Fluorescence properties of the anti-tumour alkaloid luotonin A and new synthetic analogues: pH modulation as an approach to their fluorimetric quantitation in biological samples

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dc.contributor.authorGonzález Ruiz, Víctor
dc.contributor.authorGonzález-Cuevas, Yamisley
dc.contributor.authorArunachalam, Sankaralingam
dc.contributor.authorMartín Carmona, María Antonia
dc.contributor.authorOlives Barba, Ana Isabel
dc.contributor.authorRibelles, Pascual
dc.contributor.authorRamos García, María Teresa
dc.contributor.authorMenéndez Ramos, José Carlos
dc.date.accessioned2024-02-07T10:16:23Z
dc.date.available2024-02-07T10:16:23Z
dc.date.issued2012-09
dc.description.abstractLuotonin A is an alkaloid structurally related to the natural anti-tumour agent camptothecin. The fluorescence behaviour of luotonin A and a series of six analogues is described in the present work. The influence of solvent polarity and pH on the native fluorescence properties of these alkaloids was studied, finding that in organic solvents or in aqueous solutions (pH 5.5–7.2) the neutral form of the luotonin derivatives emit in the region of 410–450 nm but, in both media, acidification to pH values below 3.0 causes a new emission band to appear at about 500 nm. An ESPT reaction occurs due to the protonation of the basic nitrogen atoms of the pentacyclic ring. Acid-base titrations of luotonin A and its derivatives in aqueous and acetonitrile media were carried out in order to determine their pKa n values which were around 2, showing these compounds to be very weak bases. In aqueous media, the absence of an iso-emissive point in the emission spectra suggests the existence of more than two species in the proton transfer equilibria. The basicity of the luotonin A derivatives is increased in organic media, and a good correlation between the pKa n values and the chemical structure was found. The protonation of luotonin A was also studied by 1 H-NMR and 13C-NMR experiments, which proved the protonation of the nitrogen atoms at the positions 5 and 6 of the pentacyclic ring. The fluorescence quantum yields were determined in ethanol and in aqueous solutions under neutral and acidic conditions. The fluorescence quantum yields were higher in water for the case of the more polar compounds, and the opposite result was obtained for the more hydrophobic ones. The remarkable and interesting fluorescence properties of luotonin A prompted the development of its fluorimetric analytical quantitation, obtaining very good analytical features
dc.description.departmentDepto. de Química en Ciencias Farmacéuticas
dc.description.facultyFac. de Farmacia
dc.description.refereedTRUE
dc.description.sponsorshipMinisterio de Ciencia, Innovación y Universidades (España)
dc.description.sponsorshipUniversidad Complutense de Madrid
dc.description.statuspub
dc.identifier.citationGonzález-Ruiz V, González-Cuevas Y, Arunachalam S, Martín MA, Olives AI, Ribelles P, et al. Fluorescence properties of the anti-tumour alkaloid luotonin A and new synthetic analogues: pH modulation as an approach to their fluorimetric quantitation in biological samples. Journal of Luminescence 2012;132:2468–75. https://doi.org/10.1016/j.jlumin.2012.03.056.
dc.identifier.doi10.1016/j.jlumin.2012.03.056
dc.identifier.issn0022-2313
dc.identifier.officialurlhttps://doi.org/10.1016/j.jlumin.2012.03.056
dc.identifier.urihttps://hdl.handle.net/20.500.14352/99858
dc.issue.number9
dc.journal.titleJournal of Luminescence
dc.language.isoeng
dc.page.final2475
dc.page.initial2468
dc.relation.projectIDinfo:eu-repo/grantAgreement/MICINN/CTQ2009-11312-BQU
dc.relation.projectIDinfo:eu-repo/grantAgreement/MICINN/CTQ2009-12320-BQU
dc.relation.projectIDinfo:eu-repo/grantAgreement/GR35/10-A-920234
dc.rights.accessRightsrestricted access
dc.subject.cdu543
dc.subject.keywordESPT
dc.subject.keywordLuotonin A
dc.subject.keywordAnti-tumour agents
dc.subject.keywordSteady-state fluorescence
dc.subject.keywordUV–Vis-spectrophotometry
dc.subject.keyword1 H- and 13C-NMR spectroscop
dc.subject.ucmQuímica analítica (Farmacia)
dc.subject.unesco2301 Química Analítica
dc.titleFluorescence properties of the anti-tumour alkaloid luotonin A and new synthetic analogues: pH modulation as an approach to their fluorimetric quantitation in biological samples
dc.typejournal article
dc.type.hasVersionAM
dc.volume.number132
dspace.entity.typePublication
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relation.isAuthorOfPublication109c167c-4d5d-41f6-be94-4ca6160136a5
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relation.isAuthorOfPublication.latestForDiscovery711c3146-caca-4061-9626-60a946a50f20
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