Highly solvatochromic and tunable fluorophores based on a 4,5-quinolimide scaffold: novel CDK5 probes

González‐Vera, Juan A.; Fueyo-González, Francisco; Alkorta, Ibón; Peyressatre, Marion; Morris, May; Herranz, Rosario

doi:10.1039/c6cc04566a

Cited by 26 publications

(20 citation statements)

References 35 publications

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“…In general, antennas that directly assemble lanthanide cations are bulky multidentate ligands able to coordinate the cations with a high coordination number. 7,8,17,21,22 However, herein we explore the potential of small-size quinolin-2(1H)-one derivatives with b-dicarbonyl character, concretely, 8-methoxy-4,5-dihydrocyclopenta[de]quinolin-2(1H)-ones 1 and 2 23 and their carbostyril analogues 3 and 4 (Chart 1) as self-assembled lanthanide sensitizers. Importantly, such complexes exhibit an extraordinary ability to sense H 2 O impurities in organic solvents.…”

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Smart lanthanide antennas for sensing water

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Smart lanthanide antennas for sensing water

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“…Photophysical Properties. The UV absorption and fluorescence emission properties of 9-aminoquinolimide derivatives 2−6 were determined in solvents of varying polarity in comparison with those of the 9-methoxyquinolimide analogue 1 26 and are summarized in Figure 1 and Table S1 (Supporting Information). Replacement of the 9methoxy group by an amino group induced a bathochromic shift of 60−142 nm both in the absorption and the emission maximum wavelengths, λ max abs and λ max em , respectively.…”

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confidence: 99%

“…9-Methoxy-quinolimide-based fluorophores A (Figure 1A) have recently demonstrated highly solvatochromic behavior and sensitivity for in cellulo imaging of the CDK5 kinase interaction with its regulatory partner protein p25 in glioblastoma cells. 26 The solvatochromic properties of these new dyes represent an interesting tool to probe different environments. Their demonstrated ability to report on protein−protein interactions paves the way to probe during the early stages of amyloid fibril formation.…”

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Environment-Sensitive Probes for Illuminating Amyloid Aggregation In Vitro and in Zebrafish

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The aberrant aggregation of certain peptides and proteins, forming extracellular plaques of fibrillar material, is one of the hallmarks of amyloid diseases, such as Alzheimer's and Parkinson's. Herein, we have designed a new family of solvatochromic dyes based on the 9-aminoquinolimide moiety capable of reporting during the early stages of amyloid fibrillization. We have rationally improved the photophysical properties of quinolimides by placing diverse amino groups at the 9-position of the quinolimide core, leading to higher solvatochromic and fluorogenic character and higher lifetime dependence on the hydrophobicity of the environment, which represent excellent properties for the sensitive detection of prefibrillar aggregates. Among the different probes prepared, the 9-azetidinylquinolimide derivative showed striking performance in the following β-amyloid peptide (Aβ) aggregation in solution in real time and identifying the formation of different types of early oligomers of Aβ, the most important species linked to cytotoxicity, using novel, multidimensional fluorescence microscopy, with one-or two-photon excitation. Interestingly, the new dye allowed the visualization of proteinaceous inclusion bodies in a zebrafish model with neuronal damage induced by the neurotoxin 1-methyl-4phenyl-1,2,3,6-tetrahydropyridine. Our results support the potential of the novel fluorophores as powerful tools to follow amyloid aggregation using fluorescence microscopy in vivo, revealing heterogeneous populations of different types of aggregates and, more broadly, to study protein interactions.

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“…Importantly, the use of N-substituted-2-methoxyacridone acridones is not a compulsory demand. Other solvatochromic dyes, with long luminescence lifetimes, such as naphthamilide or quinolimide dyes [ 19 , 20 ], may be valid candidates for implementing the method.…”

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Building Accurate Intracellular Polarity Maps through Multiparametric Microscopy

González-García

Herrero-Foncubierta

García‐Fernández

et al. 2020

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The precise knowledge of intracellular polarity, a physiological parameter that involves complex and intertwined intracellular mechanisms, may be relevant in the study of important diseases like cancer or Alzheimer’s. In this technical note, we illustrate our recently developed, accurate method for obtaining intracellular polarity maps employing potent fluorescence microscopy techniques. Our method is based on the selection of appropriate luminescent probes, in which several emission properties vary with microenvironment polarity, specifically spectral shifts and luminescence lifetime. A multilinear calibration is performed, correlating polarity vs. spectral shift vs. luminescence lifetime, to generate a powerful and error-free 3D space for reliable interpolation of microscopy data. Multidimensional luminescence microscopy is then used to obtain simultaneously spectral shift and luminescence lifetime images, which are then interpolated in the 3D calibration space, resulting in accurate, quantitative polarity maps.

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Highly solvatochromic and tunable fluorophores based on a 4,5-quinolimide scaffold: novel CDK5 probes

Cited by 26 publications

References 35 publications

Smart lanthanide antennas for sensing water

Smart lanthanide antennas for sensing water

Environment-Sensitive Probes for Illuminating Amyloid Aggregation In Vitro and in Zebrafish

Building Accurate Intracellular Polarity Maps through Multiparametric Microscopy

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