{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,8]],"date-time":"2026-07-08T05:30:06Z","timestamp":1783488606734,"version":"3.55.0"},"reference-count":48,"publisher":"MDPI AG","issue":"15","license":[{"start":{"date-parts":[[2022,7,29]],"date-time":"2022-07-29T00:00:00Z","timestamp":1659052800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Natural Science Foundation of China","award":["22064009"],"award-info":[{"award-number":["22064009"]}]},{"name":"National Natural Science Foundation of China","award":["22164009"],"award-info":[{"award-number":["22164009"]}]},{"name":"National Natural Science Foundation of China","award":["ZDYF2021SHFZ245"],"award-info":[{"award-number":["ZDYF2021SHFZ245"]}]},{"name":"National Natural Science Foundation of China","award":["322QN309"],"award-info":[{"award-number":["322QN309"]}]},{"name":"National Natural Science Foundation of China","award":["820RC641"],"award-info":[{"award-number":["820RC641"]}]},{"name":"National Natural Science Foundation of China","award":["820RC655"],"award-info":[{"award-number":["820RC655"]}]},{"name":"National Natural Science Foundation of China","award":["HYPY2020017"],"award-info":[{"award-number":["HYPY2020017"]}]},{"name":"Hainan Province Science and Technology Special Fund","award":["22064009"],"award-info":[{"award-number":["22064009"]}]},{"name":"Hainan Province Science and Technology Special Fund","award":["22164009"],"award-info":[{"award-number":["22164009"]}]},{"name":"Hainan Province Science and Technology Special Fund","award":["ZDYF2021SHFZ245"],"award-info":[{"award-number":["ZDYF2021SHFZ245"]}]},{"name":"Hainan Province Science and Technology Special Fund","award":["322QN309"],"award-info":[{"award-number":["322QN309"]}]},{"name":"Hainan Province Science and Technology Special Fund","award":["820RC641"],"award-info":[{"award-number":["820RC641"]}]},{"name":"Hainan Province Science and Technology Special Fund","award":["820RC655"],"award-info":[{"award-number":["820RC655"]}]},{"name":"Hainan Province Science and Technology Special Fund","award":["HYPY2020017"],"award-info":[{"award-number":["HYPY2020017"]}]},{"name":"Hainan Provincial Natural Science Foundation of China","award":["22064009"],"award-info":[{"award-number":["22064009"]}]},{"name":"Hainan Provincial Natural Science Foundation of China","award":["22164009"],"award-info":[{"award-number":["22164009"]}]},{"name":"Hainan Provincial Natural Science Foundation of China","award":["ZDYF2021SHFZ245"],"award-info":[{"award-number":["ZDYF2021SHFZ245"]}]},{"name":"Hainan Provincial Natural Science Foundation of China","award":["322QN309"],"award-info":[{"award-number":["322QN309"]}]},{"name":"Hainan Provincial Natural Science Foundation of China","award":["820RC641"],"award-info":[{"award-number":["820RC641"]}]},{"name":"Hainan Provincial Natural Science Foundation of China","award":["820RC655"],"award-info":[{"award-number":["820RC655"]}]},{"name":"Hainan Provincial Natural Science Foundation of China","award":["HYPY2020017"],"award-info":[{"award-number":["HYPY2020017"]}]},{"name":"Talent Program of Hainan Medical University","award":["22064009"],"award-info":[{"award-number":["22064009"]}]},{"name":"Talent Program of Hainan Medical University","award":["22164009"],"award-info":[{"award-number":["22164009"]}]},{"name":"Talent Program of Hainan Medical University","award":["ZDYF2021SHFZ245"],"award-info":[{"award-number":["ZDYF2021SHFZ245"]}]},{"name":"Talent Program of Hainan Medical University","award":["322QN309"],"award-info":[{"award-number":["322QN309"]}]},{"name":"Talent Program of Hainan Medical University","award":["820RC641"],"award-info":[{"award-number":["820RC641"]}]},{"name":"Talent Program of Hainan Medical University","award":["820RC655"],"award-info":[{"award-number":["820RC655"]}]},{"name":"Talent Program of Hainan Medical University","award":["HYPY2020017"],"award-info":[{"award-number":["HYPY2020017"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Peroxynitrite (ONOO\u2212), as an important reactive oxygen species (ROS), holds great potential to react with a variety of biologically