A water-soluble BODIPY-based fluorescent probe for rapid and selective detection of hypochlorous acid in living cells

Rutala, 1997, Uses of inorganic hypochlorite (bleach) in health-care facilities, Clin. Microbiol. Rev., 10, 597−610, 10.1128/CMR.10.4.597 Hole, 2011, Do reactive oxygen species play a role in myeloid leukemias, Blood, 117, 5816−5826, 10.1182/blood-2011-01-326025 Prokopowicz, 2010, Hypochlorous acid: a natural adjuvant that facilitates antigen processing, cross-priming, and the induction of adaptive immunity, J. Immunol., 184, 824−835, 10.4049/jimmunol.0902606 Winterbourn, 2006, Modeling the reactions of superoxide and myeloperoxidase in the neutrophil phagosome: implications for microbial killing, J. Biol. Chem., 281, 10.1074/jbc.M605898200 Steinbeck, 2007, Myeloperoxidase and chlorinated peptides in osteoarthritis: potential biomarkers of the disease, J. Orthop. Res., 25, 1128−1135, 10.1002/jor.20400 Sugiyama, 2001, Macrophage myeloperoxidase regulation by granulocyte macrophage colony-stimulating factor in human atherosclerosis and implications in acute coronary syndromes, Am. J. Pathol., 158, 879−891, 10.1016/S0002-9440(10)64036-9 Hammerschmidt, 2002, Tissue lipid peroxidation and reduced glutathione depletion in hypochlorite-induced lung injury, Chest, 121, 573−581, 10.1378/chest.121.2.573 Malle, 2003, Myeloperoxidase in kidney disease, Kidney Int., 64, 1956−1967, 10.1046/j.1523-1755.2003.00336.x Yap, 2007, Chlorinative stress: an under appreciated mediator of neurodegeneration, Cell. Signal., 19, 219−228, 10.1016/j.cellsig.2006.06.013 Güngör, 2010, Genotoxic effects of neutrophils and hypochlorous acid, Mutagenesis, 25, 149−154, 10.1093/mutage/gep053 Ding, 2013, A highly selective fluorescent chemosensor for Al(III) ion and fluorescent species formed in the solution, Inorg. Chem., 52, 7320−7322, 10.1021/ic401028u Jung, 2010, Rationally designed fluorescence turn-on sensors: a new design strategy based on orbital control, Inorg. Chem., 49, 8552−8557, 10.1021/ic101165k de Silva, 1997, Signaling recognition events with fluorescent sensors and switches, Chem. Rev., 97, 1515−1566, 10.1021/cr960386p Kobayashi, 2010, New strategies for fluorescent probe design in medical diagnostic imaging, Chem. Rev., 110, 2620−2640, 10.1021/cr900263j Callan, 2005, Luminescent sensors and switches in the early 21st century, Tetrahedron, 61, 8551−8588, 10.1016/j.tet.2005.05.043 Ding, 2015, A turn on fluorescent probe for heparin and its over sulfated chondroitin sulfate contaminant, Chem. Sci., 6, 6361−6366, 10.1039/C5SC01675D Xia, 2015, A squaraine-based colorimetric and Fˉ dependent chemosensor for recyclable CO2 gas detection: highly sensitive off-on-off response, Chem. Commun., 51, 10.1039/C5CC04755B Shi, 2017, An arylboronate locked fluorescent probe for hypochlorite, Analyst, 142, 2104−2108, 10.1039/C7AN00467B Xia, 2018, Controlling crystal structures and multiple thermo- and vapochromic behaviors of benzimidazole-based squaraine dyes, Chem. Eur. J., 24, 13205, 10.1002/chem.201801518 Xia, 2019, Reversible specifc vapoluminescence behavior in pure organic crystals through hydrogen-bonding docking strategy, Adv. Opt. Mater., 7, 10.1002/adom.201801549 Kenmoku, 2007, Development