Supramolecular optimization of the visual contrast for colorimetric indicator assays that release resorufin dye

Morsby, Janeala J.; Dharmarwardana, Madushani; McGarraugh, Hannah H.; Smith, Bradley D.

doi:10.1039/d0cc03551c

Cited by 13 publications

(6 citation statements)

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“…2e , f). This linear relationship suggests i) a high affinity of 2 to cage 1 and ii) a strongly cooperative binding of 2 to 1 , with the 2:1 complex-forming preferentially 42 to a putative 1:1 complex 43 (even in the presence of an excess of the guest; note that for a 1:1 complex, fluorescence should be preserved, at least partially 26 , 31 , 43 – 45 ).…”

Section: Resultsmentioning

confidence: 99%

“…Surprisingly, however, little attention has been devoted to the behavior of resorufin and resazurin in confined spaces, and no strong confinement effects for these two dyes have been reported to date. For example, the fluorescence of resorufin was not markedly affected by encapsulation within β -cyclodextrin 30 or within a tetralactam macrocycle incorporating two anthracene moieties 31 . Similarly, resorufin placed within micelles 32 , microemulsion droplets 33 , and one-dimensional channels of metal–organic frameworks 34 retained its strong emission.…”

Section: Introductionmentioning

confidence: 99%

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Encapsulation within a coordination cage modulates the reactivity of redox-active dyes

et al. 2022

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Confining molecules within well-defined nanosized spaces can profoundly alter their physicochemical characteristics. For example, the controlled aggregation of chromophores into discrete oligomers has been shown to tune their optical properties whereas encapsulation of reactive species within molecular hosts can increase their stability. The resazurin/resorufin pair has been widely used for detecting redox processes in biological settings; yet, how tight confinement affects the properties of these two dyes remains to be explored. Here, we show that a flexible PdII6L4 coordination cage can efficiently encapsulate both resorufin and resazurin in the form of dimers, dramatically modulating their optical properties. Furthermore, binding within the cage significantly decreases the reduction rate of resazurin to resorufin, and the rate of the subsequent reduction of resorufin to dihydroresorufin. During our studies, we also found that upon dilution, the PdII6L4 cage disassembles to afford PdII2L2 species, which lacks the ability to form inclusion complexes – a process that can be reversed upon the addition of the strongly binding resorufin/resazurin guests. We expect that the herein disclosed ability of a water-soluble cage to reversibly modulate the optical and chemical properties of a molecular redox probe will expand the versatility of synthetic fluorescent probes in biologically relevant environments.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Encapsulation within a coordination cage modulates the reactivity of redox-active dyes

et al. 2022

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“…A common commercial fluorogenic substrate for HEX(NAG) detection is 4-methylumbelliferyl- N -acetyl-β- d -glucosaminide (4-MU-NAG). Upon cleavage by HEX(NAG) enzyme, 4-MU-NAG releases 4-methylumbelliferone, a fluorescent dye which emits at 460 nm. − A recent successful effort to extend the emission band to a longer wavelength led to substrate 4 which was found to be rapidly cleaved by human HEX(NAG) to produce highly fluorescent resorufin dye for fluorescent detection at 598 nm. , Substrate 4 was first used to quantify urinary HEX(NAG) activity in a mouse model of kidney disease and subsequently validated for use in urine samples from human patients. The graph in Figure d compares the HEX(NAG) activity in 58 urine samples from renal injury patients ( n = 28) and healthy individuals ( n = 30).…”

Section: Assessing Kidney Healthmentioning

confidence: 99%

Advances in Optical Sensors of N-Acetyl-β-d-hexosaminidase (N-Acetyl-β-d-glucosaminidase)

Morsby

Smith

2022

Bioconjugate Chem.

