Detection of dsDNA with [1,3]Dioxolo[4,5‐<i>f</i>]benzodioxol (DBD) Dyes

Büchner, Dörthe; John, Leonard; Mertens, Monique; Wessig, Pablo

doi:10.1002/chem.201804057

Cited by 6 publications

(3 citation statements)

References 42 publications

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“…Meanwhile, a range of applications of DBD dyes was developed. Thus, they were used as probes to study conformational changes in proteins, , in fluorescence-lifetime-based assays, , in various fluorescence resonance energy transfer pairs, − and in potassium selective probes and probes to selectively detect double-stranded DNA . Recently, we reported further development in the synthesis of DBD dyes, facilitating the adjustment of photophysical parameters to the requirements of an application …”

Section: Introductionmentioning

confidence: 99%

Photophysics of Acyl- and Ester-DBD Dyes: Quadrupole-Induced Solvent Relaxation Investigated by Transient Absorption Spectroscopy

et al. 2019

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A new generation of wavelength-tunable, fluorescent dyes, so-called DBD ([1,3]dioxolo [4,5-f ][1,3]benzodioxole) dyes, were developed a few years ago, and they showed great potential as probes, for example, for fluorescence microscopy. However, their photophysics is not fully explored and leaves open questions regarding their large fluorescence Stokes shifts and sensitivity to solvent conditions of differently substituted DBD dyes. To improve the understanding of the influence of the substitution pattern of the DBD dyes on their respective photophysics, transient absorption spectroscopy (TAS) was used, that is, a pump−probe experiment on the femtosecond timescale. TAS allows measurements of excited states, ground state recovery, solvent relaxation, and fluorescence properties on time scales of up to several nanoseconds. Two different DBD dye samples were investigated: acyl-and estersubstituted DBD dyes. Experiments were carried out in solvents with different polarities using different excitation energies and at different viscosities. Based on the experimental data and theoretical calculations, we were able to determine the conformational changes of the molecule due to electronic excitation and were able to investigate solvent relaxation processes for both types of DBD dyes. By generalizing the theory for quadrupole-induced solvent relaxation developed by Togashi et al., we derived quadrupole moments of both molecules in the ground and excited state. Our data showed differences in the binding of polar solvent molecules to the dyes depending on the substituent on the DBD dye. In the case of water as the solvent, an additional efficient quenching process in the electronically excited state was revealed, which was indicated by the observation of solvated electrons in the TAS signals.

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Section: Introductionmentioning

confidence: 99%

Photophysics of Acyl- and Ester-DBD Dyes: Quadrupole-Induced Solvent Relaxation Investigated by Transient Absorption Spectroscopy

et al. 2019

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“…Upon binding to ds DNA the distance between quencher and fluorophore is increased and the fluorescence intensity is raised by a factor of 18. 54 The operating principle of structurally simpler probe 69 is based on the change of the environment polarity upon binding to ds DNA, associated with an increase of the fluorescence intensity. In this case the fluorescence enhancement factor is 5 (Figure 4 ).…”

Section: Applicationsmentioning

confidence: 99%

[1,3]-Dioxolo[4,5-f]benzodioxole (DBD) Fluorescent Dyes; Synthesis, Properties, and Applications

Wessig¹,

Lehmann²

2023

Synthesis

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In this review we give an overview of the syntheses and photophysical properties of the new class of fluorescent dyes based on a [1,3]-dioxolo[4,5-f]benzodioxole core and their derivatives. Starting from commercially available reactants (e.g., sesamol, 1,2,4,5-tetrachlorobenzene) the core units can be prepared in a simple manner. Then, the benzene core can be derivatized via lithiation and their photophysical properties can be adjusted as desired. The obtained fluorophores have an absorption range of 403–520 nm and an emission range of 495–665 nm. This class of fluorescent dyes is also characterized by a long fluorescence lifetime, a high stability towards photobleaching, large Stokes shifts, and small size. Thus, the DBD dyes are optimally suited for optical sensing.1 Introduction2 Synthesis3 Properties4 Applications

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“… [5a,b] The outstanding features of these dyes are very large Stokes shifts, long fluorescence lifetimes and high bleaching stability. Meanwhile, we developed numerous applications such as probes for sensing lipophilic environment, [5c] conformational changes of proteins, [5d,e] detecting carbohydrate‐lectin interactions, [5f] ds DNA, [5o] and alkaline cations [5g,h] . Furthermore, fluorescence lifetime based assays [5i,j] and FRET pairs [5k–n] were developed.…”

Section: Introductionmentioning

confidence: 99%

Sulfur Tuning of [1,3]‐Dioxolo[4.5‐f]benzodioxole (DBD) Fluorescent Dyes

et al. 2020

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Dedicated to Professor Bernd Giese on the occasion of his 80th birthday. The replacement of oxygen by sulfur atoms of [1,3]-dioxolo[4.5f]benzodioxole (DBD) fluorescent dyes is an efficient way to adjust the photophysical properties (sulfur tuning). While previously developed S 4-DBD dyes exhibit considerably redshifted absorption and emission wavelength, the heavy atom effect of four sulfur atoms cause low fluorescence quantum yields and short fluorescence lifetimes. Herein, we demonstrate that the replacement of less than four sulfur atoms (S 1-DBD, 1,2-S 2-DBD, and 1,4-S 2-DBD dyes) permits a fine-tuning of the photophysical properties. In some cases, a similar influence on the wavelength without the detrimental effect on the quantum yields and lifetimes is observed. Furthermore, the synthetic accessibility of S 1-and S 2-DBD dyes is improved, compared with S 4-DBD dyes. For coupling with biomolecules a series of reactive derivatives of the new dyes were developed (azides, OSu esters, alkynes, maleimides).

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Detection of dsDNA with [1,3]Dioxolo[4,5‐f]benzodioxol (DBD) Dyes

Cited by 6 publications

References 42 publications

Photophysics of Acyl- and Ester-DBD Dyes: Quadrupole-Induced Solvent Relaxation Investigated by Transient Absorption Spectroscopy

Photophysics of Acyl- and Ester-DBD Dyes: Quadrupole-Induced Solvent Relaxation Investigated by Transient Absorption Spectroscopy

[1,3]-Dioxolo[4,5-f]benzodioxole (DBD) Fluorescent Dyes; Synthesis, Properties, and Applications

Sulfur Tuning of [1,3]‐Dioxolo[4.5‐f]benzodioxole (DBD) Fluorescent Dyes

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