of a highly specific rhodamine-based fluorescence probe for hypochlorous acid and its application to real-time imaging of phagocytosis, J. Am. Chem. Soc., 129, 7313−7318, 10.1021/ja068740g Yuan, 2012, Fluorescent detection of hypochlorous acid from turn-on to FRET-based ratiometry by a HOCl-mediated cyclization reaction, Chem. Eur. J., 18, 2700−2706, 10.1002/chem.201101918 Xu, 2013, A highly specific fluorescent probe for hypochlorous acid and its application in imaging microbe-induced HOCl production, J. Am. Chem. Soc., 135, 9944−9949, 10.1021/ja404649m Zhang, 2016, Real-time discrimination and versatile profiling of spontaneous reactive oxygen species in living organisms with a single fluorescent probe, J. Am. Chem. Soc., 138, 3769−3778 Li, 2017, A tumor-specific and mitochondria-targeted fluorescent probe for real-time sensing of hypochlorite in living cells, Chem. Commun., 53, 5539−5541 Xiao, 2015, A colorimetric and ratiometric fluorescent probe for ClOˉ targeting in mitochondria and its application in vivo, J. Mater. Chem. B, 3, 1633−1638, 10.1039/C4TB02003K Zou, 2015, An Nd3+-sensitized upconversion nanophosphor modified with a cyanine dye for the ratiometric upconversion luminescence bioimaging of hypochlorite, Nanoscale, 7, 4105−4113, 10.1039/C4NR06407K Xu, 2015, Development of imidazoline-2-thiones based two-photon fluorescence probes for imaging hypochlorite generation in a co-culture system, Angew. Chem. Int. Ed., 54, 4890−4894 Wu, 2018, ESIPT-based fluorescence probe for the rapid detection of hypochlorite (HOCl/ClOˉ), Chem. Commun., 54, 8522−8525, 10.1039/C8CC06917D Xi, 2018, A near-infrared ratiometric fluorescent probe for rapid and selective detection of hypochlorous acid in aqueous solution and living cells, Sensors Actuators B Chem., 255, 666−671, 10.1016/j.snb.2017.08.073 Xing, 2018, A water-soluble, two-photon probe for imaging endogenous hypochlorous acid in live tissue, Chem. Eur. J., 24, 5748−5753, 10.1002/chem.201800249 Zhang, 2018, Ratiometric fluorescent probes for capturing endogenous hypochlorous acid in the lungs of mice, Chem. Sci., 9, 8207−8212, 10.1039/C8SC03226B Cheng, 2014, A near-infrared fluorescent probe for selective detection of HClO based on se-sensitized aggregation of heptamethine cyanine dye, Chem. Commun., 50, 1018−1020, 10.1039/C3CC47864E Xiao, 2015, A fast-responsive mitochondria-targeted fluorescent probe detecting endogenous hypochlorite in living RAW 264.7 cells and nude mouse, Chem. Commun., 51, 1442−1445, 10.1039/C4CC07411D Liang, 2016, A highly selective and sensitive photoinduced electron transfer (PET) based HOCl fluorescent probe in water and its endogenous imaging in living cells, Chem. Commun., 52, 7982−7985, 10.1039/C6CC02603F Tian, 2016, A HClO-specific near-infrared fluorescent probe for determination of myeloperoxidase activity and imaging mitochondrial HClO in living cells, Biosens. Bioelectron., 86, 68−74, 10.1016/j.bios.2016.06.039 Zhang, 2017, Lysosomal-targeted two-photon fluorescent probe to sense hypochlorous acid in live cells, Anal. Chem., 89, 10.1021/acs.analchem.7b02361 Wu, 2017, Photostable ratiometric pdot probe for in vitro and in vivo imaging of hypochlorous acid, J. Am. Chem. Soc., 139, 