Organoselenium compounds as fluorescent probes

Panda, Snigdha; Panda, Arunashree; Zade, Sanjio S.

doi:10.1016/j.ccr.2015.04.006

Cited by 88 publications

(32 citation statements)

References 51 publications

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“…However, excessive amounts of metal ions or the presence of toxic metal ions has severe deleterious effects on living systems. 15 In the past decades, several fluorescent probes for cations have been developed by a strategy that combines fluorophores and specific selenium-containing reaction or binding sites.…”

Section: Selenium-containing Fluorescent Probes For Cations and Anionsmentioning

confidence: 99%

“…4 Thus, selenium has drawn greater attention in recent years, and many reviews have focused on this element. [5][6][7][8][9][10][11][12][13][14][15][16] Fluorimetry is among the most simple, inexpensive, and rapid methods for detecting analytes (neutral molecules and ions). Probes based on this method have been investigated extensively and widely used in many fields because of their high levels of sensitivity and in particular their ability to be utilized for temporal and spatial sampling and in in vivo imaging applications.…”

Section: Introductionmentioning

confidence: 99%

“…Although some closely related reviews have been published in recent years, none of them have covered fluorescent probes for significant biological Se species (selenocysteine [Sec], H 2 Se, thioredoxin reductases [TrxRs], and Se(IV)), which is a newly developed field. [14][15][16] This review comprises two major sections. The first describes fluorescent probes for selenium-containing species, such as Sec, hydrogen selenide, TrxRs, and selenite.…”

Section: Introductionmentioning

confidence: 99%

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Fluorescent Probes Containing Selenium as a Guest or Host

Chen

Kwon

et al. 2016

Chem

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Selenium is an important trace element in living systems. Proteins incorporating selenium have a wide range of biological effects, ranging from anti-oxidant and antiinflammatory effects to the production of active thyroid hormones. In the past decades, selenium has drawn enormous attention because of its important role in biology, which can be ascribed partly if not solely to its redox and hard and soft donor properties. With the use of chemical mimicry, a large number of seleniumrelated fluorescent probes have been developed for monitoring physiological and pathological processes. This review, which summarizes recent progress made in this area, comprises two major sections. In the first section, fluorescent probes for selenium-containing species, such as selenocysteine (Sec), hydrogen selenide, thioredoxin reductases (TrxRs), and selenite, are described. This is followed by a discussion of fluorescent probes that contain selenium and detect reactive oxygen, nitrogen, and sulfur species, as well as cations and anions.

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Section: Selenium-containing Fluorescent Probes For Cations and Anionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Fluorescent Probes Containing Selenium as a Guest or Host

Chen

Kwon

et al. 2016

Chem

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“…In particular, organoselenium compounds as fluorescent probes for various analytes (e.g., thiols, biomolecules, mercury ions) possess certain advantages over N-, O-, and S-based fluorescent probes due to the unique properties of selenium [32]. Although organoselenium chemistry has become a well-established field of research, there is still no report on the exploration of selenium-containing functional POSS materials.…”

Section: Introductionmentioning

confidence: 99%

A Selenone-Functionalized Polyhedral Oligomeric Silsesquioxane for Selective Detection and Adsorption of Hg2+ ions in Aqueous Solutions

et al. 2019

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Developing novel functional polyhedral oligomeric silsesquioxane (POSS) for various applications is highly desirable. Herein we present the first example of a novel selenone-functionalized POSS (POSS-Se) by treating an imidazolium-containing POSS with selenium powder under mild condition. The structure of POSS-Se was characterized by FT-IR, 1 H NMR, 13 C NMR, 29 Si NMR, and elemental analysis. Acid treatment of POSS-Se results in a hydrophilic red-orange colored solid, which is highly sensitive and selective for the detection of Hg 2+ ions in aqueous solutions by visually observing the color change to pale yellow, and to white. Interestingly, POSS-Se has no activity on this detection. This finding is due to the Se-Se formation by acid-treatment and subsequent coordination-induced cleavage upon the addition of Hg 2+ ions. The detection behavior can be precisely monitored by a "turn-on" fluorescence phenomenon with the limit of detection (LOD) of 8.48 ppb, comparable to or higher than many reported Hg 2+ sensors. Moreover, POSS-Se demonstrates a selective and efficient adsorption of Hg 2+ ions with a maximum capacity of 952 mg g -1 . The value is higher than most reported adsorbents for Hg 2+ ions, typically thiol and/or thioether functional materials, indicating its promise as an efficient adsorbent for the selective removal of Hg 2+ ions from industrial wastewater. This work may open up new horizons for the exploration of selenium-containing functional POSS.

