Strategy for Detecting Carbon Monoxide: Cu2+-Assisted Fluorescent Probe and Its Applications in Biological Imaging.

Herein, a novel strategy was proposed for identifying carbon monoxide (CO), which plays a crucial part in living systems. For the first time, we have managed to design, synthesize, and characterize successfully this new Cu2+-assisted fluorescent probe (DPHP) in detecting CO. Compared with the commonly adopted Pd0-mediated Tsuji-Trost reaction recognition method, such a new strategy did not engage costly palladium (II) salt and generated no leaving group, indicating a satisfactory anti-interference ability. The recognition mechanism was confirmed by IR, 1H NMR titration, HR-MS, cyclic voltammetry, X-ray photoelectron spectroscopy, electron paramagnetic resonance, and optical properties. Surprisingly, it was found that the new method achieved high selectivity and rapid identification of CO with a lower limit of detection (1.7 × 10-8 M). More intriguingly, it could recognize endogenous and exogenous CO in HeLa cells. The cytotoxicity of this new method was so low that it allowed the detection of CO in mice and zebrafish. Basically, our results trigger a novel viewpoint of rationally designing and synthesizing advanced materials for CO detection with unique features, impelling new research in detection chemistry.

[1]  W. Chao,et al.  A hepatocyte-specific fluorescent probe for imaging endogenous carbon monoxide release in vitro and in vivo , 2021 .

[2]  J Zhang,et al.  Easily available aggregation-induced enhanced emission fluorescent material for detecting 1, 3-diaminopropane in gas-liquid-solid three-phase and bioimaging application , 2021 .

[3]  M. Karbarz,et al.  Reversible change in volume of thin hydrogel layer deposited on electrode surface using Cu(II)↔Cu(I) process , 2021 .

[4]  Yongfei Li,et al.  A novel HPQ-based fluorescent probe for the visualization of carbon monoxide in zebrafish , 2021 .

[5]  Guoqiang Feng,et al.  In Vivo Imaging and Tracking Carbon Monoxide-Releasing Molecule-3 with an NIR Fluorescent Probe. , 2021, ACS sensors.

[6]  Yongfei Li,et al.  Construction of NIR and Ratiometric Fluorescent Probe for Monitoring Carbon Monoxide under Oxidative Stress in Zebrafish. , 2021, Analytical chemistry.

[7]  Nan Zhang,et al.  Ratiometric Fluorescence Imaging for the Distribution of Nucleic Acid Content in Living Cells and Human Tissue Sections. , 2020, Analytical chemistry.

[8]  Guohui Li,et al.  Probing cell membrane damage using a molecular rotor probe with membrane-to-nucleus translocation , 2020 .

[9]  Weiying Lin,et al.  An endoplasmic reticulum targetable turn-on fluorescence probe for imaging application of carbon monoxide in living cells. , 2020, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[10]  J. Pfeilschifter,et al.  Gasotransmitter synthesis and signalling in the renal glomerulus. Implications for glomerular diseases. , 2020, Cellular signalling.

[11]  A. Ibrahim,et al.  CO oxidation over nobel metals supported on copper oxide: effect of Cu+/Cu2+ ratio , 2020 .

[12]  Chaobo Huang,et al.  Design of a novel mitochondria targetable turn-on fluorescence probe for hydrogen peroxide and its two-photon bioimaging applications , 2020 .

[13]  Guoqiang Feng,et al.  NIR fluorescent probe based on a modified rhodol-dye with good water solubility and large Stokes shift for monitoring CO in living systems. , 2020, Talanta.

[14]  Christopher J. Chang,et al.  Ligand-Directed Approach to Activity-Based Sensing: Developing Palladacycle Fluorescent Probes That Enable Endogenous Carbon Monoxide Detection. , 2020, Journal of the American Chemical Society.

[15]  Chang-qing Qu,et al.  Reversible and Selective Turn-on Fluorescent and Naked-Eye Colorimetric Sensor to Detect Cyanide in Tap Water, Food Samples, and Living Systems , 2020 .

[16]  M. Li,et al.  Recent progress in fluorescent probes for detection of carbonyl species: Formaldehyde, carbon monoxide and phosgene , 2020, Coordination Chemistry Reviews.

[17]  B. Wang,et al.  Nitro reduction-based fluorescent probes for carbon monoxide require reactivity involving a ruthenium carbonyl moiety. , 2020, Chemical communications.

[18]  K. Maslakov,et al.  XPS detection of unusual Cu(II) to Cu(I) transition on the surface of complexes with redox-active ligands , 2020 .

[19]  Guoqiang Feng,et al.  Development of a new ratiometric probe with near-infrared fluorescence and a large Stokes shift for detection of gasotransmitter CO in living cells. , 2020, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[20]  Guoqiang Feng,et al.  Rapid detection of CO in vitro and in vivo with a ratiometric probe showing near-infrared turn-on fluorescence, large Stokes shift, and high signal-to-noise ratio , 2019 .

[21]  Yuliang Zhao,et al.  Emerging Delivery Strategies of Carbon Monoxide for Therapeutic Applications: from CO Gas to CO Releasing Nanomaterials. , 2019, Small.

[22]  Hong Wang,et al.  A fluorescent probe for carbon monoxide based on allyl ether rather than allyl ester: A practical strategy to avoid the interference of esterase in cell imaging. , 2019, Talanta.

