Molecular Encapsulation of Fluorescent Dyes Affords Efficient Narrow‐band Dye Laser Operation in Water

Mohanty, Jyotirmayee; Jagtap, Krishna K.; Ray, Alok K.; Nau, Werner M.; Pal, Haridas

doi:10.1002/cphc.201000532

Cited by 64 publications

(66 citation statements)

References 40 publications

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“…Some uses for macrocyclic host molecules that take advantage of these properties include molecular recognition,6–8 catalysis,9, 10 enzymatic regulation,11 and drug delivery 12–14. Another emerging area of interest is the use of macrocycles for dye tuning 15. 16 This refers to a substantial modulation (or tuning) of the physical and spectroscopic properties of a guest dye molecule upon encapsulation by a macrocyclic host.…”

Section: Introductionmentioning

confidence: 99%

Understanding Photophysical Effects of Cucurbituril Encapsulation: A Model Study with Acridine Orange in the Gas Phase

Czar

Jockusch

2013

ChemPhysChem

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Encapsulation of dyes by cucurbituril macrocycles has proven profitable as a strategy to alter fluorescence characteristics in useful ways. Encapsulation generally results in longer fluorescence lifetimes, enhanced brightness, and solvatochromic effects not normally seen in the condensed phase. These effects have been attributed variously to both the removal of interactions with solvent molecules and to the confined environment of extremely low polarizability provided by the cucurbituril interior. It is difficult to disentangle these effects in solution. Here, we present results from gas-phase experiments designed to separate these effects, using cucurbit[7]uril (CB7), and the cationic dye acridine orange (AOH(+)) as a probe. Fluorescence properties of gaseous AOH(+) are compared with those of the gaseous AOH(+)-CB7 complex and with the properties of the dye and complex in aqueous solution. The dependence on the local environment of several spectroscopic properties is discussed, including the fluorescence excitation and emission maxima, the size of the Stokes shift, fluorescence lifetime and relative brightness. An understanding of the modulation of fluorescence properties by the local environment, such as that promoted by this work, will aid in the rational design of improved fluorophores and fluorescent sensors.

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Section: Introductionmentioning

confidence: 99%

Understanding Photophysical Effects of Cucurbituril Encapsulation: A Model Study with Acridine Orange in the Gas Phase

Czar

Jockusch

2013

ChemPhysChem

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“…The enhanced photostability may result from a combination of factors, including the inert cavity, its low polarizability, confinement of the dye, and protection from water and oxygen. [26][27][28][29] …”

Section: Improving the Photostability Of Hoechst 34580mentioning

confidence: 99%

Host–Guest Interaction of Hoechst 34580 and Cucurbit[7]uril

et al. 2011

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To track nuclear dynamic processes by fluorescence imaging, nuclear stains should be highly fluorescent, resistant to photobleaching, and inert to nuclear processes. The nuclear stains of the Hoechst family, such as Hoechst 34580, show bright fluorescence only on groove binding to DNA, and therefore may interfere with visualization of nuclear dynamic processes induced by other stimuli. We study host-guest interactions between Hoechst 34580 and Cucurbit[7]uril (CB7) in aqueous solutions. The formation of CB7-Hoechst 34580 inclusion complexes with stoichiometry of 2:1 in water and 1:1 in phosphate-buffered saline (PBS) solution (pH 7.0) is confirmed by (1)H NMR, absorption spectra, fluorescence spectra, MALDI-TOF MS, and molecular modeling. Compared to Hoechst 34580, the inclusion complex exhibits redshifted absorption, intensified fluorescence, improved photostability, weakened DNA binding affinity, comparable ability to penetrate cell nuclei, and better nuclear-staining capability, and thus a new avenue for the application of cucurbituril in fluorescence imaging is opened.

