{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,9]],"date-time":"2026-04-09T06:29:19Z","timestamp":1775716159212,"version":"3.50.1"},"reference-count":55,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2024,10,31]],"date-time":"2024-10-31T00:00:00Z","timestamp":1730332800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100014188","name":"Ministry of Science and ICT, South Korea","doi-asserted-by":"publisher","award":["2023R1A2C300453411"],"award-info":[{"award-number":["2023R1A2C300453411"]}],"id":[{"id":"10.13039\/501100014188","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100014188","name":"Ministry of Science and ICT, South Korea","doi-asserted-by":"publisher","award":["2021R1A6A1A10042944"],"award-info":[{"award-number":["2021R1A6A1A10042944"]}],"id":[{"id":"10.13039\/501100014188","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2025,1,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Herein, we present an innovative and atom\u2010efficient synthesis of trimethine cyanines (Cy3) using formaldehyde (FA) as a single\u2010carbon reagent. The widespread application of Cy3 dyes in bioimaging and genomics\/proteomics is often limited by synthetic routes plagued by low atom economy and substantial side\u2010product formation. Through systematic investigation, we have developed a practical and efficient synthetic pathway for both symmetrical and unsymmetrical Cy3 derivatives, significantly minimizing resource utilization. Notably, this approach yields water as the by\u2010product, in alignment with sustainable chemistry principles. Moreover, the efficient one\u2010pot synthesis facilitates the detection of intracellular FA levels, utilizing the fluorescence signal of Cy3 in live cells. It is also possible to detect endogenous FA in the intestinal tissues. We observed a significant decrease in FA in the small intestine of inflammatory bowel disease (IBD) mice as compared to healthy mice. This methodological advancement not only enhances the scope of fluorescent dye synthesis but also contributes to sustainable practices within chemical manufacturing, offering a significant leap forward in the development of environmentally friendly synthetic strategies.<\/jats:p>","DOI":"10.1002\/anie.202413121","type":"journal-article","created":{"date-parts":[[2024,9,18]],"date-time":"2024-09-18T08:25:57Z","timestamp":1726647957000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Atom\u2010Efficient Synthesis of Trimethine Cyanines Using Formaldehyde as a Single\u2010Carbon Source"],"prefix":"10.1002","volume":"64","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5698-9976","authenticated-orcid":false,"given":"Sun Hyeok","family":"Lee","sequence":"first","affiliation":[{"name":"Basic Science Research Institute (BSRI) Pohang University of Science and Technology (POSTECH)  Pohang 37673 Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Taek\u2010Jun","family":"Lee","sequence":"additional","affiliation":[{"name":"Department of Chemistry Pohang University of Science and Technology (POSTECH)  Pohang 37673 Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sourav","family":"Sarkar","sequence":"additional","affiliation":[{"name":"Senpro Co., Ltd.  Pohang 37673 Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Heewon","family":"Cho","sequence":"additional","affiliation":[{"name":"Department of Chemistry Pohang University of Science and Technology (POSTECH)  Pohang 37673 Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0000-9902-259X","authenticated-orcid":false,"given":"Quynh Pham Nguyen","family":"Nhu","sequence":"additional","affiliation":[{"name":"Department of Chemistry Faculty of Science Chulalongkorn University  Bangkok 10330 Thailand"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1927-3688","authenticated-orcid":false,"given":"Young\u2010Tae","family":"Chang","sequence":"additional","affiliation":[{"name":"Department of Chemistry Pohang University of Science and Technology (POSTECH)  Pohang 37673 Republic of Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2024,10,31]]},"reference":[{"key":"e_1_2_3_1_1","unstructured":"\u00a0"},{"key":"e_1_2_3_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.apcata.2005.02.029"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1152\/physrev.00034.2014"},{"key":"e_1_2_3_4_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00386"},{"key":"e_1_2_3_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.9b03128"},{"key":"e_1_2_3_6_1","unstructured":"\u00a0"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b00959"},{"key":"e_1_2_3_8_2","first-page":"85","volume":"13","author":"Beurden K.","year":"2020","journal-title":"Green Chem. Lett. Rev."