{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,6]],"date-time":"2026-03-06T10:45:34Z","timestamp":1772793934209,"version":"3.50.1"},"reference-count":44,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2022,1,1]],"date-time":"2022-01-01T00:00:00Z","timestamp":1640995200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2022,1,1]],"date-time":"2022-01-01T00:00:00Z","timestamp":1640995200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2022,1,1]],"date-time":"2022-01-01T00:00:00Z","timestamp":1640995200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2022,1,1]],"date-time":"2022-01-01T00:00:00Z","timestamp":1640995200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2022,1,1]],"date-time":"2022-01-01T00:00:00Z","timestamp":1640995200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2022,1,1]],"date-time":"2022-01-01T00:00:00Z","timestamp":1640995200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2022,1,1]],"date-time":"2022-01-01T00:00:00Z","timestamp":1640995200000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["81903571"],"award-info":[{"award-number":["81903571"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100010029","name":"Taishan Scholar Foundation of Shandong Province","doi-asserted-by":"publisher","award":["tsqn202103096"],"award-info":[{"award-number":["tsqn202103096"]}],"id":[{"id":"10.13039\/501100010029","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100010040","name":"Taishan Scholar Project of Shandong Province","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100010040","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Journal of Chromatography A"],"published-print":{"date-parts":[[2022,1]]},"DOI":"10.1016\/j.chroma.2021.462742","type":"journal-article","created":{"date-parts":[[2021,12,10]],"date-time":"2021-12-10T01:54:42Z","timestamp":1639101282000},"page":"462742","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":7,"special_numbering":"C","title":["Multi-wavelength visible-light induced [2+2] cycloaddition for identification of lipid isomers in biological samples"],"prefix":"10.1016","volume":"1662","author":[{"given":"Yuhao","family":"Han","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Panpan","family":"Chen","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zhichao","family":"Li","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xiao","family":"Wang","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Chenglong","family":"Sun","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"78","reference":[{"key":"10.1016\/j.chroma.2021.462742_bib0001","doi-asserted-by":"crossref","first-page":"888","DOI":"10.1016\/j.cell.2010.11.033","article-title":"Lipidomics: new tools and applications","volume":"143","author":"Wenk","year":"2010","journal-title":"Cell"},{"key":"10.1016\/j.chroma.2021.462742_bib0002","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1038\/nrm.2017.138","article-title":"Understanding the diversity of membrane lipid composition","volume":"19","author":"Harayama","year":"2018","journal-title":"Nat. Rev. Mol. Cell Biol."},{"key":"10.1016\/j.chroma.2021.462742_bib0003","doi-asserted-by":"crossref","first-page":"15884","DOI":"10.1021\/jacs.9b06977","article-title":"Lipid acyl chain cis double bond position modulates membrane domain registration\/anti-registration","volume":"141","author":"Zhang","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.chroma.2021.462742_bib0004","doi-asserted-by":"crossref","DOI":"10.1016\/j.celrep.2021.108738","article-title":"Apocryphal FADS2 activity promotes fatty acid diversification in cancer","volume":"34","author":"Young","year":"2021","journal-title":"Cell Rep."},{"key":"10.1016\/j.chroma.2021.462742_bib0005","doi-asserted-by":"crossref","first-page":"348","DOI":"10.1016\/j.ccr.2010.01.022","article-title":"A transcriptional signature and common gene networks link cancer with lipid metabolism and diverse human diseases","volume":"17","author":"Hirsch","year":"2010","journal-title":"Cancer Cell"},{"key":"10.1016\/j.chroma.2021.462742_bib0006","doi-asserted-by":"crossref","first-page":"403","DOI":"10.1038\/s41586-019-0904-1","article-title":"Evidence for an alternative fatty acid desaturation pathway increasing cancer plasticity","volume":"566","author":"Vriens","year":"2019","journal-title":"Nature"},{"key":"10.1016\/j.chroma.2021.462742_bib0007","doi-asserted-by":"crossref","first-page":"1701","DOI":"10.1016\/j.cmet.2021.05.016","article-title":"Peroxidation of n-3 and n-6 polyunsaturated fatty acids in the acidic tumor environment leads to ferroptosis-mediated anticancer effects","volume":"33","author":"Dierge","year":"2021","journal-title":"Cell Metab."