{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,3]],"date-time":"2026-04-03T19:53:13Z","timestamp":1775245993379,"version":"3.50.1"},"reference-count":44,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2018,10,6]],"date-time":"2018-10-06T00:00:00Z","timestamp":1538784000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Ministry of Science and Technology","award":["MOST 106-2113-M-009-023."],"award-info":[{"award-number":["MOST 106-2113-M-009-023."]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Nitroxyl (HNO) plays a critical role in many physiological processes which includes vasorelaxation in heart failure, neuroregulation, and myocardial contractility. Powerful imaging tools are required to obtain information for understanding the mechanisms involved in these in vivo processes. In order to develop a rapid and high sensitive probe for HNO detection in living cells and the zebrafish model organism, 2-((2-(benzothiazole-2yl)benzylidene) amino)benzoic acid (AbTCA) as a ligand, and its corresponding copper(II) complex Cu(II)-AbTCA were synthesized. The reaction results of Cu(II)-AbTCA with Angeli\u2019s salt showed that Cu(II)-AbTCA could detect HNO quantitatively in a range of 40\u2013360 \u00b5M with a detection limit of 9.05 \u00b5M. Furthermore, Cu(II)-AbTCA is more selective towards HNO over other biological species including thiols, reactive nitrogen, and reactive oxygen species. Importantly, Cu(II)-AbTCA was successfully applied to detect HNO in living cells and zebrafish. The collective data reveals that Cu(II)-AbTCA could be used as a potential probe for HNO detection in living systems.<\/jats:p>","DOI":"10.3390\/molecules23102551","type":"journal-article","created":{"date-parts":[[2018,10,8]],"date-time":"2018-10-08T10:44:53Z","timestamp":1538995493000},"page":"2551","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["In Vitro and in Vivo Imaging of Nitroxyl with Copper Fluorescent Probe in Living Cells and Zebrafish"],"prefix":"10.3390","volume":"23","author":[{"given":"Sathyadevi","family":"Palanisamy","sequence":"first","affiliation":[{"name":"Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, Center For Intelligent Drug Systems and Smart Bio-devices (IDS2B), National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yu-Liang","family":"Wang","sequence":"additional","affiliation":[{"name":"Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, Center For Intelligent Drug Systems and Smart Bio-devices (IDS2B), National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yu-Jen","family":"Chen","sequence":"additional","affiliation":[{"name":"Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, Center For Intelligent Drug Systems and Smart Bio-devices (IDS2B), National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chiao-Yun","family":"Chen","sequence":"additional","affiliation":[{"name":"Department of Radiology, Faculty of Medicine, College of Medicine, Kaohsiung Medical University, Kaohsiung 807, Taiwan"},{"name":"Department of Medical Imaging, Kaohsiung Medical University Hospital, Kaohsiung 807, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Fu-Te","family":"Tsai","sequence":"additional","affiliation":[{"name":"Department of Chemistry, National Tsing Hua University, Hsinchu 30043, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Wen-Feng","family":"Liaw","sequence":"additional","affiliation":[{"name":"Department of Chemistry, National Tsing Hua University, Hsinchu 30043, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yun-Ming","family":"Wang","sequence":"additional","affiliation":[{"name":"Department of Biological Science and Technology, Institute of Molecular Medicine and Bioengineering, Center For Intelligent Drug Systems and Smart Bio-devices (IDS2B), National Chiao Tung University, 75 Bo-Ai Street, Hsinchu 300, Taiwan"},{"name":"Department of Biomedical Science and Environmental Biology, Kaohsiung Medical University, Kaohsiung 807, Taiwan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2018,10,6]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1016\/j.ccr.2004.08.010","article-title":"The chemistry of nitroxyl (HNO) and implications in biology","volume":"249","author":"Miranda","year":"2005","journal-title":"Coordin. Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"H2264","DOI":"10.1152\/ajpheart.00531.2003","article-title":"Orthogonal properties of the redox siblings nitroxyl and nitric oxide in the cardiovascular system: A novel redox paradigm","volume":"285","author":"Wink","year":"2003","journal-title":"Am. J. Physiol. Heart Circ. Physiol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"593","DOI":"10.1021\/ja00210a047","article-title":"Oxidation and reduction of hemoproteins by trioxodinitrate(II). The role of nitrosyl hydride and nitrite","volume":"110","author":"Doyle","year":"1988","journal-title":"J. Am. Chem. Soc."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"546","DOI":"10.1016\/S0022-3565(25)10384-4","article-title":"The pharmacological activity of nitroxyl: A potent vasodilator with activity similar to nitric oxide and\/or endothelium-derived relaxing factor","volume":"263","author":"Fukuto","year":"1992","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"315","DOI":"10.1038\/sj.bjp.0703058","article-title":"Differential actions of L-cysteine on responses to nitric oxide, nitroxyl anions and EDRF in the rat aorta","volume":"129","author":"Ellis","year":"2000","journal-title":"Br. J. Pharmacol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"463","DOI":"10.1038\/sj.bjp.0704269","article-title":"Vascular smooth muscle relaxation mediated by nitric oxide donors: A comparison with acetylcholine, nitric oxide and nitroxyl ion","volume":"134","author":"Wanstall","year":"2001","journal-title":"Br. J. Pharmacol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"540","DOI":"10.1111\/j.1476-5381.2009.00150.x","article-title":"A role for nitroxyl (HNO) as an endothelium-derived relaxing and hyperpolarizing factor in resistance arteries","volume":"157","author":"Andrews","year":"2009","journal-title":"Br. J. Pharmacol."