},{"key":"e_1_2_3_9_1","author":"Hunger K.","year":"2000","journal-title":"Ullmann's Encyclopedia of Industrial Chemistry"},{"key":"e_1_2_3_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.1c00386"},{"key":"e_1_2_3_11_1","volume":"2013","author":"Ullah S.","year":"2013","journal-title":"J. Chem-Ny"},{"key":"e_1_2_3_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2013.08.001"},{"key":"e_1_2_3_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202003697"},{"key":"e_1_2_3_14_1","unstructured":"\u00a0"},{"key":"e_1_2_3_15_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jlumin.2017.01.038"},{"key":"e_1_2_3_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2016.04.032"},{"key":"e_1_2_3_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.snb.2023.133404"},{"key":"e_1_2_3_18_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2CS00905F"},{"key":"e_1_2_3_19_1","unstructured":"\u00a0"},{"key":"e_1_2_3_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3CS60237K"},{"key":"e_1_2_3_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bpj.2019.05.026"},{"key":"e_1_2_3_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.6b00053"},{"key":"e_1_2_3_23_2","doi-asserted-by":"publisher","DOI":"10.1126\/sciadv.adf1488"},{"key":"e_1_2_3_24_1","unstructured":"\u00a0"},{"key":"e_1_2_3_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2014.02.009"},{"key":"e_1_2_3_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB01698K"},{"key":"e_1_2_3_27_1","unstructured":"\u00a0"},{"key":"e_1_2_3_28_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41592-021-01061-2"},{"key":"e_1_2_3_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.1c00483"},{"key":"e_1_2_3_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c04178"},{"key":"e_1_2_3_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202203444"},{"key":"e_1_2_3_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200804883"},{"key":"e_1_2_3_33_1","unstructured":"\u00a0"},{"key":"e_1_2_3_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2ra22291d"},{"key":"e_1_2_3_35_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10562-017-1969-9"},{"key":"e_1_2_3_36_1","doi-asserted-by":"publisher","DOI":"10.1017\/S1551929500057060"},{"key":"e_1_2_3_37_1","unstructured":"\u00a0"},{"key":"e_1_2_3_38_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41598-021-03365-x"},{"key":"e_1_2_3_39_2","first-page":"181","volume":"21","author":"Yu Q.","year":"2020","journal-title":"Mol. Med."},{"key":"e_1_2_3_40_1","unstructured":"\u00a0"},{"key":"e_1_2_3_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm501452j"},{"key":"e_1_2_3_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.11.041"},{"key":"e_1_2_3_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/acsabm.9b00025"},{"key":"e_1_2_3_44_1","unstructured":"\u00a0"},{"key":"e_1_2_3_45_2","doi-asserted-by":"publisher","DOI":"10.1039\/b801629a"},{"key":"e_1_2_3_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.0c00928"},{"key":"e_1_2_3_47_1","doi-asserted-by":"publisher","DOI":"10.1111\/jcmm.16602"},{"key":"e_1_2_3_48_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature23481"},{"key":"e_1_2_3_49_1","doi-asserted-by":"publisher","DOI":"10.1038\/77783"},{"key":"e_1_2_3_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.7b00044"},{"key":"e_1_2_3_51_1","doi-asserted-by":"publisher","DOI":"10.1002\/0471142735.im1525s104"},{"key":"e_1_2_3_52_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0505256102"},{"key":"e_1_2_3_53_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10895-009-0470-2"},{"key":"e_1_2_3_54_1","doi-asserted-by":"publisher","DOI":"10.1002\/jssc.201600345"},{"key":"e_1_2_3_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/acsami.7b04205"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202413121","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,5,15]],"date-time":"2025-05-15T08:15:39Z","timestamp":1747296939000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202413121"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,10,31]]},"references-count":55,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2025,1,2]]}},"alternative-id":["10.1002\/anie.202413121"],"URL":"https:\/\/doi.org\/10.1002\/anie.202413121","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,10,31]]},"assertion":[{"value":"2024-07-12","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2024-10-31","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202413121"}}