{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,29]],"date-time":"2026-04-29T05:08:17Z","timestamp":1777439297351,"version":"3.51.4"},"reference-count":51,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2019,2,11]],"date-time":"2019-02-11T00:00:00Z","timestamp":1549843200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Fundamental Research Funds for the Central University","award":["2682016CX102"],"award-info":[{"award-number":["2682016CX102"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>As the members of reactive sulfur species, SO2 and biothiols play a significant role in physiological and pathological processes and directly influence numerous diseases. Furthermore, SO2 and biothiols can provide a reductive environment for lysosomes to carry out their optimal functionality. To this end, the development of single fluorescent probes for imaging SO2 and biothiols from different emission channels is highly desirable for understanding their physiological nature. Here, a lysosome-targeted fluorescent probe (BPO-DNSP) with a dual reaction site for SO2 and biothiols was presented. BPO-DNSP can sensitively and selectively respond to SO2 in the green channel with a large Stokes shift over 105 nm, and to biothiols in the near-infrared emission channel with a large Stokes shift over 109 nm. The emission shift for the two channels was as high as 170 nm. Colocalization experiments verified that BPO-DNSP can selectively enrich lysosomes. Notably, BPO-DNSP can not only be used to image intracellular SO2 and biothiols from two different channels, but also to monitor the conversion of biothiols to SO2 without adding exogenous enzymes in living HeLa cells.<\/jats:p>","DOI":"10.3390\/molecules24030618","type":"journal-article","created":{"date-parts":[[2019,2,12]],"date-time":"2019-02-12T03:18:20Z","timestamp":1549941500000},"page":"618","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Lysosome-Targeted Single Fluorescence Probe for Two-Channel Imaging Intracellular SO2 and Biothiols"],"prefix":"10.3390","volume":"24","author":[{"given":"Yue","family":"Wang","sequence":"first","affiliation":[{"name":"School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Li","family":"Liu","sequence":"additional","affiliation":[{"name":"School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xian-Li","family":"Zhou","sequence":"additional","affiliation":[{"name":"School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2047-3441","authenticated-orcid":false,"given":"Ming-Yu","family":"Wu","sequence":"additional","affiliation":[{"name":"School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2019,2,11]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1016\/j.canlet.2003.11.028","article-title":"Critical roles of intracellular thiols and calcium in parthenolide-induced apoptosis in human colorectal cancer cells","volume":"208","author":"Zhang","year":"2004","journal-title":"Cancer Lett."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1496","DOI":"10.1126\/science.1523409","article-title":"Oxidized redox state of glutathione in the endoplasmic reticulum","volume":"257","author":"Hwang","year":"1992","journal-title":"Science"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1251","DOI":"10.1038\/cddis.2014.229","article-title":"Sulfur dioxide inhibits vascular smooth muscle cell proliferation via suppressing the Erk\/MAP kinase pathway mediated by cAMP\/PKA signalling","volume":"5","author":"Liu","year":"2014","journal-title":"Cell Death Dis."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"166","DOI":"10.1016\/j.niox.2008.12.003","article-title":"The role of sulfur dioxide as an endogenous gaseous vasoactive factor in synergy with nitric oxide","volume":"20","author":"Li","year":"2009","journal-title":"Nitric Oxide"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"4904","DOI":"10.1046\/j.1432-1327.2000.01595.x","article-title":"Glutathione, oxidative stress and neurodegeneration","volume":"267","author":"Schulz","year":"2000","journal-title":"Eur. J. Biochem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"902","DOI":"10.1016\/j.jmb.2010.09.027","article-title":"Cysteine function governs its conservation and degeneration and restricts its utilization on protein surfaces","volume":"404","author":"Marino","year":"2010","journal-title":"J. Mol. Biol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1279","DOI":"10.1016\/S0891-5849(01)00710-9","article-title":"Hypothesis: The role of reactive sulfur species in oxidative stress","volume":"31","author":"Giles","year":"2001","journal-title":"Free Radical Biol. Med."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"457","DOI":"10.1038\/nchembio.1834","article-title":"Biogenesis of reactive sulfur species for signaling by hydrogen sulfide oxidation pathways","volume":"11","author":"Ishanina","year":"2015","journal-title":"Nat. Chem. Biol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"5071","DOI":"10.1021\/cr300358b","article-title":"Disulfide-cleavage-triggered chemosensors and their biological applications","volume":"113","author":"Lee","year":"2013","journal-title":"Chem. Rev."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"5972","DOI":"10.1021\/ac010541m","article-title":"Lead phthalocyanine as a selective carrier for preparation of a cysteine-selective electrode","volume":"73","author":"Shahrokhian","year":"2001","journal-title":"Anal. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"476","DOI":"10.1056\/NEJMoa011613","article-title":"Plasma homocysteine as a risk factor for dementia and Alzheimer\u2019s disease","volume":"346","author":"Seshadri","year":"2002","journal-title":"Engl. J. Med."