active substances, leading to the occurrence of various diseases such as cancer and neurodegenerative diseases. In this work, we developed a novel mitochondria-localized fluorescent probe, HDBT-ONOO\u2212, which was designed as a mitochondria-targeting two-photon fluorescence probe based on 1,8-naphthylimide fluorophore and the reactive group of 4-(bromomethyl)-benzene boronic acid pinacol ester. More importantly, the probe exhibited good biocompatibility, sensitivity, and selectivity, enabling its successful application in imaging the generation of intracellular and extracellular ONOO\u2212. Furthermore, exogenous and endogenous ONOO\u2212 products in live zebrafish were visualized. It is greatly expected that the designed probe can serve as a useful imaging tool for clarifying the distribution and pathophysiological functions of ONOO\u2212 in cells and zebrafish.<\/jats:p>","DOI":"10.3390\/molecules27154858","type":"journal-article","created":{"date-parts":[[2022,8,1]],"date-time":"2022-08-01T04:04:00Z","timestamp":1659326640000},"page":"4858","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["A Two-Photon Fluorescent Probe for the Visual Detection of Peroxynitrite in Living Cells and Zebrafish"],"prefix":"10.3390","volume":"27","author":[{"given":"Zhencai","family":"Xu","sequence":"first","affiliation":[{"name":"Guanyun People\u2019s Hospital, Lianyungang 222000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jin","family":"Qian","sequence":"additional","affiliation":[{"name":"Modern Education Technology Center, Department of Critical Care Medicine, The First Affiliated Hospital of Hainan Medical University, Hainan Medical University, Haikou 571199, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yufeng","family":"Ge","sequence":"additional","affiliation":[{"name":"Department of Emergent Trauma Surgery, Qilu Hospital of Shandong University, Jinan 250012, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yalan","family":"Wang","sequence":"additional","affiliation":[{"name":"Guanyun People\u2019s Hospital, Lianyungang 222000, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hongwei","family":"Chen","sequence":"additional","affiliation":[{"name":"Modern Education Technology Center, Department of Critical Care Medicine, The First Affiliated Hospital of Hainan Medical University, Hainan Medical University, Haikou 571199, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,7,29]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"721","DOI":"10.1021\/acs.chemrestox.8b00068","article-title":"Reaction of CO2 with ONOO\u2212: One Molecule of CO2 Is Not Enough","volume":"31","author":"Kissner","year":"2018","journal-title":"Chem. Res. Toxicol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1620","DOI":"10.1073\/pnas.87.4.1620","article-title":"Apparent hydroxyl radical production by peroxynitrite: Implications for endothelial injury from nitric oxide and superoxide","volume":"87","author":"Beckman","year":"1990","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1016\/0003-9861(92)90431-U","article-title":"Peroxynitrite-mediated tyrosine nitration catalyzed by superoxide dismutase","volume":"298","author":"Ischiropoulos","year":"1992","journal-title":"Arch. Biochem. Biophys."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1021\/cb800279q","article-title":"Chemical biology of peroxynitrite: Kinetics, diffusion, and radicals","volume":"4","author":"Radi","year":"2009","journal-title":"ACS Chem. Biol."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"834","DOI":"10.1021\/tx00030a017","article-title":"Peroxynitrite, a cloaked oxidant formed by nitric oxide and superoxide","volume":"5","author":"Koppenol","year":"1992","journal-title":"Chem. Res. Toxicol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"349","DOI":"10.1038\/nri3423","article-title":"Beyond oxidative stress: An immunologist\u2019s guide to reactive oxygen species","volume":"13","author":"Nathan","year":"2013","journal-title":"Nat. Rev. Immunol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"26464","DOI":"10.1074\/jbc.R113.472936","article-title":"Peroxynitrite, a stealthy biological oxidant","volume":"288","author":"Radi","year":"2013","journal-title":"J. Biol. