Designed Benzothiadiazole Fluorophores for Selective Mitochondrial Imaging and Dynamics

Carvalho, Pedro H. P. R.; Corrêa, José R.; Guido, Bruna C.; Gatto, Claudia C.; Oliveira, Heibbe C. B. de; Soares, Thereza A.; Neto, Brenno A. D.

doi:10.1002/chem.201404039

Cited by 46 publications

(44 citation statements)

References 57 publications

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“…binding to double-stranded DNA) or in lipid-based structures. [31][32][33][34][35] Synthesis: In the present study, we have combined the electron-withdrawing benzothiadiazole scaffold with an electron-donating substituent (dimethylaminophenyl), resulting in a push-pull fluorophore. 28 In a push-pull system, the LUMO is mainly localized on the acceptor moiety whereas the HOMO is centered on the donor fragment.…”

Section: Resultsmentioning

confidence: 99%

Specific Imaging of Intracellular Lipid Droplets Using a Benzothiadiazole Derivative with Solvatochromic Properties

et al. 2017

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Altered lipid metabolism and extensive lipid storage in cells have been associated with various medical disorders, including cancer. The development of fluorescent probes that specifically accumulate in lipid deposits is therefore of great interest in order to study pathological processes that are linked to dysregulated lipogenesis. In the present study, we present a small fluorescent benzothiadiazole dye that specifically stains lipid droplets in living and fixated cells. The photophysical characterization of the probe revealed strong solvatochromic behavior, large Stokes shifts, and high fluorescent quantum yields in hydrophobic solvents. In addition, the fluorophore exhibits a nontoxic profile and a high signal-to-noise ratio in cells (i.e., lipid droplets vs cytosol), which make it an excellent candidate for studying lipid biology using confocal fluorescent microscopy.

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Section: Resultsmentioning

confidence: 99%

Specific Imaging of Intracellular Lipid Droplets Using a Benzothiadiazole Derivative with Solvatochromic Properties

et al. 2017

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“…Owing to our interest in the development of new and selective bioprobes, especially for mitochondrial selective staining, we disclose herein our synthetic strategy for the synthesis of new fluorescent imidazole and phenazine derivatives from lapachone towards selective mitochondrial staining in live cells.…”

Section: Introductionmentioning

confidence: 99%

Redox Center Modification of Lapachones towards the Synthesis of Nitrogen Heterocycles as Selective Fluorescent Mitochondrial Imaging Probes

et al. 2017

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We describe herein a synthetic strategy for the synthesis of new fluorescent imidazole and phenazine derivatives synthesized from lapachol, a naturally occurring naphthoquinone isolated from Tabebuia species (ipê tree). The photophysical properties and computational details of these compounds have been studied, aiming at gaining a complete understanding of the potential of these derivatives as probes capable of staining mitochondria selectively. Cell imaging experiments proved the capacity of the imidazole derivatives as selective fluorescent mitochondrial imaging probes. These heterocycles present the same staining patterns as MitoTracker Red, corroborating the potential of these compounds as new mitochondria markers permeable to the cell membrane.

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“…37 Five derivatives were synthesized and tested. Four of them did not show mitochondrial selection; of these four derivatives, one showed a tendency toward this organelle, while another displayed a significant light-up effect (see Figure 6).…”

Section: Staining Of Mitochondria With Btd Fluorophoresmentioning

confidence: 99%

Benzothiadiazole Derivatives as Fluorescence Imaging Probes: Beyond Classical Scaffolds

2015

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This Account describes the origins, features, importance, and trends of the use of fluorescent small-molecule 2,1,3-benzothiadiazole (BTD) derivatives as a new class of bioprobes applied to bioimaging analyses of several (live and fixed) cell types. BTDs have been successfully used as probes for a plethora of biological analyses for only a few years, and the impressive responses obtained by using this important class of heterocycle are fostering the development of new fluorescent BTDs and expanding the biological applications of such derivatives. The first use of a fluorescent small-molecule BTD derivative as a selective cellular probe dates back to 2010, and since then impressive advances have been described by us and others. The well-known limitations of classical scaffolds urged the development of new classes of bioprobes. Although great developments have been achieved by using classical scaffolds such as coumarins, BODIPYs, fluoresceins, rhodamines, cyanines, and phenoxazines, there is still much to be done, and BTDs aim to succeed where these dyes have shown their limitations. Important organelles and cell components such as nuclear DNA, mitochondria, lipid droplets, and others have already been successfully labeled by fluorescent small-molecule BTD derivatives. New technological systems that use BTDs as the fluorophores for bioimaging experiments have been described in recent scientific literature. The successful application of BTDs as selective bioprobes has led some groups to explore their potential for use in studying membrane pores or tumor cells under hypoxic conditions. Finally, BTDs have also been used as fluorescent tags to investigate the action mechanism of some antitumor compounds. The attractive photophysical data typically observed for π-extended BTD derivatives is fostering interest in the use of this new class of bioprobes. Large Stokes shifts, large molar extinction coefficients, high quantum yields, high stability when stored in solution or as pure solids, no fading even after long periods of irradiation, bright emissions with no blinking, good signal-to-noise ratios, efficiency to transpose the cell membrane, and irradiation preferentially in the visible-light region are just some features noted by using BTDs. As the pioneering group in the use of fluorescent small-molecule BTDs for bioimaging purposes, we feel pleased to share our experience, results, advances, and personal perspectives with the readers of this Account. The readers will clearly note the huge advantages of using fluorescent BTDs over classical scaffolds, and hopefully they will be inspired and motivated to further BTD technology in the fields of molecular and cellular biology.

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Designed Benzothiadiazole Fluorophores for Selective Mitochondrial Imaging and Dynamics

Cited by 46 publications

References 57 publications

Specific Imaging of Intracellular Lipid Droplets Using a Benzothiadiazole Derivative with Solvatochromic Properties

Specific Imaging of Intracellular Lipid Droplets Using a Benzothiadiazole Derivative with Solvatochromic Properties

Redox Center Modification of Lapachones towards the Synthesis of Nitrogen Heterocycles as Selective Fluorescent Mitochondrial Imaging Probes

Benzothiadiazole Derivatives as Fluorescence Imaging Probes: Beyond Classical Scaffolds

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