{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,18]],"date-time":"2026-07-18T01:00:33Z","timestamp":1784336433436,"version":"3.55.0"},"reference-count":50,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2023,8,28]],"date-time":"2023-08-28T00:00:00Z","timestamp":1693180800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100005632","name":"National Centre for Research and Development","doi-asserted-by":"publisher","award":["POWR.03.02.00\u201300-I029\/16"],"award-info":[{"award-number":["POWR.03.02.00\u201300-I029\/16"]}],"id":[{"id":"10.13039\/501100005632","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Hydrogen sulfide (H2S) is an important gasotransmitter, but only a few methods are available for real-time detection. Fluorescent probes are attractive tools for biological applications because of their high sensitivity, convenience, rapid implementation, noninvasive monitoring capability, and simplicity in fluorescent imaging of living cells and tissues. Herein, we report on a pro-fluorescent probe, NAP-Py-N3 based on naphthalimide derivative, which was found to show high selectivity toward H2S over various other analytes, including biothiols, making it feasible to detect H2S. After reaction with H2S, this probe showed rapid and significant turn-on green fluorescent enhancement at 553 nm (about 54-fold, k2 = 9.62 M\u22121s\u22121), high sensitivity (LOD: 15.5 nM), significant Stokes shift (118 nm), and it was found that the fluorescence quantum yield of fluorescence product can reach 0.36. Moreover, the probe has also been successfully applied to detect the gaseous H2S and to confirm the presence of H2S released from modern organic donors, which in recent years have been commonly used to investigate the role of H2S in biological systems. All the results indicate that this probe is excellent and highly valuable.<\/jats:p>","DOI":"10.3390\/molecules28176299","type":"journal-article","created":{"date-parts":[[2023,8,29]],"date-time":"2023-08-29T08:59:05Z","timestamp":1693299545000},"page":"6299","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Sensitive Detection of Various Forms of Hydrogen Sulfide via Highly Selective Naphthalimide-Based Fluorescent Probe"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1398-1525","authenticated-orcid":false,"given":"Daniel","family":"S\u0142owi\u0144ski","sequence":"first","affiliation":[{"name":"Institute of Polymer and Dye Technology, Faculty of Chemistry, Lodz University of Technology, Stefanowskiego 16, 90-537 Lodz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ma\u0142gorzata","family":"\u015awierczy\u0144ska","sequence":"additional","affiliation":[{"name":"Institute of Polymer and Dye Technology, Faculty of Chemistry, Lodz University of Technology, Stefanowskiego 16, 90-537 Lodz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jaros\u0142aw","family":"Roma\u0144ski","sequence":"additional","affiliation":[{"name":"Department of Organic and Applied Chemistry, Faculty of Chemistry, University of Lodz, Tamka 12, 91-403 Lodz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7822-8182","authenticated-orcid":false,"given":"Rados\u0142aw","family":"Podsiad\u0142y","sequence":"additional","affiliation":[{"name":"Institute of Polymer and Dye Technology, Faculty of Chemistry, Lodz University of Technology, Stefanowskiego 16, 90-537 Lodz, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,8,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"118669","DOI":"10.1016\/j.jlumin.2021.118669","article-title":"A dicyanoisophorone-based near-infrared fluorescent probe with fast detection for H2S in living cells and zebrafish","volume":"243","author":"Cuiling","year":"2022","journal-title":"J. Lumin."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"129235","DOI":"10.1016\/j.snb.2020.129235","article-title":"Direct comparison of triggering motifs on chemiluminescent probes for hydrogen sulfide detection in water","volume":"329","author":"Levinn","year":"2021","journal-title":"Sens. Actuators B Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"107826","DOI":"10.1016\/j.dyepig.2019.107826","article-title":"High selective distinguishable detection GSH and H2S based on steric configuration of molecular in Vivo","volume":"172","author":"Li","year":"2020","journal-title":"Dye. Pigment."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.niox.2017.09.011","article-title":"Environmental toxicology of hydrogen sulfide","volume":"71","author":"Rubright","year":"2017","journal-title":"Nitric Oxide"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"118331","DOI":"10.1016\/j.saa.2020.118331","article-title":"A novel \u201cturn-on\u201d fluorescent probe based on hydroxy functionalized naphthalimide as a logic platform for visual recognition of H2S in environment and living cells","volume":"235","author":"Zhang","year":"2020","journal-title":"Spectrochim. Acta A Mol. Biomol. Spectrosc."