{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T15:15:06Z","timestamp":1788362106175,"version":"build-2803163510"},"reference-count":46,"publisher":"American Chemical Society (ACS)","issue":"9","license":[{"start":{"date-parts":[[2017,9,27]],"date-time":"2017-09-27T00:00:00Z","timestamp":1506470400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/501100000923","name":"Australian Research Council","doi-asserted-by":"publisher","award":["CE140100 003"],"award-info":[{"award-number":["CE140100 003"]}],"id":[{"id":"10.13039\/501100000923","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000925","name":"National Health and Medical Research Council","doi-asserted-by":"publisher","award":["1111630"],"award-info":[{"award-number":["1111630"]}],"id":[{"id":"10.13039\/501100000925","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2017,9,30]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Biologically compatible fluorescent ion sensors, particularly those that are reversible, represent a key tool for answering a range of fundamental biological questions. We report a rationally designed probe with a 6\u2032-fluoro spiropyran scaffold (5) for the reversible sensing of zinc (Zn2+) in cells. The 6\u2032-fluoro substituent overcomes several limitations normally associated with spiropyran-based sensors to provide an improved signal-to-background ratio and faster photoswitching times in aqueous solution. In vitro studies were performed with 5 and the 6\u2032-nitro analogues (6) in HEK 293 and endothelial cells. The new spiropyran (5) can detect exogenous Zn2+ inside both cell types and without affecting the proliferation of endothelial cells. Studies were also performed on dying HEK 293 cells, with results demonstrating the ability of the key compound to detect endogenous Zn2+ efflux from cells undergoing apoptosis. Biocompatibility and photoswitching of 5 were demonstrated within endothelial cells but not with 6, suggesting the future applicability of sensor 5 to study intracellular Zn2+ efflux in these systems.<\/jats:p>","DOI":"10.1021\/acsomega.7b00923","type":"journal-article","created":{"date-parts":[[2017,9,27]],"date-time":"2017-09-27T10:44:34Z","timestamp":1506509074000},"page":"6201-6210","source":"Crossref","is-referenced-by-count":25,"title":["Rationally Designed Probe for Reversible\nSensing of Zinc and Application in Cells"],"prefix":"10.1021","volume":"2","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2008-2790","authenticated-orcid":true,"given":"Sabrina","family":"Heng","sequence":"first","affiliation":[{"name":"The University of Adelaide , , , , ,","place":["Adelaide, South Australia, Australia, 5000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1549-937X","authenticated-orcid":true,"given":"Philipp","family":"Reineck","sequence":"additional","affiliation":[{"name":"RMIT University , , , ,","place":["Melbourne, Victoria, Australia, 3001"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Achini K.","family":"Vidanapathirana","sequence":"additional","affiliation":[{"name":"The University of Adelaide , , , , ,","place":["Adelaide, South Australia, Australia, 5000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Benjamin J.","family":"Pullen","sequence":"additional","affiliation":[{"name":"The University of Adelaide , , , , ,","place":["Adelaide, South Australia, Australia, 5000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniel W.","family":"Drumm","sequence":"additional","affiliation":[{"name":"RMIT University , , , ,","place":["Melbourne, Victoria, Australia, 3001"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lesley J.","family":"Ritter","sequence":"additional","affiliation":[{"name":"The University of Adelaide , , , , ,","place":["Adelaide, South Australia, Australia, 5000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nisha","family":"Schwarz","sequence":"additional","affiliation":[{"name":"The University of Adelaide , , , , ,","place":["Adelaide, South Australia, Australia, 5000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudine S.","family":"Bonder","sequence":"additional","affiliation":[{"name":"The University of Adelaide , , , , ,","place":["Adelaide, South Australia, Australia, 5000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter J.","family":"Psaltis","sequence":"additional","affiliation":[{"name":"The University of Adelaide , , , , ,","place":["Adelaide, South Australia, Australia, 5000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jeremy G.","family":"Thompson","sequence":"additional","affiliation":[{"name":"The University of Adelaide , , , , ,","place":["Adelaide, South Australia, Australia, 5000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7109-2796","authenticated-orcid":true,"given":"Brant C.","family":"Gibson","sequence":"additional","affiliation":[{"name":"RMIT University , , , ,","place":["Melbourne, Victoria, Australia, 3001"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stephen J.","family":"Nicholls","sequence":"additional","affiliation":[{"name":"The University of Adelaide , , , , ,","place":["Adelaide, South Australia, Australia, 5000"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0604-2629","authenticated-orcid":true,"given":"Andrew D.","family":"Abell","sequence":"additional","affiliation":[{"name":"The University of Adelaide , , , , ,","place":["Adelaide, South Australia, Australia, 5000"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2017,9,27]]},"reference":[{"key":"2026090210362068300_cit1","doi-asserted-by":"publisher","first-page":"4564","DOI":"10.1021\/cr400546e","article-title":"Fluorescent sensors for measuring\nmetal ions in living systems","volume":"114","author":"Carter","year":"2014","journal-title":"Chem. Rev."