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1016\/S0753-3322(03)00043-X","article-title":"The importance of glutathione in human disease","volume":"57","author":"Townsend","year":"2003","journal-title":"Biomed. Pharmacother."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1007\/s00726-009-0264-5","article-title":"Amino acids and gaseous signalling","volume":"37","author":"Li","year":"2009","journal-title":"Amino Acids"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"366","DOI":"10.1016\/0076-6879(87)43065-6","article-title":"Mammalian sulfur amino acid metabolism: An overview","volume":"143","author":"Griffith","year":"1987","journal-title":"Methods Enzymol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"226","DOI":"10.1093\/toxsci\/kfq010","article-title":"SO2 inhalation contributes to the development and progression of ischemic stroke in the brain","volume":"114","author":"Sang","year":"2010","journal-title":"Toxicol. Sci."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"4596","DOI":"10.1039\/C4CS00298A","article-title":"Chemical probes for molecular imaging and detection of hydrogen sulfide and reactive sulfur species in biological systems","volume":"44","author":"Lin","year":"2015","journal-title":"Chem. Soc. Rev."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1410","DOI":"10.1021\/acs.accounts.7b00087","article-title":"A unique \u201cintegration\u201d strategy for the rational design of optically tunable near-infrared fluorophores","volume":"50","author":"Chen","year":"2017","journal-title":"Acc. Chem. Res."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2076","DOI":"10.1039\/C6CS00719H","article-title":"Fluorescent bioimaging of pH: From design to applications","volume":"46","author":"Hou","year":"2017","journal-title":"Chem. Soc. Rev."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"533","DOI":"10.1021\/acs.analchem.7b04234","article-title":"Small-molecule fluorescent probes for imaging and detection of reactive oxygen, nitrogen, and sulfur species in biological systems","volume":"90","author":"Jiao","year":"2018","journal-title":"Anal. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"7768","DOI":"10.1021\/acs.chemrev.6b00001","article-title":"Recent development of chemosensors based on cyanine platforms","volume":"116","author":"Sun","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"13188","DOI":"10.1002\/anie.201704084","article-title":"Fluorescent probes with multiple binding sites for the discrimination of Cys, Hcy, and GSH","volume":"56","author":"Yin","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"6019","DOI":"10.1039\/c3cs60024f","article-title":"Recent progress in luminescent and colorimetric chemosensors for detection of thiols","volume":"42","author":"Jung","year":"2013","journal-title":"Chem. Soc. Rev."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"12234","DOI":"10.1039\/C4CC03312D","article-title":"Fluorescent probes for hydrogen sulfide detection and bioimaging","volume":"50","author":"Yu","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"3181","DOI":"10.1021\/jacs.6b12845","article-title":"Dual-site fluorescent probe for visualizing the metabolism of Cys in living cells","volume":"139","author":"Yue","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"992","DOI":"10.1016\/j.cclet.2017.11.011","article-title":"Dual-site fluorescent probe for highly selective and sensitive detection of sulfite and biothiols","volume":"29","author":"Li","year":"2018","journal-title":"Chine. Chem. Lett."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"21047","DOI":"10.1039\/C8RA01683F","article-title":"Novel dual-site fluorescent probe for monitoring cysteine and sulfite in living cells","volume":"8","author":"Guo","year":"2018","journal-title":"RSC Adv."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"647","DOI":"10.1016\/j.snb.2018.09.064","article-title":"Fluorescent probe detect distinguishly sulfite\/hydrogen sulfide and thiol via two emission channels in vivo","volume":"277","author":"Xie","year":"2018","journal-title":"Sens. Actuators B"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"4232","DOI":"10.1039\/C8TB01152D","article-title":"Dual-site lysosome-targeted fluorescent probe for separate detection of endogenous biothiols and SO2 in living cells","volume":"6","author":"Wu","year":"2018","journal-title":"J. Mater. Chem. B"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"11766","DOI":"10.1039\/c2cc36785h","article-title":"Imaging of lysosomal pH changes with a fluorescent sensor containing a novel lysosome-locating group","volume":"48","author":"Zhu","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2253","DOI":"10.1007\/s00467-013-2652-z","article-title":"Lysosome dysfunction in the pathogenesis of kidney diseases","volume":"29","author":"Surendran","year":"2014","journal-title":"Pediatr. Nephrol."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"25907","DOI":"10.1074\/jbc.M003459200","article-title":"Gamma-interferon-inducible lysosomal thiol reductase (GILT) maturation, activity, and mechanism of action","volume":"275","author":"Phan","year":"2000","journal-title":"J. Biol. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"8163","DOI":"10.1039\/C5OB00889A","article-title":"Lysosome targeting fluorescence probe for imaging intracellular thiols","volume":"13","author":"Kand","year":"2015","journal-title":"Org. Biomol. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"6138","DOI":"10.1021\/acs.analchem.8b00434","article-title":"Coumarinocoumarin-based two-photon fluorescent cysteine biosensor for targeting lysosome","volume":"90","author":"Chen","year":"2018","journal-title":"Anal. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"31891","DOI":"10.1074\/jbc.M114.584391","article-title":"Gamma-interferon-inducible lysosomal thiol reductase (GILT) maintains phagosomal proteolysis in alternatively activated macrophages","volume":"289","author":"Balce","year":"2014","journal-title":"J. Biol. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"7018","DOI":"10.1021\/acs.analchem.8b01406","article-title":"In situ lysosomal cysteine-specific targeting and imaging during dexamethasone induced apoptosis","volume":"90","author":"Yue","year":"2018","journal-title":"Anal. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"19562","DOI":"10.1038\/srep19562","article-title":"A two-photon fluorescent probe for lysosomal thiols in live cells and tissues","volume":"6","author":"Fan","year":"2016","journal-title":"Sci. Rep."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"11579","DOI":"10.1039\/C6CC06750F","article-title":"A lysosome-targeted fluorescent sensor for the detection of glutathione in cells with an extremely fast response","volume":"52","author":"Huang","year":"2016","journal-title":"Chem. Commun."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"338","DOI":"10.1016\/j.snb.2017.03.127","article-title":"A novel near-infrared fluorescent probe with a large stokes shift for the detection and imaging of biothiols","volume":"248","author":"Wang","year":"2017","journal-title":"Sens. Actuators B"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1896","DOI":"10.1039\/C5SC03591K","article-title":"Single near-infrared fluorescent probe with high- and low-sensitivity sites for sensing different concentration ranges of biological thiols with distinct modes of fluorescence signals","volume":"7","author":"Chen","year":"2016","journal-title":"Chem. Sci."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"274","DOI":"10.1016\/j.snb.2015.09.106","article-title":"A ratiometric fluorescent probe with DNBS group for biothiols in aqueous solution","volume":"223","author":"Dai","year":"2016","journal-title":"Sens. Actuators B"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"3836","DOI":"10.1039\/C7TB00187H","article-title":"A novel near-infrared fluorescent probe with a large Stokes shift for biothiol detection and application in in vitro and in vivo fluorescence imaging","volume":"5","author":"Liu","year":"2017","journal-title":"J. Mater. Chem. B"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"2637","DOI":"10.1039\/c3cc39161b","article-title":"Fluorescent probe for biological gas SO2 derivatives bisulfite and sulphite","volume":"49","author":"Sun","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"183","DOI":"10.1039\/C3CC46468G","article-title":"A water-soluble near-infrared probe for colorimetric and ratiometric sensing of SO2 derivatives in living cells","volume":"50","author":"Wu","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"25409","DOI":"10.1039\/C4RA15067H","article-title":"A real-time colorimetric and ratiometric fluorescent probe for rapid detection of SO2 derivatives in living cells based on a near-infrared benzopyrylium dye","volume":"5","author":"Chen","year":"2015","journal-title":"RSC Adv."},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Wu, M.-Y., Wu, J., Wang, Y., Liu, Y.-H., and Yu, X.-Q. (2018). A Novel Colorimetric Fluorescent Probe for SO2 and Its Application in Living Cells Imaging. Molecules, 23.","DOI":"10.3390\/molecules23040871"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"7060","DOI":"10.1039\/C8TB02030B","article-title":"Construction of a novel near infrared fluorescent probe with multiple fluorescence emission and its application for SO2 derivative detection in cells and living zebrafish","volume":"6","author":"Liu","year":"2018","journal-title":"J. Mat. Chem. B"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"3790","DOI":"10.1039\/C7AY01113J","article-title":"Construction of a novel ratiometric near-infrared fluorescent probe for SO2 derivatives and its application for biological imaging","volume":"9","author":"Shang","year":"2017","journal-title":"Anal. Methods"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"8292","DOI":"10.1021\/acs.analchem.5b01428","article-title":"Monitoring lipid peroxidation within foam cells by lysosome-targetable and ratiometric probe","volume":"87","author":"Zhang","year":"2015","journal-title":"Anal. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1499","DOI":"10.1021\/ac5045912","article-title":"N-Pyridineium-2-yl Darrow Red analogue: Unique near-infrared lysosome-biomarker for the detection of cancer cells","volume":"87","author":"He","year":"2015","journal-title":"Anal. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"712","DOI":"10.1039\/C7OB02881D","article-title":"A novel lysosome-targeted fluorogenic probe based on 5-triazole-quinoline for the rapid detection of hydrogen sulfide in living cells","volume":"16","author":"Dou","year":"2018","journal-title":"Org. Biomol. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"9566","DOI":"10.1016\/j.biomaterials.2013.08.081","article-title":"Analogs of Changsha near-infrared dyes with large Stokes Shifts for bioimaging","volume":"34","author":"Yuan","year":"2013","journal-title":"Biomaterials"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/3\/618\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T12:31:01Z","timestamp":1760185861000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/3\/618"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,2,11]]},"references-count":51,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2019,2]]}},"alternative-id":["molecules24030618"],"URL":"https:\/\/doi.org\/10.3390\/molecules24030618","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,2,11]]}}}