Fluorescent Arylphosphonic Acids: Synergic Interactions between Bone and the Fluorescent Core

dc.contributor.authorZorlu, Yunus
dc.contributor.authorBrown, Connor
dc.contributor.authorKeil, Claudia
dc.contributor.authorAyhan, M. Menaf
dc.contributor.authorHaase, Hajo
dc.contributor.authorThompson, Richard B.
dc.contributor.authorLengyel, Imre
dc.contributor.authorYücesan, Gündoğ
dc.date.accessioned2020-11-10T14:49:49Z
dc.date.available2020-11-10T14:49:49Z
dc.date.issued2020-07-28
dc.date.updated2020-11-09T18:07:38Z
dc.description.abstractHerein, we report the third generation of fluorescent probes (arylphosphonic acids) to target calcifications, particularly hydroxyapatite (HAP). In this study, we use highly conjugated porphyrin‐based arylphosphonic acids and their diesters, namely 5,10,15,20‐tetrakis[m‐(diethoxyphosphoryl)phenyl]porphyrin (m‐H8TPPA‐OEt8) and 5,10,15,20‐tetrakis [m‐phenylphosphonic acid]porphyrin (m‐H8TPPA), in comparison with their positional isomers 5,10,15,20‐tetrakis[p‐(diisopropoxyphosphoryl)phenyl]porphyrin (p‐H8TPPA‐iPr8) and 5,10,15,20‐tetrakis [p‐phenylphosphonic acid]porphyrin (p‐H8TPPA), which have phosphonic acid units bonded to sp2 carbon atoms of the fluorescent core. The conjugation of the fluorescent core is thus extended to the (HAP) through sp2‐bonded −PO3H2 units, which generates increased fluorescence upon HAP binding. The resulting fluorescent probes are highly sensitive towards the HAP in rat bone sections. The designed probes are readily taken up by cells. Due to the lower reported toxicity of (p‐H8TPPA), these probes could find applications in monitoring bone resorption or adsorption, or imaging vascular or soft tissue calcifications for breast cancer diagnosis etc.en
dc.description.sponsorshipTU Berlin, Open-Access-Mittel – 2020en
dc.identifier.eissn1521-3765
dc.identifier.issn0947-6539
dc.identifier.urihttps://depositonce.tu-berlin.de/handle/11303/11887
dc.identifier.urihttp://dx.doi.org/10.14279/depositonce-10778
dc.language.isoenen
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/en
dc.subject.ddc660 Chemische Verfahrenstechnikde
dc.subject.otherAlzheimer's diseaseen
dc.subject.othercalcificationsen
dc.subject.otherfluorescent imagingen
dc.subject.otherligand synthesisen
dc.subject.othervascular calcificationsen
dc.titleFluorescent Arylphosphonic Acids: Synergic Interactions between Bone and the Fluorescent Coreen
dc.typeArticleen
dc.type.versionpublishedVersionen
dcterms.bibliographicCitation.doi10.1002/chem.202001613en
dcterms.bibliographicCitation.issue49en
dcterms.bibliographicCitation.journaltitleChemistry – A European Journalen
dcterms.bibliographicCitation.originalpublishernameWileyen
dcterms.bibliographicCitation.originalpublisherplaceNew York, NYen
dcterms.bibliographicCitation.pageend11134en
dcterms.bibliographicCitation.pagestart11129en
dcterms.bibliographicCitation.volume26en
tub.accessrights.dnbfreeen
tub.affiliationFak. 3 Prozesswissenschaften::Inst. Lebensmitteltechnologie und Lebensmittelchemie::FG Lebensmittelchemie und Toxikologiede
tub.affiliation.facultyFak. 3 Prozesswissenschaftende
tub.affiliation.groupFG Lebensmittelchemie und Toxikologiede
tub.affiliation.instituteInst. Lebensmitteltechnologie und Lebensmittelchemiede
tub.publisher.universityorinstitutionTechnische Universität Berlinen

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