{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,28]],"date-time":"2026-07-28T08:53:17Z","timestamp":1785228797965,"version":"3.55.0"},"reference-count":45,"publisher":"Public Library of Science (PLoS)","issue":"3","license":[{"start":{"date-parts":[[2019,3,27]],"date-time":"2019-03-27T00:00:00Z","timestamp":1553644800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Institute of General Medical Sciences of the National Institutes of Health","award":["R01GM128508"],"award-info":[{"award-number":["R01GM128508"]}]},{"name":"National Institute of General Medical Sciences of the National Institutes of Health","award":["P20GM103549"],"award-info":[{"award-number":["P20GM103549"]}]},{"name":"National Institute of General Medical Sciences of the National Institutes of Health","award":["P30GM118247"],"award-info":[{"award-number":["P30GM118247"]}]},{"name":"National Institute of General Medical Sciences of the National Institutes of Health","award":["R01GM099959"],"award-info":[{"award-number":["R01GM099959"]}]},{"DOI":"10.13039\/100000066","name":"National Institute of Environmental Health and Sciences","doi-asserted-by":"crossref","award":["T32-ES007079"],"award-info":[{"award-number":["T32-ES007079"]}],"id":[{"id":"10.13039\/100000066","id-type":"DOI","asserted-by":"crossref"}]},{"name":"IDeA Network of Biomedical Research Excellence","award":["QH846868-K-INBRE"],"award-info":[{"award-number":["QH846868-K-INBRE"]}]}],"content-domain":{"domain":["www.plosone.org"],"crossmark-restriction":false},"short-container-title":["PLoS ONE"],"DOI":"10.1371\/journal.pone.0209726","type":"journal-article","created":{"date-parts":[[2019,3,27]],"date-time":"2019-03-27T15:25:33Z","timestamp":1553700333000},"page":"e0209726","update-policy":"https:\/\/doi.org\/10.1371\/journal.pone.corrections_policy","source":"Crossref","is-referenced-by-count":4,"title":["Aqueous synthesis of a small-molecule lanthanide chelator amenable to copper-free click chemistry"],"prefix":"10.1371","volume":"14","author":[{"given":"Stephanie C.","family":"Bishop","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Robert","family":"Winefield","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Asokan","family":"Anbanandam","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0794-2263","authenticated-orcid":true,"given":"Jed N.","family":"Lampe","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"340","published-online":{"date-parts":[[2019,3,27]]},"reference":[{"issue":"Pt 7","key":"ref1","doi-asserted-by":"crossref","first-page":"1111","DOI":"10.1107\/S0907444902006509","article-title":"Thiol-reactive lanthanide chelates for phasing protein X-ray diffraction data","volume":"58","author":"MD Purdy","year":"2002","journal-title":"Acta Crystallogr D Biol Crystallogr"},{"issue":"28","key":"ref2","doi-asserted-by":"crossref","first-page":"3682","DOI":"10.1002\/anie.200460028","article-title":"Structural origin of the high affinity of a chemically evolved lanthanide-binding peptide","volume":"43","author":"M Nitz","year":"2004","journal-title":"Angew Chem Int Ed Engl"},{"issue":"10","key":"ref3","doi-asserted-by":"crossref","first-page":"1599","DOI":"10.1002\/cbic.200600142","article-title":"Site-specific labelling of proteins with a rigid lanthanide-binding tag","volume":"7","author":"XC Su","year":"2006","journal-title":"Chembiochem"},{"issue":"1","key":"ref4","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s10858-008-9256-0","article-title":"Prospects for lanthanides in structural biology by NMR","volume":"42","author":"G. Otting","year":"2008","journal-title":"J Biomol NMR"},{"issue":"2","key":"ref5","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1016\/j.cbpa.2010.01.004","article-title":"Lanthanide-tagged proteins\u2014an illuminating partnership","volume":"14","author":"KN Allen","year":"2010","journal-title":"Curr Opin Chem Biol"},{"issue":"9","key":"ref6","doi-asserted-by":"crossref","first-page":"2847","DOI":"10.1007\/s00216-011-5047-7","article-title":"Lanthanide-based time-resolved luminescence immunoassays","volume":"400","author":"AK Hagan","year":"2011","journal-title":"Anal