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"10781","DOI":"10.1016\/j.dyepig.2019.107818","article-title":"A single fluorescent probe for one- and two-photon imaging hydrogen sulfide and hydrogen polysulfides with different fluorescence signals","volume":"172","author":"Zhao","year":"2020","journal-title":"Dye. Pigment."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1438","DOI":"10.1039\/C4RA13086C","article-title":"Performance comparison of two cascade reaction models in fluorescence off\u2013on detection of hydrogen sulfide","volume":"5","author":"Saha","year":"2015","journal-title":"RSC Adv."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"743","DOI":"10.1016\/j.snb.2018.11.136","article-title":"Dual sites fluorescence probe for hydrogen sulfide: AIEE activity and supramolecular assembly with \u03b2-cyclodextrin","volume":"282","author":"Zhu","year":"2019","journal-title":"Sens. Actuators B Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"850","DOI":"10.1016\/j.talanta.2018.12.014","article-title":"A highly sensitive and responsive fluorescent probe based on 6-azidechroman dye for detection and imaging of hydrogen sulfide in cells","volume":"195","author":"Qiao","year":"2019","journal-title":"Talanta"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"181","DOI":"10.1016\/j.alit.2020.10.003","article-title":"Hydrogen sulfide as a novel biomarker of asthma and chronic obstructive pulmonary disease","volume":"70","author":"Suzuki","year":"2021","journal-title":"Allergol. Int."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"122193","DOI":"10.1016\/j.saa.2022.122193","article-title":"A thiomorpholine-based fluorescent probe for the far-red hypochlorous acid monitoring","volume":"289","author":"Michalski","year":"2023","journal-title":"Spectrochim. Acta A Mol. Biomol. Spectrosc."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"339225","DOI":"10.1016\/j.aca.2021.339225","article-title":"Two simple but effective turn-on benzothiazole-based fluorescent probes for detecting hydrogen sulfide in real water samples and HeLa cells","volume":"1189","author":"Liu","year":"2022","journal-title":"Anal. Chim. Acta"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"112213","DOI":"10.1016\/j.jphotochem.2019.112213","article-title":"A quaternary ammonium modified fluorescent probe for hydrogen sulfide detection in living cells","volume":"389","author":"Liu","year":"2020","journal-title":"J. Photochem. Photobiol. A"},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Khattak, S., Rauf, M., Khan, N., Zhang, Q., Chen, H., Muhammad, P., Ansari, M., Alomary, M., Jahangir, M., and Zhang, C. (2022). Hydrogen sulfide biology and its role in cancer. Molecules, 27.","DOI":"10.3390\/molecules27113389"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1231","DOI":"10.1002\/bkcs.12611","article-title":"Hydrogen sulfide-activatable fluorescence turn-on azide-containing naphthalimide derivative","volume":"43","author":"Yoo","year":"2022","journal-title":"Bull. Korean Chem. Soc."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"117391","DOI":"10.1016\/j.saa.2019.117391","article-title":"Construction of ratiometric hydrogen sulfide probe with two reaction sites and its applications in solution and in live cells","volume":"224","author":"Fu","year":"2020","journal-title":"Spectrochim. Acta A Mol. Biomol. Spectrosc."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"847","DOI":"10.1113\/expphysiol.2011.057448","article-title":"Hydrogen sulfide and asthma","volume":"96","author":"Wang","year":"2011","journal-title":"Exp. Physiol."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"750","DOI":"10.1177\/0748233720945184","article-title":"Acute myocardial injury following hydrogen sulfide poisoning","volume":"36","author":"Mo","year":"2020","journal-title":"Toxicol. Ind. Health"},{"key":"ref_19","first-page":"131202","article-title":"Rapid and sensitive detection of H2S by a 4-phenylselenium coumarin as a dual-active-site fluorescent probe","volume":"354","author":"Chen","year":"2022","journal-title":"Spectrochim. Acta A Mol. Biomol. Spectrosc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"120390","DOI":"10.1016\/j.saa.2021.120390","article-title":"An ESIPT-based fluorescent probe with fast-response for detection of hydrogen sulfide in mitochondria","volume":"265","author":"Du","year":"2022","journal-title":"Spectrochim. Acta A Mol. Biomol. Spectrosc."