in vivo imaging and detection of nitroreductase in zebrafish by a new near-infrared fluorescence off–on probe

Li, Zhao; He, Xinyuan; Wang, Zhe; Yang, Ronghua; Shi, Wen; Ma, Huimin

doi:10.1016/j.bios.2014.07.024

Cited by 169 publications

(91 citation statements)

References 24 publications

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“…[17,[25][26][27][28][29] The other mechanism for the design of hypoxia-sensitive imaging probes was by exploiting the bioreductive microenvironmento fh ypoxia,r esulting in excess expression of nitro reductase (NTR), azo reductase, quinone reductase, and so forth. [30] Several hypoxia-sensitive probes, the luminescence intensity of which changes depending on bioreductionu nder hypoxia,h ave been developed by employing nitro groups, [31][32][33] azo groups, [8,10,34] quinone groups, [19,35] or QSY-21 [9] as the hypoxia-sensing moiety.…”

Section: Introductionmentioning

confidence: 99%

Iridium(III) Anthraquinone Complexes as Two‐Photon Phosphorescence Probes for Mitochondria Imaging and Tracking under Hypoxia

Sun

Chen

Kuang

et al. 2016

Chemistry A European J

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In the present study, four mitochondria-specific and two-photon phosphorescence iridium(III) complexes, Ir1-Ir4, were developed for mitochondria imaging in hypoxic tumor cells. The iridium(III) complex has two anthraquinone groups that are hypoxia-sensitive moieties. The phosphorescence of the iridium(III) complex was quenched by the functions of the intramolecular quinone unit, and it was restored through two-electron bioreduction under hypoxia. When the probes were reduced by reductase to hydroquinone derivative products under hypoxia, a significant enhancement in phosphorescence intensity was observed under one- (λ=405 nm) and two-photon (λ=720 nm) excitation, with a two-photon absorption cross section of 76-153 GM at λ=720 nm. More importantly, these probes possessed excellent specificity for mitochondria, which allowed imaging and tracking of the mitochondrial morphological changes in a hypoxic environment over a long period of time. Moreover, the probes can visualize hypoxic mitochondria in 3D multicellular spheroids and living zebrafish through two-photon phosphorescence imaging.

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Section: Introductionmentioning

confidence: 99%

Iridium(III) Anthraquinone Complexes as Two‐Photon Phosphorescence Probes for Mitochondria Imaging and Tracking under Hypoxia

Sun

Chen

Kuang

et al. 2016

Chemistry A European J

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“…[1][2][3][4][5][6][7] To a large extent, an excellent sensing system depends on the nature of chromophores themselves. Therefore, it's essential for fluorophores to have a good luminescent property, and the development of new fluorophores with satisfactory photophysical properties is highly desirable.…”

mentioning

confidence: 99%

Pyrene Derivative Emitting Red or near-Infrared Light with Monomer/Excimer Conversion and Its Application to Ratiometric Detection of Hypochlorite

Wang

Zeng

et al. 2016

ACS Appl. Mater. Interfaces

195

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Fluorescent sensors are attractive and versatile tools for both chemical sensing and biological imaging. Herein, a novel pyrene derivative fluorophore, Py-Cy, possessing the monomer/excimer conversion feature, was synthesized; and the design rationale for this fluorophore is combination of extending conjugation length and incorporating donor-π-acceptor structure. The positively charged Py-Cy shows quite good water solubility and exhibits absorption in the visible-light range, and its monomer and excimer emit red light and near-infrared light respectively, which is extremely beneficial for biosensing or bioimaging. To explore the potential utilization of this new fluorophore, we choose hypochlorite as a model analyte, which can break the double bond in the molecular structure, thereby generating the water-insoluble pyrenecarboxaldehyde; this process correspondingly leads to fluorescence changes and thus affords the ratiometric fluorescent detection of hypochlorite in real samples and cell imaging. The approach offers new insights for designing other fluorophores which emit red or near-infrared light and for devising technically simple ratiometric fluorescent sensors.

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“…Probe 1 and model compounds 1-5 ( Figure 1a nd the Supporting Information, Scheme S1) were prepared by incorporating different 3-subsituted benzyloxy moieties into aNIR fluorophore HXPI. [9,10] Thed etailed synthetic steps and characterization of probe 1 and model compounds 1-5 are given in the Supporting Information, Figures S1-S12 and Table S1.…”

mentioning

confidence: 99%

Near‐Infrared Fluorescent Probe with New Recognition Moiety for Specific Detection of Tyrosinase Activity: Design, Synthesis, and Application in Living Cells and Zebrafish

et al. 2016

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Fluorescence imaging of tyrosinase (a cancer biomarker) in living organisms is of great importance for biological studies. However, selective detection of tyrosinase remains a great challenge because current fluorescent probes that contain the 4-hydroxyphenyl moiety show similar fluorescence responses to both tyrosinase and some reactive oxygen species (ROS), thereby suffering from ROS interference. Herein, a new tyrosinase-recognition 3-hydroxybenzyloxy moiety, which exhibits distinct fluorescence responses for tyrosinase and ROS, is proposed. Using the recognition moiety, we develop a near-infrared fluorescence probe for tyrosinase activity, which effectively eliminates the interference from ROS. The high specificity of the probe was demonstrated by imaging and detecting endogenous tyrosinase activity in live cells and zebrafish and further validated by an enzyme-linked immunosorbent assay. The probe is expected to be useful for the accurate detection of tyrosinase in complex biosystems.

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in vivo imaging and detection of nitroreductase in zebrafish by a new near-infrared fluorescence off–on probe

Cited by 169 publications

References 24 publications

Iridium(III) Anthraquinone Complexes as Two‐Photon Phosphorescence Probes for Mitochondria Imaging and Tracking under Hypoxia

Iridium(III) Anthraquinone Complexes as Two‐Photon Phosphorescence Probes for Mitochondria Imaging and Tracking under Hypoxia

Pyrene Derivative Emitting Red or near-Infrared Light with Monomer/Excimer Conversion and Its Application to Ratiometric Detection of Hypochlorite

Near‐Infrared Fluorescent Probe with New Recognition Moiety for Specific Detection of Tyrosinase Activity: Design, Synthesis, and Application in Living Cells and Zebrafish

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