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Affinity Studies of Hemicyanine Derived Water Soluble Colorimetric Probes with Reactive Oxygen/Nitrogen/Sulfur Species

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Peroxynitrite (ONOO‑) is an essential endogenous reactive oxygen species (ROS) generated in mitochondria under various pathological and physiological conditions. An increase in its level in mitochondria is related to numerous diseases. In this work, we have reported a series of hemicyanine-derived water-soluble colorimetric probes (1-4) to study their reactivity with various reactive oxygen, nitrogen, and sulfur species. Probes 1-4 are formed by conjugating 1,2,3,3-tetramethyl-3H-indolium iodide and 4-hydroxybenzaldehyde or its derivatives through an alkene linkage formed by the Knoevenagel reaction. The oxidative cleavage of the electron-rich double bond of the conjugated hemicyanine dye revealed a discerning affinity of 3 towards peroxynitrite among all reactive oxygen species. The rapid color change of 3 provides a sensitive and selective method for detecting peroxynitrite with a low detection limit of 180 nM. Notably, the water solubility of the probe displays excellent performance for the selective detection of peroxynitrite among ROS, reactive nitrogen (RNS)/sulfur species (RSS). UV-vis, 1H NMR, and 13C NMR spectroscopic data and results from theoretical calculations provide further information on the interaction of peroxynitrite with probe 3.

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