Kinetics improvement of protease-mediated formation of pyronin dyes

Debieu, Sylvain; Romieu, Anthony

doi:10.1016/j.tetlet.2018.04.010

“…However, the availability of Sipyronin dyes 4 and 5 has enabled us to perform some photophysical and stability studies in simulated physiological conditions. The latter ones clearly support the relevance of molecular amino group [34][35][36], these novel (Si-)pyronin derivatives will be very useful as references to validate "covalent-assembly" fluorescent probes based on in situ formation of (Si-)pyronin triggered by the analyte to be detected [38][39][40][41][42]. Finally, tunable reactivity of their meso-position towards different nucleophiles can be used to design reversible reaction-based fluorescent probes particularly well suited for real-time imaging of redox status changes in vivo [73][74][75].…”

Section: Discussionsupporting

confidence: 55%

Synthetic Routes to Novel Fluorogenic Pyronins and Silicon Analogs with Far-Red Spectral Properties and Enhanced Aqueous Stability

Dejouy¹,

Renault²,

Valverde³

et al. 2020

Preprint

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Fluorogenic detection of reactive (bio)analytes is often achieved with "smart" probes, whose activation mechanism causes the release of aniline-based fluorophores. Indeed, the protection-deprotection of their primary amino is the simplest way to induce dramatic and valuable changes in spectral features of the fluorogenic reporter. In this context, and due to their small size and intrinsic hydrophilicity, we focused on pyronin dyes and related heteroatom analogs (i.e., formal derivatives of 3-imino-3H-xanthen-6-amine and its silicon analog) for their use as optically tunable aniline-based fluorophores. To overcome some severe limitations associated with the use of such fluorogenic scaffolds (i.e., poor aqueous stability and spectral features only in the green-yellow spectral range), the synthesis of novel unsymmetrical derivatives of (Si)-pyronins bearing a single bulky tertiary aniline (i.e., N-methylindoline and julolidine) was explored and presented in this Article. This structural alteration has been found to be beneficial to dramatically lower electrophilicity of the meso-position and to reach attractive fluorescence properties within the far-red spectral region.

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“…As a natural extension of our work, this versatile methodology could also be applied to facile their use as fluorogenic dyes in "smart" probes based on protection-deprotection of a primary amino group [34][35][36], these novel (Si-)pyronin derivatives will be very useful as references to validate "covalent-assembly" fluorescent probes based on in situ formation of (Si-)pyronin triggered by the analyte to be detected [38][39][40][41][42]. Finally, tunable reactivity of their meso-position towards different nucleophiles can be used to design reversible reaction-based fluorescent probes particularly well suited for real-time imaging of redox status changes in vivo [73][74][75].…”

Section: Resultsmentioning

confidence: 93%

“…Among the different fluorescent probe design strategies commonly used for selective detection of (bio)analytes through chemical reactions, those based either on (1) protection-deprotection of an amino group (i.e., aniline-based pro-fluorophores) [34][35][36] or (2) "covalent-assembly" principle [37] are readily implementable to pyronin scaffolds. Some recent examples of the literature illustrate this trend and highlight benefits in terms of sensing performances, that might accrue form it [38][39][40][41][42] (Fig. 1).…”

Section: Introductionmentioning

confidence: 80%

Synthetic routes to novel fluorogenic pyronins and silicon analogs with far-red spectral properties and enhanced aqueous stability

Dejouy

¹

,

Renault

²

,

Valverde

³

et al. 2020

Self Cite

View full text Add to dashboard Cite

Fluorogenic detection of reactive (bio)analytes is often achieved with "smart" probes, whose activation mechanism causes the release of aniline-based fluorophores. Indeed, the protection-deprotection of their primary amino is the simplest way to induce dramatic and valuable changes in spectral features of the fluorogenic reporter. In this context, and due to their small size and intrinsic hydrophilicity, we focused on pyronin dyes and related heteroatom analogs (i.e., formal derivatives of 3-imino-3H-xanthen-6-amine and its silicon analog) for their use as optically tunable aniline-based fluorophores. To overcome some severe limitations associated with the use of such fluorogenic scaffolds (i.e., poor aqueous stability and spectral features only in the green-yellow spectral range), the synthesis of novel unsymmetrical derivatives of (Si)-pyronins bearing a single bulky tertiary aniline (i.e., N-methylindoline and julolidine) was explored and presented in this Article. This structural alteration has been found to be beneficial to dramatically lower electrophilicity of the meso-position and to reach attractive fluorescence properties within the far-red spectral region. File list (2) download file view on ChemRxiv Publication-GD4-ChemRxiv-Preprint-31032020.pdf (837.64 KiB) download file view on ChemRxiv Publication-GD04-ChemRxiv-SI-31032020.pdf (6.54 MiB)

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“…Among the different fluorescent probe design strategies commonly used for selective detection of (bio)analytes through chemical reactions, those based either on (1) protection-deprotection of an amino group (i.e., aniline-based pro-fluorophores) [34][35][36] or (2) "covalent-assembly" principle [37] are readily implementable to pyronin scaffolds. Some recent examples of the literature illustrate this trend and highlight benefits in terms of sensing performances, that might accrue form it [38][39][40][41][42] (Fig. 1).…”

Section: Introductionmentioning

confidence: 80%

Synthetic Routes to Novel Fluorogenic Pyronins and Silicon Analogs with Far-Red Spectral Properties and Enhanced Aqueous Stability

Dejouy¹,

Renault²,

Valverde³

et al. 2020

Preprint

Self Cite

0

View full text Add to dashboard Cite

Fluorogenic detection of reactive (bio)analytes is often achieved with "smart" probes, whose activation mechanism causes the release of aniline-based fluorophores. Indeed, the protection-deprotection of their primary amino is the simplest way to induce dramatic and valuable changes in spectral features of the fluorogenic reporter. In this context, and due to their small size and intrinsic hydrophilicity, we focused on pyronin dyes and related heteroatom analogs (i.e., formal derivatives of 3-imino-3H-xanthen-6-amine and its silicon analog) for their use as optically tunable aniline-based fluorophores. To overcome some severe limitations associated with the use of such fluorogenic scaffolds (i.e., poor aqueous stability and spectral features only in the green-yellow spectral range), the synthesis of novel unsymmetrical derivatives of (Si)-pyronins bearing a single bulky tertiary aniline (i.e., N-methylindoline and julolidine) was explored and presented in this Article. This structural alteration has been found to be beneficial to dramatically lower electrophilicity of the meso-position and to reach attractive fluorescence properties within the far-red spectral region.

show abstract

Kinetics improvement of protease-mediated formation of pyronin dyes

Cited by 14 publications

References 75 publications

Synthetic Routes to Novel Fluorogenic Pyronins and Silicon Analogs with Far-Red Spectral Properties and Enhanced Aqueous Stability

Synthetic Routes to Novel Fluorogenic Pyronins and Silicon Analogs with Far-Red Spectral Properties and Enhanced Aqueous Stability

Synthetic routes to novel fluorogenic pyronins and silicon analogs with far-red spectral properties and enhanced aqueous stability

Synthetic Routes to Novel Fluorogenic Pyronins and Silicon Analogs with Far-Red Spectral Properties and Enhanced Aqueous Stability

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