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Near-infrared Cell-Permeable Hg2+-selective Ratiometric Fluorescent Chemodosimeters and Fast Indicator Paper for MeHg+ Based on Tricarbocyanines

Near-infrared Cell-Permeable Hg2+-selective Ratiometric Fluorescent Chemodosimeters and Fast Indicator Paper for MeHg+ Based on Tricarbocyanines

Zhiqian Guo, Weihong Zhu, Mingming Zhu, Xumeng Wu, He Tian

Chemistry. 2010 Dec 27;16(48):14424-32.

PMID: 21038328

Abstract:

Three tricarbocyanine dyes (IR-897, IR-877, and IR-925) with different thiourea substituents that function as dosimeter units through specific Hg(2+)-induced desulfurization have been demonstrated in a fast indicator paper for Hg(2+) and MeHg(+) ions. In comparison with available Hg(2+)-selective chemodosimeters, IR-897 and IR-877 show several advantages, such as convenient synthesis, very long wavelengths falling in the near-infrared (NIR) region (650-900 nm) with high molar extinction coefficients, a ratiometric response, and quite low disturbance with Ag(+) and Cu(2+) ions. They exhibit large redshifts, which result in a clear color change from deep blue to pea green that can be easily monitored by the naked eye for a convenient indicator paper. In emission spectra, they display a characteristic turn-off mode at 780 nm and turn-on mode at 830 nm with titration of Hg(2+) ions. Remarkably, the signal/noise (S/N) ratio with other thiophilic metal ions (Ag(+) and Cu(2+)) is greatly enhanced with ratiometric measurement of two channels: excitation spectra mode (I(810 nm)/I(670 nm), monitored at 830 nm) and emission spectra mode (I(830 nm)/I(780 nm), isosbestic absorption point at 730 nm as excitation). The distinct response is dependent upon the electron-donating effect of the thiourea substituents; that is, the stronger the electron-donating capability of the thiourea substituents, the faster the Hg(2+)-promoted cyclization. Additionally, experiments with living SW1116 cells show that these three tricarbocyanine dyes with low toxicity can exhibit special characteristics that are favorable for visualizing intracellular Hg(2+) and MeHg(+) ions in biological systems, including excellent membrane permeability, minimal interfering absorption and fluorescence from biological samples, low scattering, and deep penetration into tissues.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
TIT92401	Special indicator paper			Price

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