A highly selective chemodosimeter for fast detection and intracellular imaging of Hg²⁺ions based on a dithiocarbamate–isothiocyanate conversion in aqueous ethanol

Abstract

A new naphthalene diimide-dithiocarbamate based fluorescence probe was synthesized and its fluorogenic behavior towards various metal ions was studied. Upon addition of various metal ions, the probe afforded an irreversible change only with Hg(2+) ions in aqueous-ethanol media (4 : 1 v/v) with a fourfold enhancement of the fluorescence (Φ = 0.03 → 0.11) along with a distinct 43 nm blue shift of the emission maxima. The mechanism of the chemodosimetric behavior of the probe has been attributed to a Hg(2+) induced transformation of a weakly fluorescent dithiocarbamate to a highly fluorescent isothiocyanate which has been characterized by a number of spectroscopic techniques and a crystal structure. Intracellular detection of Hg(2+) ions was achieved using the probe.

Harnessing Brightness in Naphthalene Diimides

“…in which a weakly emissive dithiocarbamate‐NDI ( Φ f 0.03) is treated with Hg 2+ to form isothiocyanate‐NDI 53 showing a modest fluorescence enhancement with a Φ f of 0.11 in H 2 O/ethanol (4:1, v/v) (Figure a,b). An application of this specificity to Hg 2+ is shown in vitro, when human epithelial carcinoma cells are treated with both mercury cations and the dithiocarbamate‐NDI, leading to a bright‐blue intracellular emission, producing a potential indicator for mercury poisoning inside the body . Recent developments using 5 have taken the concept further.…”

“…An application of this specificity to Hg 2 + is shown in vitro, when human epithelial carcinomac ellsa re treated with both mercury cations and the dithiocarbamate-NDI, leading to ab right-blue intracellular emission, producing ap otential indicator for mercury poisoning inside the body. [52] Recent developments using 5 have taken the concept further. Upon the incorporation of Hg 2 + ,a tenfold increase in radiative quantum yield (from 0.03 to 0.32), is demonstrated throught he creation of emissive p-p stacked coordination polymer (l em,max 425 nm) in solution.…”

Sequence-Defined Dithiocarbamate Oligomers via a Scalable, Support-free, Iterative Strategy

“…Motivated by the promises of synthetic SDPs and the pressing need for developing an efficient strategy for synthesizing the same, we report here a highly efficient, support-free, and iterative strategy to yield multigram scale of a new class of monodispersed SDPs. The unique feature of this class of SDP is that its backbone harbors an important functional groupdithiocarbamate (DTC)which is reported as an excellent candidate for both material ( e.g., heavy metal sensors and vulcanizing accelerators in rubber industries) and biomedical applications ( e.g., antileishmanial, antiacute myelogenous leukaemia, antitrypanosomatids, and anticancer agents). To our knowledge, this is the first report on a DTC-based SDP.…”

New Pyridine-Bridged Ferrocene–Rhodamine Receptor for the Multifeature Detection of Hg2+ in Water and Living Cells

“… 3 − 5 Once inside the human body, Hg(II) tends to accumulate in vital organs and impairs human health even at low concentrations due to its strong affinity to thiols from enzymes and proteins. 6 − 9 For example, Hg(II) can cause the serious Minamata disease. 10 Therefore, it is significant to develop new strategies for efficiently monitoring Hg 2+ ions in aqueous media and biological systems.…”