},{"key":"10.1016\/j.chroma.2021.462742_bib0008","doi-asserted-by":"crossref","first-page":"58","DOI":"10.1021\/ja056797h","article-title":"Ozonolysis of phospholipid double bonds during electrospray ionization: a new tool for structure determination","volume":"128","author":"Thomas","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.chroma.2021.462742_bib0009","doi-asserted-by":"crossref","first-page":"4738","DOI":"10.1021\/ac1030946","article-title":"Facile determination of double bond position in unsaturated fatty acids and esters by low temperature plasma ionization mass spectrometry","volume":"83","author":"Zhang","year":"2011","journal-title":"Anal. Chem."},{"key":"10.1016\/j.chroma.2021.462742_bib0010","doi-asserted-by":"crossref","first-page":"1100","DOI":"10.1039\/C1AN15864C","article-title":"Using ambient ozone for assignment of double bond position in unsaturated lipids","volume":"137","author":"Ellis","year":"2012","journal-title":"Analyst"},{"key":"10.1016\/j.chroma.2021.462742_bib0011","doi-asserted-by":"crossref","first-page":"1292","DOI":"10.1021\/acs.analchem.7b04091","article-title":"Online ozonolysis combined with ion mobility-mass spectrometry provides a new platform for lipid isomer analyses","volume":"90","author":"Poad","year":"2018","journal-title":"Anal. Chem."},{"key":"10.1016\/j.chroma.2021.462742_bib0012","doi-asserted-by":"crossref","first-page":"10530","DOI":"10.1002\/anie.201802937","article-title":"Mass spectrometry imaging with isomeric resolution enabled by ozone-induced dissociation","volume":"57","author":"Paine","year":"2018","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"10.1016\/j.chroma.2021.462742_bib0013","doi-asserted-by":"crossref","first-page":"6492","DOI":"10.1002\/anie.201812698","article-title":"Reshaping lipid biochemistry by pushing barriers in structural lipidomics","volume":"58","author":"Porta Siegel","year":"2019","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"10.1016\/j.chroma.2021.462742_bib0014","doi-asserted-by":"crossref","first-page":"6245","DOI":"10.1021\/acs.analchem.0c00641","article-title":"Ozonization of tissue sections for MALDI MS imaging of carbon\u2013carbon double bond positional isomers of phospholipids","volume":"92","author":"Bedna\u0159\u00edk","year":"2020","journal-title":"Anal. Chem."},{"key":"10.1016\/j.chroma.2021.462742_bib0015","doi-asserted-by":"crossref","first-page":"9826","DOI":"10.1021\/acs.analchem.1c01377","article-title":"Mass spectrometry imaging of lipids with isomer resolution using high-pressure ozone-induced dissociation","volume":"93","author":"Claes","year":"2021","journal-title":"Anal. Chem."},{"key":"10.1016\/j.chroma.2021.462742_bib0016","doi-asserted-by":"crossref","first-page":"8115","DOI":"10.1039\/D1SC01614H","article-title":"Quantification and molecular imaging of fatty acid isomers from complex biological samples by mass spectrometry","volume":"12","author":"Zhang","year":"2021","journal-title":"Chem. Sci."},{"key":"10.1016\/j.chroma.2021.462742_bib0017","doi-asserted-by":"crossref","first-page":"1516","DOI":"10.1021\/acs.analchem.6b03353","article-title":"Structural characterization of phosphatidylcholines using 193 nm ultraviolet photodissociation mass spectrometry","volume":"89","author":"Klein","year":"2017","journal-title":"Anal. Chem."},{"key":"10.1016\/j.chroma.2021.462742_bib0018","doi-asserted-by":"crossref","first-page":"1406","DOI":"10.1007\/s13361-017-1668-1","article-title":"Detailed structural characterization of sphingolipids via 193 nm ultraviolet photodissociation and ultra high resolution tandem mass spectrometry","volume":"28","author":"Ryan","year":"2017","journal-title":"J. Am. Soc. Mass Spectrom."},{"key":"10.1016\/j.chroma.2021.462742_bib0019","doi-asserted-by":"crossref","first-page":"15681","DOI":"10.1021\/jacs.7b06416","article-title":"Pinpointing double bond and sn-positions in glycerophospholipids via hybrid 193 nm ultraviolet photodissociation (UVPD) mass spectrometry","volume":"139","author":"Williams","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.chroma.2021.462742_bib0020","doi-asserted-by":"crossref","first-page":"8386","DOI":"10.1021\/acs.analchem.0c00970","article-title":"Double bond characterization of free fatty acids directly from biological tissues by ultraviolet photodissociation","volume":"92","author":"Feider","year":"2020","journal-title":"Anal. Chem."