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Approaching Tryptophan-Derived Polynorbornene Fluorescent Chemosensors: Synthesis, Characterization, and Sensing
Sutthira Sutthasupa1,2, Aphiwat Pankaew3, Sukanya Thisan2,4
1Division of Packaging Technology, Faculty of Agro Industry, Chiang Mai University, Chiang Mai 50100, Thailand.
Abstract:
We present a novel group of tryptophan (Trp)-based fluorescent polymeric probes synthesized via ring-opening metathesis polymerization (ROMP) of Trp-derived norbornene monomers. These probes, in mono- and disubstituted forms, incorporate amide and ester anchoring groups. The quantity of Trp substituents did not affect fluorescence selectivity but influenced quenching percentage. Poly-diamide-Trp, Poly-monoamide-Trp, Poly-diester-Trp, and Poly-monoester-Trp probes displayed selective detection of Fe2+ and Fe3+ ions with fluorescence on-off characteristics. Poly-diamide-Trp and Poly-monoamide-Trp exhibited a limit of detection (LOD) for Fe2+ and Fe3+ ions of 0.86-11.32 μM, while Poly-diester-Trp and Poly-monoester-Trp showed higher LODs (21.8-108.7 μM). These probes exhibited high selectivity over Fe2+, a crucial metal ion in the body known for its redox properties causing oxidative stress and cell damage. Cell cytotoxicity tests in various cell types confirmed biocompatibility. Additionally, Poly-diamide-Trp displayed excellent cell permeability and iron ion detection in EA.hy926 cells, suggesting potential for bioimaging and clinical applications.