[23]  Xiaohua Ren,et al.  A metal-free near-infrared fluorescent probe for tracking the glucose-induced fluctuations of carbon monoxide in living cells and zebrafish , 2019, Sensors and Actuators B: Chemical.

[24]  B. Wang,et al.  Esterase-Sensitive and pH-Controlled Carbon Monoxide Prodrugs for Treating Systemic Inflammation. , 2019, Journal of medicinal chemistry.

[25]  A. Wojtczak,et al.  Redox active ligand and metal cooperation for C(sp2)-H oxidation: extension of the galactose oxidase mechanism in water-mediated amide formation. , 2018, Dalton transactions.

[26]  J. Mittal,et al.  Room temperature carbon monoxide gas sensor using Cu doped OMS-2 nanofibers , 2018, Sensors and Actuators B: Chemical.

[27]  Genggongwo Shi,et al.  Turn-on and Turn-off Fluorescent Probes for Carbon Monoxide Detection and Blood Carboxyhemoglobin Determination. , 2018, ACS sensors.

[28]  C. Lau,et al.  Bioluminescence Imaging of Carbon Monoxide in Living Cells and Nude Mice Based on Pd0-Mediated Tsuji-Trost Reaction. , 2018, Analytical chemistry.

[29]  L. Otterbein,et al.  Enrichment-triggered Prodrug Activation Demonstrated through Mitochondria-targeted Delivery of Doxorubicin and Carbon Monoxide , 2018, Nature Chemistry.

[30]  Z. Mao,et al.  A coumarin Schiff's base two-photon fluorescent probe for hypochlorite in living cells and zebrafish , 2018, RSC advances.

[31]  Guoqiang Feng,et al.  A readily available colorimetric and near-infrared fluorescent turn-on probe for detection of carbon monoxide in living cells and animals , 2018 .

[32]  Andrew J. P. White,et al.  Ex Vivo Tracking of Endogenous CO with a Ruthenium(II) Complex. , 2017, Journal of the American Chemical Society.

[33]  Guoqiang Feng,et al.  Colorimetric and ratiometric fluorescent detection of carbon monoxide in air, aqueous solution, and living cells by a naphthalimide-based probe , 2017 .

[34]  Jyhfu Lee,et al.  X-ray Absorption and Electron Paramagnetic Resonance Guided Discovery of the Cu-Catalyzed Synthesis of Multiaryl-Substituted Furans from Aryl Styrene and Ketones Using DMSO as the Oxidant. , 2017, Organic letters.

[35]  Guoqiang Feng,et al.  Allyl Fluorescein Ethers as Promising Fluorescent Probes for Carbon Monoxide Imaging in Living Cells. , 2017, Analytical chemistry.

[36]  R. Martínez‐Máñez,et al.  Chromo-fluorogenic probes for carbon monoxide detection. , 2016, Chemical communications.

[37]  T. Urushidani,et al.  Feedback Response to Selective Depletion of Endogenous Carbon Monoxide in the Blood. , 2016, Journal of the American Chemical Society.

[38]  Jyhfu Lee,et al.  Direct Observation of Reduction of Cu(II) to Cu(I) by P–H Compounds using XAS and EPR Spectroscopy , 2016 .

[39]  L. Magagnin,et al.  Copper electrodeposition from a chloride free deep eutectic solvent , 2015 .

[40]  Koushik Dhara,et al.  A new fluorogenic probe for the selective detection of carbon monoxide in aqueous medium based on Pd(0) mediated reaction. , 2015, Chemical communications.

[41]  Y. Naito,et al.  The Therapeutic Potential of Carbon Monoxide for Inflammatory Bowel Disease , 2015, Digestion.

[42]  G. Bernardes,et al.  Carbon-monoxide-releasing molecules for the delivery of therapeutic CO in vivo. , 2014, Angewandte Chemie.

[43]  Kaibo Zheng,et al.  A unique carbazole–coumarin fused two-photon platform: development of a robust two-photon fluorescent probe for imaging carbon monoxide in living tissues , 2014 .

[44]  Jeffrey T. Miller,et al.  Direct observation of reduction of Cu(II) to Cu(I) by terminal alkynes. , 2014, Journal of the American Chemical Society.

[45]  Christopher J. Chang,et al.  A reaction-based fluorescent probe for selective imaging of carbon monoxide in living cells using a palladium-mediated carbonylation. , 2012, Journal of the American Chemical Society.

[46]  Youngmi Lee,et al.  Improved electrochemical microsensor for the real-time simultaneous analysis of endogenous nitric oxide and carbon monoxide generation. , 2012, Analytical chemistry.

[47]  Andrea R. Gerson,et al.  Resolving surface chemical states in XPS analysis of first row transition metals, oxides and hydroxides: Sc, Ti, V, Cu and Zn , 2010 .

[48]  L. Otterbein,et al.  The therapeutic potential of carbon monoxide , 2010, Nature Reviews Drug Discovery.

[49]  A. Abbott,et al.  Electrodeposition of copper composites from deep eutectic solvents based on choline chloride. , 2009, Physical Chemistry, Chemical Physics - PCCP.

[50]  K. Kirchner,et al.  Stereospecific and reversible CO binding at iron pincer complexes. , 2008, Angewandte Chemie.