{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,25]],"date-time":"2026-06-25T17:46:07Z","timestamp":1782409567254,"version":"3.54.5"},"reference-count":34,"publisher":"Elsevier","isbn-type":[{"value":"9780443432248","type":"print"}],"license":[{"start":{"date-parts":[[2026,1,1]],"date-time":"2026-01-01T00:00:00Z","timestamp":1767225600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2026,1,1]],"date-time":"2026-01-01T00:00:00Z","timestamp":1767225600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2026,1,1]],"date-time":"2026-01-01T00:00:00Z","timestamp":1767225600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2026,1,1]],"date-time":"2026-01-01T00:00:00Z","timestamp":1767225600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,1,1]],"date-time":"2026-01-01T00:00:00Z","timestamp":1767225600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2026,1,1]],"date-time":"2026-01-01T00:00:00Z","timestamp":1767225600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,1,1]],"date-time":"2026-01-01T00:00:00Z","timestamp":1767225600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026]]},"DOI":"10.1016\/bs.mie.2026.05.012","type":"book-chapter","created":{"date-parts":[[2026,6,1]],"date-time":"2026-06-01T19:42:00Z","timestamp":1780342920000},"page":"73-98","source":"Crossref","is-referenced-by-count":0,"title":["Nitrone dipoles in bioorthogonal chemistry applications"],"prefix":"10.1016","author":[{"given":"Elexa","family":"Scott","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jason D.","family":"Josephson","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Didier A.","family":"Bilodeau","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"John Paul","family":"Pezacki","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/bs.mie.2026.05.012_bib1","doi-asserted-by":"crossref","first-page":"15046","DOI":"10.1021\/ja044996f","article-title":"A strain-promoted [3 + 2] azide\u2212alkyne cycloaddition for covalent modification of biomolecules in living systems","volume":"126","author":"Agard","year":"2004","journal-title":"Journal of the American Chemical Society"},{"key":"10.1016\/bs.mie.2026.05.012_bib2","doi-asserted-by":"crossref","first-page":"1988","DOI":"10.1039\/C9CC09473C","article-title":"Optimized aqueous kinugasa reactions for bioorthogonal chemistry applications","volume":"56","author":"Bilodeau","year":"2020","journal-title":"Chemical Communications"},{"key":"10.1016\/bs.mie.2026.05.012_bib3","doi-asserted-by":"crossref","first-page":"6699","DOI":"10.1021\/acs.chemrev.0c00832","article-title":"Bioorthogonal reactions utilizing nitrones as versatile dipoles in cycloaddition reactions","volume":"121","author":"Bilodeau","year":"2021","journal-title":"Chemical Reviews"},{"key":"10.1016\/bs.mie.2026.05.012_bib4","unstructured":"Bilodeau, D. A., & Pezacki, J. P. (2025). Developing novel bioorthogonal chemistry employing nitrone dipoles [Doctoral Thesis, University of Ottawa]. http:\/\/hdl.handle.net\/10393\/50644."},{"key":"10.1016\/bs.mie.2026.05.012_bib5","doi-asserted-by":"crossref","first-page":"2457","DOI":"10.1021\/acs.bioconjchem.1c00461","article-title":"Bioorthogonal chemistry and its applications","volume":"32","author":"Bird","year":"2021","journal-title":"Bioconjugate Chemistry"},{"key":"10.1016\/bs.mie.2026.05.012_bib6","doi-asserted-by":"crossref","first-page":"647","DOI":"10.1038\/nchembio.211","article-title":"Design, synthesis and selection of DNA-encoded small-molecule libraries","volume":"5","author":"Clark","year":"2009","journal-title":"Nature Chemical Biology"},{"key":"10.1016\/bs.mie.2026.05.012_bib7","doi-asserted-by":"crossref","first-page":"16","DOI":"10.1007\/s41061-016-0016-4","article-title":"Strain-promoted 1,3-dipolar cycloaddition of cycloalkynes and organic azides","volume":"374","author":"Dommerholt","year":"2016","journal-title":"Topics in Current Chemistry"},{"key":"10.1016\/bs.mie.2026.05.012_bib8","doi-asserted-by":"crossref","first-page":"19106","DOI":"10.1021\/acsomega.9b02322","article-title":"Nitrone-modified gold nanoparticles: Synthesis, characterization, and their potential as 18F-labeled positron emission tomography probes via I-SPANC","volume":"4","author":"Ghiassian","year":"2019","journal-title":"ACS Omega"},{"key":"10.1016\/bs.mie.2026.05.012_bib9","doi-asserted-by":"crossref","first-page":"7162","DOI":"10.1021\/ac048688b","article-title":"Using