Synthesis, properties and highly selective mitochondria staining with novel, stable and superior benzothiadiazole fluorescent probes

Neto, Brenno A. D.; Carvalho, Pedro H. P. R.; Santos, Diego C. B. D.; Gatto, Claudia C.; Ramos, Luciana M.; Vasconcelos, Nathalia Moraes de; Corrêa, José R.; Costa, Maísa Borges; Oliveira, Heibbe C. B. de; Silva, Rafael G.

doi:10.1039/c1ra00701g

Cited by 57 publications

(39 citation statements)

References 39 publications

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“…The selected series of amine derivatives in Scheme 1d emonstrates that highly aligned squaresc an in fact coexistw hile hydrogen bondingo ccurs directly on the thiadiazole (TDA) unit. Withint he 2d monomer,t he 4-NH 2 group intramolecularly Hbonds to one N TDA while the remaining N TDA engages in close, highly aligned2 S-2N squares with as econd 2d partner.R eplacing the 4-NH 2 with 4-NH-pyridyl (CSD reference code FEBYES, Scheme 1) [124] disrupts the square 2d·2 d dimer in favor of new intermolecular N TDA ···NH networks and close N TDA ···S-N CB contacts at 3.10 (angle N···S-N 169.68). Adding Figure 12.…”

Section: The Hb Interaction Class:competitionb Etween2s-2n Square Intmentioning

confidence: 99%

“…Scheme1.Crystal structures 2d, FEBYES [124] and FEBYAO [124] highlighting the co-existenceo fHBa nd CB interactions.T he red arrows indicate the position of the substituent changes. Atomc oloring: Cgreen,Nblue, Sy ellow,Brb rown.…”

Section: The Hb Interaction Class:competitionb Etween2s-2n Square Intmentioning

confidence: 99%

“…Atomc oloring: Cgreen,Nblue, Sy ellow,Brb rown. bromine to the 7-position (FEBYAO, [124] Scheme 1), or fluorine in the case of 9e [109] (Figure S12), evidently prevents the intermolecular N TDA ···NH networks and permits highly aligned squares to compete again (CB ave = 2.99 , q ave = 74.28, f ave = 0.08, F ave = 179.08).…”

Section: The Hb Interaction Class:competitionb Etween2s-2n Square Intmentioning

confidence: 99%

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Chalcogen Bonding “2S–2N Squares” versus Competing Interactions: Exploring the Recognition Properties of Sulfur

Mark

Trapp

Schwab

et al. 2018

Chemistry A European J

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Chalcogen bonding (CB) is the focus of increased attention for its applications in medicinal chemistry, materials science, and crystal engineering. However, the origin of sulfur's recognition properties remains controversial, and experimental evidence for supporting theories is still emerging. Here, a comprehensive evaluation of sulfur CB interactions is presented by investigating 2,1,3‐benzothiadiazole X‐ray crystallographic structures gathered from the Cambridge Structure Database (CSD), Protein Data Bank (PDB), and own laboratory findings. Through the systematic analysis of substituent effects on a subset library of over thirty benzothiadiazole derivatives, the competing interactions have been categorized into four main classes, namely 2S–2N CB square, halogen bonding (XB), S⋅⋅⋅S, and hydrogen‐bonding (HB). A geometric model is employed to characterize the 2S–2N CB square motifs and discuss the role of electrostatic, dipole, and orbital contributions toward the interaction.

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Section: The Hb Interaction Class:competitionb Etween2s-2n Square Intmentioning

confidence: 99%

Section: The Hb Interaction Class:competitionb Etween2s-2n Square Intmentioning

confidence: 99%

Section: The Hb Interaction Class:competitionb Etween2s-2n Square Intmentioning

confidence: 99%

See 1 more Smart Citation

Chalcogen Bonding “2S–2N Squares” versus Competing Interactions: Exploring the Recognition Properties of Sulfur

