Tuning macrocycles to design ‘turn-on’ fluorescence probes for manganese(<scp>ii</scp>) sensing in live cells

Bakthavatsalam, Subha; Sarkar, Anindita; Rakshit, Ananya; Jain, Sushma; Kumar, Amit; Datta, Ankona

doi:10.1039/c4cc09542a

Cited by 48 publications

(56 citation statements)

References 40 publications

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“…Fig. 5, which shows PE profiles for E → Z isomerism about C(3)vC (9) in HBO calculated as a function of the C(2)-C(3)-C(9)-N(10) dihedral angle, ϕ C(3)-C (9) , confirms this expectation. The displayed energy at ϕ C(3)-C(9) = 0°is the relaxed S 1 energy at R O(1)-H = 1.8 Å (see Fig.…”

Section: Resultssupporting

confidence: 57%

“…Following photoinduced tautomerism, we consider two possible fates for a keto tautomer in its S 1 state: fluorescence and internal conversion. Analogy with molecules like 2-(2′-hydroxyphenyl)benzotriazole 23 and 2-(2′-hydroxyphenyl)benzothiazole 33 suggests that E → Z isomerism around the C(3)vC (9) bond (in the case of HBO, (C(6)vC (17) in the case of HDBO)) might offer a route from the keto minimum to a minimum energy (ME)CI between the S 1 and S 0 PESs. Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Other studies have demonstrated the tunability of such supramolecular sensors. [8][9][10] Aza-crown ethers, for example, with chromophores (such as coumarin) attached to both ends, have been shown to exhibit similar, but opposite, PET and fluorescence propensities, i.e. the supramolecule fluoresces when metal-free but undergoes PET when metal-bound.…”

Section: Introductionmentioning

confidence: 99%

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Mechanistic insights into excited state intramolecular proton transfer in isolated and metal chelated supramolecular chemosensors

2016

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We report a computational study of excited state intramolecular proton transfer in a series of related and progressively more complex organic chromophores ranging from 2-(2'-hydroxyphenyl)-benzoxazole (HBO) through to the 5-(benzo[d]oxazol-2-yl)-2-(4-((bis(pyridin-2-ylmethyl)amino)methyl)benzo[d]oxazol-2-yl)-4 hydroxyphenolate (HDBO') anion. The latter chelates group 12 metal cations (X = Zn, Cd and Hg), and can serve as a fluorescence-based sensor for such metals. Initial π* ←π excitation of the ground (S) state enol-tautomer induces charge separation in the first excited singlet (S) state and drives the subsequent proton transfer (i.e. enol→keto tautomerism). The keto-tautomer constitutes a local minimum on the S PES, and is responsible for highly Stokes shifted fluorescent emission; S(enol) → S fluorescence is proposed to account for the shorter wavelength emission from the X-HDBO' complexes. Derivatives of HDBO' that should retain the favourable visible absorption and heavily Stokes shifted emission properties but, additionally, offer higher fluorescence quantum yields (i.e. enhanced metal sensing capability) are proposed.

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Section: Resultssupporting

confidence: 57%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Mechanistic insights into excited state intramolecular proton transfer in isolated and metal chelated supramolecular chemosensors

2016

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“…The penta-azamacrocycles 44 and 45 , which are appended with a BOIDPY fluorophore, been reported as ‘off-on’ sensors for Mn 2+ ( Figure 19 ) [ 120 ]. Selectivity for Mn 2+ was observed, but some interactions with Zn 2+ and Cu 2+ were also evident.…”

Section: Other Macrocyclic Sensorsmentioning

confidence: 99%

Recent Advances in Macrocyclic Fluorescent Probes for Ion Sensing

2017

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Small-molecule fluorescent probes play a myriad of important roles in chemical sensing. Many such systems incorporating a receptor component designed to recognise and bind a specific analyte, and a reporter or transducer component which signals the binding event with a change in fluorescence output have been developed. Fluorescent probes use a variety of mechanisms to transmit the binding event to the reporter unit, including photoinduced electron transfer (PET), charge transfer (CT), Förster resonance energy transfer (FRET), excimer formation, and aggregation induced emission (AIE) or aggregation caused quenching (ACQ). These systems respond to a wide array of potential analytes including protons, metal cations, anions, carbohydrates, and other biomolecules. This review surveys important new fluorescence-based probes for these and other analytes that have been reported over the past five years, focusing on the most widely exploited macrocyclic recognition components, those based on cyclam, calixarenes, cyclodextrins and crown ethers; other macrocyclic and non-macrocyclic receptors are also discussed.

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“…15 Ca 2+ , Mg 2+ , Na + , and K + ions are important interferents due to their high abundance in physiological samples as well as in natural waters. 16 Therefore, selectivity is an important requirement for the analysis of manganese ions and there is a need to develop new analytical procedures especially focusing on selectivity and sensitivity problems. Previous studies on the determination of Mn 2+ ions are compared in detail in Table 1 in terms of the sensing dye, the analysis media, linear working range, detection limit, and selectivity.…”

Section: Tolu D Ne Bluementioning

confidence: 99%

Suppression of interfering ions by using ionic liquid and micelle moieties in spectrofluorimetric analysis of manganese

Öter¹,

Aydin²,

Ertekin³

2016

Turk J Chem

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Eosin-Y exhibits high affinity and emission based spectral response to most of the major ions in water samples. In the present study we performed selective spectrofluorimetric analysis of manganese with eosin-Y in the presence of potential interferents. We employed green chemistry reagents, ionic liquids (ILs) and two different micelles, to suppress the effect of conventional cations and anions on the response of eosin-Y. The experimental data revealed that different test moieties caused enhanced analytical response to Mn 2+ . The highest analytical signal of eosin-Y was obtained in the presence of Triton X-100 at a concentration of 2.0 × 10 −3 mol L −1 . Presence of the green chemistry reagents ILs enhanced the limit of quantification for Mn 2+ 10-fold with respect to the IL-free moieties. The interfering effects of the metal ions of Ca 2+ , Cu 2+ , Hg + , Hg 2+ , As 5+ , Li + , Al 3+ , Cr 3+ , Co 2+ , Ni 2+ , and the anionic groups were completely suppressed in the presence of the ILs and micelles. Additionally, the tolerance limit of Na + and Zn 2+ ions increased 6-fold in the presence of IL and sodium dodecyl sulfate. The presented method did not use any harmful conventional solvents and was employed successfully for the detection of Mn 2+ ions in real water samples.

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Tuning macrocycles to design ‘turn-on’ fluorescence probes for manganese(ii) sensing in live cells

Cited by 48 publications

References 40 publications

Mechanistic insights into excited state intramolecular proton transfer in isolated and metal chelated supramolecular chemosensors

Mechanistic insights into excited state intramolecular proton transfer in isolated and metal chelated supramolecular chemosensors

Recent Advances in Macrocyclic Fluorescent Probes for Ion Sensing

Suppression of interfering ions by using ionic liquid and micelle moieties in spectrofluorimetric analysis of manganese

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