{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,29]],"date-time":"2026-07-29T00:36:52Z","timestamp":1785285412810,"version":"3.55.0"},"reference-count":49,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2023,8,25]],"date-time":"2023-08-25T00:00:00Z","timestamp":1692921600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Research Excellence Initiative of the University of Silesia in Katowice (MK)","award":["2019\/35\/B\/NZ5\/04208"],"award-info":[{"award-number":["2019\/35\/B\/NZ5\/04208"]}]},{"DOI":"10.13039\/501100004281","name":"National Science Centre","doi-asserted-by":"publisher","award":["2019\/35\/B\/NZ5\/04208"],"award-info":[{"award-number":["2019\/35\/B\/NZ5\/04208"]}],"id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>This paper presents the photophysical and biological properties of eight 3-imino-1,8-naphthalimides. The optical properties of the compounds were investigated in the solvents that differed in their polarity (dichloromethane, acetonitrile, and methanol), including three methods of sample preparation using different pre-dissolving solvents such as dimethyl sulfoxide or chloroform. In the course of the research, it was found that there are strong interactions between the tested compounds and DMSO, which was visible as a change in the maximum emission band (\u03bbem) of the neat 3-imino-1,8-naphthalimides (\u03bbem = 470\u2013480 nm) and between the compounds and DMSO (\u03bbem = 504\u2013514 nm). The shift of the emission maximum that was associated with the presence of a small amount of DMSO in the sample was as much as 41 nm. In addition, the susceptibility of imines to hydrolysis in the methanol\/water mixture with increasing water content and in the methanol\/water mixture (v\/v; 1:1) in the pH range from 1 to 12 was discussed. The studies showed that the compounds are hydrolysed in the CH3OH\/H2O system in an acidic environment (pH in the range of 1 to 4). In addition, it was found that partial hydrolysis occurs in systems with an increased amount of water, and its degree may depend on the type of substituent on the imine bond. The compounds tended to quench the emission (ACQ) in the aggregated state and increase the emission related to the protonation of the imine bond. Moreover, it was found that the substituent in the imine bonds influenced a compound\u2019s individual photophysical properties. Biological tests, including cytotoxicity studies and cellular localisation, were also performed for all of the molecules. All of the tested compounds exhibited green fluorescence in the MCF-7 cells and showed co-localisation in the mitochondria, endoplasmic reticulum, and lysosome. The obtained photophysical and biological results indicate the promising potential use of the tested compounds as cellular dyes.<\/jats:p>","DOI":"10.3390\/molecules28176255","type":"journal-article","created":{"date-parts":[[2023,8,28]],"date-time":"2023-08-28T06:10:22Z","timestamp":1693203022000},"page":"6255","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Spectroscopic and Biological Properties of the 3-Imino-1,8-naphthalimide Derivatives as Fluorophores for Cellular Imaging"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8658-1031","authenticated-orcid":false,"given":"Mateusz","family":"Korzec","sequence":"first","affiliation":[{"name":"Institute of Chemistry, University of Silesia in Katowice, 9 Szkolna Str., 40-006 Katowice, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6021-0892","authenticated-orcid":false,"given":"Sonia","family":"Kotowicz","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, University of Silesia in Katowice, 9 Szkolna Str., 40-006 Katowice, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4283-3126","authenticated-orcid":false,"given":"Katarzyna","family":"Malarz","sequence":"additional","affiliation":[{"name":"August Chelkowski Institute of Physics, University of Silesia in Katowice, 1A 75 Pu\u0142ku Piechoty Str., 41-500 Chorzow, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2228-1475","authenticated-orcid":false,"given":"Anna","family":"Mrozek-Wilczkiewicz","sequence":"additional","affiliation":[{"name":"August Chelkowski Institute of Physics, University of Silesia in Katowice, 1A 75 Pu\u0142ku Piechoty Str., 41-500 Chorzow, Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,8,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1007\/s10853-021-06602-w","article-title":"A systematic review on 1,8-naphthalimide derivatives as emissive materials in organic light-emitting diodes","volume":"57","author":"Kagatikar","year":"2022","journal-title":"J. Mater. Sci."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"16328","DOI":"10.1016\/j.synthmet.2020.116328","article-title":"A review of investigation on 4-substituted 1,8-naphthalimide derivatives","volume":"262","author":"Gudeika","year":"2020","journal-title":"Synth. Met."