An "enhanced PET"-based fluorescent probe with ultrasensitivity for imaging basal and elesclomol-induced HClO in cancer cells.

Abstract

Reactive oxygen species (ROS) and cellular oxidant stress have long been associated with cancer. Unfortunately, the role of HClO in tumor biology is much less clear than for other ROS. Herein, we report a BODIPY-based HClO probe (BClO) with ultrasensitivity, fast response (within 1 s), and high selectivity, in which the pyrrole group at the meso position has an "enhanced PET" effect on the BODIPY fluorophore. The detection limit is as low as 0.56 nM, which is the highest sensitivity achieved to date. BClO can be facilely synthesized by a Michael addition reaction of acryloyl chloride with 2,4-dimethylpyrrole and applied to image the basal HClO in cancer cells for the first time and the time-dependent HClO generation in MCF-7 cells stimulated by elesclomol, an effective experimental ROS-generating anticancer agent.

• Authors: Hao Zhu, Jiangli Fan, Jingyun Wang, Huiying Mu, Xiaojun Peng
• Journal: Journal of the American Chemical Society (J Am Chem Soc) Vol. 136 Issue 37 Pg. 12820-3 (Sep 17 2014) ISSN: 1520-5126 [Electronic] United States
• PMID: 25171114 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• Antineoplastic Agents
• Boron Compounds
• Fluorescent Dyes
• Hydrazines
• elesclomol
• Hypochlorous Acid

Topics

• Animals
• Antineoplastic Agents (pharmacology)
• Boron Compounds (chemistry)
• Breast (drug effects, metabolism, pathology)
• Breast Neoplasms (drug therapy, metabolism, pathology)
• COS Cells
• Chlorocebus aethiops
• Female
• Fluorescent Dyes (chemistry)
• Humans
• Hydrazines (pharmacology)
• Hypochlorous Acid (analysis, metabolism)
• MCF-7 Cells
• Optical Imaging
• Positron-Emission Tomography