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1016\/S0378-4274(02)00507-6","article-title":"Multiple pathways of peroxynitrite cytotoxicity","volume":"140\u2013141","author":"Szabo","year":"2003","journal-title":"Toxicol. Lett."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1007\/s00726-003-0018-8","article-title":"Peroxynitrite reactivity with amino acids and proteins","volume":"25","author":"Alvarez","year":"2003","journal-title":"Amino Acids"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1338","DOI":"10.1021\/acs.chemrev.7b00568","article-title":"Biochemistry of Peroxynitrite and Protein Tyrosine Nitration","volume":"118","author":"Campolo","year":"2018","journal-title":"Chem. Rev."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"662","DOI":"10.1038\/nrd2222","article-title":"Peroxynitrite: Biochemistry, pathophysiology and development of therapeutics","volume":"6","author":"Szabo","year":"2007","journal-title":"Nat. Rev. Drug Discov."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"315","DOI":"10.1152\/physrev.00029.2006","article-title":"Nitric oxide and peroxynitrite in health and disease","volume":"87","author":"Pacher","year":"2007","journal-title":"Physiol. Rev."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1016\/S0165-0173(99)00014-4","article-title":"Neurodegenerative disorders: The role of peroxynitrite","volume":"30","author":"Torreilles","year":"1999","journal-title":"Brain Res. Rev."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"713","DOI":"10.1111\/j.1476-5381.2008.00086.x","article-title":"Role of nitrosative stress in the pathogenesis of diabetic vascular dysfunction","volume":"156","author":"Szabo","year":"2009","journal-title":"Br. J. Pharmacol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"910","DOI":"10.1021\/cb900159n","article-title":"Manganese corroles prevent intracellular nitration and subsequent death of insulin-producing cells","volume":"4","author":"Okun","year":"2009","journal-title":"ACS Chem. Biol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1080\/10715760410001659773","article-title":"Detection of superoxide and peroxynitrite in model systems and mitochondria by the luminol analogue L-012","volume":"38","author":"Daiber","year":"2004","journal-title":"Free Radic Res."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1006\/bbrc.1998.8936","article-title":"Detection of superoxide radicals and peroxynitrite by 1-hydroxy-4-phosphonooxy-2,2,6,6-tetramethylpiperidine: Quantification of extracellular superoxide radicals formation","volume":"248","author":"Dikalov","year":"1998","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"5313","DOI":"10.1021\/ac000701e","article-title":"Amperometric ultramicrosensors for peroxynitrite detection and its application toward single myocardial cells","volume":"72","author":"Xue","year":"2000","journal-title":"Anal. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"608","DOI":"10.1038\/nchembio.2105","article-title":"Fluorescence probes to detect lipid-derived radicals","volume":"12","author":"Yamada","year":"2016","journal-title":"Nat. Chem. Biol."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"10409","DOI":"10.1021\/jacs.9b04412","article-title":"Fluorescence Detection of Prostate Cancer by an Activatable Fluorescence Probe for PSMA Carboxypeptidase Activity","volume":"141","author":"Kawatani","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"e202113191","DOI":"10.1002\/anie.202113191","article-title":"Rational Design of a Two-Photon Fluorescent Probe for Human Cytochrome P450 3A and the Visualization of Mechanism-Based Inactivation","volume":"61","author":"Ning","year":"2022","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1288","DOI":"10.1080\/10715762.2018.1446530","article-title":"A 1,8-naphthalimide-based turn-on fluorescent probe for imaging mitochondrial hydrogen peroxide in living cells","volume":"52","author":"Dai","year":"2018","journal-title":"Free Radic Res."