},{"key":"10.1016\/j.chroma.2021.462742_bib0021","doi-asserted-by":"crossref","first-page":"2592","DOI":"10.1002\/anie.201310699","article-title":"Pinpointing double bonds in lipids by Patern\u00f2-B\u00fcchi reactions and mass spectrometry","volume":"53","author":"Ma","year":"2014","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"10.1016\/j.chroma.2021.462742_bib0022","doi-asserted-by":"crossref","first-page":"2573","DOI":"10.1073\/pnas.1523356113","article-title":"Identification and quantitation of lipid C=C location isomers: a shotgun lipidomics approach enabled by photochemical reaction","volume":"113","author":"Ma","year":"2016","journal-title":"Proc. Natl. Acad. Sci. U. S. A."},{"key":"10.1016\/j.chroma.2021.462742_bib0023","doi-asserted-by":"crossref","first-page":"8545","DOI":"10.1021\/acs.analchem.7b02375","article-title":"Determination of double bond positions in polyunsaturated fatty acids using the photochemical Patern\u00f2-B\u00fcchi reaction with acetone and tandem mass spectrometry","volume":"89","author":"Murphy","year":"2017","journal-title":"Anal. Chem."},{"key":"10.1016\/j.chroma.2021.462742_bib0024","doi-asserted-by":"crossref","first-page":"4744","DOI":"10.1039\/C7AN01158J","article-title":"Selective phosphatidylcholine double bond fragmentation and localisation using Patern\u00f2-B\u00fcchi reactions and ultraviolet photodissociation","volume":"142","author":"W\u00e4ldchen","year":"2017","journal-title":"Analyst"},{"key":"10.1016\/j.chroma.2021.462742_bib0025","doi-asserted-by":"crossref","first-page":"4880","DOI":"10.1002\/anie.201801330","article-title":"Entropy-driven diastereoselectivity improvement in the Patern\u00f2-B\u00fcchi reaction of 1-naphthyl aryl ethenes with a chiral cyanobenzoate through remote alkylation","volume":"57","author":"Nagasaki","year":"2018","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"10.1016\/j.chroma.2021.462742_bib0026","doi-asserted-by":"crossref","first-page":"11816","DOI":"10.1021\/jacs.9b05868","article-title":"Reactive matrix-assisted laser desorption\/ionization mass spectrometry imaging using an intrinsically photoreactive Patern\u00f2-B\u00fcchi matrix for double-bond localization in isomeric phospholipids","volume":"141","author":"W\u00e4ldchen","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.chroma.2021.462742_bib0027","doi-asserted-by":"crossref","first-page":"10740","DOI":"10.1039\/C9SC03521D","article-title":"A lipidomic workflow capable of resolving sn- and C=C location isomers of phosphatidylcholines","volume":"10","author":"Zhao","year":"2019","journal-title":"Chem. Sci."},{"key":"10.1016\/j.chroma.2021.462742_bib0028","doi-asserted-by":"crossref","first-page":"11380","DOI":"10.1021\/acs.analchem.0c02245","article-title":"Combining mass spectrometry with Patern\u00f2-B\u00fcchi reaction to determine double-bond positions in lipids at the single-cell level","volume":"92","author":"Zhu","year":"2020","journal-title":"Anal. Chem."},{"key":"10.1016\/j.chroma.2021.462742_bib0029","doi-asserted-by":"crossref","first-page":"14130","DOI":"10.1021\/acs.analchem.0c03150","article-title":"Multifunctional Reactive MALDI matrix enabling high-lateral resolution dual polarity MS imaging and lipid C=C position-resolved MS2 imaging","volume":"92","author":"W\u00e4ldchen","year":"2020","journal-title":"Anal. Chem."},{"key":"10.1016\/j.chroma.2021.462742_bib0030","doi-asserted-by":"crossref","first-page":"5612","DOI":"10.1021\/acs.analchem.7b04675","article-title":"Rapid In situ profiling of lipid C=C location isomers in tissue using ambient mass spectrometry with photochemical reactions","volume":"90","author":"Tang","year":"2018","journal-title":"Anal. Chem."},{"key":"10.1016\/j.chroma.2021.462742_bib0031","doi-asserted-by":"crossref","first-page":"32","DOI":"10.1016\/j.aca.2018.04.046","article-title":"Benzophenone used as the photochemical reagent for pinpointing C=C locations in unsaturated lipids through shotgun and liquid chromatography-mass spectrometry approaches","volume":"1028","author":"Xu","year":"2018","journal-title":"Anal. Chim. Acta"},{"key":"10.1016\/j.chroma.2021.462742_bib0032","doi-asserted-by":"crossref","first-page":"6446","DOI":"10.1021\/acs.analchem.9b05588","article-title":"Double derivatization strategy for high-sensitivity and high-coverage localization of double bonds in free fatty acids by mass spectrometry","volume":"92","author":"Xu","year":"2020","journal-title":"Anal. Chem."},{"key":"10.1016\/j.chroma.2021.462742_bib0033","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1038\/s41467-018-07963-8","article-title":"Online photochemical derivatization enables comprehensive mass spectrometric analysis of unsaturated phospholipid isomers","volume":"10","author":"Zhang","year":"2019","journal-title":"Nat. Commun."