6911−6918, 10.1021/jacs.7b01545 Deng, 2018, Development of an enhanced turn-on fluorescent HOCl probe with a large stokes shift and its use for imaging HOCl in cells and zebrafish, Sensors Actuators B Chem., 255, 963−969, 10.1016/j.snb.2017.08.146 Zhu, 2014, An “enhanced PET”-based fluorescent probe with ultrasensitivity for imaging basal and elesclomol-induced HClO in cancer cells, J. Am. Chem. Soc., 136, 10.1021/ja505988g Fan, 2015, Recognition of HClO in live cells with separate signals using a ratiometric fluorescent sensor with fast response, Ind. Eng. Chem. Res., 54, 8842−8846, 10.1021/acs.iecr.5b01904 Yuan, 2015, Development of targetable two-photon fluorescent probes to image hypochlorous acid in mitochondria and lysosome in live cell and inflamed mouse model, J. Am. Chem. Soc., 137, 5930−5938, 10.1021/jacs.5b00042 Zhu, 2018, A highly specific and ultrasensitive near-infrared fluorescent probe for imaging basal hypochlorite in the mitochondria of living cells, Biosens. Bioelectron., 107, 218−223, 10.1016/j.bios.2018.02.023 Mao, 2018, Design of a ratiometric two-photon probe for imaging of hypochlorous acid (HClO) in wounded tissues, Chem. Sci., 9, 6035−6040, 10.1039/C8SC01697F Jiao, 2018, Small-molecule fluorescent probes for imaging and detection of reactive oxygen, nitrogen, and sulfur species in biological systems, Anal. Chem., 90, 533−555, 10.1021/acs.analchem.7b04234 Lopez, 2005, Process development of an inherently safer oxidation: synthesis of 2-chloro-6-methylbenzoic acid in the R411 manufacturing process, Org. Process. Res. Dev., 9, 1003−1008, 10.1021/op050083+ Xing, 2018, Water solubility is essential for fluorescent probes to image hypochlorous acid in live cells, Chem. Commun., 54, 9889−9892, 10.1039/C8CC04631J Loudet, 2007, BODIPY dyes and their derivatives: syntheses and spectroscopic properties, Chem. Rev., 107, 4891−4932, 10.1021/cr078381n Niu, 2012, BODIPY-based ratiometric fluorescent sensor for highly selective detection of glutathione over cysteine and homocysteine, J. Am. Chem. Soc., 134, 10.1021/ja309079f Kowada, 2015, BODIPY-based probes for the fluorescence imaging of biomolecules in living cells, Chem. Soc. Rev., 44, 4953−4972, 10.1039/C5CS00030K Jia, 2015, BODIPY-based fluorometric sensor for the simultaneous determination of Cys, Hcy, and GSH in human serum, ACS Appl. Mater. Interfaces, 7, 5907−5914, 10.1021/acsami.5b00122 Kolemen, 2018, Reaction-based BODIPY probes for selective bio-imaging, Coordin. Chem. Rev., 354, 121−134, 10.1016/j.ccr.2017.06.021 Turksoy, 2019, Photosensitization and controlled photosensitization with BODIPY dyes, Coordin. Chem. Rev., 379, 47−64, 10.1016/j.ccr.2017.09.029 X. Jiang, J. Zhang, X. Shao, W. Zhao, A selective fluorescent turn-on NIR probe for cysteine, Org. Biomol. Chem. 10 (2012) 1966–1968. Shao, 2015, Highly selective and sensitive 1-amino BODIPY-based red fluorescent probe for thiophenols with high off-to-on contrast ratio, Anal. Chem., 87, 399−405, 10.1021/ac5028947 Zhang, 2015, Dual emission channels for sensitive discrimination of Cys/Hcy and GSH in plasma and cells, Chem. Commun., 51, 4245−4248 Zhang, 2016, A mitochondria-targeted turn-on fluorescent probe for the detection of glutathione in