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N-Acetyl-β-d-hexosaminidases (EC 3.2.1.52) are exo-acting glycosyl hydrolases that remove N-acetyl-β-d-glucosamine (Glc-NAc) or N-acetyl-β-d-galactosamine (Gal-NAc) from the nonreducing ends of various biomolecules including oligosaccharides, glycoproteins, and glycolipids. The same enzymes are sometimes called N-acetyl-β-d-glucosaminidases, and this review article employs the shorthand descriptor HEX(NAG) to indicate that the terms HEX or NAG are used interchangeably in the literature. The wide distribution of HEX(NAG) throughout the biosphere and its intracellular location in lysosomes combine to make it an important enzyme in food science, agriculture, cell biology, medical diagnostics, and chemotherapy. For more than 50 years, researchers have employed chromogenic derivatives of N-acetyl-β-d-glucosaminide in basic assays for biomedical research and clinical chemistry. Recent conceptual and synthetic innovations in molecular fluorescence sensors, along with concurrent technical improvements in instrumentation, have produced a growing number of new fluorescent imaging and diagnostics methods. A systematic summary of the recent advances in optical sensors for HEX(NAG) is provided under the following headings: assessing kidney health, detection and treatment of infectious disease, fluorescence imaging of cancer, treatment of lysosomal disorders, and reactive probes for chemical biology. The article concludes with some comments on likely future directions.

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“…16−18 In addition, the independence of the availability without power sources could bring unprecedented portability and usability. 19,20 Therefore, it is much desirable for developing colorimetric indicators with rapid response and high sensitivity in trace water detection applications.…”

Section: ■ Introductionmentioning

confidence: 99%

Metal–Organic Framework Flowers as a Naked-Eye Colorimetric Indicator of Trace Water

Shao

Zhang

et al. 2023

ACS Appl. Mater. Interfaces

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Convenient and sensitive trace water indication is of great significance in various industrial processes. Here, a flower-like metal–organic framework Cu-FMM is assembled from ultrathin nanosheets that change its coordination structure reversibly with the capture and loss of water molecules, enabling sensitive trace water naked-eye colorimetric indication ability. A recognizable black/yellow color change can be observed when the dried Cu-FMM is exposed to the atmosphere or solvent with trace water as low as RH 3% and a water content of 0.25‰ (v/v) and further enables potential trace water imaging applications. The excellent accessibility of the multi-scale pore structure of Cu-FMM contributes to a fast response time of 3.8 s with good reversibility (>100 cycles), outperforming traditional coordination polymer humidity sensors. The present study provides new inspirations for the design of sensitive and applicable naked-eye water indicator materials that are applicable to in situ and continuous monitoring in industrial processes.

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Supramolecular optimization of the visual contrast for colorimetric indicator assays that release resorufin dye

Abstract:
A tetralactam macrocycle acts as a novel supramolecular adjuvant to capture a released resorufin dye and create a higher contrasting yellow/blue color change for enhanced naked eye interpretation of a...

Cited by 13 publications

References 37 publications

Encapsulation within a coordination cage modulates the reactivity of redox-active dyes

Encapsulation within a coordination cage modulates the reactivity of redox-active dyes

Advances in Optical Sensors of N-Acetyl-β-d-hexosaminidase (N-Acetyl-β-d-glucosaminidase)

Metal–Organic Framework Flowers as a Naked-Eye Colorimetric Indicator of Trace Water

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Supramolecular optimization of the visual contrast for colorimetric indicator assays that release resorufin dye

Abstract: A tetralactam macrocycle acts as a novel supramolecular adjuvant to capture a released resorufin dye and create a higher contrasting yellow/blue color change for enhanced naked eye interpretation of a...

Cited by 13 publications

References 37 publications

Encapsulation within a coordination cage modulates the reactivity of redox-active dyes

Encapsulation within a coordination cage modulates the reactivity of redox-active dyes

Advances in Optical Sensors of N-Acetyl-β-d-hexosaminidase (N-Acetyl-β-d-glucosaminidase)

Metal–Organic Framework Flowers as a Naked-Eye Colorimetric Indicator of Trace Water

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Product

Resources

About

Abstract:
A tetralactam macrocycle acts as a novel supramolecular adjuvant to capture a released resorufin dye and create a higher contrasting yellow/blue color change for enhanced naked eye interpretation of a...