},{"key":"2026090210362068300_cit2","doi-asserted-by":"publisher","first-page":"244","DOI":"10.1038\/nmeth.3256","article-title":"A general\nmethod to improve fluorophores for live-cell and single-molecule microscopy","volume":"12","author":"Grimm","year":"2015","journal-title":"Nat. Methods"},{"key":"2026090210362068300_cit3","doi-asserted-by":"publisher","first-page":"4010","DOI":"10.1039\/c2cs35015g","article-title":"Molecular switches\nas photocontrollable \u201csmart\u201d receptors","volume":"41","author":"Natali","year":"2012","journal-title":"Chem. Soc. Rev."},{"key":"2026090210362068300_cit4","doi-asserted-by":"publisher","first-page":"12727","DOI":"10.1021\/acsami.6b03565","article-title":"Microstructured Optical Fiber-based\nBiosensors: Reversible and Nanoliter-Scale Measurement of Zinc Ions","volume":"8","author":"Heng","year":"2016","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"2026090210362068300_cit5","doi-asserted-by":"publisher","first-page":"148","DOI":"10.1039\/C3CS60181A","article-title":"Spiropyran-based\ndynamic materials","volume":"43","author":"Klajn","year":"2014","journal-title":"Chem. Soc. Rev."},{"key":"2026090210362068300_cit6","doi-asserted-by":"publisher","first-page":"8308","DOI":"10.1039\/c3ra40321a","article-title":"Nanoliter-scale,\nregenerable ion sensor: sensing with a surface functionalized microstructured\noptical fibre","volume":"3","author":"Heng","year":"2013","journal-title":"RSC Adv."},{"key":"2026090210362068300_cit7","doi-asserted-by":"publisher","first-page":"3268","DOI":"10.1021\/ac500619z","article-title":"Dual sensor for\nCd(II) and Ca(II): selective nanoliter-scale sensing of metal ions","volume":"86","author":"Heng","year":"2014","journal-title":"Anal. Chem."},{"key":"2026090210362068300_cit8","doi-asserted-by":"publisher","first-page":"1238","DOI":"10.1002\/cmdc.201400014","article-title":"SpiroZin1: a reversible\nand pH-Insensitive, reaction-based, red-fluorescent probe for imaging\nbiological mobile zinc","volume":"9","author":"Rivera-Fuentes","year":"2014","journal-title":"ChemMedChem"},{"key":"2026090210362068300_cit9","doi-asserted-by":"publisher","first-page":"7612","DOI":"10.1016\/j.tet.2010.07.035","article-title":"A photoswitchable Zn (II) selective\nspiropyran-based sensor","volume":"66","author":"Natali","year":"2010","journal-title":"Tetrahedron"},{"key":"2026090210362068300_cit10","doi-asserted-by":"publisher","first-page":"3376","DOI":"10.1021\/bm401040v","article-title":"Microstructured\noptical fibers and live cells: a water-soluble, photochromic zinc\nsensor","volume":"14","author":"Heng","year":"2013","journal-title":"Biomacromolecules"},{"key":"2026090210362068300_cit11","doi-asserted-by":"publisher","first-page":"4944","DOI":"10.1002\/anie.200600112","article-title":"A spiropyran-based ensemble for visual recognition and quantification\nof cysteine and homocysteine at physiological levels","volume":"45","author":"Shao","year":"2006","journal-title":"Angew. 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Protoc."},{"key":"2026090210362068300_cit29","doi-asserted-by":"publisher","first-page":"32","DOI":"10.1021\/acssensors.5b00022","article-title":"Reaction-Based Probes for Imaging Mobile Zinc in Live\nCells and Tissues","volume":"1","author":"Zastrow","year":"2016","journal-title":"ACS Sens."},{"key":"2026090210362068300_cit30","doi-asserted-by":"publisher","first-page":"202","DOI":"10.1039\/C4MT00230J","article-title":"Analyzing\nfree zinc(II) ion concentrations in cell biology with fluorescent\nchelating molecules","volume":"7","author":"Maret","year":"2015","journal-title":"Metallomics"},{"key":"2026090210362068300_cit31","doi-asserted-by":"publisher","first-page":"385","DOI":"10.1021\/cb500617c","article-title":"Peptide-based, two-fluorophore, ratiometric\nprobe for quantifying mobile zinc in biological solutions","volume":"10","author":"Zhang","year":"2015","journal-title":"ACS Chem. Biol."},{"key":"2026090210362068300_cit32","doi-asserted-by":"publisher","first-page":"L165","DOI":"10.1152\/ajplung.00459.2005","article-title":"Alterations in zinc homeostasis underlie\nendothelial cell death induced by oxidative stress from acute exposure\nto hydrogen peroxide","volume":"292","author":"Wiseman","year":"2007","journal-title":"Am. J. Physiol.: Lung\nCell. Mol. Physiol."