Revisit of a dipropargyl rhodamine probe reveals its alternative ion sensitivity in both a solution and live cells

Li, Kaibin; Wei, Xiaoli; Zang, Yi; He, Xiao‐Peng; Chen, Guorong; Li, Jia; Chen, Kaixian

doi:10.1039/c3an01379k

Cited by 15 publications

(11 citation statements)

References 19 publications

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“…30 Here, we use the CuAAC click reaction to simply couple 1 with a water-soluble PEG tail to enhance the water solubility. In addition, since the as-formed bis-triazolyl motif is envisioned to chelate more strongly and selectively a metal ion, 34−41 a monotriazolyl PEG rhodamine derivative was synthesized for analyzing the structure activity relationship.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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One-Step Click Engineering Considerably Ameliorates the Practicality of an Unqualified Rhodamine Probe

Wang

Zang

et al. 2014

ACS Appl. Mater. Interfaces

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This study describes the exploitation of click chemistry in the one-step molecular engineering of an unqualified rhodamine probe, leading to its considerable functional enhancement in terms of water solubility, ion selectivity, and usefulness in detecting biological and environmental samples. A dipropargyl rhodamine dye previously identified as an unselective and poorly water-soluble mercury(II) probe was used to couple with an azido polyethylene glycol (PEG) by the Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition click reaction in almost quantitative yield. The simple click-engineered rhodamine probe shows, remarkably, better water solubility and mercury(II) selectivity comparing to the raw counterpart, and can be used to sensitively image mercury ions internalized by live cells and to accurately quantify the ion spiked in river water specimens. This study provides insights into the simple functional improvement of unqualified molecular dye probes via the efficient "click engineering".

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Section: ■ Results and Discussionmentioning

confidence: 99%

“…Compounds 1, 30 13 4 , and Cu(ClO 4 ) 2 were prepared in deionized water. The fluorescence measurements were carried out with a path length of 10 mm and an excitation wavelength at 530 nm by scanning the spectra between 540 and 750 nm.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

One-Step Click Engineering Considerably Ameliorates the Practicality of an Unqualified Rhodamine Probe

Wang

Zang

et al. 2014

ACS Appl. Mater. Interfaces

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“…38 This is mainly due to the difficulty in glycosylation of phenolic alcohols with other hexoses. [39][40][41][42][43] In particular, L-fucose as a 6-deoxy sugar is more electron rich than its parent hexose hence more prone to hydrolysis of its glycosidic bond. [44][45] As a consequence, a new platform strategy for visualizing a more diverse range of glycosidases implicated in the myriad of biologically and pathologically important cellular events is highly needed.…”

Section: Introductionmentioning

confidence: 99%

A General Strategy to the Intracellular Sensing of Glycosidases using AIE-Based Glycoclusters

Dong

Zhang

Han

et al. 2021

Preprint

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Glycosidases, which are the enzymes responsible for removal of residual monosaccharides from glycoconjugates, are implicated in a myriad of biological and pathological events. The ability to detect sensitively the activity and spatiotemporal distribution of glycosidases in cells may facilitate the study of glycobiology, and add useful diagnostic tools. However, the currently developed fluorogenic probes for glycosidases are generally based on glycosylation of a phenol group of a donor-acceptor type fluorogen. This general molecular scaffold has potential drawbacks in terms of substrate scope, sensitivity because of aggregation-caused quenching (ACQ), and the inability for long-term cell tracking. Here, we developed glycoclusters characterized by aggregation-induced emission (AIE) properties as a general platform for the sensing of a variety of glycosidases. To overcome the low chemical reactivity during phenol glycosylation, we synthesized an AIE-based dye composed of tetraphenylethylene conjugated with dicyanomethylene-4H-pyran (TPE-DCM) with a red fluorescence emission. Subsequently, a pair of dendritic linkages was introduced to both sides of the fluorophore, to which six copies of different monosaccharides (D-glucose, D-galactose and L-fucose) were conjugated through azide-alkyne click chemistry. The resulting AIE-active glycoclusters were shown to be capable of (1) fluorogenic sensing of a diverse range of glycosidases including β-D-galactosidase, β-D-glucosidase and α-L-fucosidase through the AIE mechanism, (2) fluorescence imaging of the endogenous glycosidase activities in healthy and cancer cells, and during cell senescence, and (3) glycosidase-activated, long-term imaging of cells. The present study provides a general strategy to the functional imaging of glycosidase activities through the multivalent display of sugar epitopes of interest onto AIE-active dyes.

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“…Some interesting studies on this "OFF-ON" type of uorescent sensors have been reported since Czarnik's pioneering work on the breaking of the spirolactum ring of rhodamine B derivative in the presence of Cu 2+ afforded strong uorescence. [42][43][44][45][46][47][48][49][50][51] Particularly, only few reports were available on detection of aluminium or uoride. [52][53][54][55] Besides, 8hydroxyquinoline is a kind of important chelators for metal ions and has been widely used to construct functional ionophores for recognizing metal ions.…”

Section: Introductionmentioning

confidence: 99%

A rhodamine–quinoline type molecular switch as a highly selective sequential sensor for Al³⁺and F⁻in aqueous solution

Liang

Chen

et al. 2014

RSC Adv.

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A novel optical rhodamine-quinoline type chemosensor (REQ) was successfully synthesized and characterized as a reversible molecular switch. It displayed high selectivity toward Al 3+ among 19 metal ions and the resultant complex [REQ-Al 3+ ] acted as a sequential chemosensor toward F À among 16 anions in neutral aqueous media (ethanol-water, v/v ¼ 3/7, Tris-HNO 3 , 20 mM, pH 7.0). Moreover, detecting fluoride at concentrations below the maximum contaminant level in drinking water defined by the U. S. Environmental Protection Agency (4.0 mg L À1 , 211 mM) could be achieved with a detection limit (LOD) estimated to be down to 8.0 mM. The reversible ring-open mechanism of the rhodamine spirolactam induced by Al 3+ binding and the 1 : 1 stoichiometric structure between REQ and Al 3+ were adequately supported by Job plot evaluation, optical titration, and 1 H NMR study. Finally, it could be conveniently used for the determination of Al 3+ and F À with the "naked eye" due to the obvious color change of the testing solution, showing its potential practical application.

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Revisit of a dipropargyl rhodamine probe reveals its alternative ion sensitivity in both a solution and live cells

Cited by 15 publications

References 19 publications

One-Step Click Engineering Considerably Ameliorates the Practicality of an Unqualified Rhodamine Probe

One-Step Click Engineering Considerably Ameliorates the Practicality of an Unqualified Rhodamine Probe

A General Strategy to the Intracellular Sensing of Glycosidases using AIE-Based Glycoclusters

A rhodamine–quinoline type molecular switch as a highly selective sequential sensor for Al³⁺and F⁻in aqueous solution

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Revisit of a dipropargyl rhodamine probe reveals its alternative ion sensitivity in both a solution and live cells

Cited by 15 publications

References 19 publications

One-Step Click Engineering Considerably Ameliorates the Practicality of an Unqualified Rhodamine Probe

One-Step Click Engineering Considerably Ameliorates the Practicality of an Unqualified Rhodamine Probe

A General Strategy to the Intracellular Sensing of Glycosidases using AIE-Based Glycoclusters

A rhodamine–quinoline type molecular switch as a highly selective sequential sensor for Al3+and F−in aqueous solution

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A rhodamine–quinoline type molecular switch as a highly selective sequential sensor for Al³⁺and F⁻in aqueous solution