{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,20]],"date-time":"2026-09-20T12:15:28Z","timestamp":1789906528886,"version":"4.0.1"},"reference-count":37,"publisher":"American Chemical Society (ACS)","issue":"31","license":[{"start":{"date-parts":[[2020,7,27]],"date-time":"2020-07-27T00:00:00Z","timestamp":1595808000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_ccbyncnd_termsofuse.html"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2020,8,11]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Fluorescence sensing of oxalate has garnered some attention in the past two decades as a result of this anion\u2019s prominence and impact on society. Previous work on oxalate sensors and other divalent anion sensors has led to the conclusion that the sensors are selective for the anion under investigation. However, sensor selectivity is often determined by testing against a relatively small array of \u201cguest\u201d molecules or analytes and studies often exclude potentially interfering compounds. For example, studies on oxalate sensors have excluded compounds such as citrate and urate, which are anions in the biological matrices where oxalate is measured (e.g., urine, blood, and bacterial lysate). In the present study, we reassessed the selectivity of a dinuclear copper(II) macrocycle (Cu2L) in an eosin Y displacement assay using biologically relevant anions. Although previously reported as selective for oxalate, we found greater indicator displacement (fluorescence response) for urate and oxaloacetate and a significant response to citrate. These anions are larger than oxalate and do not appear to fit into the putative binding pocket of Cu2L. Consistent with previous reports, Cu2L did not release eosin Y in the presence of several other dicarboxylates, including adipate, glutarate, malate (except at 10 mM), fumarate, succinate, or malonate (except at 10 mM), and the monocarboxylate acetate. This was demonstrated by the failure of the anions to reverse eosin Y quenching by Cu2L. We also assessed, for the first time, other monocarboxylates, including butyrate, pyruvate, lactate, propionate, and formate. None of these anions were able to displace eosin Y, indicating no interaction with Cu2L that interfered with the eosin Y binding site. Single-crystal X-ray crystallography revealed that nonselective binding of the anions is likely partly caused by readily accessible copper(II) ions on the external surface of Cu2L. In addition, \u03c0\u2013\u03c0 stacking of urate with the aromatic groups of Cu2L cannot be ruled out as a contributor to binding. We conclude that Cu2L is not suitable for oxalate sensing in a biological matrix unless interfering compounds are selectively removed or masked.<\/jats:p>","DOI":"10.1021\/acsomega.0c01655","type":"journal-article","created":{"date-parts":[[2020,7,27]],"date-time":"2020-07-27T15:35:35Z","timestamp":1595864135000},"page":"19469-19477","source":"Crossref","is-referenced-by-count":20,"title":["A Copper(II) Macrocycle Complex for Sensing Biologically\nRelevant Organic Anions in a Competitive Fluorescence Assay: Oxalate\nSensor or Urate Sensor?"],"prefix":"10.1021","volume":"5","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3217-8164","authenticated-orcid":true,"given":"David","family":"Hontz","sequence":"first","affiliation":[{"name":"Wilkes University , , 84 W South St. , , ,","place":["Wilkes-Barre, Pennsylvania, United States, 18766"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jayden","family":"Hensley","sequence":"additional","affiliation":[{"name":"Wilkes University , , 84 W South St. , , ,","place":["Wilkes-Barre, Pennsylvania, United States, 18766"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kayla","family":"Hiryak","sequence":"additional","affiliation":[{"name":"Wilkes University , , 84 W South St. , , ,","place":["Wilkes-Barre, Pennsylvania, United States, 18766"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jennifer","family":"Lee","sequence":"additional","affiliation":[{"name":"Wilkes University , , 84 W South St. , , ,","place":["Wilkes-Barre, Pennsylvania, United States, 18766"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jared","family":"Luchetta","sequence":"additional","affiliation":[{"name":"Wilkes University , , 84 W South St. , , ,","place":["Wilkes-Barre, Pennsylvania, United States, 18766"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maria","family":"Torsiello","sequence":"additional","affiliation":[{"name":"Wilkes