},{"key":"2026090210362068300_cit33","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1007\/s00394-016-1343-5","article-title":"Cardiac changes in apoptosis, inflammation,\noxidative stress, and nitric oxide system induced by prenatal and\npostnatal zinc deficiency in male and female rats","author":"Juriol","year":"2016","journal-title":"Eur. J. Nutr."},{"key":"2026090210362068300_cit34","doi-asserted-by":"publisher","first-page":"634","DOI":"10.1021\/acsbiomaterials.6b00035","article-title":"In Vitro Cytotoxicity, Adhesion,\nand Proliferation of Human Vascular Cells Exposed to Zinc","volume":"2","author":"Shearier","year":"2016","journal-title":"ACS Biomater. Sci. Eng."},{"key":"2026090210362068300_cit35","doi-asserted-by":"publisher","first-page":"C811","DOI":"10.1152\/ajpcell.00643.2008","article-title":"Nitric oxide-mediated protection\nof endothelial cells from hydrogen peroxide is mediated by intracellular\nzinc and glutathione","volume":"296","author":"Cortese-Krott","year":"2009","journal-title":"Am. J. Physiol.: Cell\nPhysiol."},{"key":"2026090210362068300_cit36","doi-asserted-by":"publisher","first-page":"744","DOI":"10.1016\/S0899-9007(99)00148-3","article-title":"Zinc nutrition and apoptosis of vascular endothelial\ncells: implications in atherosclerosis","volume":"15","author":"Hennig","year":"1999","journal-title":"Nutrition"},{"key":"2026090210362068300_cit37","doi-asserted-by":"crossref","first-page":"81","DOI":"10.1093\/ajcn\/71.1.81","article-title":"Zinc protects against apoptosis of\nendothelial cells induced by linoleic acid and tumor\nnecrosis factor alpha","volume":"71","author":"Meerarani","year":"2000","journal-title":"Am. J. Clin. Nutr."},{"key":"2026090210362068300_cit38","doi-asserted-by":"publisher","first-page":"11169","DOI":"10.1103\/PhysRevB.54.11169","article-title":"Efficient\niterative schemes for ab initio total-energy calculations using a\nplane-wave basis set","volume":"54","author":"Kresse","year":"1996","journal-title":"Phys. Rev. B: Condens.\nMatter Mater. Phys."},{"key":"2026090210362068300_cit39","doi-asserted-by":"publisher","first-page":"8308","DOI":"10.1039\/c3ra40321a","article-title":"Nanoliter-scale, regenerable ion\nsensor: sensing with a surface functionalized microstructured optical\nfiber","volume":"3","author":"Heng","year":"2013","journal-title":"RSC Adv."},{"key":"2026090210362068300_cit40","doi-asserted-by":"crossref","first-page":"1459s","DOI":"10.1093\/jn\/130.5.1459S","article-title":"Cellular zinc fluxes\nand the regulation of apoptosis\/gene-directed cell death","volume":"130","author":"Truong-Tran","year":"2000","journal-title":"J. Nutr."},{"key":"2026090210362068300_cit41","doi-asserted-by":"publisher","first-page":"245","DOI":"10.1016\/S0143-4160(02)00053-2","article-title":"Measuring\nzinc in living cells. A new generation of sensitive and selective\nfluorescent probes","volume":"31","author":"Gee","year":"2002","journal-title":"Cell Calcium"},{"key":"2026090210362068300_cit42","doi-asserted-by":"publisher","first-page":"1135","DOI":"10.1083\/jcb.200903097","article-title":"Accuracy\nand precision in quantitative fluorescence microscopy","volume":"185","author":"Waters","year":"2009","journal-title":"J. Cell Biol."},{"key":"2026090210362068300_cit43","first-page":"L1172","article-title":"Visualization\nof labile zinc and its role in apoptosis of primary airway epithelial\ncells and cell lines","volume":"279","author":"Truong-Tran","year":"2000","journal-title":"Am. J. Physiol.: Lung\nCell. Mol. Physiol."},{"key":"2026090210362068300_cit44","doi-asserted-by":"crossref","first-page":"272","DOI":"10.1046\/j.1440-1711.1999.00825.x","article-title":"Regulation of caspase activation and apoptosis by cellular zinc fluxes and zinc deprivation: A review.","volume":"77","author":"Chai","year":"1999","journal-title":"Immunol. Cell Biol."},{"key":"2026090210362068300_cit45","doi-asserted-by":"publisher","first-page":"3354","DOI":"10.1038\/sj.onc.1204436","article-title":"Staurosporine\ninduces apoptosis through both caspase-dependent and caspase-independent\nmechanisms","volume":"20","author":"Belmokhtar","year":"2001","journal-title":"Oncogene"},{"key":"2026090210362068300_cit46","doi-asserted-by":"publisher","first-page":"1459","DOI":"10.1021\/tx100123g","article-title":"Determination of spiropyran\ncytotoxicity by high content screening and analysis for safe application\nin bionanosensing","volume":"23","author":"Movia","year":"2010","journal-title":"Chem. Res. Toxicol."}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.7b00923","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/2\/9\/6201\/67798978\/acsomega.7b00923.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/2\/9\/6201\/67798978\/acsomega.7b00923.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T14:36:28Z","timestamp":1788359788000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/2\/9\/6201\/751154\/Rationally-Designed-Probe-for-Reversible-Sensing"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,9,27]]},"references-count":46,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2017,9,27]]},"published-print":{"date-parts":[[2017,9,30]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.7b00923","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,9,27]]}}}