    Department of General Surgery, Jinhua Central Hospital
  • Jiang Keyi
    Institute of Bioengineering, Zhejiang University of Technology (Chaohui Campus)
  • Zhu Qing
    Institute of Bioengineering, Zhejiang University of Technology (Chaohui Campus)

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Epoxide hydrolase plays an important role in the detoxification of genotoxic compounds and in the control of physiological signaling molecules. Altered levels of epoxide hydrolase activity are associated with many diseases, such as emphysema, lung cancer, ovarian cancer, and laryngeal carcinoma. We designed and synthesized a resorufin-based fluorogenic probe, 7-(2-(oxiran-2-yl)ethoxy) resorufin, which was hydrolyzed by microsomal epoxide hydrolase to form the corresponding diol, which upon further treatment with sodium periodate released the strongly fluorescent resorufin. The probe exhibits good biological compatibility and photophysical properties, such as long wavelength excitation (571 nm) and emission (585 nm) and a wide working pH range (from 6.0 to 10.0), and thus facilitates the determination of the activity of microsomal epoxide hydrolase.

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