Discrimination of cis–trans isomers by dinuclear metal cryptates at physiological pH: selectivity for fumarate vs. maleate

Xie, Gaoyi; Jiang, Long; Lu, Tong‐Bu

doi:10.1039/c3dt51501j

Cited by 17 publications

(31 citation statements)

References 45 publications

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“…In a completely different approach, a selective detection of fumarate over its cis-analog maleate was reported by Lu and coworkers using dinuclear metal (Cu 2 + and Zn 2 + ) complexes (85). [170] Fumarate, due to its trans conformation, can easily be encapsulated inside the rigid core of the cryptand moiety and formed coordination with both the metal ion centers simultaneously. Employing similar strategy, Pasini and his group employed [9]aneN 3 decorated Bisphenol probe (86) for selective binding of (S,S)tartaric acid over its (R,R)/meso forms.…”

Section: Differentiation Among Biologically Relevant Carboxylatesmentioning

confidence: 99%

Switchable Optical Probes for Simultaneous Targeting of Multiple Anions

Dey

Bhattacharya

2020

Chemistry An Asian Journal

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Traditional optical probes primarily work on the concept of one-to-one recognition strategy. Therefore, simultaneous detection of multiple anions is difficult using this kind of sensory systems. Similarly, designing of multiresponsive array-based materials is synthetically challenging as well as difficult to optimize. Thus, researchers across the globe became interested in developing single molecular probes, capable of detecting multiple anions (or anionic biomolecules) by simultaneously activating optically distinguishable output channels. Here, the modes of interaction largely depend on the structural features of the binding sites (cleft size, number of available coordination sites etc.), characteristics of the anions (ionic radius, hydration enthalpy, basicity, coordination number, pk a of corresponding acids etc.) and the microenvironment around the probe molecules (micropolarity, viscosity, dielectric constant etc.) in the host matrix. In this review, we are mostly focusing on the structure-activity relationships of such multiple anions sensing optical probes and their stimuli-responsive properties.

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Section: Differentiation Among Biologically Relevant Carboxylatesmentioning

confidence: 99%

Switchable Optical Probes for Simultaneous Targeting of Multiple Anions

Dey

Bhattacharya

2020

Chemistry An Asian Journal

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“…There has been one very recent report by Xie et al on the discrimination of cis-trans isomers by dinuclear metal cryptates at physiological pH [13], in which some degree of selective recognition of cis-trans isomers has been reported. Naturally, the development of this seminal study toward a more fundamental and systematic search for tailored and more controllable and reliable cis-trans isomeric separation gains a logical currency and momentum: the separation and purification of cis-trans isomers is a challenging industrial and experimental task, so we want the design and synthesis of novel structures to achieve isomeric separation.…”

Section: Introductionmentioning

confidence: 96%

Theoretical studies of separation of cis–trans isomers using dinuclear (Cu2+- and Zn2+-based) cryptates

2014

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Theoretical investigations have been carried out using density functional theory, with the M06L functional and SMD solvent-modeling, to study the binding interactions of geometrical cis-trans isomers of fumarate (fum(2-)), maleate (male(2-)) and 1,2-cyclopropane dicarboxylate with Cu(2+)- and Zn(2+)-based dinuclear cryptates. It was found that cis-trans isomers of these groups of compounds bind strongly to metal cryptates, and the binding ability of the cryptates is controlled by the shape of the 'incoming' isomer (cis or trans); trans isomers bind more strongly than cis. Due to the size and shape of the cis and trans isomers, the cryptates can bind selectively and, to a large extent, 'recognize' the various cis-trans isomers, suggesting the tantalising possibility of isomeric separation/purification and recognition.

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“…For these reasons, many cation sensors have been described and synthesized; fluorescent chemosensors, in particular, are very intriguing thanks to the low detection limits of the fluorescence technique [7][8][9][10][11]. Functionalized polyamine macrocycles and macrobicycles are often used as receptors; however, by introducing fluorescent signaling units in the molecular skeleton (e.g., anthracene or naphthalene), they can be also converted into efficient chemosensors [12][13][14][15]. In this field, bistren azacryptands have been deeply investigated, due to the possibility of modulating their cavity shape [16][17][18][19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Study in Solution of a New Dansyl-Modified Azacryptand

Bergamaschi

Miljkovic

Marcheggiani

et al. 2016

International Journal of Inorganic Chemistry

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We report the synthesis of a new asymmetric azacryptand (L1), characterized by three p-xylyl spacers, one of which carries a dansyl side arm. The fluorescent sensor has been studied by potentiometric, UV-Vis, and emission studies in MeOH : water 3 : 2 mixture (0.07 M NaNO3), determining, in particular, the protonation constants of the free ligand and metal ion complexation equilibria. Interestingly, the obtained results revealed that the new receptor is fluorescent at neutral pH with a typical emission band of the dansyl group. Metal addition induced a partial quenching of the dansyl emission band; this behavior is more pronounced with Cu(II) that reduces the receptor’s emission by 60%. With all the studied cations, quenching follows the formation of a dimetallic complex. Similar studies on the model compound L2 confirmed that fluorescence quenching is mainly driven by a static mechanism, attributable to the formation of the inclusion dicopper complex [L1Cu2]4+. In order to test the stability of copper complexes under physiological conditions, spectrofluorimetric titrations with Cu(II) were performed in water buffered at pH = 8 (HEPES 0.07 M) and the values of binding constants, K11 and K12, were determined.

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Discrimination of cis–trans isomers by dinuclear metal cryptates at physiological pH: selectivity for fumarate vs. maleate

Cited by 17 publications

References 45 publications

Switchable Optical Probes for Simultaneous Targeting of Multiple Anions

Switchable Optical Probes for Simultaneous Targeting of Multiple Anions

Theoretical studies of separation of cis–trans isomers using dinuclear (Cu2+- and Zn2+-based) cryptates

Synthesis and Study in Solution of a New Dansyl-Modified Azacryptand

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