New Sensitive Fluorophores for Selective DNA Detection

Neto, Brenno A. D.; Lapis, Alexandre A. M.; Mancilha, Fabiana Szczesny; Vasconcelos, Igor B.; Thum, Caroline; Basso, Luiz Augusto; Santos, Daniel Silas Veras dos; Dupont, Jaı̈rton

doi:10.1021/ol701708y

Cited by 68 publications

(45 citation statements)

References 30 publications

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“…156 Benzothiadiazole containing dyes 213 stained selectively nuclear DNA in human stem cells. 167 4-Substituted benzothiadiazole derivatives 214 exhibit high cellular selectivity and stain only mitochondria in different cell lines (Figure 7).…”

Section: Biological Applicationsmentioning

confidence: 99%

“…Sometimes instead of an organic base, a mixture of potassium carbonate and triphenylphosphine was used 155. In contrast to Suzuki and Stille couplings, monoalkynyl derivatives 130 can be obtained from 4,7-dibromo-2,1,3-benzothiadiazole(112) in high yields employing practically the same conditions as those used for the synthesis of dialkynyl benzothiadiazoles, with a smaller amount of terminal alkyne (Scheme 63) 156,157. It was shown that four ethynyl groups can be inserted to benzothiadiazole molecule in one step giving so called "carbon-rich BTD series."…”

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confidence: 99%

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Recent Developments in the Synthesis and Applications of 1,2,5-Thia- and Selenadiazoles. A Review

Konstantinova

Knyazeva

Ракитин

2014

Organic Preparations and Procedures International

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Section: Biological Applicationsmentioning

confidence: 99%

mentioning

confidence: 99%

Recent Developments in the Synthesis and Applications of 1,2,5-Thia- and Selenadiazoles. A Review

Konstantinova

Knyazeva

Ракитин

2014

Organic Preparations and Procedures International

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“…In 2007, we demonstrated the first application of fluorescent small-molecule BTD derivatives as sensitive fluorophores for double-stranded DNA (dsDNA)-selective detection and quantification. 18 In the same year, another group reported that polymeric BTD-containing derivatives are also efficient for DNA concentration determination. 19 Later, we also demonstrated that some BTDs proved to be efficient fluorophores for real-time PCR analyses.…”

Section: Introductionmentioning

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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“…Based on this intercalative mechanism, many cationic planar, polycyclic dyes derived from quinolizinium, benzooxazolinium, benzothiazolinium, and acridizinium have been developed as powerful optical probes for DNA detection [9,10]. These DNA-selective probes demonstrate a variety of potential applications in pharmaceutical studies and molecular biology, and can be used as probes for electron and/or energy transfer and gene modulators [11][12][13][14][15][16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

A Novel Styryldehydropyridocolinium Homodimer: Synthesis and Fluorescence Properties Upon Interaction with DNA

et al. 2015

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A novel homodimer of the styryldehydropyridocolinium dye (TPTP) has been synthesized and characterized. Free TPTP exhibited low fluorescence quantum yield and large Stokes shift (over 160 nm) in water. However, it showed a significant fluorescence turn-on effect upon intercalation into DNA base pairs. Meanwhile, the fluorescence intensity of the intercalated structures formed by TPTP and DNA decreased quickly upon addition of deoxyribonuclease I, indicating that the dye can be used to monitor deoxyribonuclease I activity and DNA hydrolysis. Electrophoresis analysis revealed that the dye had intercalative binding to DNA and can potentially be used for DNA staining in electrophoresis. Thus, the innate nature of large Stokes shift and excellent fluorescence turn on effect upon interaction with DNA endue the dye with a wide range of applications.

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New Sensitive Fluorophores for Selective DNA Detection

Abstract: 4,7-Disubstituted benzothiadiazoles containing 1-arylethynyl and 4-methoxyphenyl groups are selective photoluminescent "light up" probes to duplex DNA with unprecedented sensibility in both spectrophotometric and spectrofluorimetric measurements.

Cited by 68 publications

References 30 publications

Recent Developments in the Synthesis and Applications of 1,2,5-Thia- and Selenadiazoles. A Review

Recent Developments in the Synthesis and Applications of 1,2,5-Thia- and Selenadiazoles. A Review

Benzothiadiazole Derivatives as Fluorescence Imaging Probes: Beyond Classical Scaffolds

A Novel Styryldehydropyridocolinium Homodimer: Synthesis and Fluorescence Properties Upon Interaction with DNA

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