A triphenylamine-based near-infrared fluorescence turn off probe for nitroreductase imaging

Article Chemistry, Analytical

A highly sensitive NIR fluorescence probe for hypoxia imaging in cells and ulcerative colitis

Sheng Wang et al.

Summary: A new fluorescence probe was developed for hypoxia imaging in ulcerative colitis, showing high sensitivity and low detection limit. The probe demonstrated promising application potential in live cells, tumors, and mouse models.

TALANTA (2023)

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Review Chemistry, Inorganic & Nuclear

Recent advances in organic near-infrared ratiometric small-molecule fluorescent probes

Ya-Lin Qi et al.

Summary: In recent years, there has been great interest in the development of organic near-infrared (NIR) ratiometric fluorescent probes. Traditional intensity-based probes lack an internal standard method, resulting in unreliable and inaccurate detection signals as well as an inability to achieve quantitative determination of analytes. Smart dual emission probes with built-in correction ability have overcome the limitations of single channel fluorescent probes and enable reliable quantitative image analysis. Moreover, fluorescent chemosensors in the NIR window offer advantages such as high signal-to-noise ratio, low tissue damage, and deep tissue penetration. The combination of the advantages of ratiometric fluorescent probes and single-intensity-based NIR probes in NIR ratiometric fluorescent probes has led to their widespread application in biomedical research and clinical practice. This review provides a systematic summary of the recent advances (2020-2022) in this field, discussing the design strategies, sensing mechanisms, and bioapplications of these intelligent fluorescent probes. The challenges and prospects in this promising field are also addressed, with the anticipation that this work will inspire the development of organic NIR ratiometric fluorescent probes.

COORDINATION CHEMISTRY REVIEWS (2023)

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Article Chemistry, Analytical

A novel pyrimidine-based two-photon fluorogenic probe for rapidly visualizing nitroreductase activity in hypoxic cancer cells and in vivo

Jia Zhou et al.

Summary: This study developed a NTR probe (ZJ) that can accurately and rapidly detect the overexpressed NTR activity in tumor cells. ZJ showed responsive turn-on two-photon excited fluorescence by NTR recognition in both cells and in vivo. The probe demonstrated favorable stability and specificity, and successfully visualized the distribution of overexpressed NTR in hypoxic cancer cells and zebrafish, indicating its potential application in studying the relationship between tumor hypoxic microenvironment and cancer.

SENSORS AND ACTUATORS B-CHEMICAL (2023)

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Article Spectroscopy

Rational design of a ratiometric fluorescent probe for imaging lysosomal nitroreductase activity

Wenjun Bai et al.

Summary: In this study, a ratiometric fluorescent probe based on extended 7C-7C conjugation of a triphenylamine unit was designed for the detection of NTR and lysosomes imaging. The probe showed high selectivity, rapid response, and a wide pH range towards NTR. It also exhibited low cytotoxicity in both normal and tumor cells, as well as excellent lysosomes colocalization.

SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY (2023)

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Article Chemistry, Physical

A novel nitroreductase-responsive turn-off fluorescent probe based on AIEgen and its bioimaging application

Ruxin Li et al.

Summary: This study presents a novel NTR-responsive turnoff fluorescent probe, TPEDCH-PBN, based on AIEgen. The probe shows high selectivity towards NTR and has a detection limit of 0.68 μg/mL. Computational calculations and docking studies were employed to determine the structure-function relationship between the probe and NTR. Cell imaging experiments confirmed the NTR detection ability of the probe.

JOURNAL OF MOLECULAR STRUCTURE (2023)

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Review Chemistry, Multidisciplinary

Activity-based NIR fluorescent probes based on the versatile hemicyanine scaffold: design strategy, biomedical applications, and outlook

Haidong Li et al.

Summary: The discovery of hemicyanine dyes as near-infrared fluorescent chromophores has significant implications in detection, bioimaging, and medical therapeutic applications. These dyes possess superior optical properties and structural tailorability, making them promising tools for monitoring biomolecules and diagnosing diseases.

CHEMICAL SOCIETY REVIEWS (2022)

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Article Chemistry, Applied

Hypoxia degradable AIE photosensitizer with high efficiency of photodynamic therapy and improved biological safety

Jizhong Shi et al.

