Synthesis of a new long-wavelength latent fluorimetric indicator for analytes determination in the DT-Diaphorase coupling dehydrogenase assay system

Huang, Sheng‐Tung; Peng, Yi-Xiang; Wang, Kun‐Li

doi:10.1016/j.bios.2008.02.015

Cited by 26 publications

(5 citation statements)

References 39 publications

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“…Despite the very long history and wide use of coumarin dyes (figure 2), their structure-property relationships are not studied in depth [67,[70][71][72][73][74][75][76][77][78][79][80][81][82][83][84][85][86][87][88][89]. Large Stokes shifts in coumarins are provided by using intramolecular charge transfer (ICT) and (rarely) excited state intramolecular proton transfer (ESIPT) mechanisms [66].…”

Section: Fluorophores With Large Stokes Shifts Caused By Intramolecul...mentioning

confidence: 99%

“…Thus, new 'masked' fluorescent dyes probing the activity of the highly efficient bio-catalysts were created [84]. A similar approach was used in the course of creating the fluorimetric sensors for other enzymes or physiologically active thiols which trigger the (cascade) reactions and liberate the free hydroxyl group at C-7 (responsible for fluorescence) [85,86,88].…”

Section: Fluorophores With Large Stokes Shifts Caused By Intramolecul...mentioning

confidence: 99%

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Fluorescent dyes with large Stokes shifts for super-resolution optical microscopy of biological objects: a review

Sednev

Belov

Hell

2015

Methods Appl. Fluoresc.

187

177

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The review deals with commercially available organic dyes possessing large Stokes shifts and their applications as fluorescent labels in optical microscopy based on stimulated emission depletion (STED). STED microscopy breaks Abbe's diffraction barrier and provides optical resolution beyond the diffraction limit. STED microscopy is non-invasive and requires photostable fluorescent markers attached to biomolecules or other objects of interest. Up to now, in most biology-related STED experiments, bright and photoresistant dyes with small Stokes shifts of 20-40 nm were used. The rapid progress in STED microscopy showed that organic fluorophores possessing large Stokes shifts are indispensable in multi-color super-resolution techniques. The ultimate result of the imaging relies on the optimal combination of a dye, the bio-conjugation procedure and the performance of the optical microscope. Modern bioconjugation methods, basics of STED microscopy, as well as structures and spectral properties of the presently available fluorescent markers are reviewed and discussed. In particular, the spectral properties of the commercial dyes are tabulated and correlated with the available depletion wavelengths found in STED microscopes produced by LEICA Microsytems, Abberior Instruments and Picoquant GmbH.

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Section: Fluorophores With Large Stokes Shifts Caused By Intramolecul...mentioning

confidence: 99%

Section: Fluorophores With Large Stokes Shifts Caused By Intramolecul...mentioning

confidence: 99%

Fluorescent dyes with large Stokes shifts for super-resolution optical microscopy of biological objects: a review

Sednev

Belov

Hell

2015

Methods Appl. Fluoresc.

187

177

View full text Add to dashboard Cite

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“…The trimethyl lock can also be adapted to produce probes for enzymes that cannot usually be targeted with xanthene-and coumarinbased compounds. Huang and co-workers used the reduction of an electrophilic quinone by DT diaphorase (DTP) to form the phenolic alcohol required for the self-immolation and were able to develop two probes that were stable for several months in PBS but showed a rapid increase in fluorescence in the presence of DTP [313,314]. Ho et al used a pbenzyloxycarbonyl linker (12) to allow the cleavage of an O-glycoside linker by βgalactoside to release their previously developed NIR fluorophore [315].…”

Section: Fluorogenic Compoundsmentioning

confidence: 99%

Activatable Optical Probes for the Detection of Enzymes

Drake¹,

Miller²,

Jones³

2011

COS

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The early detection of many human diseases is crucial if they are to be treated successfully. Therefore, the development of imaging techniques that can facilitate early detection of disease is of high importance. Changes in the levels of enzyme expression are known to occur in many diseases, making their accurate detection at low concentrations an area of considerable active research. Activatable fluorescent probes show immense promise in this area. If properly designed they should exhibit no signal until they interact with their target enzyme, reducing the level of background fluorescence and potentially endowing them with greater sensitivity. The mechanisms of fluorescence changes in activatable probes vary. This review aims to survey the field of activatable probes, focusing on their mechanisms of action as well as illustrating some of the in vitro and in vivo settings in which they have been employed.

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“…From the plot shown in Figure 3, we obtained K m = 3.86 ± 0.79 μ M, V max = 0.037 ± 0.002 μ mol min −1 mg · NQO1 −1 , k cat = 0.019 ± 0.001 s −1 , and k cat / K m = 4.94 ± 0.33 × 10 3 M −1 s −1 . Due to the presence of the non-bulky ethanolamine linker and the need of only a single activation step to reveal reporter fluorescence, the kinetic constants are significantly higher than those of other NQO1 activatable fluorophores, 31,34,35 thereby ensuring sufficient signal enhancement for fast detection of hNQO1 activity.…”

Section: Resultsmentioning

confidence: 99%

Profluorogenic Reductase Substrate for Rapid, Selective, and Sensitive Visualization and Detection of Human Cancer Cells that Overexpress NQO1

Silvers¹,

Prasai²,

et al. 2012

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Achieving the vision of identifying and quantifying cancer-related events and targets for future personalized oncology is predicated on the existence of synthetically accessible and economically viable probe molecules fully able to report the presence of these events and targets in a rapid, and highly selective and sensitive fashion. Delineated here are the design and evaluation of a newly synthesized turn-on probe whose intense fluorescent reporter signature is revealed only through probe activation by a specific intracellular enzyme present in tumor cells of multiple origins. Quenching of molecular probe fluorescence is achieved through unique photo-induced electron transfer (PeT) between the naphthalimide dye reporter and a covalently attached, quinone-based enzyme substrate. Fluorescence of the reporter dye is turned on by rapid removal of the quinone quencher, an event that immediately occurs only after highly selective, two-electron reduction of the sterically and conformationally restricted quinone substrate by the cancer-associated human NAD(P)H:quinone oxidoreductase isozyme 1 (hNQO1). Successes of the approach include rapid differentiation of NQO1-expressing and non-expressing cancer cell lines via the unaided eye, flow cytometry, fluorescence imaging, and two-photon microscopy. The potential for use of the turn-on probe in longer-term cellular studies is indicated by its lack of influence on cell viability and its in vitro stability.

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Synthesis of a new long-wavelength latent fluorimetric indicator for analytes determination in the DT-Diaphorase coupling dehydrogenase assay system

Cited by 26 publications

References 39 publications

Fluorescent dyes with large Stokes shifts for super-resolution optical microscopy of biological objects: a review

Fluorescent dyes with large Stokes shifts for super-resolution optical microscopy of biological objects: a review

Activatable Optical Probes for the Detection of Enzymes

Profluorogenic Reductase Substrate for Rapid, Selective, and Sensitive Visualization and Detection of Human Cancer Cells that Overexpress NQO1

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