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"13501","DOI":"10.1039\/D0TC03681A","article-title":"1,8-Naphthalimide-based fluorescent chemosensors: Recent advances and perspectives","volume":"8","author":"Dong","year":"2020","journal-title":"J. Mater. Chem. C"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1016\/j.ejmech.2018.09.055","article-title":"l,8-Naphthalimide based DNA intercalators and anticancer agents. A systematic review from 2007 to 2017","volume":"159","author":"Tomczyk","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"214019","DOI":"10.1016\/j.ccr.2021.214019","article-title":"Recent advances in 1,8-naphthalimide-based small-molecule fluorescent probes for organelles imaging and tracking in living cells","volume":"444","author":"Yua","year":"2021","journal-title":"Coord. Chem. Rev."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Fu, Y., Pang, X.X., Wang, Z.Q., Qu, H.T., and Ye, F. (2018). Synthesis and Fluorescent Property Study of Novel 1,8-Naphthalimide-Based Chemosensors. Molecules, 23.","DOI":"10.3390\/molecules23020376"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"310","DOI":"10.1039\/B614529A","article-title":"Highly selective 4-amino-1,8-naphthalimide based fluorescent photoinduced electron transfer (PET) chemosensors for Zn(II) under physiological pH conditions","volume":"5","author":"Parkesh","year":"2007","journal-title":"Org. Biomol. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"5569","DOI":"10.1002\/chem.201705546","article-title":"Expanding the Breadth of 4-Amino-1,8-naphthalimide Photophysical Properties through Substitution of the Naphthalimide Core","volume":"24","author":"Leslie","year":"2018","journal-title":"Chem. Eur. J."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1685","DOI":"10.1039\/D1CC05798G","article-title":"Development of 1,8-naphthalimide dyes for rapid imaging of subcellular compartments in plants","volume":"58","author":"Kusano","year":"2022","journal-title":"Chem. Comm."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1016\/j.inoche.2014.02.035","article-title":"4-Amino-1,8-naphthalimide-based fluorescent sensor with high selectivity and sensitivity for Zn2+ imaging in living cells","volume":"43","author":"Liu","year":"2014","journal-title":"Inorg. Chem. Commun."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"5642","DOI":"10.1039\/c3ob40370j","article-title":"The effect of the 4-amino functionality on the photophysical and DNA binding properties of alkyl-pyridinium derived 1,8-naphthalimides","volume":"11","author":"Banerjee","year":"2013","journal-title":"Org. Biomol. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"4040","DOI":"10.1021\/ol9013602","article-title":"4-Amino-1,8-naphthalimide-Based Troger\u2019s Bases As High Affinity DNA Targeting Fluorescent Supramolecular Scaffolds","volume":"11","author":"Veale","year":"2009","journal-title":"Org. Lett."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"10064","DOI":"10.1002\/chem.202002088","article-title":"Synthesis of Nitro-Aryl Functionalised 4-Amino-1,8-Naphthalimides and Their Evaluation as Fluorescent Hypoxia Sensors","volume":"26","author":"Adair","year":"2020","journal-title":"Chem. Eur. J."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"135","DOI":"10.1016\/j.dyepig.2014.05.006","article-title":"Synthesis of 4-amino substituted 1,8-naphthalimide derivatives using palladium-mediated amination","volume":"109","author":"Fleming","year":"2014","journal-title":"Dyes Pigm."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"112626","DOI":"10.1016\/j.molliq.2020.112626","article-title":"Synthesis, photophysical properties and solvatochromic analysis of some naphthalene-1,8-dicarboxylic acid derivatives","volume":"303","author":"Nicolescu","year":"2020","journal-title":"J. Mol. Liq."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"114690","DOI":"10.1016\/j.molliq.2020.114690","article-title":"Colorimetric assay of fluoride goes digital: On the spot testing of F\u2212 ions in water using smartphone\u2019s digital imaging and test strip assay by a novel chromofluorogenic receptor based on 1,8-naphthalimide","volume":"324","author":"Yadav","year":"2021","journal-title":"J. Mol. Liq."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"121796","DOI":"10.1016\/j.molliq.2023.121796","article-title":"Novel 4,4\u2032-Binaphthalimidyl derivatives with carboxyalkyl side chains: Synthesis, Aggregation-induced emission, Hydrogel and Cell imaging","volume":"381","author":"Wang","year":"2023","journal-title":"J. Mol. Liq."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"112549","DOI":"10.1016\/j.molliq.2020.112549","article-title":"A naked-eye visible colorimetric and fluorescent chemosensor for rapid detection of fluoride anions: Implication for toxic fluorine-containing pesticides detection","volume":"302","author":"Wu","year":"2020","journal-title":"J. Mol. Liq."