{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,7]],"date-time":"2026-09-07T20:24:01Z","timestamp":1788812641044,"version":"build-2803163510"},"reference-count":28,"publisher":"American Chemical Society (ACS)","issue":"28","license":[{"start":{"date-parts":[[2025,7,11]],"date-time":"2025-07-11T00:00:00Z","timestamp":1752192000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/100010940","name":"University of Nebraska Kearney","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100010940","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["1U54GM115458"],"award-info":[{"award-number":["1U54GM115458"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["5P20GM103427"],"award-info":[{"award-number":["5P20GM103427"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2025,7,22]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Hydroxy-1,8-naphthalimides are a class of fluorophores known for their strong photoacidity, which facilitates excited-state proton transfer (ESPT) and results in red-shifted fluorescence emission. Based on this unique photophysical behavior, we synthesized and evaluated four reaction-based fluorescent probes (L1\u2013L4) for the selective detection of hydrogen sulfide (H2S). Structure\u2013function analysis revealed that the position of the hydroxyl substituent plays a critical role in modulating ESPT efficiency, emission wavelength, and overall probe sensitivity. Specifically, L1 (3-hydroxy) and L3 (4-hydroxy) exhibited distinct fluorescence maxima at 617 and 550 nm, respectively. Both probes demonstrated exceptionally fast reactivity with H2S, with L3 showing enhanced sensitivity attributed to the increased stability of its 4-naphtholate intermediate. In contrast, L4, bearing a 2,4-dinitrobenzene ether (DNBE) group, showed reduced sensitivity but maintained high selectivity for H2S over biologically relevant thiols such as l-cysteine and glutathione. These results defined key structure\u2013activity relationships and offered design strategies for developing naphthalimide-based fluorescent probes for detecting reactive sulfur species.<\/jats:p>","DOI":"10.1021\/acsomega.5c05047","type":"journal-article","created":{"date-parts":[[2025,7,11]],"date-time":"2025-07-11T16:07:17Z","timestamp":1752250037000},"page":"31138-31146","source":"Crossref","is-referenced-by-count":10,"title":["Structure\u2013Function Analysis of Hydroxy-1,8-Naphthalimide\nPhotoacids for ESPT-Driven H2S Probes"],"prefix":"10.1021","volume":"10","author":[{"given":"Trevor","family":"Dvorak","sequence":"first","affiliation":[{"name":"University of Nebraska at Kearney , , 2504 Ninth Avenue , , ,","place":["Kearney, Nebraska, United States, 68849"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sunayn","family":"Cheku","sequence":"additional","affiliation":[{"name":"University of Nebraska at Kearney , , 2504 Ninth Avenue , , ,","place":["Kearney, Nebraska, United States, 68849"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Linus","family":"Borer","sequence":"additional","affiliation":[{"name":"University of Nebraska at Kearney , , 2504 Ninth Avenue , , ,","place":["Kearney, Nebraska, United States, 68849"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Haley","family":"Hernandez-Sandoval","sequence":"additional","affiliation":[{"name":"University of Nebraska at Kearney , , 2504 Ninth Avenue , , ,","place":["Kearney, Nebraska, United States, 68849"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kimberly A.","family":"Carlson","sequence":"additional","affiliation":[{"name":"University of Nebraska at Kearney , , 2504 Ninth Avenue , , ,","place":["Kearney, Nebraska, United States, 68849"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6789-0998","authenticated-orcid":true,"given":"Haishi","family":"Cao","sequence":"additional","affiliation":[{"name":"University of Nebraska at Kearney , , 2504 Ninth Avenue , , ,","place":["Kearney, Nebraska, United States, 68849"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2025,7,11]]},"reference":[{"key":"2026081813065804600_cit1","doi-asserted-by":"publisher","first-page":"6984","DOI":"10.1021\/jp9902295","article-title":"Photochemistry\nof \u201cSuper\u201d-Photoacids.\nSolvent Effects","volume":"103","author":"Solntsev","year":"1999","journal-title":"J. Phys. Chem. A"},{"key":"2026081813065804600_cit2","doi-asserted-by":"publisher","first-page":"13","DOI":"10.1021\/jp047465m","article-title":"Elementary\nSteps in Excited-State Proton Transfer","volume":"109","author":"Agmon","year":"2005","journal-title":"Phys.