{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,26]],"date-time":"2026-02-26T15:01:33Z","timestamp":1772118093508,"version":"3.50.1"},"reference-count":96,"publisher":"Wiley","issue":"12","license":[{"start":{"date-parts":[[2023,5,5]],"date-time":"2023-05-05T00:00:00Z","timestamp":1683244800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001665","name":"Agence Nationale de la Recherche","doi-asserted-by":"publisher","award":["ANR-18-CE07-0045"],"award-info":[{"award-number":["ANR-18-CE07-0045"]}],"id":[{"id":"10.13039\/501100001665","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001665","name":"Agence Nationale de la Recherche","doi-asserted-by":"publisher","award":["ANR-18-CE39-0014"],"award-info":[{"award-number":["ANR-18-CE39-0014"]}],"id":[{"id":"10.13039\/501100001665","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001665","name":"Agence Nationale de la Recherche","doi-asserted-by":"publisher","award":["ANR-21-CE07-0019-02"],"award-info":[{"award-number":["ANR-21-CE07-0019-02"]}],"id":[{"id":"10.13039\/501100001665","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["aces.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry \u0097 An Asian Journal"],"published-print":{"date-parts":[[2023,6,15]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Latent cyclic carbon\u2010centered nucleophiles (latent\n                    <jats:italic>C<\/jats:italic>\n                    \u2010nucleophiles) are recently proving their value in the field of reaction\u2010based fluorescent probes, far beyond their primary utility in organic synthesis. They are typically used to introduce a Michael acceptor moiety acting as a recognition\/reaction site for analyte to be detected or as a kinetic promoter of fluorogenic cascade reactions triggered by a reactive species.\n                    <jats:italic>C<\/jats:italic>\n                    \u2010nucleophiles bearing a further reactive handle offer an additional opportunity for tuning the physicochemical\/targeting properties or providing drug\u2010releasing capabilities to these probes, through the covalent attachment of\n                    <jats:italic>ad hoc<\/jats:italic>\n                    chemical moiety. In order to implement such strategy to fluorogenic\/chromogenic enzyme substrates based on the \u201ccovalent\u2010assembly\u201d principle, we have explored the potential of some functionalized derivatives of barbituric acid, piperidine\u20102,4\u2010dione and Meldrum's acid. Our investigations based on the rational design and analytical validations of enzyme\u2010responsive caged precursors of fluorescent pyronin dyes and 7\u2010(diethylamino)coumarin\u20103\u2010carboxylic acid, led to identify a versatile candidate suitable for this late\u2010stage structural optimization approach. This Meldrum's acid derivative enables to either enhance water solubility or achieve the reversible conjugation of a targeting ligand, while promoting\n                    <jats:italic>in\u2005situ<\/jats:italic>\n                    formation of fluorophore upon enzymatic activation. This study opens the way to novel multifunctional fluorescence imaging probes and optically modulated small conjugate\u2010based theranostics.\n                  <\/jats:p>","DOI":"10.1002\/asia.202300258","type":"journal-article","created":{"date-parts":[[2023,4,24]],"date-time":"2023-04-24T05:00:54Z","timestamp":1682312454000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Arylidene Meldrum's Acid: A Versatile Structural Motif for the Design of Enzyme\u2010Responsive \u201cCovalent\u2010Assembly\u201d Fluorescent Probes with Tailor\u2010Made Properties**"],"prefix":"10.1002","volume":"18","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4427-8146","authenticated-orcid":false,"given":"K\u00e9vin","family":"Renault","sequence":"first","affiliation":[{"name":"Institut de Chimie Mol\u00e9culaire de l'Universit\u00e9 de Bourgogne UMR 6302 CNRS Universit\u00e9 de Bourgogne  9, Avenue Alain Savary 21000 Dijon France"},{"name":"Present address: Department of Chemistry Laboratory of Bio-Organic Chemistry Namur Research Institute for Life Sciences (NARILIS) University of Namur (UNamur)  5000 Namur Belgium"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8624-2665","authenticated-orcid":false,"given":"Yoan","family":"Capello","sequence":"additional","affiliation":[{"name":"Institut