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Synthesis and Chemiluminescent Properties of Amino-Acylated luminol Derivatives Bearing Phosphonium Cations

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Synthesis and Chemiluminescent Properties of Amino-Acylated luminol Derivatives Bearing Phosphonium Cations

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dc.contributor.author Pantelia, Anna es_ES
dc.contributor.author Daskalaki, Ira es_ES
dc.contributor.author Cuquerella Alabort, Maria Consuelo es_ES
dc.contributor.author Rotas, Georgios es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.contributor.author Vougioukalakis, Georgios C. es_ES
dc.date.accessioned 2021-01-20T04:32:13Z
dc.date.available 2021-01-20T04:32:13Z
dc.date.issued 2019-11 es_ES
dc.identifier.issn 1420-3049 es_ES
dc.identifier.uri http://hdl.handle.net/10251/159530
dc.description.abstract [EN] The monitoring of reactive oxygen species in living cells provides valuable information on cell function and performance. Lately, the development of chemiluminescence-based reactive oxygen species monitoring has gained increased attention due to the advantages posed by chemiluminescence, including its rapid measurement and high sensitivity. In this respect, specific organelle-targeting trackers with strong chemiluminescence performance are of high importance. We herein report the synthesis and chemiluminescence properties of eight novel phosphonium-functionalized amino-acylated luminol and isoluminol derivatives, designed as mitochondriotropic chemiluminescence reactive oxygen species trackers. Three different phosphonium cationic moieties were employed (phenyl, p-tolyl, and cyclohexyl), as well as two alkanoyl chains (hexanoyl and undecanoyl) as bridges/linkers. Synthesis is accomplished via the acylation of the corresponding phthalimides, as phthalhydrazide precursors, followed by hydrazinolysis. This method was chosen because the direct acylation of (iso)luminol was discouraging. The new derivatives' chemiluminescence was evaluated and compared with that of the parent molecules. A relatively poor chemiluminescence performance was observed for all derivatives, with the isoluminol-based ones being the poorest. This result is mainly attributed to the low yield of the fluorescence species formation during the chemiluminescence oxidation reaction. es_ES
dc.description.sponsorship This project was financially supported by the European Union's Horizon 2020 framework program for research and innovation under grant agreement no. 712921, as well as a Greek State Scholarships Foundation (I.K.Y.) fellowship to A.P. es_ES
dc.language Inglés es_ES
dc.publisher MDPI AG es_ES
dc.relation.ispartof Molecules es_ES
dc.rights Reconocimiento (by) es_ES
dc.subject Phthalhydrazide es_ES
dc.subject Luminol es_ES
dc.subject Chemiluminescence es_ES
dc.subject Peroxide es_ES
dc.subject Phosphonium es_ES
dc.subject Mitochondria es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Synthesis and Chemiluminescent Properties of Amino-Acylated luminol Derivatives Bearing Phosphonium Cations es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.3390/molecules24213957 es_ES
dc.relation.projectID info:eu-repo/grantAgreement/EC/H2020/712921/EU/A paradigm shift in cancer therapy – using mitochondria-powered chemiluminescence to non-invasively treat inaccessible tumours/ es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.description.bibliographicCitation Pantelia, A.; Daskalaki, I.; Cuquerella Alabort, MC.; Rotas, G.; Miranda Alonso, MÁ.; Vougioukalakis, GC. (2019). Synthesis and Chemiluminescent Properties of Amino-Acylated luminol Derivatives Bearing Phosphonium Cations. Molecules. 24(21):1-16. https://doi.org/10.3390/molecules24213957 es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.3390/molecules24213957 es_ES
dc.description.upvformatpinicio 1 es_ES
dc.description.upvformatpfin 16 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 24 es_ES
dc.description.issue 21 es_ES
dc.identifier.pmid 31683732 es_ES
dc.identifier.pmcid PMC6865176 es_ES
dc.relation.pasarela S\406752 es_ES
dc.contributor.funder European Commission es_ES
dc.contributor.funder General Secretariat for Research and Technology, Grecia es_ES
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