University , , 84 W South St. , , ,","place":["Wilkes-Barre, Pennsylvania, United States, 18766"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Michael","family":"Venditto","sequence":"additional","affiliation":[{"name":"Wilkes University , , 84 W South St. , , ,","place":["Wilkes-Barre, Pennsylvania, United States, 18766"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Del","family":"Lucent","sequence":"additional","affiliation":[{"name":"Wilkes University , , 84 W South St. , , ,","place":["Wilkes-Barre, Pennsylvania, United States, 18766"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"William","family":"Terzaghi","sequence":"additional","affiliation":[{"name":"Wilkes University , , 84 W South St. , , ,","place":["Wilkes-Barre, Pennsylvania, United States, 18766"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Donald","family":"Mencer","sequence":"additional","affiliation":[{"name":"Wilkes University , , 84 W South St. , , ,","place":["Wilkes-Barre, Pennsylvania, United States, 18766"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ajay","family":"Bommareddy","sequence":"additional","affiliation":[{"name":"Wilkes University , , 84 W South St. , , ,","place":["Wilkes-Barre, Pennsylvania, United States, 18766"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7255-7639","authenticated-orcid":true,"given":"Adam L.","family":"VanWert","sequence":"additional","affiliation":[{"name":"Wilkes University , , 84 W South St. , , ,","place":["Wilkes-Barre, Pennsylvania, United States, 18766"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2020,7,27]]},"reference":[{"key":"2026090206032586900_cit1","doi-asserted-by":"publisher","first-page":"49","DOI":"10.1016\/bs.aambs.2018.10.001","article-title":"Oxalic Acid,\na Molecule\nat the Crossroads of Bacterial-Fungal Interactions","volume":"106","author":"Palmieri","year":"2019","journal-title":"Adv. Appl. Microbiol."},{"key":"2026090206032586900_cit2","doi-asserted-by":"publisher","first-page":"585","DOI":"10.1038\/ki.2008.626","article-title":"Recent Advances\nin the Pathophysiology of Nephrolithiasis","volume":"75","author":"Sakhaee","year":"2009","journal-title":"Kidney\nInt."},{"key":"2026090206032586900_cit3","doi-asserted-by":"publisher","first-page":"445","DOI":"10.1080\/02773818308085175","article-title":"The Formation of Oxalic\nAcid During Bleaching of Kraft\nPulp","volume":"3","author":"Krasowski","year":"2007","journal-title":"J. Wood Chem. Technol."},{"key":"2026090206032586900_cit4","doi-asserted-by":"publisher","first-page":"1467","DOI":"10.1056\/NEJMicm1704369","article-title":"Calcium Oxalate Crystals in Ethylene\nGlycol Toxicity","volume":"377","author":"Hanouneh","year":"2017","journal-title":"N. Engl. J. Med."},{"key":"2026090206032586900_cit5","doi-asserted-by":"publisher","first-page":"254","DOI":"10.1039\/B9AY00247B","article-title":"A Novel Urinary Oxalate\nDetermination Method via a Catalase Model Compound with Oxalate Oxidase","volume":"2","author":"Zuo","year":"2010","journal-title":"Anal. Methods"},{"key":"2026090206032586900_cit6","unstructured":"Oxalic Acid Colorimetric Assay Kit; https:\/\/www.sigmaaldrich.com\/catalog\/product\/sigma\/mak179 (accessed Jun 10, 2020)."},{"key":"2026090206032586900_cit7","doi-asserted-by":"publisher","first-page":"893","DOI":"10.1093\/chromsci\/bms186","article-title":"Analysis of\nGlyoxal and Related Substances\nby Means of High-Performance Liquid Chromatography with Refractive\nIndex Detection","volume":"51","author":"Zhang","year":"2013","journal-title":"J. Chromatogr. Sci."},{"key":"2026090206032586900_cit8","doi-asserted-by":"publisher","first-page":"2296","DOI":"10.1373\/clinchem.2006.075275","article-title":"Quantification of Urinary Oxalate\nby Liquid Chromatography-Tandem\nMass Spectrometry with Online Weak Anion Exchange Chromatography","volume":"52","author":"Keevil","year":"2006","journal-title":"Clin. Chem."},{"key":"2026090206032586900_cit9","doi-asserted-by":"publisher","first-page":"227","DOI":"10.1016\/0009-8981(87)90132-X","article-title":"Development of a Reference\nMethod for Determining Urinary Oxalate by Means of Isotope Dilution\u2500Mass\nSpectrometry (ID-MS) and Its Usefulness in Testing Existing Assays\nfor Urinary Oxalate","volume":"170","author":"Koolstra","year":"1987","journal-title":"Clin. Chim. Acta"},{"key":"2026090206032586900_cit10","unstructured":"Aminex Organic Acid and Alcohol Analysis Columns; https:\/\/www.bio-rad.com\/en-us\/product\/aminex-organic-acid-alcohol-analysis-columns?ID=cdc9d572-65ea-4e55-8e3a-dda17b1aa1ea (accessed Jun 10, 2020)."