A cell-membrane-permeable europium complex as an efficient luminescent probe for singlet oxygen

Dai, Zhichao; Tian, Ling; Xiao, Yunna; Ye, Zhiqiang; Zhang, Run; Yuan, Jingli

doi:10.1039/c2tb00350c

Cited by 65 publications

(44 citation statements)

References 27 publications

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“…For instance, 1 O2 can readily react with a diene moiety in a [4+2] cycloaddition reaction, as in the europium complex [Eu.27], reported by Yuan [45] . A terpyridine--based platform, extensively discussed above, was used with a 10--methyl--9--anthryl moiety.…”

Section: Sensing Of Biologically Relevant Anionsmentioning

confidence: 99%

Responsive, Water‐Soluble Europium(III) Luminescent Probes

Shuvaev

Starck

Parker

2017

Chemistry A European J

113

103

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Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. E-mail: david.parker@dur.ac.uk; sergey.shuvaev@dur.ac.uk Abstract: The design principles, mechanism of action and performance of europium(III) complexes that serve as strongly emissive and responsive molecular probes in water are critically discussed. Examples of systems designed to assess pH, selected metal ions and anions, including chiral species, as well as selected small molecules and biopolymers are considered, and prospects evaluated for improved performance in more complex biological media such as in bio--fluids and within living cells. Modulation of the emission spectral form, lifetime and degree of circular polarisation can be used to quantify the spectral response and permit calibration. IntroductionThe genesis of lanthanide bio--imaging probes can be traced to two discoveries: the observation of the red emission of europium by Crookes in 1885 and the report of its sensitised emission made by Weissman in 1942 [1] . Each discovery epitomises the advantageous optical features of lanthanide complexes - narrow bands in emission with energies only slightly affected by the nature of the ligand, and a large separation (a "pseudo--Stokes' shift") between the absorbing (ligand--antenna) and emitting (lanthanide ion) photon energies. These favourable optical properties create a myriad of opportunities to devise responsive systems by judicious ligand design. Europium(III) complexes have particular advantages over other lanthanide complexes in biologically relevant applications: the higher transparency of biological tissue towards the red region of the visible spectrum; their high inherent brightness and low sensitivity to quenching by oxygen; the presence of three excited states ( 5 D2, 5 D1 and 5 D0) spanning the range 17500--21000 cm --1 that are lower in energy than the triplet levels of many different types of ligands; the presence of an environmentally insensitive magnetic--dipole transition 5 D0 to 7 F1 in the luminescence spectrum, (Figure 1), that can be used as an internal reference to the hypersensitive transition bands around 620 ( 5 D0 --7 F2) and 700 nm ( 5 D0 to 7 F4), and the high emission anisotropy factors, gem, in circularly polarised luminescence (CPL) spectra.

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Section: Sensing Of Biologically Relevant Anionsmentioning

confidence: 99%

Responsive, Water‐Soluble Europium(III) Luminescent Probes

Shuvaev

Starck

Parker

2017

Chemistry A European J

113

103

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“…We have previously reported that the ruthenium complex has a broad single-photon absorption spectrum from 350 to 550 nm17181920. For in vivo application of deep-tissue imaging, we first evaluated the two-photon absorption spectrum of these two-photon dual imaging probes.…”

Section: Resultsmentioning

confidence: 99%

“…We have previously reported the specificity and in vitro cellular uptake properties of these probes17181920. To further examine their applicability for detecting cellular GSH and ROS levels using FLIM, probes (30 μM) were incubated with a mouse hepatocyte cell line (AML12) in culture media for 2 h. Figure 2E displays the spatial distribution of the fluorescence lifetime signal of P-GSH in the AML12 cells in two emission channels.…”

Section: Resultsmentioning

confidence: 99%

“…PBS was purchased from Invitrogen (Carlsbad, CA, USA). The P-GSH, P-HP and P-HA were synthesized according to the literature17181920. AML12 cells were obtained from ATCC (Manassas, VA, USA) and maintained in vitro under cell culture conditions recommended by ATCC.…”