de Chimie Mol\u00e9culaire de l'Universit\u00e9 de Bourgogne UMR 6302 CNRS Universit\u00e9 de Bourgogne  9, Avenue Alain Savary 21000 Dijon France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shun","family":"Yao","sequence":"additional","affiliation":[{"name":"Centre de Recherches sur les Macromol\u00e9cules V\u00e9g\u00e9tales (CERMAV) UPR 5301 CNRS Universit\u00e9 Grenoble Alpes  38000 Grenoble France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9673-1099","authenticated-orcid":false,"given":"Sami","family":"Halila","sequence":"additional","affiliation":[{"name":"Centre de Recherches sur les Macromol\u00e9cules V\u00e9g\u00e9tales (CERMAV) UPR 5301 CNRS Universit\u00e9 Grenoble Alpes  38000 Grenoble France"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2300-4499","authenticated-orcid":false,"given":"Anthony","family":"Romieu","sequence":"additional","affiliation":[{"name":"Institut de Chimie Mol\u00e9culaire de l'Universit\u00e9 de Bourgogne UMR 6302 CNRS Universit\u00e9 de Bourgogne  9, Avenue Alain Savary 21000 Dijon France"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2023,5,5]]},"reference":[{"key":"e_1_2_8_1_1","volume-title":"Encyclopedia of Reagents for Organic Synthesis","author":"Argintaru O. A.","year":"2011"},{"key":"e_1_2_8_2_1","first-page":"1","volume-title":"Advances in Heterocyclic Chemistry, Vol.\u200598","author":"El Ashry E. S. H.","year":"2009"},{"key":"e_1_2_8_3_1","unstructured":"\u00a0"},{"key":"e_1_2_8_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/cs9780700345"},{"key":"e_1_2_8_5_2","volume-title":"Encyclopedia of Reagents for Organic Synthesis","author":"Yonemitsu O.","year":"2010"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1OB00395J"},{"key":"e_1_2_8_7_1","unstructured":"For selected examples see:"},{"key":"e_1_2_8_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol802363x"},{"key":"e_1_2_8_9_2","doi-asserted-by":"publisher","DOI":"10.1117\/12.849452"},{"key":"e_1_2_8_10_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3ra42633e"},{"key":"e_1_2_8_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.aca.2014.09.018"},{"key":"e_1_2_8_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201801660"},{"key":"e_1_2_8_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/slct.201901254"},{"key":"e_1_2_8_14_1","unstructured":"For selected examples see:"},{"key":"e_1_2_8_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC04907A"},{"key":"e_1_2_8_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/pola.28467"},{"key":"e_1_2_8_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201900362"},{"key":"e_1_2_8_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2022.135031"},{"key":"e_1_2_8_19_1","unstructured":"For selected examples see:"},{"key":"e_1_2_8_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc36838b"},{"key":"e_1_2_8_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molliq.2019.02.129"},{"key":"e_1_2_8_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2020.108459"},{"key":"e_1_2_8_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2019.108144"},{"key":"e_1_2_8_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.snb.2021.130850"},{"key":"e_1_2_8_25_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11696-022-02475-8"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0QM00872A"},{"key":"e_1_2_8_27_1","unstructured":"\u00a0"},{"key":"e_1_2_8_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2018.04.010"},{"key":"e_1_2_8_29_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9OB01773A"},{"key":"e_1_2_8_30_1","unstructured":"\u00a0"},{"key":"e_1_2_8_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5SC02569A"},{"key":"e_1_2_8_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201901251"},{"key":"e_1_2_8_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.macromol.9b00533"},{"key":"e_1_2_8_34_1","unstructured":"For selected reviews see:"},{"key":"e_1_2_8_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar500179y"},{"key":"e_1_2_8_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201500088"},{"key":"e_1_2_8_36_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201500088"},{"key":"e_1_2_8_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00372"},{"key":"e_1_2_8_38_1","unstructured":"To the best of our knowledge