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4-Amino-1,8-naphthalimide based fluorescent photoinduced electron transfer (PET) pH sensors as liposomal cellular imaging agents: The effect of substituent patterns on PET directional quenching

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frontiers of Chemical Science and Engineering 2020年第1期14卷 61-75页

作者： Miguel Martinez-Calvo Sandra A.Bright Emma B.Veale adam f.henwood D.Clive Williams Thorfinnur Gunnlaugsson School of Chemistry and Trinity Biomedical Sciences Institute(TBSI) Trinity College DublinThe University of DublinDublin 2Ireland School of Biochemistry and Immunology and Trinity Biomedical Sciences Institute(TBSI) Trinity College DublinThe University of DublinDublin 2Ireland Centro Singular de Investigacion en Quimica Bioloxica e Materiais Moleculares(CIQUS)and Departamento de Quimica Organica Universidade de Santiago de Compostela Rua Jenaro de la Fuente s/n15782Santiago de CompostelaSpain

four new fluorescent sensors(1-4)based on the 4-amino-1,8-naphthalimide fluorophores(Naps)have been synthesized based on the classical fluorophore-spacer-receptor *** four compounds all gave rise to emission bands centred at ca.535 nm,which were found to be highly pH dependent,the emission being‘switched on’in acidic media,while being quenched due to PET from the amino moieties to the excited state of the Nap at more alkaline *** luminescent pH dependence for these probes was found to be highly dependent on the substitution on the imide site,as well as the polyamine chain attached to the position 4-amino *** the case of sensor 2 the presence of the 4-amino-aniline dominated the pH dependent ***,at higher pH,PET quenching was also found to occur from the polyamine ***,2 is better described as a receptor1-spacer1-fluorophore-spacer2-receptor2 system,where the dominant PET process is due to(normally less favourable)‘directional’PET quenching from the 4-amino-aniline unit to the Nap *** trends and pH fluorescence dependences were also seen for 3 and *** compounds were also tested for their imaging potential and toxicity against HeLa cells(using DRAQ5 as nuclear stain which does now show pH dependent changes in acidic and neutral pH)and the results demonstrated that these compounds have reduced cellular viability at moderately high concentrations(with IC50 values between ca.8-30μmol?L^?1),but were found to be suitable for intracellular pH determination at 1μmol?L^?1 concentrations,where no real toxicity was *** allowed us to employ these as lysosomal probes at sub-toxic concentrations,where the Nap based emission was found to be pH depended,mirroring that seen in aqueous solution for 1-4,with the main fluorescence changes occurring within acidic to neutral pH.

关键词： sensors pH photoinduced electron transfer cellular imaging confocal microscopy

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