Summary: Photodynamic therapy (PDT) is a promising cancer treatment method, but it still faces challenges, such as the toxic effects of residual photosensitizers (PSs) on normal tissues. In this study, a novel PS NTPy was synthesized and successfully applied for cancer therapy. NTPy has aggregation-induced emission (AIE) characteristics, high reactive oxygen species generation efficiency, and strong fluorescence emission. Additionally, NTPy exhibits excellent mitochondria targeting capacity and the ability to detect the hypoxic microenvironment of tumors. The results show that NTPy can reduce the side effects of PS on normal tissues after effective PDT treatment, providing a new strategy for intelligent PDT treatment and increasing the biological safety of PDT.

DYES AND PIGMENTS (2022)

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Article Chemistry, Applied

Synthesis and fluorescence property modulation of α-cyano-1,4-diphenylbutadiene derivatives containing triphenylamine structure

Pei-Ting Li et al.

Summary: In this study, a series of alpha-cyano-1,4-diphenylbutadiene derivatives containing triphenylamine structure were designed and synthesized. By changing the connection mode, the fluorescent wavelengths of the compounds were further regulated.

DYES AND PIGMENTS (2022)

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Article Chemistry, Multidisciplinary

Monitoring mitochondrial nitroreductase activity in tumors and a hind-limb model of ischemia in mice using a novel activatable NIR fluorescent probe

Xiaosheng Liu et al.

Summary: In this study, a mitochondria-targeted nitroreductase (NTR)-activated near-infrared fluorescent probe, CS-NO2, was developed. The probe demonstrated high sensitivity in measuring overexpressed NTR in mitochondria. Most importantly, it successfully monitored NTR activity in solid tumors and an ischemic hind-limb model in mice. These findings highlight the potential utility of the probe in diagnosing solid tumors and hypoxia-associated diseases.

CHEMICAL COMMUNICATIONS (2022)

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Article Chemistry, Multidisciplinary

Acid-induced tunable white light emission based on triphenylamine derivatives

Xi Liu et al.

Summary: A series of TPA derivatives with different substituent groups were prepared and showed unique absorption and fluorescence characteristics due to the substituent effect. The presence of pyridine units in these derivatives enabled acid-induced tunable multicolor fluorescence emission, making them suitable for constructing stimuli-responsive fluorescent films and inks for inkjet printing.

CHINESE CHEMICAL LETTERS (2021)

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Article Chemistry, Analytical

A novel long-wavelength off-on fluorescence probe for nitroreductase analysis and hypoxia imaging

Aixian Zheng et al.

Summary: The study presented a fluorescence probe RCO-NTR for hypoxia analysis, which achieved fluorescence signal enhancement under the action of NTR by introducing nitrobenzyl. This probe can be used for nitroreductase analysis and hypoxia imaging.

ANALYTICA CHIMICA ACTA (2021)

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Article Chemistry, Medicinal

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

Sanu Karan et al.

Summary: This study presents a cancer cell-selective and hypoxia-responsive probe for direct cancer monitoring. The probe shows superior fluorescence signal under hypoxic conditions.

JOURNAL OF MEDICINAL CHEMISTRY (2021)

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Article Chemistry, Analytical

An AIEgen-based photosensitizer for lysosome imaging and photodynamic therapy in tumor

Wendi Huang et al.

Summary: A lysosome-targeting photosensitizer MP-TPEDCH with excellent photostability and lysosome targeting specificity has been designed in this work, showing significantly enhanced antitumor effect under NIR irradiation.

SENSORS AND ACTUATORS B-CHEMICAL (2021)

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Review Chemistry, Analytical

Small-molecule probes for fluorescent detection of cellular hypoxia-related nitroreductase

Jian Qiao et al.

Summary: Nitroreductase catalyzes the conversion of nitro aromatic compounds to aromatic amines. Its upregulation in hypoxic tumor cells is directly related to the degree of hypoxia, making effective detection of nitroreductase important for cellular hypoxia studies, tumor diagnosis, and treatment. The latest advances in small-molecule fluorescent probes for nitroreductase detection and the development trends in this field were summarized in this review.

JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS (2021)

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Article Biochemistry & Molecular Biology

A Novel NIR Fluorescent Probe for Highly Selective Detection of Nitroreductase and Hypoxic-Tumor-Cell Imaging

Feng Liu et al.