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"98","DOI":"10.1016\/j.biomaterials.2018.02.044","article-title":"A ratiometric fluorescence probe for lysosomal polarity","volume":"164","author":"Li","year":"2018","journal-title":"Biomaterials"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"9347","DOI":"10.1021\/acs.analchem.8b01960","article-title":"A Two-Photon Fluorescent Probe for Imaging Endogenous ONOO\u2212 near NMDA Receptors in Neuronal Cells and Hippocampal Tissues","volume":"90","author":"Lee","year":"2018","journal-title":"Anal. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1016\/j.biomaterials.2016.08.032","article-title":"A new class of fast-response and highly selective fluorescent probes for visualizing peroxynitrite in live cells, subcellular organelles, and kidney tissue of diabetic rats","volume":"107","author":"Miao","year":"2016","journal-title":"Biomaterials"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"849","DOI":"10.1016\/j.bios.2017.01.027","article-title":"In vitro and in vivo imaging of peroxynitrite by a ratiometric boronate-based fluorescent probe","volume":"91","author":"Palanisamy","year":"2017","journal-title":"Biosens. Bioelectron."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1016\/j.talanta.2019.01.065","article-title":"Construction of a novel far-red fluorescence light-up probe for visualizing intracellular peroxynitrite","volume":"197","author":"Qu","year":"2019","journal-title":"Talanta"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"6004","DOI":"10.1021\/ja0603756","article-title":"A highly selective fluorescent probe for the detection and imaging of peroxynitrite in living cells","volume":"128","author":"Yang","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1275","DOI":"10.1002\/bio.3546","article-title":"Dual site-controlled two-photon fluorescent probe for the imaging of lysosomal pH in living cells","volume":"33","author":"Wang","year":"2018","journal-title":"Luminescence"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"7473","DOI":"10.1002\/anie.201800293","article-title":"Enhancing the Anti-Solvatochromic Two-Photon Fluorescence for Cirrhosis Imaging by Forming a Hydrogen-Bond Network","volume":"57","author":"Ren","year":"2018","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1048","DOI":"10.1002\/bio.3507","article-title":"A new xanthene-based two-photon fluorescent probe for the imaging of 1,4-dithiothreitol (DTT) in living cells","volume":"33","author":"Wang","year":"2018","journal-title":"Luminescence"},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Czernel, G., Matwijczuk, A., Karcz, D., Gorecki, A., Niemczynowicz, A., Szczes, A., Gladyszewski, G., Matwijczuk, A., Gladyszewska, B., and Niewiadomy, A. (2018). Spectroscopic Studies of Dual Fluorescence in 2-(4-Fluorophenylamino)-5-(2,4-dihydroxybenzeno)-1,3,4-thiadiazole: Effect of Molecular Aggregation in a Micellar System. Molecules, 23.","DOI":"10.3390\/molecules23112861"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"629","DOI":"10.1146\/annurev.pharmtox.47.120505.105110","article-title":"Targeting antioxidants to mitochondria by conjugation to lipophilic cations","volume":"47","author":"Murphy","year":"2007","journal-title":"Annu. Rev. Pharmacol. Toxicol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1009","DOI":"10.1016\/j.bbagen.2010.06.001","article-title":"Rapid uptake of lipophilic triphenylphosphonium cations by mitochondria in vivo following intravenous injection: Implications for mitochondria-specific therapies and probes","volume":"1800","author":"Porteous","year":"2010","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"6686","DOI":"10.1039\/C5OB00928F","article-title":"Mitochondrially targeted redox probe reveals the variations in oxidative capacity of the haematopoietic cells","volume":"13","author":"Kaur","year":"2015","journal-title":"Org. Biomol. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"909","DOI":"10.1023\/A:1007540005737","article-title":"Potentiation of carbachol-induced Ca2+ release by peroxynitrite in human neuroblastoma SH-SY5Y cells","volume":"25","author":"Saeki","year":"2000","journal-title":"Neurochem. Res."