Neutral derivatives of Thioflavin T do not exhibit viscosity-dependent fluorescence

Gogoleva, S. D.; Kalganova, Elena V.; Маскевич, А. А.; Lugovski, A. A.; Kuzmitsky, V. A.; Goswami, Mausumi; Буганов, О. В.; Тихомиров, С. А.; Stsiapura, V. I.

doi:10.1016/j.jphotochem.2018.03.003

Cited by 11 publications

(22 citation statements)

References 71 publications

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“…greater than unity in all cases (2.6-16.7), supporting the attribution of low measured ΦFl1 values (<0.1) to excited-state quenching induced by dye-dye hydrophobic interactions 45. excitation and fluorescence measurements of the dyes free in PBS buffer (denoted by subscript 1).…”

supporting

confidence: 73%

“…A reduction in oscillator strength may result from the absence of the positive charge and thus contribute to the lower ε 1 compared to ThT. The long and short wavelength peaks seen in the absorption spectra of the PAP dyes may result from protonation of N -5, forming a mixture of neutral and cationic molecules as previously described …”

mentioning

confidence: 69%

“…spectra of the PAP dyes may result from protonation of N-5, forming a mixture of neutral and cationic molecules as previously described. 45 The ΦFl1 of the PAP derivatives were ~10´ greater than ThT. This can be partially explained by the existence of a higher energy barrier to rotation about the C-C σ bond between phenyl and benzothiazolium rings, 46 which increases the probability that photo-excited PAP dyes will occupy a LE state rather than a TICT state in low viscosity media.…”

mentioning

confidence: 98%

“…48 The PAP dyes showed longer lifetimes (~1 ns, Figure S5C), in accordance with their greater ΦFl1 and further supporting their minimal rotor behaviour. 45 All the dyes displayed altered photophysical properties in response to amyloid incorporation.…”

mentioning

confidence: 99%

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A Comparative Photophysical Study of Structural Modifications of Thioflavin T-Inspired Fluorophores

Needham

Weber

Pearson

et al. 2020

J. Phys. Chem. Lett.

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The benzothiazolium salt, Thioflavin T (ThT), has been widely adopted as the 'gold-standard' fluorescent reporter of amyloid in vitro. Its properties as a molecular rotor result in a largescale (~1000-fold) fluorescence turn-on upon binding to β-sheets in amyloidogenic proteins.However, the complex photophysics of ThT combined with the intricate and varied nature of the amyloid binding motif means these interactions are poorly understood. To study this important class of fluorophore, we present a detailed photophysical characterisation and comparison of a novel library of twelve ThT-inspired fluorescent probes for amyloid protein (PAPs), where both the charge and donor capacity of the heterocyclic and aminobenzene components have been interrogated, respectively. This enables direct photophysical juxtaposition of two structural groups; Class 1 the neutral 'PAP' and Class 2 the charged 'mPAP' fluorophores. We quantify binding and optical properties at both the bulk and singleaggregate levels with some derivatives showing higher aggregate affinity and brightness than ThT. Finally, we demonstrate their abilities to perform super-resolution imaging of αsynuclein fibrils with localisation precisions of ~16 nm. The properties of the derivatives provide new insights into the relationship between chemical structure and function of benzothiazole probes.

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supporting

confidence: 73%

mentioning

confidence: 69%

mentioning

confidence: 98%

mentioning

confidence: 99%

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A Comparative Photophysical Study of Structural Modifications of Thioflavin T-Inspired Fluorophores

Needham

Weber

Pearson

et al. 2020

J. Phys. Chem. Lett.

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“…When ThT is in a free state the dihedral angle rotated by the C-C bond between the BZT and DMAB moieties is 90°and molecule has the lowest quantum yield possible [39]. As ThT is embedded into the G-quadruplex its hidden fluorescence property will emerge with the suppression of steric hindrance [38][39][40]. So that aptamers with Gquadruplex sequences are good candidates for designing ThT based turn-off sensors.…”

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confidence: 99%

Label-free G-Quadruplex aptamer and Thioflavin-T based turn-off fluorescent detection of ethanolamine

Bayraç

Acar

2020

Dyes and Pigments

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Dual Functional Microcapsule based on Monodisperse Short PEG Amphiphile for Drug Encapsulation and Protein Affinity Controlled Release

Ketkar,

Dey,

Sodnawar

et al. 2024

Chemistry An Asian Journal

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A short monodisperse poly(ethylene glycol) (PEG) and a neutral organic rotamer conjugate TEG‐BTA‐2 amphiphile was designed for the construction of a stimuli‐responsive switchable self‐assembled structure for drug encapsulation by noncovalent interaction and targeted controlled delivery. A short PEG, tetraethylene glycol (TEG) was covalently attached with a neutral organic rotamer benzothiazole dye (BTA‐2) affording the neutral TEG‐BTA‐2 (<500 D). The TEG‐BTA‐2 is self‐assembled into a microsphere in an aqueous medium, but remarkably undergoes morphology change switching to a rice‐like microcapsule for curcumin encapsulation. Curcumin‐loaded microcapsules were stable in an aqueous solution, however, were noticed disintegrating upon the addition of BSA protein. This is possibly due to an interaction with BSA protein leading to a protein affinity‐controlled curcumin release in a neutral PBS buffer. Moreover, cell internalization of the neutral amphiphile TEG‐BTA‐2 into A549 cells was observed by fluorescence microscopy, providing an opportunity for application as a molecular vehicle for targeted drug delivery and monitoring.

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Neutral derivatives of Thioflavin T do not exhibit viscosity-dependent fluorescence

Cited by 11 publications

References 71 publications

A Comparative Photophysical Study of Structural Modifications of Thioflavin T-Inspired Fluorophores

A Comparative Photophysical Study of Structural Modifications of Thioflavin T-Inspired Fluorophores

Label-free G-Quadruplex aptamer and Thioflavin-T based turn-off fluorescent detection of ethanolamine

Dual Functional Microcapsule based on Monodisperse Short PEG Amphiphile for Drug Encapsulation and Protein Affinity Controlled Release

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