Bioanal Chem"},{"issue":"22","key":"ref7","doi-asserted-by":"crossref","first-page":"4353","DOI":"10.1016\/j.jmb.2013.07.006","article-title":"The structure of the cytochrome p450cam-putidaredoxin complex determined by paramagnetic NMR spectroscopy and crystallography","volume":"425","author":"Y Hiruma","year":"2013","journal-title":"J Mol Biol"},{"issue":"16","key":"ref8","doi-asserted-by":"crossref","first-page":"6813","DOI":"10.1021\/ac901049w","article-title":"Mass cytometry: technique for real time single cell multitarget immunoassay based on inductively coupled plasma time-of-flight mass spectrometry","volume":"81","author":"DR Bandura","year":"2009","journal-title":"Anal Chem"},{"issue":"4","key":"ref9","first-page":"780","article-title":"Mass Cytometry: Single Cells","volume":"165","author":"MH Spitzer","year":"2016","journal-title":"Many Features. Cell"},{"issue":"25","key":"ref10","doi-asserted-by":"crossref","first-page":"8255","DOI":"10.1021\/ja00441a060","article-title":"Terbium (III) emission as a probe of calcium(II) binding sites in proteins","volume":"98","author":"HG Brittain","year":"1976","journal-title":"J Am Chem Soc"},{"key":"ref11","doi-asserted-by":"crossref","first-page":"495","DOI":"10.1016\/0076-6879(93)26023-3","article-title":"Luminescence spectroscopy","volume":"226","author":"WD Horrocks Jr.","year":"1993","journal-title":"Methods Enzymol"},{"issue":"4","key":"ref12","doi-asserted-by":"crossref","first-page":"529","DOI":"10.1007\/s10895-005-2826-6","article-title":"Progress in lanthanides as luminescent probes","volume":"15","author":"I Hemmila","year":"2005","journal-title":"J Fluoresc"},{"issue":"23","key":"ref13","doi-asserted-by":"crossref","first-page":"2757","DOI":"10.1039\/b514637b","article-title":"Engineering emissive europium and terbium complexes for molecular imaging and sensing","author":"S Pandya","year":"2006","journal-title":"Dalton Trans"},{"key":"ref14","doi-asserted-by":"crossref","DOI":"10.1007\/978-1-4757-3061-6","article-title":"Principles of Fluorescence Spectroscopy","author":"JR Lakowicz","year":"1999"},{"issue":"7088","key":"ref15","doi-asserted-by":"crossref","first-page":"1227","DOI":"10.1038\/nature04673","article-title":"Detecting transient intermediates in macromolecular binding by paramagnetic NMR","volume":"440","author":"J Iwahara","year":"2006","journal-title":"Nature"},{"issue":"9","key":"ref16","doi-asserted-by":"crossref","first-page":"4108","DOI":"10.1021\/cr900033p","article-title":"Theory, practice, and applications of paramagnetic relaxation enhancement for the characterization of transient low-population states of biological macromolecules and their complexes","volume":"109","author":"GM Clore","year":"2009","journal-title":"Chem Rev"},{"issue":"44","key":"ref17","doi-asserted-by":"crossref","first-page":"8259","DOI":"10.1002\/anie.200902561","article-title":"Use of relaxation enhancements in a paramagnetic environment for the structure determination of proteins using NMR spectroscopy","volume":"48","author":"T Madl","year":"2009","journal-title":"Angew Chem Int Ed Engl"},{"issue":"7","key":"ref18","doi-asserted-by":"crossref","first-page":"3834","DOI":"10.1021\/ac5045466","article-title":"Click conjugation of a binuclear terbium(III) complex for real-time detection of tyrosine phosphorylation","volume":"87","author":"H Akiba","year":"2015","journal-title":"Anal Chem"},{"issue":"1","key":"ref19","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1517\/17460441.2011.537322","article-title":"Fluorescence polarization assays in small molecule screening","volume":"6","author":"WA Lea","year":"2011","journal-title":"Expert Opin Drug Discov"},{"issue":"32","key":"ref20","doi-asserted-by":"crossref","first-page":"10486","DOI":"10.1021\/ja803741f","article-title":"A dipicolinic acid tag for rigid lanthanide tagging of proteins and paramagnetic NMR spectroscopy","volume":"130","author":"XC Su","year":"2008","journal-title":"J Am Chem Soc"},{"issue":"41","key":"ref21","doi-asserted-by":"crossref","first-page":"14761","DOI":"10.1021\/ja903233w","article-title":"DOTA-M8: An extremely rigid, high-affinity lanthanide chelating tag for PCS NMR spectroscopy","volume":"131","author":"D Haussinger","year":"2009","journal-title":"J Am Chem Soc"},{"issue":"21","key":"ref22","doi-asserted-by":"crossref","first-page":"10600","DOI":"10.1021\/ic200858c","article-title":"Gd(III) chelates as NMR probes of protein-protein interactions. Case study: rubredoxin and cytochrome c3","volume":"50","author":"RM Almeida","year":"2011","journal-title":"Inorg Chem"},{"issue":"2","key":"ref23","doi-asserted-by":"crossref","first-page":"983","DOI":"10.1007\/s00726-011-1164-z","article-title":"Site-specific DOTA\/europium-labeling of recombinant human relaxin-3 for receptor-ligand interaction studies","volume":"43","author":"WJ Zhang","year":"2012","journal-title":"Amino Acids"},{"issue":"3","key":"ref24","doi-asserted-by":"crossref","first-page":"1013","DOI":"10.1016\/0006-291X(76)91247-X","article-title":"Circularly polarized emission of terbium(III) substituted bovine cardiac troponin-C","volume":"68","author":"HG Brittain","year":"1976","journal-title":"Biochem Biophys Res Commun"},{"key":"ref25","doi-asserted-by":"crossref","first-page":"468","DOI":"10.1016\/j.talanta.2014.11.049","article-title":"Novel approach for labeling of biopolymers with DOTA complexes using in situ click chemistry for quantification","volume":"134","author":"Y He","year":"2015","journal-title":"Talanta"},{"issue":"88","key":"ref26","doi-asserted-by":"crossref","first-page":"15898","DOI":"10.1039\/C5CC07121F","article-title":"Protein conformation by EPR spectroscopy using gadolinium tags clicked to genetically encoded p-azido-L-phenylalanine","volume":"51","author":"EH Abdelkader","year":"2015","journal-title":"Chem Commun (Camb)"},{"issue":"3","key":"ref27","doi-asserted-by":"crossref","first-page":"601","DOI":"10.1039\/C5CC05827A","article-title":"A rigid lanthanide binding tag to aid NMR studies of a 70 kDa homodimeric coat protein of human norovirus","volume":"52","author":"A Mallagaray","year":"2016","journal-title":"Chem Commun (Camb)"},{"issue":"4","key":"ref28","doi-asserted-by":"crossref","first-page":"1674","DOI":"10.1021\/acs.inorgchem.5b02605","article-title":"Luminescent Alkyne-Bearing Terbium(III) Complexes and Their Application to Bioorthogonal Protein Labeling","volume":"55","author":"WI O'Malley","year":"2016","journal-title":"Inorg Chem"},{"key":"ref29","first-page":"21","article-title":"Cellular Uptake and Photo-Cytotoxicity of a Gadolinium(III)-DOTA-Naphthalimide Complex "Clicked" to a Lipidated Tat Peptide","author":"WI O'Malley","year":"2016","journal-title":"Molecules"},{"issue":"8","key":"ref30","doi-asserted-by":"crossref","first-page":"3688","DOI":"10.1021\/ac500123z","article-title":"Click chemistry mediated Eu-tagging: activity-based specific quantification and simultaneous activity evaluation of CYP3A4 using 153Eu species-unspecific isotope dilution inductively coupled plasma mass spectrometry","volume":"86","author":"Y Liang","year":"2014","journal-title":"Anal Chem"},{"issue":"16","key":"ref31","doi-asserted-by":"crossref","first-page":"4805","DOI":"10.1016\/j.bmcl.2010.06.111","article-title":"A DOTA-peptide conjugate by copper-free click chemistry","volume":"20","author":"ME Martin","year":"2010","journal-title":"Bioorg Med Chem Lett"},{"issue":"17","key":"ref32","doi-asserted-by":"crossref","first-page":"5018","DOI":"10.1002\/chem.200903379","article-title":"Binuclear terbium(III) complex as a probe for tyrosine phosphorylation","volume":"16","author":"H Akiba","year":"2010","journal-title":"Chemistry"},{"issue":"2","key":"ref33","doi-asserted-by":"crossref","first-page":"260","DOI":"10.1021\/bc300631z","article-title":"Lanthanide tags for site-specific ligation to an unnatural amino acid and generation of pseudocontact shifts in proteins","volume":"24","author":"CT Loh","year":"2013","journal-title":"Bioconjug Chem"},{"issue":"10","key":"ref34","doi-asserted-by":"crossref","first-page":"1706","DOI":"10.1039\/b924784j","article-title":"Clickable bifunctional radiometal chelates for peptide labeling","volume":"46","author":"AY