\nChem. A"},{"key":"2026081813065804600_cit3","doi-asserted-by":"publisher","first-page":"4658","DOI":"10.1021\/jp994454y","article-title":"Photochemistry of\n\u201cSuper\u201d Photoacids. 2. Excited-State Proton Transfer\nin Methanol\/Water Mixtures","volume":"104","author":"Solntsev","year":"2000","journal-title":"J. Phys. Chem. A"},{"key":"2026081813065804600_cit4","doi-asserted-by":"publisher","first-page":"114669","DOI":"10.1016\/j.ejmech.2022.114669","article-title":"A Water-Dependent Reversible Photoacidity Strategy for Cancer Treatment","volume":"242","author":"Kang","year":"2022","journal-title":"Eur. J. Med. Chem."},{"issue":"2","key":"2026081813065804600_cit5","doi-asserted-by":"publisher","DOI":"10.1002\/wnan.1408","article-title":"Photoactivated\nDrug Delivery and Bioimaging","volume":"9","author":"Yang","year":"2017","journal-title":"Wiley Interdiscip\nRev. Nanomed Nanobiotechnol"},{"key":"2026081813065804600_cit6","doi-asserted-by":"publisher","first-page":"32023","DOI":"10.1039\/C5CP05548B","article-title":"Photoacids\nas a New Fluorescence Tool For Tracking Structural Transitions of\nProteins: Following The Concentration-Induced Transition of Bovine\nSerum Albumin","volume":"17","author":"Amdursky","year":"2015","journal-title":"Phys. Chem. Chem. Phys."},{"key":"2026081813065804600_cit7","doi-asserted-by":"publisher","first-page":"10593","DOI":"10.1021\/ja00102a028","article-title":"Photoexcited Proton Transfer from Enhanced Photoacids","volume":"116","author":"Tolbert","year":"1994","journal-title":"J. E. J. Am. Chem. Soc."},{"key":"2026081813065804600_cit8","doi-asserted-by":"publisher","first-page":"8163","DOI":"10.1021\/ja00178a049","article-title":"Enhanced\nphotoacidities of cyanonaphthols","volume":"112","author":"Tolbert","year":"1990","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026081813065804600_cit9","doi-asserted-by":"publisher","first-page":"2515","DOI":"10.1021\/jp508334s","article-title":"Synthesis and Spectroscopic\nCharacterization of 1,8-Naphthalimide Derived \u201cSuper\u201d\nPhotoacids","volume":"119","author":"Kumpulainen","year":"2015","journal-title":"J. Phys. Chem. B"},{"key":"2026081813065804600_cit10","doi-asserted-by":"publisher","first-page":"6166","DOI":"10.1021\/acs.jpca.8b04417","article-title":"Excited-State\nProton Transfer from the Photoacid 2-Naphthol-8-sulfonate to Acetonitrile\/Water\nMixtures","volume":"122","author":"Gajst","year":"2018","journal-title":"J. Phys. Chem. A"},{"key":"2026081813065804600_cit11","doi-asserted-by":"publisher","first-page":"19","DOI":"10.1021\/ar990109f","article-title":"Excited-State Proton Transfer: From\nConstrained Systems\nto \u201cSuper\u201d Photoacids to Superfast Proton Transfer","volume":"35","author":"Tolbert","year":"2002","journal-title":"Acc. Chem. Res."},{"key":"2026081813065804600_cit12","doi-asserted-by":"publisher","first-page":"4594","DOI":"10.1021\/jp308746x","article-title":"Ultrafast Excited-State\nProton-Transfer Reaction of\n1-Naphthol-3,6-Disulfonate and Several 5-Substituted 1-Naphthol Derivatives","volume":"117","author":"Pre\u0301mont-Schwarz","year":"2013","journal-title":"J. Phys. Chem. B"},{"key":"2026081813065804600_cit13","doi-asserted-by":"publisher","first-page":"4124","DOI":"10.1021\/acs.chemrev.3c00683","article-title":"Activity-Based\nFluorescent Probes for Hydrogen Sulfide\nand Related Reactive Sulfur Species","volume":"124","author":"Fosnacht","year":"2024","journal-title":"Chem. Rev."},{"key":"2026081813065804600_cit14","doi-asserted-by":"publisher","first-page":"126415","DOI":"10.1016\/j.saa.2025.126415","article-title":"A portable\nsensing platform using a novel dipyrrolopyrazinedione-based aza-BODIPY\ndimer for highly efficient detection of hypochlorite and hydrazine","volume":"341","author":"Zhang","year":"2025","journal-title":"Spectrochim. Acta, Part A"},{"key":"2026081813065804600_cit15","doi-asserted-by":"publisher","first-page":"126286","DOI":"10.1016\/j.saa.2025.126286","article-title":"Rational\ndesign of an acid-sensitive fluorophore from 8-hydroxy quinoline derivative\nexhibiting proton activated charge transfer characteristics","volume":"339","author":"Akhil\nKumar","year":"2025","journal-title":"Spectrochim. Acta, Part A"},{"key":"2026081813065804600_cit16","doi-asserted-by":"publisher","first-page":"125900","DOI":"10.1016\/j.saa.2025.125900","article-title":"A new dithieno\u00ad[2,3-b]\u00adpyridine-fused\nBODIPY fluorescent probe for specific Cu2+ recognition","volume":"333","author":"Zhou","year":"2025","journal-title":"Spectrochim. Acta, Part A"},{"key":"2026081813065804600_cit17","doi-asserted-by":"publisher","first-page":"4767","DOI":"10.1039\/c2cc30730h","article-title":"Selective Turn-on\nFluorescent Probes for Imaging Hydrogen\nSulfide in Living Cells","volume":"48","author":"Montoya","year":"2012","journal-title":"Chem. Commun."