Development of a sensitive long-wavelength fluorogenic probe for nitroreductase: A new fluorimetric indictor for analyte determination by dehydrogenase-coupled biosensors

Huang, Hun Chung; Wang, Kun Li; Huang, Sheng‐Tung; Lin, Hung‐Yi; Lin, Chun Mao

doi:10.1016/j.bios.2011.01.036

Cited by 54 publications

(19 citation statements)

References 34 publications

(35 reference statements)

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“…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 Intramoleculmentioning

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.

180

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 Intramoleculmentioning

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.

180

177

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“…Such an off-on switch concept has been exploited as a signal transducer in fluorescent probes (vide infra). [10] Despite the well-known emission quencher, fluorescent nitro chromophores are sporadically found and applied in several research fields. These include the fundamental approach on fluorescence of the nitro compounds standing on the excited-state twisted intramolecular charge transfer (TICT), [11] the application of the nitro-chromophores in two-photon absorption (TPA) nonlinear spectroscopy, [12] and nitro-containing fluorescent probes where fluorescence spectral shifts from the nitro group to its chemically converted form could be exploited as the signal transducer.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent Chromophores Containing the Nitro Group: Relatively Unexplored Emissive Properties

Chen

Chou

2020

ChemPlusChem

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Apart from numerous applications, for example in azo dye precursors, explosives, and industrial processes, the nitro group (−NO2) appears on countless molecules in photochemical research owing to its unique characteristics such as a strong electron‐withdrawing ability and facile conversion to the reduced substituent. Although it is well known as a fluorescence quencher, fluorescent chromophores that contain the nitro group have also emerged, with 3‐nitrophenothiazine being recently reported to have 100 % emission quantum yield in nonpolar solvents. The diverse characters of nitro‐containing chromophores motivated us to systematically review those chromophores with nitro substituents, their associated photophysical properties, and applications. In this Review, we succinctly elaborate the advance of the fluorescent nitro chromophores in fields of intramolecular charge transfer, fluorescent probes and nonlinear properties. Special attention is paid to the rationalization of the associated emission spectroscopy, so that the readers can gain insights into the structure‐photophysics relationship and hence gain insights for the strategic design of nitro chromophores.

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“…Based on this switch mechanism, various prodrug or activatable imaging probes have been designed with nitro groups as substrates to be triggered upon reduction by NTR. 2 The dicoumarin carbonate-based latent fluorophore was devised for the application in imaging to improve selectivity for NTR and aqueous solubility. 2b Furthermore, NTR was employed in development of gene-directed enzyme prodrug cancer therapies (GDEPT), antibody-directed enzyme prodrug therapy (ADEPT) and drug screening as exemplified with 2,4-dinitrobenzamide (CB1954).…”

mentioning

confidence: 99%

“…2 The dicoumarin carbonate-based latent fluorophore was devised for the application in imaging to improve selectivity for NTR and aqueous solubility. 2b Furthermore, NTR was employed in development of gene-directed enzyme prodrug cancer therapies (GDEPT), antibody-directed enzyme prodrug therapy (ADEPT) and drug screening as exemplified with 2,4-dinitrobenzamide (CB1954). 3 The basis of CB1954 activation has been fully elucidated and the molecule has advanced into clinical trials.…”

mentioning

confidence: 99%

“…2–4 To design NTR activatable agents with combined imaging and therapeutic function, the selection of an appropriate reporter is of great importance. Among various reporters, fluorophores with emission in the far red and near-infrared (NIR), in the range of 600–1000 nm, are widely utilized in relevant research settings to overcome the limitation of poor tissue penetration owing to the interference from background auto-fluorescence from biomolecules.…”

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confidence: 99%

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Nitroreductase-triggered activation of a novel caged fluorescent probe obtained from methylene blue

et al. 2015

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Development of a sensitive long-wavelength fluorogenic probe for nitroreductase: A new fluorimetric indictor for analyte determination by dehydrogenase-coupled biosensors

Cited by 54 publications

References 34 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

Fluorescent Chromophores Containing the Nitro Group: Relatively Unexplored Emissive Properties

Nitroreductase-triggered activation of a novel caged fluorescent probe obtained from methylene blue

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