},{"key":"2026090206032586900_cit11","doi-asserted-by":"publisher","first-page":"193","DOI":"10.1002\/(SICI)1099-0801(199609)10:5&lt;193::AID-BMC591&gt;3.0.CO;2-B","article-title":"Ultraviolet\nand Fluorescence Derivatization Reagents\nfor Carboxylic Acids Suitable for High Performance Liquid Chromatography:\nA Review","volume":"10","author":"Mukherjee","year":"1996","journal-title":"Biomed. Chromatogr."},{"key":"2026090206032586900_cit12","doi-asserted-by":"publisher","first-page":"7105","DOI":"10.1039\/c7cs00240h","article-title":"Fluorescent Chemosensors:\nThe Past Present and Future","volume":"46","author":"Wu","year":"2017","journal-title":"Chem. Soc. Rev."},{"key":"2026090206032586900_cit13","doi-asserted-by":"publisher","first-page":"9397","DOI":"10.1021\/ja00099a094","article-title":"Real-Time Assay of Inorganic Pyrophosphatase Using\na High-Affinity Chelation-Enhanced Fluorescence Chemosensor","volume":"116","author":"Vance","year":"1994","journal-title":"J. Am. Chem. Soc."},{"key":"2026090206032586900_cit14","doi-asserted-by":"publisher","first-page":"4777","DOI":"10.1002\/anie.200453914","article-title":"A Fluorescent Pyrophosphate Sensor\nwith High Selectivity over ATP in Water","volume":"43","author":"Lee","year":"2004","journal-title":"Angew.\nChem."},{"key":"2026090206032586900_cit15","doi-asserted-by":"publisher","first-page":"7769","DOI":"10.1021\/jacs.5b03131","article-title":"Expanded\nPorphyrin-Anion Supramolecular\nAssemblies: Environmentally Responsive Sensors for Organic Solvents\nand Anions","volume":"137","author":"Zhang","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"2026090206032586900_cit16","doi-asserted-by":"publisher","first-page":"6837","DOI":"10.1021\/jacs.5b01881","article-title":"Fluorescent Probe HKSOX-1\nfor Imaging\nand Detection of Endogenous Superoxide in Live Cells and In Vivo","volume":"137","author":"Hu","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"2026090206032586900_cit17","doi-asserted-by":"publisher","first-page":"4618","DOI":"10.1039\/c3dt53467g","article-title":"Colourimetric and\nFluorescent Detection of Oxalate in Water by a New Macrocycle-Based\nDinuclear Nickel Complex: A Remarkable Red Shift of the Fluorescence\nBand","volume":"43","author":"Rhaman","year":"2014","journal-title":"Dalton Trans."},{"key":"2026090206032586900_cit18","doi-asserted-by":"publisher","first-page":"1548","DOI":"10.1056\/NEJMcpc049016","article-title":"Normal\nReference Laboratory Values","volume":"351","author":"Kratz","year":"2004","journal-title":"N. Engl. 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Acta"},{"key":"2026090206032586900_cit22","doi-asserted-by":"publisher","first-page":"12606","DOI":"10.1021\/ja804753n","article-title":"Tight Binding and\nFluorescent Sensing\nof Oxalate in Water","volume":"130","author":"Tang","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"2026090206032586900_cit23","doi-asserted-by":"publisher","first-page":"286","DOI":"10.1038\/s41598-017-18322-w","article-title":"Highly Selective\nand Sensitive Macrocycle-Based Dinuclear Foldamer for Fluorometric\nand Colorimetric Sensing of Citrate in Water","volume":"8","author":"Rhaman","year":"2018","journal-title":"Sci. Rep."},{"key":"2026090206032586900_cit24","doi-asserted-by":"publisher","first-page":"1337","DOI":"10.1007\/s12039-016-1124-y","article-title":"A Fluorescent Sensor Based on Binaphthol-Quinoline\nSchiff Base for Relay Recognition of Zn2+ and Oxalate in\nAqueous Media","volume":"128","author":"Tang","year":"2016","journal-title":"J. Chem. Sci."},{"key":"2026090206032586900_cit25","doi-asserted-by":"publisher","first-page":"6951","DOI":"10.1039\/c2cc33191h","article-title":"Highly Selective and Sensitive Fluorescent Sensing\nof Oxalate in\nWater","volume":"48","author":"Hu","year":"2012","journal-title":"Chem. Commun."},{"key":"2026090206032586900_cit26","doi-asserted-by":"publisher","first-page":"6895","DOI":"10.1016\/S0040-4020(01)96145-9","article-title":"The Synthesis of\nNew Binucleating Polyaza Macrocyclic\nand Macrobicyclic Ligands: Dioxygen Affinities of the Cobalt Complexes","volume":"47","author":"Chen","year":"1991","journal-title":"Tetrahedron"},{"key":"2026090206032586900_cit27","doi-asserted-by":"publisher","first-page":"3811","DOI":"10.1002\/1521-3773(20021018)41:20&lt;3811::AID-ANIE3811&gt;3.0.CO;2-W","article-title":"Pyrophosphate\nDetection in Water by Fluorescence Competition Assays: Inducing Selectivity\nthrough the Choice of the Indicator","volume":"41","author":"Fabbrizzi","year":"2002","journal-title":"Angew.