},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Pipicz, M., Kocsis, G.F., Sarvary-Arantes, L., Bencsik, P., Varga, Z.V., Ferdinandy, P., and Csont, T. (2017). Low-Dose Endotoxin Induces Late Preconditioning, Increases Peroxynitrite Formation, and Activates STAT3 in the Rat Heart. Molecules, 22.","DOI":"10.3390\/molecules22030433"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1188","DOI":"10.1016\/j.neuint.2007.12.009","article-title":"Activation of p38 MAPK induced peroxynitrite generation in LPS plus IFN-gamma-stimulated rat primary astrocytes via activation of iNOS and NADPH oxidase","volume":"52","author":"Yoo","year":"2008","journal-title":"Neurochem. Int."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1046\/j.1341-8076.2003.00066.x","article-title":"Involvement of peroxynitrite in LPS-induced apoptosis of trophoblasts","volume":"29","author":"Asagiri","year":"2003","journal-title":"J. Obstet. Gynaecol. Res."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"254","DOI":"10.1159\/000027606","article-title":"Lipopolysaccharide-induced expression of reactive oxygen species and peroxynitrite in the guinea pig vestibular organ","volume":"60","author":"Takumida","year":"1998","journal-title":"ORL J. Otorhinolaryngol. Relat. Spec."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"4596","DOI":"10.1021\/ja711480f","article-title":"An ICT-Based Approach to Ratiometric Fluorescence Imaging of Hydrogen Peroxide Produced in Living Cells","volume":"130","author":"Srikun","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"9301","DOI":"10.1021\/acs.analchem.8b01879","article-title":"A Dual-Modal Molecular Probe for Near-infrared Fluorescence and Photoacoustic Imaging of Peroxynitrite","volume":"90","author":"Zhang","year":"2018","journal-title":"Anal. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"9947","DOI":"10.1039\/C4CC04192E","article-title":"A Highly Selective Water-Soluble Optical Probe for Endogenous Peroxynitrite","volume":"50","author":"Hou","year":"2014","journal-title":"Chem. Comm."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"9353","DOI":"10.1039\/C4CC02943G","article-title":"A Boronate-Based Fluorescent Probe for the Selective Detection of Cellular Peroxynitrite","volume":"50","author":"Kim","year":"2014","journal-title":"Chem. Comm."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"118960","DOI":"10.1016\/j.saa.2020.118960","article-title":"Investigations of drug-induced liver injury by a peroxynitrite activatable two-photon fluorescence probe","volume":"246","author":"Wang","year":"2020","journal-title":"Spectrochim. Acta Part A Mol. Biomol. Spectrosc."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"431","DOI":"10.1016\/j.talanta.2019.06.032","article-title":"A Selective Fluorescent Turn-On Probe for Imaging Peroxynitrite in Living Cells and Drug Damaged Liver Tissues","volume":"9140","author":"Xia","year":"2019","journal-title":"Talanta"},{"key":"ref_47","first-page":"120934","article-title":"A Novel Highly Selective Fluorescent Probe with New Chalcone Fluorophore for Monitoring and Imaging Endogenous Peroxynitrite in Living Cells and Drug-Damaged Liver Tissue","volume":"1","author":"Chen","year":"2020","journal-title":"Talanta"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"129069","DOI":"10.1016\/j.snb.2020.129069","article-title":"An Ict-Based Fluorescent Probe for Ratiometric Monitoring the Fluctuations of Peroxynitrite in Mitochondria","volume":"1","author":"Cui","year":"2021","journal-title":"Sens. Actuators B Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/15\/4858\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:59:06Z","timestamp":1760140746000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/15\/4858"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,7,29]]},"references-count":48,"journal-issue":{"issue":"15","published-online":{"date-parts":[[2022,8]]}},"alternative-id":["molecules27154858"],"URL":"https:\/\/doi.org\/10.3390\/molecules27154858","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,7,29]]}}}