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"32304","DOI":"10.1039\/C7RA05423H","article-title":"Naphthalimide\u2013coumarin conjugate: Ratiometric fluorescent receptor for self-calibrating quantification of cyanide anions in cells","volume":"7","author":"Shiraishi","year":"2017","journal-title":"RSC Adv."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"130343","DOI":"10.1016\/j.molstruc.2021.130343","article-title":"A naked-eye visible colorimetric and ratiometric chemosensor based on Schiff base for fluoride anion detection","volume":"1236","author":"Yang","year":"2021","journal-title":"J. Mol. Struct."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"119112","DOI":"10.1016\/j.saa.2020.119112","article-title":"Dual-channel ratiometric recognition of Al3+ and F\u2212 ions through an ESIPT-ESICT signalling mechanism. Spectrochim","volume":"247","author":"Kumar","year":"2021","journal-title":"Acta A Mol. Biomol."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Hearn, K.N., Ashton, T.D., Acharya, R., Feng, Z., Gueven, N., and Pfeffer, F.M. (2021). Direct Amidation to Access 3-Amido-1,8-Naphthalimides Including Fluorescent Scriptaid Analogues as HDAC Inhibitors. Cells, 10.","DOI":"10.3390\/cells10061505"},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Shiraishi, Y., Nakatani, R., Takagi, S., Yamada, C., and Hirai, T. (2020). A Naphthalimide\u2013Sulfonylhydrazine Conjugate as a Fluorescent Chemodosimeter for Hypochlorite. Chemosensors, 8.","DOI":"10.3390\/chemosensors8040123"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"131921","DOI":"10.1016\/j.snb.2022.131921","article-title":"A 3,4-dimethoxy-1,8-naphthalimide for lipid droplet imaging in live and fixed cells","volume":"365","author":"Johnson","year":"2022","journal-title":"Sens. Actuators B Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"5829","DOI":"10.1021\/acsomega.8b03638","article-title":"Synthesis of a 3,4-Disubstituted 1,8-Naphthalimide-Based DNA Intercalator for Direct Imaging of Legionella pneumophila","volume":"4","author":"Sharma","year":"2019","journal-title":"ACS Omega"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/j.dyepig.2018.05.017","article-title":"Novel 1,8-naphthalimides substituted at 3-C position: Synthesis and evaluation of thermal, electrochemical and luminescent properties","volume":"158","author":"Kotowicz","year":"2018","journal-title":"Dyes Pigm."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3812","DOI":"10.1007\/s10853-019-04210-3","article-title":"Novel b-ketoenamines versus azomethines for organic electronics: Characterization of optical and electrochemical properties supported by theoretical studies","volume":"55","author":"Korzec","year":"2020","journal-title":"J. Mater. Sci."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"118442","DOI":"10.1016\/j.saa.2020.118442","article-title":"Live cell imaging by 3-imino-(2-phenol)-1,8-naphthalimides: The effect of ex vivo hydrolysis. Spectrochim","volume":"238","author":"Korzec","year":"2020","journal-title":"Acta A Mol. Biomol."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Kotowicz, S., Korzec, M., Malarz, K., Krystkowska, A., Mrozek-Wilczkiewicz, A., Golba, S., Siwy, M., Ma\u0107kowski, S., and Schab-Balcerzak, E. (2021). Luminescence and Electrochemical Activity of New Unsymmetrical 3-Imino-1,8-naphthalimide Derivatives. Materials, 14.","DOI":"10.3390\/ma14195504"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"109508","DOI":"10.1016\/j.dyepig.2021.109508","article-title":"1,8-Naphthalimides 3-substituted with imine or \u03b2-ketoenamine unit evaluated as compounds for organic electronics and cell imaging","volume":"193","author":"Korzec","year":"2021","journal-title":"Dyes Pigm."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"7604","DOI":"10.1039\/C6RA27547H","article-title":"A fluorescent dye with large Stokes shift and high stability: Synthesis and application to live cell imaging","volume":"7","author":"Gao","year":"2017","journal-title":"RSC Adv."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"62","DOI":"10.1021\/ja310324q","article-title":"A Photostable AIE Luminogen for Specific Mitochondrial Imaging and Tracking","volume":"135","author":"Leung","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"10940","DOI":"10.1039\/C9CC05624F","article-title":"A photo-stable and reversible pH-responsive nano-agent based on the NIR phenazine dye for photoacoustic imaging-guided photothermal therapy","volume":"55","author":"Yongchao","year":"2019","journal-title":"Chem. Commun."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"103144","DOI":"10.1016\/j.bioorg.2019.103144","article-title":"Lysosome imaging in cancer cells by pyrene-benzothiazolium dyes: An alternative imaging approach for LAMP-1 expression based visualization methods to avoid background interference","volume":"91","author":"Chathura","year":"2019","journal-title":"Bioorg. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"3102","DOI":"10.1038\/s41467-020-16924-z","article-title":"Organic NIR-II molecule with long blood half-life for in vivo dynamic vascular imaging","volume":"11","author":"Li","year":"2020","journal-title":"Nat. Commun."},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Kotowicz, S., Korzec, M., Ma\u0142ecki, J.G., Siwy, M., Ma\u0107kowski, S., and Schab-Balcerzak, E. (2022). Six New Unsymmetrical Imino-1,8-naphthalimide Derivatives Substituted at 3-C position\u2013Photophysical Investigations. Materials, 15.","DOI":"10.3390\/ma15197043"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"6207","DOI":"10.1021\/bi3005285","article-title":"The Extent of Pyrene Excimer Fluorescence Emission Is a Reflector of Distance and Flexibility: Analysis of the Segment Linking the LDL Receptor-Binding and Tetramerization Domains of Apolipoprotein E3","volume":"31","author":"Bains","year":"2012","journal-title":"Biochemistry"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"7909","DOI":"10.3390\/molecules16097909","article-title":"Pyrene: A Probe to Study Protein Conformation and Conformational Changes","volume":"16","author":"Bains","year":"2011","journal-title":"Molecules"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"318","DOI":"10.1016\/j.jphotochem.2017.08.030","article-title":"Excimer formation from particially overlapped anthracene dimer based on saddle-shaped cyclooctatetrathiophene as spacer","volume":"355","author":"Zhao","year":"2018","journal-title":"J. Photochem. Photobiol. A Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"621","DOI":"10.1515\/phys-2016-0071","article-title":"Hydrogen-bonding study of photoexcited 4-nitro-1,8-naphthalimide in hydrogen-donating solvents","volume":"14","author":"Cao","year":"2016","journal-title":"Open Phys."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"3641","DOI":"10.1039\/D2CC00474G","article-title":"Activating room-temperature phosphorescence of 1,8-naphthalimide by doping into aromatic dicarboxylic acids","volume":"58","author":"Wang","year":"2022","journal-title":"Chem. Commun."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"12081","DOI":"10.1021\/acsami.7b14473","article-title":"Functional 1,8-Naphthalimide AIE\/AIEEgens: Recent Advances and Prospects","volume":"10","author":"Gopikrishna","year":"2018","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"12832","DOI":"10.1021\/acs.jpcb.1c08126","article-title":"Emergence of Aggregation Induced Emission (AIE), Room-Temperature Phosphorescence (RTP), and Multistimuli Response from a Single Organic Luminogen by Directed Structural Modification","volume":"125","author":"Chatterjee","year":"2021","journal-title":"J. Phys. Chem. B"},{"key":"ref_44","first-page":"3655","article-title":"Aggregation-Induced Emission or Hydrolysis by Water? The Case of Schiff Bases in Aqueous Organic Solvents","volume":"122","author":"Pramanik","year":"2018","journal-title":"J. Phys. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"112020","DOI":"10.1016\/j.jphotobiol.2020.112020","article-title":"Hydrolysis of Schiff bases with phenyl-ethynyl-phenyl system: The importance for biological and physicochemical studies","volume":"212","author":"Vasylieva","year":"2020","journal-title":"J. Photochem. Photobiol. B Biol."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1237","DOI":"10.1515\/pac-2013-1025","article-title":"Naphthalimides for labeling and sensing applications","volume":"86","author":"Jia","year":"2014","journal-title":"Pure Appl. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"Georgiev, N.I., Bakov, V.V., and Bojinov, V.B. (2022). Photoinduced Electron Transfer and Aggregation-Induced Emission in 1,8-Naphthalimide Probes as a Platform for Detection of Acid\/Base Vapors. Photonics, 9.","DOI":"10.3390\/photonics9120994"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"24263","DOI":"10.1021\/acs.jpcc.9b07275","article-title":"Fluorescence Quenching of 4,4\u2032-Dimethoxytriphenylamine-Substituted Diketopyrrolopyrrole via Intramolecular Photoinduced Electron Transfer","volume":"39","author":"Hwang","year":"2019","journal-title":"Phys. Chem. C"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1111\/j.1365-2818.2006.01706.x","article-title":"A guided tour into subcellular colocalization analysis in light microscopy","volume":"224","author":"Bolte","year":"2006","journal-title":"J. Microsc."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/17\/6255\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T20:39:24Z","timestamp":1760128764000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/17\/6255"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,8,25]]},"references-count":49,"journal-issue":{"issue":"17","published-online":{"date-parts":[[2023,9]]}},"alternative-id":["molecules28176255"],"URL":"https:\/\/doi.org\/10.3390\/molecules28176255","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,8,25]]}}}