biofunctionalized nanoparticles to probe pathogenic bacteria","volume":"76","author":"Ho","year":"2004","journal-title":"Analytical Chemistry"},{"key":"10.1016\/bs.mie.2026.05.012_bib10","first-page":"357","article-title":"1,3-Dipolar cycloadditions","author":"Huisgen","year":"1961","journal-title":"Proceedings of the Chemical Society"},{"key":"10.1016\/bs.mie.2026.05.012_bib11","doi-asserted-by":"crossref","first-page":"565","DOI":"10.1002\/anie.196305651","article-title":"1,3\u2010Dipolar cycloadditions. Past and future","volume":"2","author":"Huisgen","year":"1963","journal-title":"Angewandte Chemie International Edition"},{"key":"10.1016\/bs.mie.2026.05.012_bib12","doi-asserted-by":"crossref","first-page":"3688","DOI":"10.1021\/ja100014q","article-title":"Rapid Cu-free click chemistry with readily synthesized biarylazacyclooctynones","volume":"132","author":"Jewett","year":"2010","journal-title":"Journal of the American Chemical Society"},{"key":"10.1016\/bs.mie.2026.05.012_bib13","doi-asserted-by":"crossref","first-page":"2444","DOI":"10.1021\/ja809451w","article-title":"Cellular lipid metabolism is influenced by the coordination environment of copper","volume":"131","author":"Kennedy","year":"2009","journal-title":"Journal of the American Chemical Society"},{"key":"10.1016\/bs.mie.2026.05.012_bib14","doi-asserted-by":"crossref","first-page":"17993","DOI":"10.1021\/ja2083027","article-title":"Cellular consequences of copper complexes used to catalyze bioorthogonal click reactions","volume":"133","author":"Kennedy","year":"2011","journal-title":"Journal of the American Chemical Society"},{"key":"10.1016\/bs.mie.2026.05.012_bib15","doi-asserted-by":"crossref","first-page":"2004","DOI":"10.1002\/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5","article-title":"Click chemistry: Diverse chemical function from a few good reactions","volume":"40","author":"Kolb","year":"2001","journal-title":"Angewandte Chemie International Edition"},{"key":"10.1016\/bs.mie.2026.05.012_bib16","doi-asserted-by":"crossref","first-page":"12519","DOI":"10.1002\/anie.201206749","article-title":"Situ probing of newly synthesized peptidoglycan in live bacteria with fluorescent D-amino acids","volume":"51","author":"Kuru","year":"2012","journal-title":"Angewandte Chemie International Edition"},{"key":"10.1016\/bs.mie.2026.05.012_bib17","doi-asserted-by":"crossref","first-page":"1046","DOI":"10.1002\/anie.201509396","article-title":"Conferring phosphorogenic properties on iridium(III)\u2010based bioorthogonal probes through modification with a nitrone unit","volume":"55","author":"Lee","year":"2016","journal-title":"Angewandte Chemie International Edition"},{"key":"10.1016\/bs.mie.2026.05.012_bib18","doi-asserted-by":"crossref","first-page":"12501","DOI":"10.1039\/C5CC04901F","article-title":"Bioorthogonal labeling of living bacteria using unnatural amino acids containing nitrones and a nitrone derivative of vancomycin","volume":"51","author":"MacKenzie","year":"2015","journal-title":"Chemical Communications"},{"key":"10.1016\/bs.mie.2026.05.012_bib19","doi-asserted-by":"crossref","DOI":"10.1016\/j.ejmcr.2025.100315","article-title":"Synthetic developments and biological insights of 1,2,3-triazoles: Unravelling scope for drug discovery","volume":"16","author":"Martis","year":"2026","journal-title":"European Journal of Medicinal Chemistry Reports"},{"key":"10.1016\/bs.mie.2026.05.012_bib20","doi-asserted-by":"crossref","first-page":"10040","DOI":"10.1039\/c1cc13808a","article-title":"Strain-promoted cycloadditions of cyclic nitrones with cyclooctynes for labeling human cancer cells","volume":"47","author":"McKay","year":"2011","journal-title":"Chemical Communications"},{"key":"10.1016\/bs.mie.2026.05.012_bib21","doi-asserted-by":"crossref","first-page":"1893","DOI":"10.1016\/j.tetlet.2009.02.035","article-title":"Studies of multicomponent kinugasa reactions in aqueous media","volume":"50","author":"McKay","year":"2009","journal-title":"Tetrahedron Letters"},{"key":"10.1016\/bs.mie.2026.05.012_bib22","doi-asserted-by":"crossref","first-page":"931","DOI":"10.1039\/B921630H","article-title":"Nitrones as dipoles for rapid strain-promoted 1,3-dipolar cycloadditions with cyclooctynes","volume":"46","author":"McKay","year":"2010","journal-title":"Chemical