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This approach frequently relies on organic photoremovable protecting groups (photocages) that combine stability in living systems with controlled uncaging under visible or near\u2010infrared (NIR) light. Here, we report novel, redshifted\n                    <jats:italic>o<\/jats:italic>\n                    \u2010nitrophenethyl (\n                    <jats:italic>o<\/jats:italic>\n                    \u2010NPE) photocages based on an electron\u2010rich julolidine scaffold that enable the traceless release of amine\u2010bearing payloads upon visible\u2010light or two\u2010photon NIR activation. Electron donor\u2010enhanced\n                    <jats:italic>o<\/jats:italic>\n                    \u2010NPE photoremovable protecting groups with redshifted absorption were conjugated to doxorubicin and a combretastatin A\u20104 (CA\u2010A4) analogue, yielding stable prodrugs under biomimetic dark conditions. Upon UV\/visible irradiation or two\u2010photon NIR excitation, these prodrugs undergo light\u2010triggered uncaging via an\n                    <jats:italic>aci<\/jats:italic>\n                    \u2010nitro\/\n                    <jats:italic>\u03b2<\/jats:italic>\n                    \u2010elimination pathway. The resulting photoactivated prodrugs exhibit robust light\u2010dependent cytotoxicity with negligible dark activity, achieving selective activation in cancer cell lines. These findings position redshifted julolidine\u2010based\n                    <jats:italic>o<\/jats:italic>\n                    \u2010NPE cages as versatile platforms for visible\/NIR\u2010addressable amine prodrugs and establish design principles that advance organic photocaging strategies toward in vivo application and clinical translation.\n                  <\/jats:p>","DOI":"10.1002\/chem.71842","type":"journal-article","created":{"date-parts":[[2026,10,24]],"date-time":"2026-10-24T07:00:21Z","timestamp":1792825221000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Photoactivated Prodrugs Based on Julolidine\u2010\n                    <i>o<\/i>\n                    \u2010Nitrophenethyl Photocages for Traceless Release of Amine Payloads"],"prefix":"10.1002","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1954-6949","authenticated-orcid":false,"given":"Jo\u00e3o","family":"Vaz","sequence":"first","affiliation":[{"name":"Research Institute for Medicines (Imed.Ulisboa), Faculdade de Farm\u00e1cia Universidade de Lisboa  Lisboa Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Am\u00edlcar","family":"Duque\u2010Prata","sequence":"additional","affiliation":[{"name":"CQC\u2010IMS, Coimbra Chemistry Centre Institute of Molecular Sciences, University of Coimbra  Coimbra Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3515-0781","authenticated-orcid":false,"given":"Vanda","family":"Marques","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (Imed.Ulisboa), Faculdade de Farm\u00e1cia Universidade de Lisboa  Lisboa Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0004-1598-5495","authenticated-orcid":false,"given":"Bruno","family":"Castro","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (Imed.Ulisboa), Faculdade de Farm\u00e1cia Universidade de Lisboa  Lisboa Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4829-754X","authenticated-orcid":false,"given":"Cec\u00edlia","family":"Rodrigues","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (Imed.Ulisboa), Faculdade de Farm\u00e1cia Universidade de Lisboa  Lisboa Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8110-2740","authenticated-orcid":false,"given":"Maria de Jesus","family":"Perry","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (Imed.Ulisboa), Faculdade de Farm\u00e1cia Universidade de Lisboa  Lisboa Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3223-4819","authenticated-orcid":false,"given":"Lu\u00eds G.","family":"Arnaut","sequence":"additional","affiliation":[{"name":"CQC\u2010IMS, Coimbra Chemistry Centre Institute of Molecular Sciences, University of Coimbra  Coimbra Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0727-9852","authenticated-orcid":false,"given":"Rui","family":"Moreira","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (Imed.Ulisboa), Faculdade de Farm\u00e1cia Universidade de Lisboa  Lisboa Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,10,23]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"crossref","first-page":"21021","DOI":"10.1021\/acsami.8b01114","article-title":"Applications of Light\u2010Responsive Systems for Cancer Theranostics","volume":"10","author":"Chen H.","year":"2018","journal-title":"ACS Applied Materials & Interfaces"},{"issue":"48","key":"e_1_2_8_3_1","doi-asserted-by":"crossref","first-page":"10690","DOI":"10.1039\/b917753a","article-title":"Photoactivated Chemotherapy (PACT): The Potential of Excited\u2010State D\u2010Block Metals in Medicine","volume":"38","author":"Farrer N. 