Publication: A rapid access to activity-based and mitochondria targeting rhodol-like chromenoxanthene dyes for selective bioimaging
dc.contributor.coauthor | Knysh, Iryna | |
dc.contributor.coauthor | Jacquemin, Denis | |
dc.contributor.department | Department of Chemistry | |
dc.contributor.department | Graduate School of Sciences and Engineering | |
dc.contributor.kuauthor | Bosson, Johann | |
dc.contributor.kuauthor | Kölemen, Safacan | |
dc.contributor.kuauthor | Dırak, Musa | |
dc.contributor.schoolcollegeinstitute | College of Sciences | |
dc.contributor.schoolcollegeinstitute | GRADUATE SCHOOL OF SCIENCES AND ENGINEERING | |
dc.date.accessioned | 2025-01-19T10:29:30Z | |
dc.date.issued | 2024 | |
dc.description.abstract | Chromenoxanthenes are colorful dyes which do not suffer from any fluorescence turn -off induced by spirocyclic forms as usually observed for conventional rhodamine and fluorescein xanthene analogues. In that way, wide variety of applications in particular in bioimaging can be foreseen for those underexplored fluorophores. Herein, a one-pot synthesis of rhodol-like chromenoxanthene dyes is reported, which are further modified at the periphery of the core structure to tune the optical properties. Resulting neutral derivatives are bright fluorophores in the orange -red spectral window, while cationic counterparts are almost non-emissive. These optical properties are fully characterized and are also rationalized via first-principles calculations. In particular, the occurrence of twisted intramolecular charge transfers is shown to account for the dark -state quenching occurring in the charged compounds. This feature is harvested in the construction of an activity-based fluorescent probe for mitochondria imaging. Excellent organelle localization is achieved, while the emission signal is proportional to the hydrogen peroxide concentration in the mitochondria. Furthermore, the absence of cytotoxicity bestows rhodol-like chromenoxanthene dyes a bright future in cellular imaging applications. | |
dc.description.indexedby | WOS | |
dc.description.indexedby | Scopus | |
dc.description.publisherscope | International | |
dc.description.sponsoredbyTubitakEu | N/A | |
dc.description.sponsorship | J.B. thanks the financial support of the European Union (Horizon 2020) and the Scientific and Technological Research Institution of Tuerkiye (TUEBITAK) in the framework of the 2236 Co -Funded Brain Circulation Scheme 2 [CoCirculation2, grant agreement No 801509, project No 120C080] . J.B. thanks Prof. Onder Metin (Koc University) for offering lab space in his research group. I.K. and D.J. are indebted to the French Agence Nationale de la Recherche (ANR) [Contract No. ANR-20- CE29-0005 (BSE-Forces) ] . This work used computational resources generously provided by the CCIPL/GliCID computational center installed in Nantes. The authors are grateful to Dr Sundus Erbas Cakmak for providing B16-F10 cells. The authors thank Dr. Bengisu Y & imath;lmaz and Prof. Ug ur UEnal (Koc University) for their assistance in recording cyclic voltammograms. The authors thank the Koc University Surface Science and Technology Center (KUYTAM) for providing access to their spectrophotometers. The authors gratefully acknowledge the use of the services and facilities of the Koc University Research Center for Translational Medicine (KUTTAM) , funded by the Presidency of Tuerkiye, Head of Strategy and Budget. | |
dc.description.volume | 223 | |
dc.identifier.doi | 10.1016/j.dyepig.2024.111952 | |
dc.identifier.eissn | 1873-3743 | |
dc.identifier.issn | 0143-7208 | |
dc.identifier.quartile | Q1 | |
dc.identifier.scopus | 2-s2.0-85181980198 | |
dc.identifier.uri | https://doi.org/10.1016/j.dyepig.2024.111952 | |
dc.identifier.uri | https://hdl.handle.net/20.500.14288/25883 | |
dc.identifier.wos | 1162046700001 | |
dc.keywords | Xanthene dye | |
dc.keywords | Chromenoxanthene | |
dc.keywords | Activity-based probe | |
dc.keywords | Mitochondria | |
dc.keywords | Twisted intramolecular charge transfer | |
dc.language.iso | eng | |
dc.publisher | Elsevier Sci Ltd | |
dc.relation.grantno | European Union [801509, 120C080]; French Agence Nationale de la Recherche (ANR); [ANR-20-CE29-0005] | |
dc.relation.ispartof | Dyes and Pigments | |
dc.subject | Chemistry, applied | |
dc.subject | Engineering, chemical | |
dc.subject | Materials science, textiles | |
dc.title | A rapid access to activity-based and mitochondria targeting rhodol-like chromenoxanthene dyes for selective bioimaging | |
dc.type | Journal Article | |
dspace.entity.type | Publication | |
local.contributor.kuauthor | Bosson, Johann | |
local.contributor.kuauthor | Dırak, Musa | |
local.contributor.kuauthor | Kölemen, Safacan | |
local.publication.orgunit1 | College of Sciences | |
local.publication.orgunit1 | GRADUATE SCHOOL OF SCIENCES AND ENGINEERING | |
local.publication.orgunit2 | Department of Chemistry | |
local.publication.orgunit2 | Graduate School of Sciences and Engineering | |
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