Fluorescence detected circular dichroism (FDCD) for supramolecular host–guest complexes

Prabodh, Amrutha; Wang, Yichuan; Sinn, Stephan; Albertini, Paolo; Spies, Christian; Spuling, Eduard; Yang, Liu‐Pan; Jiang, Wei; Bräse, Stefan; Biedermann, Frank

doi:10.1039/d1sc01411k

Cited by 22 publications

(19 citation statements)

References 94 publications

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“…The great performance of these chirality sensors and the blossoming of this topic augur well for future applications. In addition, CPL, [39a, 42, 45] vibrational CD, [69] and fluorescence‐detected CD spectroscopy [70] may also be employed for chirality sensing together with CD spectroscopy.…”

Section: Discussionmentioning

confidence: 99%

Circular Dichroism Based Chirality Sensing with Supramolecular Host–Guest Chemistry

2022

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Optical methods are promising to address the ever‐increasing demands for chirality analysis in drug discovery and related fields because they are amenable to high‐throughput screening. Circular dichroism‐based chiroptical sensing using host‐guest chemistry is especially appealing due to the fast equilibrium kinetics, wide substrate scope, and potential for sustainable development. In this Minireview, we give an overview on this emerging field. General aspects of molecular recognition and chirality transfer are analyzed. Chirality sensors are discussed by dividing them into three classes according to their structural features. Applications of these chirality sensors for chirality analysis of the products of asymmetric reactions and for the real‐time monitoring of reaction kinetics are demonstrated with selected examples. Moreover, challenges and research directions in this field are also highlighted.

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Section: Discussionmentioning

confidence: 99%

Circular Dichroism Based Chirality Sensing with Supramolecular Host–Guest Chemistry

2022

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“…However, to acquire observable CD signals, a relatively high concentration of the sample or a long optical path length is necessary. For chiral molecules lacking chromophores, the CD signals located in the far-ultraviolet (UV) region are quite weak or they even become CD-silent. , Therefore, there is an urgent demand to explore alternative methods to improve the discrimination sensitivity.…”

Section: Introductionmentioning

confidence: 99%

Chiral Detection of Glucose: An Amino Acid-Assisted Surface-Enhanced Raman Scattering Strategy Showing Opposite Enantiomeric Effects on SERS Signals

et al. 2022

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It is of considerable concern to establish chiral detection methods for revealing enantioselective interactions among chiral molecules. Surfaceenhanced Raman scattering (SERS) spectroscopy is sensitive to molecular interaction due to bond variations. However, its application in chiral detection is underexplored. Inspired by the chiral selectivity toward glucose and amino acids in life, we herein propose a SERS strategy based on molecular interactions for the discrimination of D-and L-glucose (Glu) using chiral phenylalanine (Phe) decorated on gold nanoparticles as a chirality selector and Raman reporter. Interestingly, the SERS signal of L-Phe is enhanced by D-Glu but suppressed by L-Glu. In contrast, the SERS signal of D-Phe is increased by L-Glu but decreased by D-Glu. According to the above-observed intensity change (ΔI) of the SERS signal of Phe induced by Glu, it is easy to determine the chiral configurations (judged by the positive or negative sign of ΔI), enantiomeric excess (ee) values, and concentrations (estimated by the magnitude of ΔI) of Glu. Taking advantage of the high SERS enhancement and opposite enantiomeric effects on SERS signals, the proposed strategy enables enantiomeric discrimination at a low Glu concentration (10 −6 mol/L) and is further exerted for the noninvasive detection of D-/L-Glu in saliva samples. In contrast, the common chiroptical analysis tool of circular dichroism (CD) spectroscopy failed to directly detect Glu enantiomers.

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“…Nevertheless, sensing of less strongly binding metabolites or drugs has so far required the preparation and use of a library of differentially selective chemosensors in combination with multivariant data analysis. ,− In principle, it would be thus desirable to develop additional CB n derivatives and conjugates that display differential selectivity for particular biorelevant analytes of interest. However, despite many creative attempts yielding structurally fascinating CB n analogues such as chiral CB n , nor-seco-CB n , or acyclic CB n , ,,, significant improvements of the native binding selectivity of CB n macrocycles have not been achieved yet. , …”

Section: Introductionmentioning

confidence: 99%

“…9,48−50 In principle, it would be thus desirable to develop additional CBn derivatives and conjugates that display differential selectivity for particular biorelevant analytes of interest. However, despite many creative attempts yielding structurally fascinating CBn analogues such as chiral CBn, norseco-CBn, or acyclic CBn, 18,19,51,52 significant improvements of the native binding selectivity of CBn macrocycles have not been achieved yet. 53,54 Herein, we introduce a new concept that turns the shortcomings of cucurbit[n]urils�their wide analyte-binding scope (→ low selectivity) and their propensity to bind metal cations (→ CBn•guest complex disintegration in saline media)�into distinctive and desirable features.…”

Section: ■ Introductionmentioning

confidence: 99%

Further Dimensions for Sensing in Biofluids: Distinguishing Bioorganic Analytes by the Salt-Induced Adaptation of a Cucurbit[7]uril-Based Chemosensor

Jochmann

Chakraborty

et al. 2022

J. Am. Chem. Soc.

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Insufficient binding selectivity of chemosensors often renders biorelevant metabolites indistinguishable by the widely used indicator displacement assay. Array-based chemosensing methods are a common workaround but require additional effort for synthesizing a chemosensor library and setting up a sensing array. Moreover, it can be very challenging to tune the inherent binding preference of macrocyclic systems such as cucurbit[n]urils (CBn) by synthetic means. Using a novel cucurbit[7]uril-dye conjugate that undergoes salt-induced adaptation, we now succeeded in distinguishing 14 bioorganic analytes from each other through the facile stepwise addition of salts. The salt-specific concentration-resolved emission provides additional information about the system at a low synthetic effort. We present a data-driven approach to translate the human-visible curve differences into intuitive pairwise difference measures. Ion mobility experiments combined with density functional theory calculations gave further insights into the binding mechanism and uncovered an unprecedented ternary complex geometry for CB7. TThis work introduces the non-selectively binding, salt-adaptive cucurbit[n]uril system for sensing applications in biofluids such as urine, saliva, and blood serum.

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Fluorescence detected circular dichroism (FDCD) for supramolecular host–guest complexes

Abstract: Fluorescence-detected circular dichroism (FDCD) spectroscopy is applied for the first time to supramolecular host-guest and host-protein systems and compared to the more known electronic circular dichroism (ECD). We find that...

Cited by 22 publications

References 94 publications

Circular Dichroism Based Chirality Sensing with Supramolecular Host–Guest Chemistry

Circular Dichroism Based Chirality Sensing with Supramolecular Host–Guest Chemistry

Chiral Detection of Glucose: An Amino Acid-Assisted Surface-Enhanced Raman Scattering Strategy Showing Opposite Enantiomeric Effects on SERS Signals

Further Dimensions for Sensing in Biofluids: Distinguishing Bioorganic Analytes by the Salt-Induced Adaptation of a Cucurbit[7]uril-Based Chemosensor

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