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“…logK values obtained by absorbance-based indicator displacement assay with l abs = 370 nm in D 2 O. [58,59,60,61,62] Moreover, CBn and certain acyclic CBn derivatives are biologically benign, e. g., non-toxic, such that ex vivo and in vivo use of CBn-based materials and sensors is in reach. [58,59,60,61,62] Moreover, CBn and certain acyclic CBn derivatives are biologically benign, e. g., non-toxic, such that ex vivo and in vivo use of CBn-based materials and sensors is in reach.…”

Section: Analytementioning

confidence: 99%

“…[59,60,61,74,116,117] In contrast CB8-mediated excimer formation (1 : 2 complexes) is usually characterized by a bathochromic shifted (and reduced) emission. For instance, a hypsochromic shift of the (usually enhanced) emission is often found for 1 : 1 CBn-dye complexes, pointing towards polarity differences between bulk water and the CBn cavity.…”

Section: Absorbance Fluorescence and Circular Dichroismmentioning

confidence: 99%

“…[59,60,61,74,116,117] In contrast CB8-mediated excimer formation (1 : 2 complexes) is usually characterized by a bathochromic shifted (and reduced) emission. [59,60,61,116,117,129,130,131,132,133] The enhancement of the excited-state lifetimes of chromophores upon CBn complexation is also frequently found and can be exploited for time-resolved sensing applications. [128] Besides, chromophore deaggregation (preventing aggregation-caused quenching, ACQ) often leads to significant emission enhancement and absorbance spectra changes.…”

Section: Absorbance Fluorescence and Circular Dichroismmentioning

confidence: 99%

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Chemical Sensors Based on Cucurbit[n]uril Macrocycles

Sinn

Biedermann

2018

Israel Journal of Chemistry

147

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Cucurbit[n]urils (CBn) are glycoluril‐based macrocyclic hosts that bind many biologically, medicinally and environmentally relevant analytes with record high affinities in aqueous media. They are therefore prime candidates for the design of chemosensors that are operational in biological fluids, waste and drinking water and have promising potential to be utilized for in vitro and in vivo sensing and imaging applications. Unlike protein‐based antibodies, CBn can be prepared in multi kilogram scales, they are chemically robust and they show a desired fast analyte‐binding kinetics. Unlike protein‐based antibodies, CBn can be prepared in multi kilogram scales, are chemically robust and show a desired fast analyte‐binding kinetics Selective analyte detection and differentiation is possible owing to the charge‐ and size‐selective binding characteristics of the CBn members and due to the wide range of cyclic and acyclic CBn derivatives that differ in their analyte binding preference. Because CBn hosts are spectroscopically silent in the visible electromagnetic spectrum, optical signal transduction with CBn based chemosensing ensembles is typically performed by indicator displacement assays (IDA), which are easy to implement and applicable to both aliphatic and aromatic analytes. The extension to array‐based sensing with CBn chemosensors is straightforward. Associative binding assays (ABA), which are uniquely available with CB8‐based self‐assembled receptors offer superior analyte differentiation possibility due to emerging spectral fingerprints in the absorbance, circular dichroism (CD) and emission spectra for the receptor•analyte complexes. Direct signal generation is promising for inherently spectroscopically active analytes, for instance through absorbance, CD, emission and surface enhanced Raman spectroscopy (SERS). Sensitive NMR (19F, 129Xe) techniques, electron spin resonance (ESR), redox, and mass spectrometry are also valuable signal transduction options for specific analytes. CBn based chemosensors were successfully utilized for the monitoring of biophysical processes and enzymatic reactions with label free analytes or substrates in real time. These applications capitalize on the fast equilibration kinetics of CBn‐analyte complexes and the bio‐compatibility of CBn hosts. The tabulated large body of data extracted from reported CBn‐based binding studies is hoped to provide the reader with a valuable starting point for designing practically applicable CBn‐based sensors.

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Molecular Encapsulation of Fluorescent Dyes Affords Efficient Narrow‐band Dye Laser Operation in Water

Cited by 64 publications

References 40 publications

Understanding Photophysical Effects of Cucurbituril Encapsulation: A Model Study with Acridine Orange in the Gas Phase

Understanding Photophysical Effects of Cucurbituril Encapsulation: A Model Study with Acridine Orange in the Gas Phase

Host–Guest Interaction of Hoechst 34580 and Cucurbit[7]uril

Chemical Sensors Based on Cucurbit[n]uril Macrocycles

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