Mark

Trapp

Schwab

et al. 2018

Chemistry A European J

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“…Considering the possibility of cellular selection (mitochondrial selection) with only one π extension, we very recently tested two novel monosubstituted BTD derivatives with an ESIPT site by envisaging a more intense fluorescence emission and efficient stabilization in the excited state (Scheme ) 129. Indeed, the strategy proved to be very good and dyes 174 and 175 stained only mitochondria in MCF‐7 and Caco‐2 cancer cell lines.…”

Section: Biological Applicationsmentioning

confidence: 99%

2,1,3‐Benzothiadiazole and Derivatives: Synthesis, Properties, Reactions, and Applications in Light Technology of Small Molecules

et al. 2012

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2,1,3‐Benzothiadiazole (BTD) is one of the most important nuclei used in the chemistry of photoluminescent compounds and applicable for light technology. The understanding of its properties and reactions is fundamental for the design and application of these derivatives in molecular organic electronic devices and for other technologies. As a result of their potential as constituents of organic light‐emitting diodes, solar cells, liquid crystals, dyes, photovoltaic cells, and many others, attention has been focused on BTD π‐extended derivatives with potential use in this exciting area. Herein, we describe their syntheses, properties, reactions, and selected examples of applications in light technology using by BTD (small molecules) as the core.

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“…In fact, 2,1,3-benzothiadiazoles are members of ar elatively prominent class of photoluminescent compounds and have been considered as potential staininga gents for cellular organelles in fluorescence microscopy. [11] Usually characterised by emissions above ca. 500 nm and by reasonable quantum yields (0.20-0.65), these compounds are indeed very promising candidates for biological applications.I tw as challenging to find variants that would allow complexation to the metal withoute ncountering steric hindrancei ssues due to the influence of the relatively large cone angle of triphenylphosphine, in particular.…”

Section: Resultsmentioning

confidence: 99%

Highly Sensitive and Selective Molecular Probes for Chromo‐Fluorogenic Sensing of Carbon Monoxide in Air, Aqueous Solution and Cells

Toscani

Marín‐Hernández

Robson

et al. 2019

Chemistry A European J

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Optical sensing offers a low‐cost and effective means to sense carbon monoxide in air and in solution. This contribution reports the synthesis of a new series of vinyl complexes [Ru(CH=CHR)Cl(CO)(TBTD)(PPh3)2] (R=aryl, TBTD=5‐(3‐thienyl)‐2,1,3‐benzothiadiazole) and shows them to be highly sensitive and selective probes for carbon monoxide in both solution and air. Depending on the vinyl substituent, chromogenic and fluorogenic responses signalled the presence of this invisible, odourless, tasteless and toxic gas. Adsorbing the complexes on silica produced colorimetric probes for the ′naked eye′ detection of CO in the gas phase with a limit of detection as low as 8 ppm in some cases, while the release of the TBTD fluorophore allowed detection at much lower concentrations through the fluorescence response. Structural data were obtained by single‐crystal X‐ray diffraction techniques, while the photophysical behaviour was explored computationally using TD‐DFT experiments. The systems were also shown to be selective for CO over all other gases tested, including water vapour and common organic solvents. By introducing a poly(ethylene)glycol chain to the vinyl functionality, water compatibility was achieved and these non‐cytotoxic complexes were employed in the sensing of CO in HeLa cells, offering a simple and rapid system for sensing this gasotransmitter in this challenging medium.

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Synthesis, properties and highly selective mitochondria staining with novel, stable and superior benzothiadiazole fluorescent probes

Cited by 57 publications

References 39 publications

Chalcogen Bonding “2S–2N Squares” versus Competing Interactions: Exploring the Recognition Properties of Sulfur

Chalcogen Bonding “2S–2N Squares” versus Competing Interactions: Exploring the Recognition Properties of Sulfur

2,1,3‐Benzothiadiazole and Derivatives: Synthesis, Properties, Reactions, and Applications in Light Technology of Small Molecules

Highly Sensitive and Selective Molecular Probes for Chromo‐Fluorogenic Sensing of Carbon Monoxide in Air, Aqueous Solution and Cells

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