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1301","DOI":"10.1161\/01.HYP.0000072010.54901.DE","article-title":"NO-activates soluble guanylate cyclase and Kv channels to vasodilate resistance arteries","volume":"41","author":"Irvine","year":"2003","journal-title":"Hypertension"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"461","DOI":"10.1016\/S0896-6273(00)80859-4","article-title":"Attenuation of NMDA receptor activity and neurotoxicity by nitroxyl anion, NO","volume":"24","author":"Kim","year":"1999","journal-title":"Neuron"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"14617","DOI":"10.1073\/pnas.96.25.14617","article-title":"Opposite effects of nitric oxide and nitroxyl on postischemic myocardial injury","volume":"96","author":"Ma","year":"1999","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1247","DOI":"10.1021\/ac702024t","article-title":"Xerogel optical sensor films for quantitative detection of nitroxyl","volume":"80","author":"Dobmeier","year":"2008","journal-title":"Anal. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"5362","DOI":"10.1021\/bi973153g","article-title":"Reaction between S-nitrosothiols and thiols: Generation of nitroxyl (HNO) and subsequent chemistry","volume":"37","author":"Wong","year":"1998","journal-title":"Biochemistry"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"11675","DOI":"10.1021\/ja203652z","article-title":"Rapid and selective nitroxyl (HNO) trapping by phosphines: Kinetics and new aqueous ligations for HNO detection and quantitation","volume":"133","author":"Reisz","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1274","DOI":"10.1016\/j.freeradbiomed.2011.02.008","article-title":"Detection of nitroxyl (HNO) by membrane inlet mass spectrometry","volume":"50","author":"Cline","year":"2011","journal-title":"Free Radic. Biol. Med."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"676","DOI":"10.1038\/358676a0","article-title":"Nitric oxide release from a single cell measured in situ by a porphyrinic-based microsensor","volume":"358","author":"Malinski","year":"1992","journal-title":"Nature"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1235","DOI":"10.1021\/cr010152s","article-title":"Bioimaging of nitric oxide","volume":"102","author":"Nagano","year":"2002","journal-title":"Chem. Rev."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"223","DOI":"10.1006\/abio.2000.4583","article-title":"A spectrophotometric method for the direct detection and quantitation of nitric oxide, nitrite, and nitrate in cell culture media","volume":"281","author":"Ridnour","year":"2000","journal-title":"Anal. Biochem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"622","DOI":"10.1039\/C2CS35313J","article-title":"Far-red to near infrared analyte-responsive fluorescent probes based on organic fluorophore platforms for fluorescence imaging","volume":"42","author":"Yuan","year":"2013","journal-title":"Chem. Soc. Rev."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1462","DOI":"10.1021\/ar300273v","article-title":"FRET-based small-molecule fluorescent probes: Rational design and bioimaging applications","volume":"46","author":"Yuan","year":"2013","journal-title":"Acc. Chem. Res."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"5754","DOI":"10.1039\/C4CC10382C","article-title":"A two-photon fluorescent turn-on probe for nitroxyl (HNO) and its bioimaging application in living tissues","volume":"51","author":"Zheng","year":"2015","journal-title":"Chem. Commun."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"2719","DOI":"10.1021\/ol900914s","article-title":"Reductive phosphine-mediated ligation of nitroxyl (HNO)","volume":"11","author":"Reisz","year":"2009","journal-title":"Org. Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"10018","DOI":"10.1002\/anie.201303179","article-title":"A unique family of rigid analogues of the GFP chromophore with tunable two-photon action cross-sections for biological imaging","volume":"52","author":"Yuan","year":"2013","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"993","DOI":"10.1002\/poc.1871","article-title":"Detection of nitroxyl (HNO) by a prefluorescent probe","volume":"24","author":"Cline","year":"2011","journal-title":"J. Phys. Org. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"5536","DOI":"10.1021\/ja909148v","article-title":"Direct detection of nitroxyl in aqueous solution using a tripodal copper(II) BODIPY complex","volume":"132","author":"Rosenthal","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"162","DOI":"10.1016\/j.jinorgbio.2012.08.025","article-title":"Physical and structural properties of [Cu(BOT1)Cl]Cl, a fluorescent imaging probe for HNO","volume":"118","author":"Royzen","year":"2013","journal-title":"J. Inorg. Biochem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1290","DOI":"10.1021\/ol103077q","article-title":"Visualization of nitroxyl in living cells by a chelated copper(II) coumarin complex","volume":"13","author":"Zhou","year":"2011","journal-title":"Org. Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3285","DOI":"10.1021\/ic302793w","article-title":"Detection of nitric oxide and nitroxyl with benzoresorufin-based fluorescent sensors","volume":"52","author":"Apfel","year":"2013","journal-title":"Inorg. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"4697","DOI":"10.1021\/ja500315x","article-title":"A fast and selective near-infrared fluorescent sensor for multicolor imaging of biological nitroxyl (HNO)","volume":"136","author":"Wrobel","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"4867124","DOI":"10.1155\/2016\/4867124","article-title":"Nitroxyl (HNO): A reduced form of nitric oxide with distinct chemical, pharmacological, and therapeutic properties","volume":"2016","author":"Shoman","year":"2016","journal-title":"Oxid. Med. Cell. Longev."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"10860","DOI":"10.1073\/pnas.88.23.10860","article-title":"Reversible conversion of nitroxyl anion to nitric oxide by superoxide dismutase","volume":"88","author":"Murphy","year":"1991","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"414","DOI":"10.1016\/j.snb.2012.08.067","article-title":"Nitroxyl induced fluorescence enhancement via reduction of a copper(II) coumarin-ester complex: Its application for bioimaging in vivo","volume":"174","author":"Zhou","year":"2012","journal-title":"Sens. Actuat. B-Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"727","DOI":"10.1016\/j.snb.2015.06.013","article-title":"A highly sensitive and reductant-resistant fluorescent chemodosimeter for the rapid detection of nitroxyl","volume":"220","author":"Liu","year":"2015","journal-title":"Sens. Actuat. B-Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"23946","DOI":"10.1021\/jp505025t","article-title":"Detection of nitroaromatic explosives based on fluorescence quenching of silafluorene- and silole-containing polymers: A time-dependent density functional theory study","volume":"118","author":"Dedeoglu","year":"2014","journal-title":"J. Phys. Chem. C"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"6140","DOI":"10.1039\/c3cc43202e","article-title":"Extremely fast and highly selective detection of nitroaromatic explosive vapours using fluorescent polymer thin films","volume":"49","author":"Demirel","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"5007","DOI":"10.1039\/c2cc31606d","article-title":"Fluoranthene based fluorescent chemosensors for detection of explosive nitroaromatics","volume":"48","author":"Venkatramaiah","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Ye, F., Chai, Q., Liang, X.M., Li, M.Q., Wang, Z.Q., and Fu, Y. (2017). A highly selective and sensitive fluorescent turn-off probe for Cu2+ based on a guanidine derivative. Molecules, 22.","DOI":"10.3390\/molecules22101741"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2333","DOI":"10.1016\/j.ccr.2012.03.009","article-title":"Probing oxidative stress: Small molecule fluorescent sensors of metal ions, reactive oxygen species, and thiols","volume":"256","author":"Hyman","year":"2012","journal-title":"Coord. Chem. Rev."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"4131","DOI":"10.1039\/C5SC00880H","article-title":"Solid-phase synthesis provides a modular, lysine-based platform for fluorescent discrimination of nitroxyl and biological thiols","volume":"6","author":"Loas","year":"2015","journal-title":"Chem. Sci."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2671","DOI":"10.1021\/ac00175a005","article-title":"Fiber-optic sensor for the determination of glucose using micellar enhanced chemiluminescence of the peroxyoxalate reaction","volume":"60","author":"Guilbault","year":"1988","journal-title":"Anal. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"15309","DOI":"10.1021\/ja308194w","article-title":"Stibonium ions for the fluorescence turn-on sensing of F- in drinking water at parts per million concentrations","volume":"134","author":"Ke","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1092","DOI":"10.1139\/cjc-2014-0011","article-title":"Simple quinoline-based \u201cturn-on\u201d fluorescent sensor for imaging copper (II) in living cells","volume":"92","author":"Zhou","year":"2014","journal-title":"Can. J. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"10092","DOI":"10.1021\/ic3018437","article-title":"A dinitrosyliron complex within the homoleptic Fe(NO)4 anion: NO as nitroxyl and nitrosyl ligands within a single structure","volume":"51","author":"Lin","year":"2012","journal-title":"Inorg. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Valeur, B., and Berberan-Santos, M.N. (2001). Molecular Fluorescence: Principles and Applications, Wiley-VCH.","DOI":"10.1002\/3527600248"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2795","DOI":"10.1021\/ja910090v","article-title":"Development and application of a near-infrared fluorescence probe for oxidative stress based on differential reactivity of linked cyanine dyes","volume":"132","author":"Oushiki","year":"2010","journal-title":"J. Am. Chem. Soc."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/10\/2551\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,4,3]],"date-time":"2026-04-03T18:57:31Z","timestamp":1775242651000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/10\/2551"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,10,6]]},"references-count":44,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2018,10]]}},"alternative-id":["molecules23102551"],"URL":"https:\/\/doi.org\/10.3390\/molecules23102551","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,10,6]]}}}