Near-Infrared Fluorescent Probe Activated by Nitroreductase for <i>In Vitro</i> and <i>In Vivo</i> Hypoxic Tumor Detection

Karan, Sanu; Cho, Mi Young; Lee, Hyunseung; Lee, Hwunjae; Park, Hye Sun; Sundararajan, Mahesh; Sessler, Jonathan L.; Hong, Kwan Soo

doi:10.1021/acs.jmedchem.0c02162

Cited by 59 publications

(30 citation statements)

References 65 publications

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“…Such -NO2 terminal group has a strong electronwithdrawing ability, making the intramolecular charge transfer (ICT) in the acceptor unit interdict (Figure 4a and S29). 64,65 Consequently, it led to the interruption of iECL-RET, and the ECL emission was mainly contributed by the LU donor. Interestingly, the nitro-group could be quantitatively reduced to amino-group with a much lower electron-withdrawing capacity by a facile enzymatic reaction using nitroreductase (NTR) and NADH.…”

Section: Resultsmentioning

confidence: 99%

Lighting up Electrochemiluminescent Inactive Dyes by Intramolecular Resonance Energy Transfer

Zheng¹,

Ye²,

Zhao³

et al. 2021

Preprint

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By virtue of near-zero optical background and photobleaching, electrochemiluminescence (ECL), an optical phenomenon excited by electrochemical reactions, has drawn extensive attention in both fundamental studies and wide applications especially of ultrasensitive bioassay. Developing diverse ECL emitters is crucial to unlock their multiformity and performances, but remains a formidable challenge, due to the rigorous requirements for ECL. Herein, we report a general intramolecular ECL resonance energy transfer (iECL-RET) strategy to light up ECL-inactive dyes in aqueous solutions using an existing high-performance ECL initiators. As a proof-of-concept, a series of luminol donor-dye acceptor based ECL emitters with near unity RET efficiency and coarse/fine tunable emission wavelengths were demonstrated. Different to previous exploitation of new molecule single-handedly to address all the prerequisites of ECL, each unit in the proposed ECL ensemble performed maximally its own functions. The iECL-RET strategy would greatly expand the family members of ECL emitters for more demanding future applications.

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Section: Resultsmentioning

confidence: 99%

Lighting up Electrochemiluminescent Inactive Dyes by Intramolecular Resonance Energy Transfer

Zheng¹,

Ye²,

Zhao³

et al. 2021

Preprint

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“…Karan et al . developed probe 12 to target hypoxia stimulated cancer cells [50] . Probe 12 contains core BODIPY conjugated with folate subunit and p ‐nitrobenzyl ether to detect NTR.…”

Section: Small Molecule Based Ntr Probesmentioning

confidence: 99%

Small Molecule Fluorescent Probes for Sensing and Bioimaging of Nitroreductase

et al. 2022

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Hypoxia is a condition caused by a decrease in oxygen and is often seen in cases of cardiac ischemia, solid tumors, inflammation, and other diseases. Tumor hypoxia can result in cancer invasion, metastasis, decreased apoptosis, and resistance to various therapies (chemotherapy, immunotherapy, and radiotherapy), ultimately reducing overall survival rates. These effects of hypoxia underline the need to monitor hypoxia‐associated specific markers for more effective therapeutic intervention. Nitroreductase (NTR) is a common biomarker of hypoxia, via its reduction activity with nitroaromatic compounds to corresponding amino derivatives using NADH and NADPH as cofactor. The NTR expression level can be correlated to cellular hypoxia. Therefore, developing a diagnostic tool for measuring NTR activity is of immense importance for improving treatment efficacies. To leverage NTR activity as a proxy of hypoxia, small molecule based fluorescent probes have been developed as quantifiable probes. To date, several NTR‐sensitive fluorescent probes have been reported. This review is focuses on the advances in these fluorescent NTR probes over the last five years.

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“…Kwan Soo Hong and coworkers reported a near‐infrared fluorescence NTR probe ( probe 33 , Figure 21A) [56] . The near‐ infrared fluorescence precursor was synthesized by combining folic acid with BODIPY, and then the fluorescence precursor was linked to the NTR response site by conjugated bonds to construct a phenolic probe 33 .…”

Section: Nitro Reductase (Ntr) Fluorescent Probementioning

confidence: 99%

Recent Advances in the Fluorescent Probes for Flavinase Activity: Design and Applications

Yang

Zhai

Yuan

et al. 2022

Chemistry An Asian Journal

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Flavinases, including monoamine oxidase (MAO-A/ MAO-B), quinone oxidoreductase (NQO1), thioredoxin reductase (TrxR), nitroreductase (NTR) and so on, are important redox enzymes in organisms. They are considered as biomarkers of cell energy metabolism and cell vitality. Importantly, their aberrant expression is related to various disease processes. Therefore, the accurate measurement of flavinase is useful for the early diagnosis of diseases, which has aroused great concern in the scientific community. Various methods are also available for the detection of flavinases, fluorescence probes are considered to be one of the best detection methods due to their easy and accurate sensing capability. This review aims to introduce the advances in the design and application of flavinase probes in the last five years. This study focuses on analyzing the design strategies and reaction mechanisms of flavinases fluorescent probes and discusses the current challenges, which will further advance the development of diagnostic and therapeutic approaches for flavinase-related diseases.

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Near-Infrared Fluorescent Probe Activated by Nitroreductase for In Vitro and In Vivo Hypoxic Tumor Detection

Cited by 59 publications

References 65 publications

Lighting up Electrochemiluminescent Inactive Dyes by Intramolecular Resonance Energy Transfer

Lighting up Electrochemiluminescent Inactive Dyes by Intramolecular Resonance Energy Transfer

Small Molecule Fluorescent Probes for Sensing and Bioimaging of Nitroreductase

Recent Advances in the Fluorescent Probes for Flavinase Activity: Design and Applications

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