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"129343","DOI":"10.1016\/j.snb.2020.129343","article-title":"A multi-signal mitochondria-targetable fluorescent probe for simultaneously discriminating Cys\/Hcy\/H2S, GSH, and SO2 and visualizing the endogenous generation of SO2 in living cells","volume":"330","author":"Zheng","year":"2020","journal-title":"Sens. Actuators B Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1126309","DOI":"10.3389\/fchem.2023.1126309","article-title":"H2S-based fluorescent imaging for pathophysiological processes","volume":"11","author":"Jia","year":"2023","journal-title":"Front. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"264","DOI":"10.1016\/j.jphotochem.2018.11.011","article-title":"Triggered emission for rapid detection of hydrogen sulfide chaperoned by large Stokes shift","volume":"317","author":"Biswas","year":"2019","journal-title":"J. Photochem. Photobiol. A."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1016\/bs.mie.2014.11.011","article-title":"Four-azide-based fluorescent probes: Imaging hydrogen sulfide in living systems","volume":"554","author":"Lin","year":"2015","journal-title":"Meth. Enzymol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"109059","DOI":"10.1016\/j.dyepig.2020.109059","article-title":"Si-coumarin-based fluorescent probes for ultrafast monitoring H2S in vivo","volume":"186","author":"Sun","year":"2021","journal-title":"Dye. Pigment."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"10078","DOI":"10.1021\/ja203661j","article-title":"Reaction-based fluorescent probes for selective imaging of hydrogen sulfide in living cells","volume":"133","author":"Lippert","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"183","DOI":"10.1016\/j.dyepig.2018.11.050","article-title":"A near-infrared fluorescent probe based on SNAr reaction for H2S\/GSH detection in living cells and zebrafish","volume":"163","author":"Zhang","year":"2019","journal-title":"Dye. Pigment."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1016\/j.talanta.2018.12.031","article-title":"A long-wavelength-emitting fluorescent probe for simultaneous discrimination of H2S\/Cys\/GSH and its bio-imaging applications","volume":"196","author":"Niu","year":"2019","journal-title":"Talanta"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"152","DOI":"10.1016\/j.aca.2018.10.048","article-title":"A ratiometric time-gated luminescence probe for hydrogen sulfide based on copper (II)-coupled lanthanide complexes","volume":"1049","author":"Tang","year":"2019","journal-title":"Anal. Chim. Acta"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2272","DOI":"10.1002\/ejic.201500070","article-title":"A Copper Porphyrin for Sensing H2S in Aqueous Solution via a \u201cCoordinative-Based\u201d Approach","volume":"13","author":"Mirra","year":"2015","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_31","first-page":"3900","article-title":"A Cyclam-Based Fluorescent Ligand as a Molecular Beacon for Cu2+ and H2S Detection. Eur","volume":"33","author":"Mirra","year":"2017","journal-title":"J. Inorg. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"16697","DOI":"10.1021\/ja408909h","article-title":"Chemiluminescent Detection of Enzymatically-Produced Hydrogen Sulfide: Substrate Hydrogen Bonding Influences Selectivity for H2S over Biological Thiols","volume":"135","author":"Bailey","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"787","DOI":"10.1016\/j.dyepig.2018.09.001","article-title":"A red to near-infrared fluorescent probe featuring a super large Stokes shift for light-up detection of endogenous H2S","volume":"160","author":"Hong","year":"2019","journal-title":"Dye. Pigment."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"497","DOI":"10.1124\/pr.117.014050","article-title":"International union of basic and clinical pharmacology. CII: Pharmacological modulation of H2S levels: H2S Donors and H2S biosynthesis inhibitors","volume":"69","author":"Szabo","year":"2017","journal-title":"Pharmacol Rev."},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Corvino, A., Frecentese, F., Magli, E., Perissutti, E., Santagada, V., Scognamiglio, A., Caliendo, G., Fiorino, F., and Severino, B. (2021). Trends in H2S-donors chemistry and their effects in cardiovascular diseases. Antioxidants, 10.","DOI":"10.3390\/antiox10030429"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"613989","DOI":"10.3389\/fphar.2021.613989","article-title":"GYY4137 and sodium hydrogen sulfide relaxations are inhibited by L-Cysteine and KV7 channel blockers in rat small mesenteric arteries","volume":"2","author":"Abramavicius","year":"2021","journal-title":"Front. Pharmacol."