there are currently only three examples of enzyme-responsive caged precursors of coumarins rationally designed to act as fluorogenic prodrugs see:"},{"key":"e_1_2_8_39_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC02932A"},{"key":"e_1_2_8_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.8b00511"},{"key":"e_1_2_8_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.9b00564"},{"key":"e_1_2_8_42_1","unstructured":"For reviews about \u201ccovalent-assembly\u201d fluorescent probes see:"},{"key":"e_1_2_8_43_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CC00542H"},{"key":"e_1_2_8_44_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1RA08037G"},{"key":"e_1_2_8_45_1","unstructured":"\u00a0"},{"key":"e_1_2_8_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010601)40:11<2004::AID-ANIE2004>3.0.CO;2-5"},{"key":"e_1_2_8_46_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010601)113:11<2056::AID-ANGE2056>3.0.CO;2-W"},{"key":"e_1_2_8_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo011148j"},{"key":"e_1_2_8_48_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB00370F"},{"key":"e_1_2_8_49_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2020.108496"},{"key":"e_1_2_8_50_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CS00841D"},{"key":"e_1_2_8_51_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201205369"},{"key":"e_1_2_8_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201205369"},{"key":"e_1_2_8_52_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7NJ01735A"},{"key":"e_1_2_8_53_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo026469p"},{"key":"e_1_2_8_54_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.saa.2020.119179"},{"key":"e_1_2_8_55_1","unstructured":"Unpublished results."},{"key":"e_1_2_8_56_1","unstructured":"\u00a0"},{"key":"e_1_2_8_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c02287"},{"key":"e_1_2_8_58_2","doi-asserted-by":"publisher","DOI":"10.1002\/cptc.202100268"},{"key":"e_1_2_8_59_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200352075"},{"key":"e_1_2_8_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200352075"},{"key":"e_1_2_8_60_1","doi-asserted-by":"publisher","DOI":"10.1039\/b502199p"},{"key":"e_1_2_8_61_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB02076F"},{"key":"e_1_2_8_62_1","unstructured":"For selected examples see:"},{"key":"e_1_2_8_63_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2NJ04920A"},{"key":"e_1_2_8_64_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2021.110054"},{"key":"e_1_2_8_65_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.snb.2021.131024"},{"key":"e_1_2_8_66_2","doi-asserted-by":"publisher","DOI":"10.1002\/adhm.202200400"},{"key":"e_1_2_8_67_2","doi-asserted-by":"publisher","DOI":"10.1039\/D2AN00030J"},{"key":"e_1_2_8_68_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2022.111004"},{"key":"e_1_2_8_69_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.cej.2022.139020"},{"key":"e_1_2_8_70_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.6b02111"},{"key":"e_1_2_8_71_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8NJ00383A"},{"key":"e_1_2_8_72_1","doi-asserted-by":"publisher","DOI":"10.1039\/p19940002975"},{"key":"e_1_2_8_73_1","unstructured":"\u00a0"},{"key":"e_1_2_8_74_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC01037G"},{"key":"e_1_2_8_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.9b00214"},{"key":"e_1_2_8_76_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.trac.2021.116189"},{"key":"e_1_2_8_77_2","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202102895"},{"key":"e_1_2_8_78_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5OB01624J"},{"key":"e_1_2_8_79_1","doi-asserted-by":"publisher","DOI":"10.1039\/c8pp00362a"},{"key":"e_1_2_8_80_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00042"},{"key":"e_1_2_8_81_1","unstructured":"\u00a0"},{"key":"e_1_2_8_82_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9NR00913B"},{"key":"e_1_2_8_83_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.analchem.9b02917"},{"key":"e_1_2_8_84_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotobiol.2020.112043"},{"key":"e_1_2_8_85_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2013.02.063"},{"key":"e_1_2_8_86_1","unstructured":"For 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