Publication:
A rapid access to activity-based and mitochondria targeting rhodol-like chromenoxanthene dyes for selective bioimaging

dc.contributor.coauthorKnysh, Iryna
dc.contributor.coauthorJacquemin, Denis
dc.contributor.departmentDepartment of Chemistry
dc.contributor.departmentGraduate School of Sciences and Engineering
dc.contributor.kuauthorBosson, Johann
dc.contributor.kuauthorKölemen, Safacan
dc.contributor.kuauthorDırak, Musa
dc.contributor.schoolcollegeinstituteCollege of Sciences
dc.contributor.schoolcollegeinstituteGRADUATE SCHOOL OF SCIENCES AND ENGINEERING
dc.date.accessioned2025-01-19T10:29:30Z
dc.date.issued2024
dc.description.abstractChromenoxanthenes 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.indexedbyWOS
dc.description.indexedbyScopus
dc.description.publisherscopeInternational
dc.description.sponsoredbyTubitakEuN/A
dc.description.sponsorshipJ.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.volume223
dc.identifier.doi10.1016/j.dyepig.2024.111952
dc.identifier.eissn1873-3743
dc.identifier.issn0143-7208
dc.identifier.quartileQ1
dc.identifier.scopus2-s2.0-85181980198
dc.identifier.urihttps://doi.org/10.1016/j.dyepig.2024.111952
dc.identifier.urihttps://hdl.handle.net/20.500.14288/25883
dc.identifier.wos1162046700001
dc.keywordsXanthene dye
dc.keywordsChromenoxanthene
dc.keywordsActivity-based probe
dc.keywordsMitochondria
dc.keywordsTwisted intramolecular charge transfer
dc.language.isoeng
dc.publisherElsevier Sci Ltd
dc.relation.grantnoEuropean Union [801509, 120C080]; French Agence Nationale de la Recherche (ANR); [ANR-20-CE29-0005]
dc.relation.ispartofDyes and Pigments
dc.subjectChemistry, applied
dc.subjectEngineering, chemical
dc.subjectMaterials science, textiles
dc.titleA rapid access to activity-based and mitochondria targeting rhodol-like chromenoxanthene dyes for selective bioimaging
dc.typeJournal Article
dspace.entity.typePublication
local.contributor.kuauthorBosson, Johann
local.contributor.kuauthorDırak, Musa
local.contributor.kuauthorKölemen, Safacan
local.publication.orgunit1College of Sciences
local.publication.orgunit1GRADUATE SCHOOL OF SCIENCES AND ENGINEERING
local.publication.orgunit2Department of Chemistry
local.publication.orgunit2Graduate School of Sciences and Engineering
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