Summary: A novel NIR fluorescent probe Py-SiRh-NTR with excellent sensitivity and selectivity for nitroreductase detection was synthesized in this study. The probe showed enhanced fluorescence in HepG-2 cells treated under hypoxic conditions, indicating overexpression of NTR. This promising probe could facilitate research on anticancer mechanisms.

MOLECULES (2021)

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Article Chemistry, Analytical

An activatable NIR fluorescent rosol for selectively imaging nitroreductase activity

Jessica L. Klockow et al.

SENSORS AND ACTUATORS B-CHEMICAL (2020)

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Review Chemistry, Inorganic & Nuclear

Recent progress in the design principles, sensing mechanisms, and applications of small-molecule probes for nitroreductases

Ya-Lin Qi et al.

COORDINATION CHEMISTRY REVIEWS (2020)

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Article Chemistry, Analytical

A ratiometric fluorescent biosensor based on conjugated polymers for sensitive detection of nitroreductase and hypoxia diagnosis in tumor cells

Ziqi Zhang et al.

SENSORS AND ACTUATORS B-CHEMICAL (2020)

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Article Chemistry, Applied

A benzothiazole-based water soluble and pH-independent probe for nitroreductase with a dramatic change of chromogenic and fluorogenic properties

Sang-Yun Na et al.

DYES AND PIGMENTS (2019)

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Article Chemistry, Multidisciplinary

Single-Molecule Imaging of Active Mitochondrial Nitroreductases Using a Photo-Crosslinking Fluorescent Sensor

Zacharias Thiel et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Physical

The centenary of the Stern-Volmer equation of fluorescence quenching: From the single line plot to the SV quenching map

Marcelo H. Gehlen

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY C-PHOTOCHEMISTRY REVIEWS (2019)

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Article Chemistry, Multidisciplinary

Substituent effects of AIE-active -cyanostilbene-containing triphenylamine derivatives on electrofluorochromic behavior

Sin-Yu Chen et al.

NANOSCALE (2019)

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Article Chemistry, Multidisciplinary

A dual-function fluorescent probe for monitoring the degrees of hypoxia in living cells via the imaging of nitroreductase and adenosine triphosphate

Yu Fang et al.

CHEMICAL COMMUNICATIONS (2018)

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Review Chemistry, Multidisciplinary

Recent progress in small molecule fluorescent probes for nitroreductase

Wenjing Qin et al.

CHINESE CHEMICAL LETTERS (2018)

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Review Chemistry, Multidisciplinary

Recent advances in near-infrared II fluorophores for multifunctional biomedical imaging

Feng Ding et al.

CHEMICAL SCIENCE (2018)

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Article Materials Science, Biomaterials

Dimeric BODIPY-loaded liposomes for dual hypoxia marker imaging and activatable photodynamic therapy against tumors

Huachao Chen et al.

JOURNAL OF MATERIALS CHEMISTRY B (2018)

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Article Medicine, Research & Experimental

Hypoxia-triggered single molecule probe for high-contrast NIR II/PA tumor imaging and robust photothermal therapy

Xiaoqing Meng et al.

THERANOSTICS (2018)

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Article Chemistry, Analytical

A fast-responsive two-photon fluorescent turn-on probe for nitroreductase and its bioimaging application in living tissues

An Xu et al.

SENSORS AND ACTUATORS B-CHEMICAL (2017)

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Article Chemistry, Analytical

meso-ester BODIPYs for the imaging of hypoxia in tumor cells

Tae-Il Kim et al.

SENSORS AND ACTUATORS B-CHEMICAL (2017)

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Review Engineering, Biomedical

Near-infrared fluorophores for biomedical imaging

Guosong Hong et al.

NATURE BIOMEDICAL ENGINEERING (2017)

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Article Chemistry, Multidisciplinary

Real time detection of ESKAPE pathogens by a nitroreductase-triggered fluorescence turn-on probe

Shengnan Xu et al.

CHEMICAL COMMUNICATIONS (2017)

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Article Chemistry, Applied

A novel donor-two-acceptor type fluorophore-based probe for fast detection and intracellular imaging of nitroreductase

Dandan Li et al.

DYES AND PIGMENTS (2017)

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Review Chemistry, Multidisciplinary

Tissue-Specific Near-Infrared Fluorescence Imaging

Eric A. Owens et al.