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T.","year":"2023","journal-title":"Polymer Chemistry"},{"key":"e_1_2_8_23_1","doi-asserted-by":"crossref","first-page":"9410","DOI":"10.1021\/acs.orglett.9b03624","article-title":"Green\u2010Light Activatable, Water\u2010Soluble Red\u2010Shifted Coumarin Photocages","volume":"21","author":"Bojt\u00e1r M.","year":"2019","journal-title":"Organic Letters"},{"key":"e_1_2_8_24_1","doi-asserted-by":"crossref","first-page":"3611","DOI":"10.1039\/D4SC06578F","article-title":"Precise Photorelease in Living Cells by High\u2010Viscosity Activatable Coumarin\u2010Based Photocages","volume":"16","author":"Huang X.","year":"2025","journal-title":"Chemical Science"},{"key":"e_1_2_8_25_1","doi-asserted-by":"crossref","first-page":"14334","DOI":"10.1021\/acs.joc.2c01781","article-title":"Efficiency of Functional Group Caging With Second\u2010Generation Green\u2010 and Red\u2010Light\u2010Labile BODIPY Photoremovable Protecting Groups","volume":"87","author":"Shrestha P.","year":"2022","journal-title":"Journal of Organic Chemistry"},{"key":"e_1_2_8_26_1","doi-asserted-by":"crossref","first-page":"9525","DOI":"10.1002\/anie.200803964","article-title":"Molecular Engineering of Photoremovable Protecting Groups for Two\u2010Photon Uncaging","volume":"47","author":"Gug S.","year":"2008","journal-title":"Angewandte Chemie International Edition"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jphotochemrev.2021.100423"},{"key":"e_1_2_8_28_1","doi-asserted-by":"crossref","first-page":"1225","DOI":"10.3390\/encyclopedia2030082","article-title":"Photoremovable Protecting Groups","volume":"2","author":"Dunkel P.","year":"2022","journal-title":"Encyclopedia"},{"key":"e_1_2_8_29_1","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/j.csbj.2019.11.007","article-title":"Long\u2010Wavelength Photoremovable Protecting Groups: On the Way to In Vivo Application","volume":"18","author":"Vorobev A. Y.","year":"2020","journal-title":"Computational and Structural Biotechnology Journal"},{"key":"e_1_2_8_30_1","doi-asserted-by":"crossref","first-page":"726","DOI":"10.1021\/acs.joc.9b02780","article-title":"Two\u2010Photon Excitable Photoremovable Protecting Groups Based on the Quinoline Scaffold for Use in Biology","volume":"85","author":"Hennig A. L. K.","year":"2020","journal-title":"Journal of Organic Chemistry"},{"key":"e_1_2_8_31_1","doi-asserted-by":"crossref","first-page":"578","DOI":"10.1039\/c2pp05360h","article-title":"The Donor\u2010Acceptor Biphenyl Platform: A Versatile Chromophore for the Engineering of Highly Efficient Two\u2010Photon Sensitive Photoremovable Protecting Groups","volume":"11","author":"Specht A.","year":"2012","journal-title":"Photochemical and Photobiological Sciences"},{"key":"e_1_2_8_32_1","doi-asserted-by":"crossref","first-page":"1822","DOI":"10.1021\/acs.jmedchem.1c00750","article-title":"One\u2010 and Two\u2010Photon Uncaging of Carbon Monoxide (CO) With Real\u2010Time Monitoring: On\u2010Demand Carbazole\u2010Based Dual CO\u2010Releasing Platform to Test Over Single and Combinatorial Approaches for the Efficient Regression of Orthotopic Murine Melanoma In Vivo","volume":"65","author":"Venkatesh Y.","year":"2022","journal-title":"Journal of Medicinal Chemistry"},{"key":"e_1_2_8_33_1","doi-asserted-by":"crossref","first-page":"291","DOI":"10.1007\/s10847-021-01071-9","article-title":"Photolytical Reactions for Light Induced Biological Effectors Release: On the Road to the Phototherapeutic Window","volume":"101","author":"Morville C.","year":"2021","journal-title":"Journal of Inclusion Phenomena and Macrocyclic Chemistry"},{"key":"e_1_2_8_34_1","doi-asserted-by":"crossref","first-page":"1821","DOI":"10.1039\/c5pp00245a","article-title":"Two\u2010photon Uncageable Enzyme Inhibitors Bearing Targeting Vectors","volume":"14","author":"Anstaett P.","year":"2015","journal-title":"Photochemical & Photobiological Sciences"},{"key":"e_1_2_8_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/cplu.201900139"},{"key":"e_1_2_8_36_1","doi-asserted-by":"crossref","first-page":"15888","DOI":"10.1021\/acs.joc.2c01987","article-title":"Tris(4\u2032\u2010Nitrobiphenyl)Amine\u2500An Octupolar Chromophore With High Two\u2010Photon Absorption Cross\u2010Section and Its Application for Uncaging of Calcium Ions in the Near\u2010Infrared Region","volume":"87","author":"Nguyen L. 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