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“…[1][2][3][4][5][6] A vast library of chemosensors has been proposed so far, but only recently organoselenium and organotellurium compounds have been used for this purpose. 7,8,9 Heavy chalcogen-containing derivatives, and in particular those containing selenium, are of great interest because selenium compounds play an important role as enzymatic antioxidants participating in the conversion of hydrogen peroxides in water in biological systems. 10 In the particular case of seleniumcontaining chemosensors, the formation of highly stable selenoxides is often the event that triggers the optical recognition of analytes such as reactive oxygen species (ROS) superoxide, 11 hypochlorite 12 or reactive nitrogen species (RNS, for instance peroxynitrate).…”

mentioning

confidence: 99%

A new class of silica-supported chromo-fluorogenic chemosensors for anion recognition based on a selenourea scaffold

et al. 2017

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The development of optical chemosensors for neutral and charged species recognition has been one of the most active research field in Supramolecular Chemistry in the last 20 years. 1-6 A vast library of chemosensors has been proposed so far, but only recently organoselenium and organotellurium compounds have been used for this purpose. 7,8,9 Heavy chalcogen-containing derivatives, and in particular those containing selenium, are of great interest because selenium compounds play an important role as enzymatic antioxidants participating in the conversion of hydrogen peroxides in water in biological systems. 10 In the particular case of seleniumcontaining chemosensors, the formation of highly stable selenoxides is often the event that triggers the optical recognition of analytes such as reactive oxygen species (ROS) superoxide, 11 hypochlorite 12 or reactive nitrogen species (RNS, for instance peroxynitrate). 13 However, very few examples of selenium-containing optical chemosensors for "classic" anions such as fluoride 14 or carboxylates 15 have been described. In reported selenium-containing probes, the sensing mechanism of fluoride is based on a deprotonation event of an amino group, while carboxylate recognition depends on the formation of hydrogen bonds between the guest and pyrimidine and amide protons of the receptor. However, in both cases, selenium is contained in a selenodiazole moiety and do not actively participate to the sensing event.One of the most common strategy for the design of anion chemosensors is the use of hydrogen-bond donor groups such as urea or thiourea. In the case of thiourea-based chemosensors, due to the more acidic nature of the NHs protons (compared to those of the analogous urea derivatives), the recognition event is often caused by the deprotonation of the receptor that usually leads to a remarkable modification in the electronic properties of the system resulting in colour or emission changes. However, in this scenario, and, to the best of our knowledge, examples of selenourea-based anion sensors have never been reported in the literature to date despite selenoureas are interesting organoseleno compounds that show anticancer activity, antioxidant properties, enzyme inhibition, and DNA binding properties. [16][17][18][19][20] Taking these concepts into account and following our interest in anion recognition and sensing [21][22][23][24][25] we decided to explore the potential use of selenoureas as a new scaffold for the design of anion chemosensors.In particular, here, we describe the ability of the asymmetric 1-(4-methyl-2-oxo-2H-chromen-7-yl)-3-phenylselenourea (L) to act as a colorimetric and/or fluorescent sensor for S 2-and CNrecognition. L was obtained according to the reaction shown in Scheme 1.Scheme 1. Synthesis of 1-(4-methyl-2-oxo-2H-chromen-7-yl)-3-phenylselenourea (L).Phenylisoselenocyanate was synthesised following a literature procedure. 26 Reaction with 7-amino-4-methylcoumarin in DCM/EtOH (1:1, v/v) at 40°C for 3 hours under N2 atmosphere (Fig. 1) and CN -(see ESI...

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Organoselenium compounds as fluorescent probes

Cited by 88 publications

References 51 publications

Fluorescent Probes Containing Selenium as a Guest or Host

Fluorescent Probes Containing Selenium as a Guest or Host

A Selenone-Functionalized Polyhedral Oligomeric Silsesquioxane for Selective Detection and Adsorption of Hg2+ ions in Aqueous Solutions

A new class of silica-supported chromo-fluorogenic chemosensors for anion recognition based on a selenourea scaffold

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