The basis for the molecular recognition and the selective time-gated luminescence detection of ATP and GTP by a lanthanide complex

Weitz, Evan A.; Chang, Joseph; Rosenfield, Adam H.; Morrow, Elizabeth A.; Pierre, Valérie C.

doi:10.1039/c3sc51583d

Cited by 69 publications

(65 citation statements)

References 71 publications

(45 reference statements)

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“…pyrimidines and purines, as shown by Pierre [31] . A phenanthridine moiety attached to an amide arm of the cyclen--based europium complex, [Eu.14], can participate in favourable π--π stacking interactions with nitrogenous base of nucleotides.…”

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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“…19 The peripheral amines of the nanoparticles were then conjugated either to the macrocyclic ligand DOTA-Phen ( 5 ) or to the acid-functionalized Ru(bpy′)(phen)(dppz) using standard amide coupling conditions. The syntheses of Fe 3 O 4 @oleic acid nanoparticles, 42 the catechol-terminated polymer Dop-PEG-NH 2 ( 3 ), 41 the macrocyclic ligand DOTA-Phen ( 5 ), 20,25 and the ruthenium intercalating complex, Ru(bpy′)(phen)(dppz) ( 6 ) 26,43–45 were performed as previously reported. The iron/lanthanide composite is then obtained by heating the DOTA-Phen coated nanoparticles at 40°C with an excess of EuCl 3 at neutral pH.…”

Section: Resultsmentioning

confidence: 99%

“…This observation correlates to photoelectron transfer of guanosine, and to a lesser extent, adenosine, to the phenanthridine. 20–25 As a result Fe 3 O 4 @Dop-PEG-Eu-DOTAm-Phen ( 1 ) is expected to behave as a turn-off magnetic light switch. On the other hand, the luminescence of the ruthenium dppz complex in aqueous solution increases over 10 fold upon intercalation in the major groove of dsDNA, 26–34 such that Fe 3 O 4 @Dop-PEG-Ru(bpy′)(phen)(dppz) ( 2 ) was designed as a turn-on light switch.…”

Section: Introductionmentioning

confidence: 99%

Magnetoluminescent Light Switches – Dual Modality in DNA Detection

et al. 2013

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The synthesis and properties of two responsive magnetoluminescent iron oxide nanoparticles for dual detection of DNA by MRI and luminescence spectroscopy are presented. These magnetoluminescent agents consist of iron oxide nanoparticles conjugated with metallointercalators via a polyethylene glycol linker. Two metallointercalators were investigated: Ru(bpy′)(phen)(dppz), which turns on upon DNA intercalation, and Eu-DOTAm-Phen, which turns off. The characteristic light-switch responses of the metallointercalators are not affected by the iron oxide nanoparticles; upon binding to DNA the luminescence of the ruthenium complexes increases by ca. 20 fold, whereas that of the europium complex is > 95 % quenched. Additionally, the 17–20 nm magnetite cores, having permeable PEG coatings and stable dopamide anchors, render the two constructs efficient responsive contrast agents for MRI with unbound longitudinal and transverse relaxivities of 12.4 – 9.2 mM−1Fes−1 and 135 – 128 mM−1Fes−1, respectively. Intercalation of the metal complexes in DNA results in the formation of large clusters of nanoparticles with a resultant decrease of both r1 and r2 by 32 – 63 % and 24 – 38 %, respectively. The potential application of these responsive magnetoluminescent assemblies and their reversible catch-and-release properties for the purification of DNA is presented.

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“…Anion binding can be signalled by changes in the intensity ratio of two Ln III emission bands or by changes in emission lifetime of the complex . However, examples of Ln III complexes that bind to NPP anions such as ATP are rare . Binding to ATP is usually weak and causes quenching of luminescence due to energy transfer to the nucleotide base or displacement of a coordinated sensitizing ligand from the Ln III ion (decomplexation) .…”

Section: Introductionmentioning

confidence: 99%

Cationic Europium Complexes for Visualizing Fluctuations in Mitochondrial ATP Levels in Living Cells

Mailhot

Traviss-Pollard

Pál

et al. 2018

Chemistry A European J

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The ability to study cellular metabolism and enzymatic processes involving adenosine triphosphate (ATP) is impeded by the lack of imaging probes capable of signalling the concentration and distribution of intracellular ATP rapidly, with high sensitivity. We report here the first example of a luminescent lanthanide complex capable of visualizing changes in the concentration of ATP in the mitochondria of living cells. Four cationic europium(III) complexes [Eu.1–4]+ have been synthesized and their binding capabilities towards nucleoside polyphosphate anions examined in aqueous solution at physiological pH. Complexes [Eu.1]+ and [Eu.3]+ bearing hydrogen bond donor groups in the pendant arms showed excellent discrimination between ATP, ADP and monophosphate species. Complex [Eu.3]+ showed relatively strong binding to ATP (logK a=5.8), providing a rapid, long‐lived luminescent signal that enabled its detection in a highly competitive aqueous medium containing biologically relevant concentrations of Mg2+, ADP, GTP, UTP and human serum albumin. This EuIII complex responds linearly to ATP within the physiological concentration range (1–5 mm), and was used to continuously monitor the apyrase‐catalyzed hydrolysis of ATP to ADP in vitro. We demonstrate that [Eu.3]+ can permeate mammalian (NIH‐3T3) cells efficiently and localize to the mitochondria selectively, permitting real‐time visualization of elevated mitochondrial ATP levels following treatment with a broad spectrum kinase inhibitor, staurosporine, as well as depleted ATP levels upon treatment with potassium cyanide under glucose starvation conditions.

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The basis for the molecular recognition and the selective time-gated luminescence detection of ATP and GTP by a lanthanide complex

Cited by 69 publications

References 71 publications

Responsive, Water‐Soluble Europium(III) Luminescent Probes

Responsive, Water‐Soluble Europium(III) Luminescent Probes

Magnetoluminescent Light Switches – Dual Modality in DNA Detection

Cationic Europium Complexes for Visualizing Fluctuations in Mitochondrial ATP Levels in Living Cells

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