Electrochemical quenching of the fluorescence produced by NBD-labelled cell penetrating peptides: A contribution to the study of their internalization in large unilamellar vesicles

Oliveira, Raquel; Durand, Mathieu; Challier, Lylian; Messina, Pierluca; Swiecicki, Jean-Marie; Pisa, Margherita Di; Chassaing, Gérard; Lavielle, Solange; Buriez, Olivier; Labbé, Éric

doi:10.1016/j.jelechem.2017.02.006

Cited by 5 publications

(7 citation statements)

References 31 publications

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“…Though reversible electrochemical fluorescence modulation is particularly interesting and sought in the development of electrofluorochromic devices, irreversible processes can also be relevant notably in the discrimination between species internalized and not internalized in lipid vesicles. This approach was recently developed to quantify amounts of cell-penetrating peptides (CPP) that had crossed vesicular lipid membranes [22]. CPP were labeled with NBD (7-nitrobenz-2-oxa-1,3-diazole), a small organic dye displaying a strong fluorescence in non-polar media such as phospholipids.…”

Section: Direct Electrochemical Switch Of Organic Fluorescent Moleculesmentioning

confidence: 99%

Electrochemical Fluorescence Switch of Organic Fluorescent or Fluorogenic Molecules

Guille‐Collignon

Delacotte

Lemaître

et al. 2021

The Chemical Record

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This short review is aimed at emphasizing the most prominent recent works devoted to the fluorescence modulation of organic fluorescent or fluorogenic molecules by electrochemistry. This still expanding research field not only addresses the smart uses of known molecules or the design of new ones, but also investigates the development of instrumentation providing time-and space-resolved information at the molecular level. Important considerations including fluorescent/fluorogenic probes, reversible/irreversible fluorescence switch, direct/indirect fluorescence modulation, or environment properties are especially scrutinized in recent works dealing with bioanalysis perspectives.

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Section: Direct Electrochemical Switch Of Organic Fluorescent Moleculesmentioning

confidence: 99%

Electrochemical Fluorescence Switch of Organic Fluorescent or Fluorogenic Molecules

Guille‐Collignon

Delacotte

Lemaître

et al. 2021

The Chemical Record

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“…Reduction of NBD could possibly be achieved according to aH 2 -mediatedp rocess, and/ or OH À that is known to switch off the NBD fluorescence through ap Hj ump. [45,46] However,t he pH increasep ossibly triggered through the productiono fh ydroxyl anionsw ould be compensated by the generation of protons at the anode through water oxidation since the auxiliary and working electrodes are not separated in the well. Additionally,w es howed that bubbling H 2 in aN BD-glycine-containings olution did not quencht he fluorescence.…”

Section: Electrochemical Bleaching Of the Outer Leaflet Of Nbd-labelementioning

confidence: 99%

Selective Electrochemical Bleaching of the Outer Leaflet of Fluorescently Labeled Giant Liposomes

Jimenez

Challier

Delacotte

et al. 2017

Chemistry A European J

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Electrochemistry and confocal fluorescence microscopy were successfully combined to selectively bleach and monitor the fluorescence of NBD (7-nitrobenz-2-oxa-1,3-diazole)-labeled phospholipids of giant liposomes. Three types of giant unilamellar vesicles have been investigated, the fluorescent phospholipids being localized either mainly on their outer-, inner-, or both inner/outer leaflets. We established that only the fluorescent lipids incorporated in the outer leaflet of the vesicles underwent electrochemical bleaching upon reduction. The relative fluorescence intensity decay was quantified all along the electrochemical extinction through an original fluorescence loss in electrobleaching (FLIE) assay. As expected, the reorganization of the fluorescent phospholipids followed diffusion-driven dynamics. This was also evidenced by comparison with fluorescence loss in photobleaching (FLIP) and the corresponding numerical model. The value of the lateral diffusion coefficient of phospholipids was found to be similar to that obtained by other methods reported in the literature. This versatile and selective bleaching procedure appears reliable to explore important biological and pharmacological issues.

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“…Some of us recently uncovered the redox switchable properties of ferrocene–rhodamine dyads [ 28 ], as well as the selective electrochemical bleaching of the fluorescence emitted by NBD-tagged lipids and peptides [ 29 , 30 ] (NBD = 7-nitrobenz-2-oxa-1,3-diazole). Here, we report the synthesis of P797 ( Chart 1 ), the first fluorescent member of the ferrocifen family for which a coumarin fluorophore was connected to the ferrociphenol skeleton via a spacer arm of 4-carbon alkyl chain ( Chart 1 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Electrochemical and Fluorescence Properties of the First Fluorescent Member of the Ferrocifen Family and of Its Oxidized Derivatives

et al. 2022

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The first fluorescent ferrociphenol derivative (P797) has been synthesized via McMurry cross-coupling followed by copper-catalyzed [3 + 2] azide-alkyne cycloaddition of the fluorescent group coumarin. Cyclic voltammograms of P797 exhibit either a monoelectronic oxidation wave ascribed to the ferrocene Fe(II) → Fe(III) conversion or a three-electron oxidation process in the presence of a base, leading to a Fe(III) quinone methide adduct. This general sequence is consistent with those previously described for non-fluorescent ferrociphenols. Furthermore, the fluorescence properties of P797 and its oxidized intermediates appear to strongly depend on the redox state of the ferrocene group. Indeed, electrochemical generation of Fe(III) (ferrocenium) states markedly increases the fluorescence emission intensity. In contrast, the emission of the Fe(II) (ferrocene) states is partially quenched by photoinduced electron transfer (PET) from the Fe(II) donor to the coumarin acceptor and by concentration-dependent self-quenching. Owing to its switchable fluorescence properties, complex P797 could represent an innovative and useful tool to study the biodistribution and the redox state of ferrocifens in cancer cells.

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Electrochemical quenching of the fluorescence produced by NBD-labelled cell penetrating peptides: A contribution to the study of their internalization in large unilamellar vesicles

Cited by 5 publications

References 31 publications

Electrochemical Fluorescence Switch of Organic Fluorescent or Fluorogenic Molecules

Electrochemical Fluorescence Switch of Organic Fluorescent or Fluorogenic Molecules

Selective Electrochemical Bleaching of the Outer Leaflet of Fluorescently Labeled Giant Liposomes

Synthesis, Electrochemical and Fluorescence Properties of the First Fluorescent Member of the Ferrocifen Family and of Its Oxidized Derivatives

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