Section: Methodsmentioning

confidence: 99%

“…Up to now, however, no such dual-mode probe has been developed for in vivo real-time molecular imaging. We have previously synthesized a transition-metal complex-based sensing platform for detecting cellular GSH and ROS levels in vitro 17181920. This sensing platform consists of three probes, which exhibit favorable photophysical properties including high photostability, selective and quantitative response.…”

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confidence: 99%

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Two-photon dual imaging platform for in vivo monitoring cellular oxidative stress in liver injury

Wang

Zhang

Bridle

et al. 2017

Sci Rep

Self Cite

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Oxidative stress reflects an imbalance between reactive oxygen species (ROS) and antioxidants, which has been reported as an early unifying event in the development and progression of various diseases and as a direct and mechanistic indicator of treatment response. However, highly reactive and short-lived nature of ROS and antioxidant limited conventional detection agents, which are influenced by many interfering factors. Here, we present a two-photon sensing platform for in vivo dual imaging of oxidative stress at the single cell-level resolution. This sensing platform consists of three probes, which combine the turn-on fluorescent transition-metal complex with different specific responsive groups for glutathione (GSH), hydrogen peroxide (H2O2) and hypochlorous acid (HOCl). By combining fluorescence intensity imaging and fluorescence lifetime imaging, these probes totally remove any possibility of crosstalk from in vivo environmental or instrumental factors, and enable accurate localization and measurement of the changes in ROS and GSH within the liver. This precedes changes in conventional biochemical and histological assessments in two distinct experimental murine models of liver injury. The ability to monitor real-time cellular oxidative stress with dual-modality imaging has significant implications for high-accurate, spatially configured and quantitative assessment of metabolic status and drug response.

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Heptazine‐Based TADF Materials for Nanoparticle‐Based Nonlinear Optical Bioimaging

Mayder

Hojo

Primrose

et al. 2022

Adv Funct Materials

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s‐Heptazines are emerging as strong electron acceptors for efficient thermally activated delayed fluorescent (TADF) materials, yet the difficulties in synthesizing them have limited their practical use. Here, three novel s‐heptazine TADF materials with green to deep‐red emission (λmax = 525–664 nm) and high photoluminescence quantum yields, synthesized by either pseudoelectrophilic substitution or Negishi coupling routes, are described. These materials also demonstrate strong nonlinear optical absorption, with two‐photon cross sections up to 1260 GM. With deep‐red fluorescence, strong two‐photon absorption, high quantum yield, and delayed fluorescence, the emitter HAP‐3MeOTPA is ideally suited for use in nanoparticle‐based bioimaging experiments. The two kinds of luminescent nanoparticle are prepared, namely hostless, aggregate‐based organic dots (a‐Odots) and rigid, glassy Odots (g‐Odots) as biocompatible and water‐dispersible TADF probes. The g‐Odots are shown to retain the nonlinear optical properties, high photoluminescence quantum yield, and TADF observed in the constituent heptazine dye. These g‐Odots are then used as biological imaging probes with immortalized human kidney cancer (HEK293) cells, and single and multi‐photon‐excited microscopy coupled with time‐gated luminescence measurements are demonstrated. This work not only describes new routes to efficient heptazine‐based TADF materials, but also demonstrates their potential as nanoparticle‐based bioimaging probes combining several advanced optical functions.

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A cell-membrane-permeable europium complex as an efficient luminescent probe for singlet oxygen

Cited by 65 publications

References 27 publications

Responsive, Water‐Soluble Europium(III) Luminescent Probes

Responsive, Water‐Soluble Europium(III) Luminescent Probes

Two-photon dual imaging platform for in vivo monitoring cellular oxidative stress in liver injury

Heptazine‐Based TADF Materials for Nanoparticle‐Based Nonlinear Optical Bioimaging

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