ACCOUNTS OF CHEMICAL RESEARCH (2016)

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Article Chemistry, Analytical

Real-Time Bioluminescence Imaging of Nitroreductase in Mouse Model

Ping Feng et al.

ANALYTICAL CHEMISTRY (2016)

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Article Chemistry, Multidisciplinary

A New Tetraphenylethylene-Derived Fluorescent Probe for Nitroreductase Detection and Hypoxic-Tumor-Cell Imaging

Xue You et al.

CHEMISTRY-AN ASIAN JOURNAL (2016)

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Article Chemistry, Multidisciplinary

A Lysosome-Targeting Fluorescence Off-On Probe for Imaging of Nitroreductase and Hypoxia in Live Cells

Jin Zhou et al.

CHEMISTRY-AN ASIAN JOURNAL (2016)

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Article Chemistry, Multidisciplinary

Unraveling the aggregation effect on amorphous phase AIE luminogens: a computational study

Xiaoyan Zheng et al.

NANOSCALE (2016)

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Article Chemistry, Analytical

A highly sensitive near-infrared ratiometric fluorescent probe for detecting nitroreductase and cellular imaging

Dongjian Zhu et al.

SENSORS AND ACTUATORS B-CHEMICAL (2016)

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Article Chemistry, Analytical

Efficient Two-Photon Fluorescent Probe for Nitroreductase Detection and Hypoxia Imaging in Tumor Cells and Tissues

Jing Zhang et al.

ANALYTICAL CHEMISTRY (2015)

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Article Biophysics

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

Zhao Li et al.

BIOSENSORS & BIOELECTRONICS (2015)

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Article Chemistry, Multidisciplinary

N-Heterotriangulenes: Fascinating Relatives of Triphenylamine

Natalie Hammer et al.

CHEMICAL RECORD (2015)

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Review Chemistry, Multidisciplinary

Aggregation-Induced Emission: Together We Shine, United We Soar!

Ju Mei et al.

CHEMICAL REVIEWS (2015)

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Article Chemistry, Multidisciplinary

Restriction of Intramolecular Motions: The General Mechanism behind Aggregation-Induced Emission

Nelson L. C. Leung et al.

CHEMISTRY-A EUROPEAN JOURNAL (2014)

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Article Chemistry, Multidisciplinary

High selectivity imaging of nitroreductase using a near-infrared fluorescence probe in hypoxic tumor

Kehua Xu et al.

CHEMICAL COMMUNICATIONS (2013)

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Article Chemistry, Multidisciplinary

Biocompatible Nanoparticles with Aggregation-Induced Emission Characteristics as Far-Red/Near-Infrared Fluorescent Bioprobes for In Vitro and In Vivo Imaging Applications

Wei Qin et al.

ADVANCED FUNCTIONAL MATERIALS (2012)

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Article Chemistry, Multidisciplinary

A Twisting Donor-Acceptor Molecule with an Intercrossed Excited State for Highly Efficient, Deep-Blue Electroluminescence

Weijun Li et al.

ADVANCED FUNCTIONAL MATERIALS (2012)

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Article Biophysics

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

Hun-Chung Huang et al.

BIOSENSORS & BIOELECTRONICS (2011)

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Review Oncology

Targeting hypoxia in cancer therapy

William R. Wilson et al.

NATURE REVIEWS CANCER (2011)

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Article Chemistry, Multidisciplinary

Changing the Behavior of Chromophores from Aggregation-Caused Quenching to Aggregation-Induced Emission: Development of Highly Efficient Light Emitters in the Solid State

Wang Zhang Yuan et al.

ADVANCED MATERIALS (2010)

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Article Chemistry, Multidisciplinary

Aggregation-induced and crystallization-enhanced emissions of 1,2-diphenyl-3,4-bis(diphenylmethylene)-1-cyclobutene

Yongqiang Dong et al.

CHEMICAL COMMUNICATIONS (2007)

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Article Biochemistry & Molecular Biology

Structural and mechanistic studies of Escherichia coli nitroreductase with the antibiotic nitrofurazone -: Reversed binding orientations in different redox states of the enzyme

PR Race et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2005)

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Article Biochemistry & Molecular Biology

Structures of nitroreductase in three states - Effects of inhibitor binding and reduction

CA Haynes et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2002)

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A triphenylamine-based near-infrared fluorescence turn off probe for nitroreductase imaging

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