Lebedev","year":"2010","journal-title":"Chem Commun (Camb)"},{"issue":"21","key":"ref35","doi-asserted-by":"crossref","first-page":"6082","DOI":"10.1002\/chem.200700231","article-title":"Synthesis of novel 1,4,7,10-tetraazacyclodecane-1,4,7,10-tetraacetic acid (DOTA) derivatives for chemoselective attachment to unprotected polyfunctionalized compounds","volume":"13","author":"S Knor","year":"2007","journal-title":"Chemistry"},{"issue":"18","key":"ref36","doi-asserted-by":"crossref","first-page":"2163","DOI":"10.2174\/0929867054637617","article-title":"Copper as a biocidal tool","volume":"12","author":"G Borkow","year":"2005","journal-title":"Curr Med Chem"},{"issue":"10","key":"ref37","doi-asserted-by":"crossref","first-page":"644","DOI":"10.1021\/cb6003228","article-title":"A comparative study of bioorthogonal reactions with azides","volume":"1","author":"NJ Agard","year":"2006","journal-title":"ACS Chem Biol"},{"issue":"34","key":"ref38","doi-asserted-by":"crossref","first-page":"11486","DOI":"10.1021\/ja803086r","article-title":"Second-generation difluorinated cyclooctynes for copper-free click chemistry","volume":"130","author":"JA Codelli","year":"2008","journal-title":"J Am Chem Soc"},{"issue":"43","key":"ref39","doi-asserted-by":"crossref","first-page":"16793","DOI":"10.1073\/pnas.0707090104","article-title":"Copper-free click chemistry for dynamic in vivo imaging","volume":"104","author":"JM Baskin","year":"2007","journal-title":"Proc Natl Acad Sci U S A"},{"issue":"31","key":"ref40","doi-asserted-by":"crossref","first-page":"9026","DOI":"10.1021\/ja027007w","article-title":"Addition of p-azido-L-phenylalanine to the genetic code of Escherichia coli","volume":"124","author":"JW Chin","year":"2002","journal-title":"J Am Chem Soc"},{"issue":"4","key":"ref41","doi-asserted-by":"crossref","first-page":"1272","DOI":"10.1039\/b901970g","article-title":"Cu-free click cycloaddition reactions in chemical biology","volume":"39","author":"JC Jewett","year":"2010","journal-title":"Chem Soc Rev"},{"issue":"22","key":"ref42","doi-asserted-by":"crossref","first-page":"9199","DOI":"10.1021\/ja3000936","article-title":"Reactivity of biarylazacyclooctynones in copper-free click chemistry","volume":"134","author":"CG Gordon","year":"2012","journal-title":"J Am Chem Soc"},{"issue":"2","key":"ref43","doi-asserted-by":"crossref","first-page":"958","DOI":"10.1021\/ic00253a038","article-title":"Thermodynamic study of lanthanide complexes of 1,4,7-Triazacyclononane-N,N\u2019,N\u201d-triacetic Acid and 1,4,7,10-Tetraazacyclododecane-N,N\u2019,N\u201d,N\u201d\u2018-tetraacetic Acid","volume":"26","author":"WP Cacheris","year":"1987","journal-title":"Inorg Chem"},{"issue":"9","key":"ref44","doi-asserted-by":"crossref","first-page":"L45","DOI":"10.1529\/biophysj.107.119073","article-title":"In vivo measurement of intramolecular distances using genetically encoded reporters","volume":"93","author":"W Sandtner","year":"2007","journal-title":"Biophys J"},{"issue":"2","key":"ref45","first-page":"185","article-title":"Cross-bridged macrocyclic chelators for stable complexation of copper radionuclides for PET imaging","volume":"52","author":"CJ Anderson","year":"2008","journal-title":"Q J Nucl Med Mol Imaging"}],"container-title":["PLOS ONE"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/dx.plos.org\/10.1371\/journal.pone.0209726","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2020,5,9]],"date-time":"2020-05-09T09:50:24Z","timestamp":1589017824000},"score":1,"resource":{"primary":{"URL":"https:\/\/dx.plos.org\/10.1371\/journal.pone.0209726"}},"subtitle":[],"editor":[{"given":"Mohammad","family":"Shahid","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"editor"}]}],"short-title":[],"issued":{"date-parts":[[2019,3,27]]},"references-count":45,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2019,3,27]]}},"URL":"https:\/\/doi.org\/10.1371\/journal.pone.0209726","relation":{"has-preprint":[{"id-type":"doi","id":"10.1101\/531087","asserted-by":"object"}]},"ISSN":["1932-6203"],"issn-type":[{"value":"1932-6203","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,3,27]]}}}