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"347","DOI":"10.1016\/j.dyepig.2013.03.008","article-title":"Comparative analysis of the PET and ICT sensor properties of 1,8-naphthalimides containing aza-15-crown-5 ether moiety","volume":"98","author":"Panchenko","year":"2013","journal-title":"Dye. Pigment."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"4196","DOI":"10.1021\/acs.orglett.5b01962","article-title":"Diallyl trisulfide is a fast H2S donor, but diallyl disulfide is a slow one: The reaction pathways and intermediates of glutathione with polysulfides","volume":"17","author":"Liang","year":"2015","journal-title":"Org. Lett."},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Lee, Z., Zhou, J., Chen, C., Zhao, Y., Tan, C., Li, L., Moore, P., and Deng, L. (2011). The slow-releasing hydrogen sulfide donor, GYY4137, exhibits novel anti- cancer effects in vitro and in vivo. PLoS ONE, 6.","DOI":"10.1371\/journal.pone.0021077"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1099","DOI":"10.1021\/ja01223a023","article-title":"The kinetics of diffusion controlled molecular and ionic reactions in solution as determined by measurements of the quenching of fluorescence","volume":"67","author":"Umberger","year":"1945","journal-title":"J. Am. Chem. Soc."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"109765","DOI":"10.1016\/j.dyepig.2021.109765","article-title":"Hymecromone naph-thoquinone ethers as probes for hydrogen sulfide detection","volume":"196","author":"Grzelakowska","year":"2021","journal-title":"Dye. Pigment."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"5696","DOI":"10.1039\/C6TC01241H","article-title":"A thermoresponsive fluorescent rotor based on a hinged naphthalimide for a viscometer and a viscosity-related thermometer","volume":"4","author":"Xia","year":"2016","journal-title":"J. Mater. Chem. C"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"624","DOI":"10.1016\/j.dyepig.2018.10.072","article-title":"A mitochondria-targeted dual-reactable fluorescent probe for fast detection of H2S in living cells","volume":"162","author":"Ma","year":"2019","journal-title":"Dye. Pigment."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"5115","DOI":"10.1039\/c4ob00285g","article-title":"A colorimetric and ratiometric fluorescent probe for the imaging of endogenous hydrogen sulphide in living cells and sulphide determination in mouse hippocampus","volume":"12","author":"Zhang","year":"2014","journal-title":"Org. Biomol. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"3586","DOI":"10.1002\/asia.201402808","article-title":"O-fluorination of aromatic azides yields improved azido-based fluorescent probes for hydrogen sulfide: Synthesis, spectra, and bioimaging","volume":"9","author":"Wei","year":"2014","journal-title":"Chem. Asian J."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"134","DOI":"10.1016\/j.talanta.2017.02.012","article-title":"A ratiometric two-photon fluorescent probe for imaging hydrogen sulfide in lysosomes","volume":"167","author":"Feng","year":"2017","journal-title":"Talanta"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1016\/j.aca.2014.12.054","article-title":"A ratiometric fluorescent probe for gasotransmitter hydrogen sulfide based on a coumarin-benzopyrylium platform","volume":"859","author":"Duan","year":"2015","journal-title":"Anal. Chim. Acta"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"10216","DOI":"10.1021\/jacs.5b04196","article-title":"Bright fluorescent probe for H2S enables analyte-responsive, 3D imaging in live zebrafishu light sheet fluorescence microscopy","volume":"137","author":"Hammers","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"4214","DOI":"10.1039\/C3CC49605H","article-title":"A new fluorescent probe for gasotransmitter H2S: High sensitivity, excellent selectivity, and a significant fluorescence off\u2013on response","volume":"50","author":"Zhang","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"13594","DOI":"10.1039\/C9NJ02849H","article-title":"An instantaneous fluorescent probe for detecting hydrogen sulfide in biological systems","volume":"43","author":"Fang","year":"2019","journal-title":"New J. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/17\/6299\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T20:41:17Z","timestamp":1760128877000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/17\/6299"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,8,28]]},"references-count":50,"journal-issue":{"issue":"17","published-online":{"date-parts":[[2023,9]]}},"alternative-id":["molecules28176299"],"URL":"https:\/\/doi.org\/10.3390\/molecules28176299","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,8,28]]}}}