},{"key":"2026081813065804600_cit18","doi-asserted-by":"publisher","first-page":"95920","DOI":"10.1039\/C6RA20478C","article-title":"Investigation of a Sensing Approach Based on a Rapid Reduction of\nAzide to Selectively Measure Bioavailability of H2S","volume":"6","author":"Kim","year":"2016","journal-title":"RSC Adv."},{"key":"2026081813065804600_cit19","doi-asserted-by":"publisher","first-page":"11643","DOI":"10.1039\/C9NJ02813G","article-title":"A Reversible\nand Turn-on Type Fluorescence\nBehaviour of Hydrogen Sulfide Via a Redox Cycle Between Selenoxide\nand Selenide","volume":"43","author":"Annaka","year":"2019","journal-title":"New J. Chem."},{"key":"2026081813065804600_cit20","doi-asserted-by":"publisher","first-page":"18003","DOI":"10.1021\/ja207851s","article-title":"Development of a Highly Selective Fluorescence Probe\nfor Hydrogen Sulfide","volume":"133","author":"Sasakura","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"2026081813065804600_cit21","doi-asserted-by":"publisher","first-page":"118437","DOI":"10.1016\/j.saa.2020.118437","article-title":"Fluorescent Probe for Detecting Hydrogen\nSulfide Based on Disulfide Nucleophilic Substitution-Addition","volume":"238","author":"Wu","year":"2020","journal-title":"Spectrochim. Acta, Part A"},{"key":"2026081813065804600_cit22","doi-asserted-by":"publisher","first-page":"1021","DOI":"10.1016\/j.freeradbiomed.2011.01.025","article-title":"Measurement of Plasma\nHydrogen Sulfide in vivo and\nin vitro","volume":"50","author":"Shen","year":"2011","journal-title":"Free Radic. Biol. Med."},{"key":"2026081813065804600_cit23","doi-asserted-by":"publisher","first-page":"2677","DOI":"10.1021\/jacsau.3c00427","article-title":"Advances and Opportunities\nin H2S Measurement\nin Chemical Biology","volume":"3","author":"Smith","year":"2023","journal-title":"JACS Au"},{"key":"2026081813065804600_cit24","doi-asserted-by":"publisher","first-page":"850","DOI":"10.1002\/asia.202100041","article-title":"BODIPY-based\nFluorescent Probe for Fast Detection of Hydrogen Sulfide and Lysosome-targeting\nApplications in Living Cells","volume":"16","author":"Yue","year":"2021","journal-title":"Chem.\ue5f8Asian\nJ."},{"key":"2026081813065804600_cit25","doi-asserted-by":"publisher","first-page":"32507","DOI":"10.1021\/acsomega.0c04659","article-title":"A Fluorescent Probe\nfor Selective Facile Detection of H2S in Serum Based on an Albumin-Binding\nFluorophore and Effective Masking Reagent","volume":"5","author":"Lee","year":"2020","journal-title":"ACS\nOmega"},{"issue":"1","key":"2026081813065804600_cit26","doi-asserted-by":"publisher","first-page":"50","DOI":"10.1038\/nrm2820","article-title":"Sensors and Regulators of Intracellular\npH","volume":"11","author":"Casey","year":"2010","journal-title":"Nat. Rev. Mol. Cell Biol."},{"key":"2026081813065804600_cit27","doi-asserted-by":"publisher","first-page":"24383","DOI":"10.1039\/C9CP05269K","article-title":"Divergent\nExcited State Proton Transfer Reactions of Bifunctional Photoacids\n1-Ammonium-2-naphthol and 3-Ammonium-2-naphthol in Water and Methanol","volume":"21","author":"Nelson","year":"2019","journal-title":"Phys. Chem. Chem. Phys."},{"key":"2026081813065804600_cit28","doi-asserted-by":"publisher","first-page":"58","DOI":"10.1039\/d1ay01700d","article-title":"Dinitrobenzene Ether\nReactive Turn-on Fluorescence Probes for the Selective Detection of\nH2S","volume":"14","author":"Dhivya","year":"2022","journal-title":"Anal. Methods"}],"container-title":["ACS Omega"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acsomega.5c05047","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/10\/28\/31138\/40845579\/ao5c05047.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/acsodf\/article-pdf\/10\/28\/31138\/40845579\/ao5c05047.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T18:42:55Z","timestamp":1787078575000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/acsodf\/article\/10\/28\/31138\/3655141\/Structure-Function-Analysis-of-Hydroxy-1-8"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,7,11]]},"references-count":28,"journal-issue":{"issue":"28","published-online":{"date-parts":[[2025,7,11]]},"published-print":{"date-parts":[[2025,7,22]]}},"URL":"https:\/\/doi.org\/10.1021\/acsomega.5c05047","relation":{},"ISSN":["2470-1343"],"issn-type":[{"value":"2470-1343","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,7,11]]}}}