Communications"},{"key":"10.1016\/bs.mie.2026.05.012_bib23","doi-asserted-by":"crossref","first-page":"1075","DOI":"10.1016\/j.chembiol.2014.09.002","article-title":"Click chemistry in complex mixtures: Bioorthogonal bioconjugation","volume":"21","author":"McKay","year":"2014","journal-title":"Chemistry & Biology"},{"key":"10.1016\/bs.mie.2026.05.012_bib24","doi-asserted-by":"crossref","first-page":"4684","DOI":"10.1021\/acs.chemrev.8b00476","article-title":"Synthesis and transformations of nitrones for organic synthesis","volume":"119","author":"Murahashi","year":"2019","journal-title":"Chemical Reviews"},{"key":"10.1016\/bs.mie.2026.05.012_bib25","doi-asserted-by":"crossref","first-page":"29306","DOI":"10.1039\/D0RA05092J","article-title":"Predicting reactivity for bioorthogonal cycloadditions involving nitrones","volume":"10","author":"Nakajima","year":"2020","journal-title":"RSC Advances"},{"key":"10.1016\/bs.mie.2026.05.012_bib26","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1038\/s43586-021-00028-z","article-title":"Bioorthogonal chemistry","volume":"1","author":"Scinto","year":"2021","journal-title":"Nature Reviews Methods Primers"},{"key":"10.1016\/bs.mie.2026.05.012_bib27","doi-asserted-by":"crossref","first-page":"46966","DOI":"10.1039\/C4RA07851A","article-title":"Copper-catalysed cycloaddition reactions of nitrones and alkynes for bioorthogonal labeling of living cells","volume":"4","author":"Sherratt","year":"2014","journal-title":"RSC Advances"},{"key":"10.1016\/bs.mie.2026.05.012_bib28","doi-asserted-by":"crossref","first-page":"1222","DOI":"10.1021\/acs.bioconjchem.6b00063","article-title":"Dual strain-promoted alkyne\u2013nitrone cycloadditions for simultaneous labeling of bacterial peptidoglycans","volume":"27","author":"Sherratt","year":"2016","journal-title":"Bioconjugate Chemistry"},{"key":"10.1016\/bs.mie.2026.05.012_bib29","unstructured":"Sherratt, A. R., Chigrinova, M., McKay, C. S., Beaulieu, L.-P. B., Rouleau, Y., & Pezacki, J. P. (2014)."},{"key":"10.1016\/bs.mie.2026.05.012_bib30","doi-asserted-by":"crossref","first-page":"3057","DOI":"10.1021\/jo011148j","article-title":"Peptidotriazoles on solid phase: [1,2,3]-Triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides","volume":"67","author":"Torn\u00f8e","year":"2002","journal-title":"Journal of Organic Chemistry"},{"key":"10.1016\/bs.mie.2026.05.012_bib31","doi-asserted-by":"crossref","first-page":"2596","DOI":"10.1002\/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4","article-title":"A stepwise huisgen cycloaddition process: Copper(I)-catalyzed regioselective \u201cLigation\u201d of azides and terminal alkynes","volume":"41","author":"Rostovtsev","year":"2002","journal-title":"Angewandte Chemie International Edition"},{"key":"10.1016\/bs.mie.2026.05.012_bib32","doi-asserted-by":"crossref","first-page":"848","DOI":"10.1021\/acsestwater.2c00607","article-title":"Dosage-dependent toxicity of universal solvent dimethyl sulfoxide to the partial nitrification wastewater treatment process","volume":"3","author":"Wang","year":"2023","journal-title":"ACS EST Water"},{"key":"10.1016\/bs.mie.2026.05.012_bib33","doi-asserted-by":"crossref","first-page":"2491","DOI":"10.1016\/j.bmcl.2008.02.043","article-title":"\u03b2-Lactam congeners of orlistat as inhibitors of fatty acid synthase","volume":"18","author":"Zhang","year":"2008","journal-title":"Bioorganic & Medicinal Chemistry Letters"},{"key":"10.1016\/bs.mie.2026.05.012_bib34","doi-asserted-by":"crossref","first-page":"4697","DOI":"10.1002\/chem.201304056","article-title":"Synthesis of 18F\u2010labeled \u03b2\u2010lactams by using the kinugasa reaction","volume":"20","author":"Zlatopolskiy","year":"2014","journal-title":"Chemistry \u2013 A European Journal"}],"container-title":["Methods in Enzymology","Bioorthogonal Labeling"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0076687926001278?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0076687926001278?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2026,6,25]],"date-time":"2026-06-25T16:52:21Z","timestamp":1782406341000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0076687926001278"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026]]},"ISBN":["9780443432248"],"references-count":34,"URL":"https:\/\/doi.org\/10.1016\/bs.mie.2026.05.012","relation":{},"ISSN":["0076-6879"],"issn-type":[{"value":"0076-6879","type":"print"}],"subject":[],"published":{"date-parts":[[2026]]}}}