4.8 Article

Development of Rofecoxib-Based Fluorescent Probes and Investigations on Their Solvatochromism, AIE Activity, Mechanochromism, and COX-2-Targeted Bioimaging

Journal

ANALYTICAL CHEMISTRY
Volume 93, Issue 35, Pages 11991-12000

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.analchem.1c01978

Keywords

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Funding

  1. National Institutes of Health [GM070737]
  2. Strategic Priority Research Program of the CAS [XDB20000000]
  3. NSFC [51872048, 21975257, 21771185, 21406143]
  4. NSF of Fujian Province [2019I0029]
  5. Shenyang Pharmaceutical University
  6. Texas CPRIT [RP180863]

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A new class of COX-2-specific fluorescent probes has been developed in this study with attractive fluorescence properties, showing potential for identifying COX-2 in cancer cells and tissues.
Cyclooxygenase-2 (COX-2) fluorescent probes are promising tools for early diagnosis of cancer. Traditionally, COX-2 probes were designed by connecting two parts, a fluorophore and a COX-2 binding unit, via a flexible linker. Herein, a new class of COX-2-specific fluorescent probes have been developed via one-step modification from rofecoxib by an integrative approach to combine the binding unit and the fluorophore into one. Among them, several new rofecoxib analogues not only exhibited still potent COX-2 binding ability but also exhibited attractive fluorescence properties, such as tunable blue-red emission, solvatochromism, aggression-induced emission behavior, and mechanochromism. Notably, the emission of 2a16 can be switched between green-yellow in the crystalline state and red-orange in the amorphous state by grinding and fuming treatments. Furthermore, the highly fluorescent compound 2a16 (Phi(f) = 0.94 in powder) displayed a much stronger fluorescence imaging of COX-2 in HeLa cancer cells overexpressing COX-2 than RAW264.7 normal cells with a minimal expression of COX-2. Most importantly, 2a16 can light up human cancer tissues from adjacent normal tissues with a much brighter fluorescence by targeting the COX-2 enzyme. These results demonstrated the potential of 2a16 as a new red fluorescent probe for human cancer imaging in clinical applications.

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