\nChem. Int. Ed"},{"key":"2026090206032586900_cit28","doi-asserted-by":"publisher","first-page":"313","DOI":"10.1007\/s00240-017-0998-6","article-title":"A Randomised\nPhase II\/III Study to\nEvaluate the Efficacy and Safety of Orally Administered Oxalobacter\nFormigenes to Treat Primary Hyperoxaluria","volume":"46","author":"Milliner","year":"2018","journal-title":"Urolithiasis"},{"key":"2026090206032586900_cit29","doi-asserted-by":"publisher","first-page":"334","DOI":"10.3109\/21681805.2014.996251","article-title":"Oxalobacter\nFormigenes: Opening the\nDoor to Probiotic Therapy for the Treatment of Hyperoxaluria","volume":"49","author":"Jairath","year":"2015","journal-title":"Scand. J. Urol."},{"key":"2026090206032586900_cit30","doi-asserted-by":"publisher","first-page":"3983","DOI":"10.1016\/j.ica.2005.06.052","article-title":"Polynuclear\nNickel (II) and Copper (II) Complexes of Hexaazamacrocycles Incorporating\nPairs of Diethylenetriamine Subunits Separated by Aromatic Spacers","volume":"358","author":"Graham","year":"2005","journal-title":"Inorganica Chim. Acta"},{"key":"2026090206032586900_cit31","doi-asserted-by":"publisher","first-page":"10483","DOI":"10.1021\/acs.jpcb.9b08487","article-title":"Inclusion of Theobromine Modifies Uric Acid Aggregation with Possible\nChanges in Melamine\u2013Uric Acid Clusters Responsible for Kidney\nStones","volume":"123","author":"Chattaraj","year":"2019","journal-title":"J. Phys. Chem. B"},{"key":"2026090206032586900_cit32","doi-asserted-by":"publisher","first-page":"1126","DOI":"10.1134\/S1063774519070149","article-title":"Crystal Structure\nof Urate Oxidase from Bacillus Subtilis 168","volume":"64","author":"Nayab","year":"2019","journal-title":"Crystallogr. Rep."},{"key":"2026090206032586900_cit33","doi-asserted-by":"publisher","first-page":"315","DOI":"10.1016\/j.bioorg.2017.03.002","article-title":"Selective\nFluorescence Sensing and Quantification of Uric Acid by Naphthyridine-Based\nReceptor in Biological Sample","volume":"71","author":"Sahoo","year":"2017","journal-title":"Bioorg. Chem."},{"key":"2026090206032586900_cit34","doi-asserted-by":"publisher","first-page":"1271","DOI":"10.1515\/cclm-2014-0944","article-title":"Relevance\nof EDTA Carryover during Blood Collection","volume":"53","author":"Cadamuro","year":"2015","journal-title":"Clin.\nChem. Lab. Med."},{"key":"2026090206032586900_cit35","doi-asserted-by":"publisher","first-page":"301","DOI":"10.1016\/j.jnutbio.2010.06.010","article-title":"The Significance\nof Copper Chelators in Clinical and\nExperimental Application","volume":"22","author":"Ding","year":"2011","journal-title":"J. Nutr. Biochem."},{"key":"2026090206032586900_cit36","doi-asserted-by":"publisher","first-page":"39","DOI":"10.1016\/j.ab.2012.05.027","article-title":"Development of a\nSandwich Format, Amperometric Screen-Printed Uric Acid Biosensor for\nUrine Analysis","volume":"428","author":"Kanyong","year":"2012","journal-title":"Anal. Biochem."},{"key":"2026090206032586900_cit37","doi-asserted-by":"publisher","first-page":"347","DOI":"10.1111\/j.1365-2958.1994.tb01295.x","article-title":"Klebsiella Pneumoniae Genes for Citrate\nLyase and Citrate\nLyase Ligase: Localization, Sequencing, and Expression","volume":"14","author":"Bott","year":"1994","journal-title":"Mol. Microbiol."}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.0c01655","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/5\/31\/19469\/67683939\/acsomega.0c01655.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/5\/31\/19469\/67683939\/acsomega.0c01655.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T10:03:33Z","timestamp":1788343413000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/5\/31\/19469\/1377193\/A-Copper-II-Macrocycle-Complex-for-Sensing"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,7,27]]},"references-count":37,"journal-issue":{"issue":"31","published-online":{"date-parts":[[2020,7,27]]},"published-print":{"date-parts":[[2020,8,11]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.0c01655","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,7,27]]}}}