},{"key":"10.1016\/j.chroma.2021.462742_bib0034","doi-asserted-by":"crossref","first-page":"513","DOI":"10.1039\/C9AN01515A","article-title":"Analysis of ether glycerophosphocholines at the level of C=C locations from human plasma","volume":"145","author":"Lin","year":"2020","journal-title":"Analyst"},{"key":"10.1016\/j.chroma.2021.462742_bib0035","doi-asserted-by":"crossref","first-page":"1971","DOI":"10.1007\/s13361-018-2023-x","article-title":"Charging and charge switching of unsaturated lipids and apolar compounds using Patern\u00f2-B\u00fcchi reactions","volume":"29","author":"Esch","year":"2018","journal-title":"J. Am. Soc. Mass Spectrom."},{"key":"10.1016\/j.chroma.2021.462742_bib0036","doi-asserted-by":"crossref","first-page":"2256","DOI":"10.1039\/C9AN02260K","article-title":"Investigating C=C positions and hydroxylation sites in lipids using Patern\u00f2\u2013B\u00fcchi functionalization mass spectrometry","volume":"145","author":"Esch","year":"2020","journal-title":"Analyst"},{"key":"10.1016\/j.chroma.2021.462742_bib0037","doi-asserted-by":"crossref","first-page":"8487","DOI":"10.1021\/acs.analchem.0c01241","article-title":"Profiling of Cholesteryl esters by coupling charge-tagging Patern\u00f2-B\u00fcchi reaction and liquid chromatography-mass spectrometry","volume":"92","author":"Xie","year":"2020","journal-title":"Anal. Chem."},{"key":"10.1016\/j.chroma.2021.462742_bib0038","doi-asserted-by":"crossref","first-page":"375","DOI":"10.1038\/s41467-019-14180-4","article-title":"Large-scale lipid analysis with C=C location and sn-position isomer resolving power","volume":"11","author":"Cao","year":"2020","journal-title":"Nat. Commun."},{"key":"10.1016\/j.chroma.2021.462742_bib0039","doi-asserted-by":"crossref","first-page":"7244","DOI":"10.1039\/D0SC01149E","article-title":"A visible-light activated [2+2] cycloaddition reaction enables pinpointing carbon\u2013carbon double bonds in lipids","volume":"11","author":"Feng","year":"2020","journal-title":"Chem. Sci."},{"key":"10.1016\/j.chroma.2021.462742_bib0040","doi-asserted-by":"crossref","first-page":"3499","DOI":"10.1021\/jacs.9b12120","article-title":"Visible-light-driven [2+2] photocycloadditions between benzophenone and C=C bonds in unsaturated lipids","volume":"142","author":"Li","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"10.1016\/j.chroma.2021.462742_bib0041","doi-asserted-by":"crossref","first-page":"10034","DOI":"10.1002\/anie.201709766","article-title":"Visible-light photocatalysis: does it make a difference in organic synthesis?","volume":"57","author":"Marzo","year":"2018","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"10.1016\/j.chroma.2021.462742_bib0042","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1016\/j.ab.2016.09.014","article-title":"Advances and unresolved challenges in the structural characterization of isomeric lipids","volume":"524","author":"Hancock","year":"2017","journal-title":"Anal. Biochem."},{"key":"10.1016\/j.chroma.2021.462742_bib0043","article-title":"A novel on-tissue cycloaddition reagent for mass spectrometry imaging of lipid C=C position isomers in biological tissues","author":"Sun","year":"2021","journal-title":"Chin. Chem. Lett."},{"key":"10.1016\/j.chroma.2021.462742_bib0044","doi-asserted-by":"crossref","first-page":"13470","DOI":"10.1021\/acs.analchem.0c02896","article-title":"Next-generation Patern\u00f2-B\u00fcchi reagents for lipid analysis by mass spectrometry","volume":"92","author":"Zhao","year":"2020","journal-title":"Anal. Chem."}],"container-title":["Journal of Chromatography A"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0021967321008645?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0021967321008645?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,9,19]],"date-time":"2025-09-19T06:11:37Z","timestamp":1758262297000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0021967321008645"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,1]]},"references-count":44,"alternative-id":["S0021967321008645"],"URL":"https:\/\/doi.org\/10.1016\/j.chroma.2021.462742","relation":{},"ISSN":["0021-9673"],"issn-type":[{"value":"0021-9673","type":"print"}],"subject":[],"published":{"date-parts":[[2022,1]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Multi-wavelength visible-light induced [2+2] cycloaddition for identification of lipid isomers in biological samples","name":"articletitle","label":"Article Title"},{"value":"Journal of Chromatography A","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.chroma.2021.462742","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2021 Elsevier B.V. All rights reserved.","name":"copyright","label":"Copyright"}],"article-number":"462742"}}