living cells, Biosens. Bioelectron., 85, 164−170 Zhang, 2018, Pyridinium substituted BODIPY as NIR fluorescent probe for simultaneous sensing of hydrogen sulphide/glutathione and cysteine/homocysteine, Sensors Actuators B Chem., 257, 1076−1082, 10.1016/j.snb.2017.10.133 Zhang, 2018, Meso-heteroaryl BODIPY dyes as dual-responsive fluorescent probes for discrimination of Cys from Hcy and GSH, Sensors Actuators B Chem., 260, 861−869, 10.1016/j.snb.2018.01.016 Bodio, 2019, Investigation of B-F substitution on BODIPY and aza-BODIPY dyes: development of B-O and B-C BODIPYs, Dyes Pigments, 160, 700−710, 10.1016/j.dyepig.2018.08.062 Hudnall, 2008, A BODIPY boronium cation for the sensing of fluoride ions, Chem. Commun., 4596, 10.1039/b808740g Zhang, 2014, A ratiometric fluorescent probe for sensing HOCl based on a coumarin-rhodamine dyad, Chem. Commun., 50 Cao, 2018, A chemiluminescent probe for cellular peroxynitrite using a self-immolative oxidative decarbonylation reaction, Chem. Sci., 9, 2552−2558, 10.1039/C7SC05087A Zeng, 2018, Visualizing the regulation of hydroxyl radical level by superoxide dismutase via a specific molecular probe, Anal. Chem., 90, 1317−1324, 10.1021/acs.analchem.7b04191 Li, 2004, 4,5-Dimethylthio-4′-[2-(9-anthryloxy)ethylthio]tetrathiafulvalene, a highly selective and sensitive chemiluminescence probe for singlet oxygen, J. Am. Chem. Soc., 126, 10.1021/ja0481530 Zhang, 2013, A BODIPY-based fluorescent dye for mitochondria in living cells, with low cytotoxicity and high photostability, Org. Biomol. Chem., 11, 555−558 Sun, 2008, A highly specific BODIPY-based fluorescent probe for the detection of hypochlorous acid, Org. Lett., 10, 2171−2174, 10.1021/ol800507m Kim, 2014, A water-soluble sulfonate-BODIPY based fluorescent probe for selective detection of HOCl/OClˉ in aqueous media, Analyst, 139, 2986−2989, 10.1039/C4AN00466C Wang, 2013, A reversible fluorescence probe based on Se-BODIPY for the redox cycle between HClO oxidative stress and H2S repair in living cells, Chem. Commun., 49, 1014−1016 Mulay, 2016, Enhanced fluorescence turn-on imaging of hypochlorous acid in living immune and cancer cells, Chem. Eur. J., 22, 9642−9648, 10.1002/chem.201601270 Qiao, 2017, An ultrafast responsive BODIPY-based fluorescent probe for the detection of endogenous hypochlorite in live cells, J. Mater. Chem. B, 5, 525−530, 10.1039/C6TB02774A Shen, 2017, Near-infrared BODIPY-based two-photon ClOˉ probe based on thiosemicarbazide desulfurization reaction: naked-eye detection and mitochondrial imaging, J. Mater. Chem. B, 5, 5854−5861, 10.1039/C7TB01344B Li, 2017, A mitochondria-targeting fluorescence turn-on probe for hypochlorite and its applications for in vivo imaging, Sensors Actuators B Chem., 252, 127−133, 10.1016/j.snb.2017.05.138 Palma, 2009, New on-bead near-infrared fluorophores and fluorescent sensor constructs, Org. Lett., 11, 3638−3641, 10.1021/ol901413u Jiang, 2012, Development of mono- and di-AcO substituted BODIPYs on the boron center, Org. Lett., 14, 248−251, 10.1021/ol2030229 Tahtaoui, 2007, Convenient method to access new 4,4-dialkoxyand 4,4-diaryloxy-diaza-s-indacene dyes: synthesis and spectroscopic evaluation, J. Org. Chem., 72, 269−272, 10.1021/jo061567m