Recent advances in the development of responsive probes for selective detection of cysteine

Recent advances in recognition, sensing and extraction of phosphates: 2015 onwards

Recent developments in molecular sensor designs for inorganic pyrophosphate detection and biological imaging

Reversible colorimetric and NIR fluorescent probe for sensing SO2/H2O2 in living cells and food samples.

Differential chemosensors have emerged as next-generation systems due to their simplicity and favourable responsive properties to produce different signals upon selective binding of various analytes simultaneously. Nevertheless, given their inadequate fluorescence response and laborious synthetic procedures, only a few differential chemosensors have been developed so far. In this work, we have employed a single pot synthesis strategy to establish a new benzimidazole-based Schiff base type fluorogenic chemosensor (DFB) which differentially detects Cu2+ (detection limit (LOD) = 24.4 ± 0.5 nM) and Zn2+ (LOD = 2.18 ± 0.1 nM) through fluorescence “off-on” manner over the library of other metal cations in an aqueous medium. The DFB-derived ‘in situ’ complexes DFB-Cu2+ and DFB-Zn2+ showed fluorescence revival “on-off” responses toward cyanide (CN−) and bio-relevant pyrophosphate (P2O7 4--PPi) ions with a significantly low LOD of 9.43 ± 0.2 and 2.9 ± 0.1 nM, respectively, in water. We have demonstrated the phosphate group-specific binding capability of DFB-Zn2+ , by testing it with both ssDNA and dsDNA samples which displayed fluorescence “turn-off” response (LOD ∼10-7 M), similar to the PPi binding in an aqueous medium, indicating that it interacts explicitly with the phosphate backbone of DNA. We have also harnessed the DFB as a sequential fluorescent probe to detect Cu2+, Zn2+, CN− and P2O7 4- ions in human cervical (HeLa) and breast (MCF-7 and MDA-MB-231 (aggressive and invasive)) cancer cell lines. Moreover, we have explored the PPi recognition capability of DFB-Zn2+ in the polymerase-chain-reaction (PCR) products where PPi is one of the primary by-products during amplification of DNA.

A benzimidazole-based new fluorogenic differential/sequential chemosensor for Cu2+, Zn2+, CN-, P2O74-, DNA, its live-cell imaging and pyrosequencing applications

There is growing interest in monitoring the level of pyrophosphate (PPi) in biological processes due to its significant roles in live organisms. In this paper, we described a Cu2+ ensemble based chemosensor (GN-Cu2+) for highly selective detection of PPi in an aqueous medium and live cells. The fluorescence silent ensemble, GN-Cu2+, was facilely prepared by complexing of the glucosamine-1,8-naphthalimide fluorescent ligand (GN) with paramagnetic Cu2+. The structure of GN was confirmed using 1H NMR, 13C NMR and high-resolution mass spectroscopy (HRMS) assays. The spectroscopic characteristics of GN-Cu2+ were verified in detail through fluorescence emission and UV-vis spectra titration. The decomplexation of GN-Cu2+ by PPi led to the liberation of the fluorescent ligand, GN, and thus the fluorescence was switched on. Spectroscopic studies revealed that GN-Cu2+ possesses excellent tolerance to various anions and even other phosphate series, such as AMP, ADP, ATP, and inorganic phosphate (Pi). The detection limit for PPi was calculated to be 1.0 μM. GN-Cu2+ features several advantages, such as high selectivity, reliability at physiological pH and low cytotoxicity. Intracellular fluorescence imaging measurements indicated that GN-Cu2+ is cell membrane permeable and has been successfully used for the detection of PPi in live MD-AMB-231 cells.

A novel glucosamine-linked fluorescent chemosensor for the detection of pyrophosphate in an aqueous medium and live cells

The development of well-designed fluorescence probes for the monitoring of redox homeostasis in biosystems has attracted significant research interest owing to their non-invasive and real-time detection capability in vivo. In this work, a reversible near-infrared (NIR) fluorescence probe (XC) was designed and synthesized for the monitoring of HSO3−/H2O2-regulated cycles in vivo. The XC probe contains a D–π–A–π–D conjugated structure with a reactive CC double bond in the benzopyrylium moiety. In the presence of HSO3−, a nucleophilic addition reaction with the unsaturated carbon atom of XC occurred and rearranged the structure from the positively charged benzopyrylium moiety to neutral chromene. The HSO3−-induced nucleophilic addition product (XC-SO3) can be oxidized to the native XC, resulting in the reversible responses to HSO3−/H2O2 cycles. In the presence of HSO3−, XC presented a significant decrease in the absorption and emission spectra, as well as a solution colour change from blue to colourless under physiological conditions (pH = 7.4), which allows for the detection of HSO3− by the “naked eye”. By further incubation of XC-SO3 with H2O2, the spectroscopic and colour signals were recovered. Biologically relevant species including anions, reactive oxygen species (ROS), biothiols and cations induced negligible spectroscopic responses. The detection limits of XC for HSO3− and XC-SO3 for H2O2 were calculated to be 1.02 μM and 0.84 μM, respectively. XC has several advantages such as high selectivity, reliability at physiological pH and low cytotoxicity, which enable its application in biological samples. Fluorescence imaging experiments in live adult zebrafish and live nude mice demonstrated that XC has the potential to monitor the HSO3−/H2O2-regulated redox homeostasis in biosystems. The practical applications of XC were also demonstrated by the quantitative analysis of HSO3− in white wine and sugar samples.

A reversible near-infrared fluorescence probe for the monitoring of HSO3−/H2O2-regulated cycles in vivo

The invention provides a fluorescent probe, and a preparation method and an application thereof in reversible detection of hydrosulfite/hydrogen peroxide in vivo, and relates to the technical field offluorescent probes. The fluorescent probe provided by the invention has a structure represented by a formula 1, wherein in the formula 1, R is -CH3, -CH2CH3, -CH2CH2CH3, -CH2CH2CH2OH or a group described in the specification. The fluorescent probe provided by the invention has the advantages of near-infrared fluorescence emission, high specificity, high sensitivity, suitability for physiologicalpH and low cytotoxicity; redox balance regulated and controlled by hydrosulfite and hydrogen peroxide can be reversibly detected, particularly, redox balance regulated and controlled by hydrosulfite and hydrogen peroxide in a living body can be reversibly detected, and the blank of application of a conventional fluorescent probe is filled up. The invention provides the preparation method of the fluorescent probe, and the preparation method provided by the invention is simple in process, easy in condition control and prone to realization of large-scale production.

Fluorescent probe, and preparation method and application thereof in reversible detection of hydrosulfite/hydrogen peroxide in vivo

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A novel glucosamine-linked fluorescent chemosensor for the detection of pyrophosphate in an aqueous medium and live cells

A reversible near-infrared fluorescence probe for the monitoring of HSO3−/H2O2-regulated cycles in vivo

Fluorescent probe, and preparation method and application thereof in reversible detection of hydrosulfite/hydrogen peroxide in vivo