Tuning the Sensitivity of Fluorescent Porphyrin Dimers to Viscosity and Temperature

Vyšniauskas, Aurimas; Ding, Dong; Qurashi, Maryam; Boczarow, Igor; Baláž, Milan; Anderson, Harry L.; Kuimova, Marina K.

doi:10.1002/chem.201700740

Cited by 37 publications

(27 citation statements)

References 40 publications

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“…Therefore, it is necessary to exclude certain distortion effects for accurate viscosity measurement using the FL intensity of molecular rotors. To this end, ratiometric molecular rotors have been developed that exhibit dual emission of viscosity sensitive (probe) and insensitive (reference) FL signals . Ratiometric analysis of the viscosity‐dependent probe signal with respect to the internal reference provides normalized data accounting for probe concentration.…”

Section: Remarkable Issuesmentioning

confidence: 99%

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Fluorescent Molecular Rotors for Viscosity Sensors

Lee

Heo

Woo

et al. 2018

Chemistry A European J

216

117

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Fluorescent molecular rotors (FMRs) can act as viscosity sensors in various media including subcellular organelles and microfluidic channels. In FMRs, the rotation of rotators connected to a fluorescent π-conjugated bridge is suppressed by increasing environmental viscosity, resulting in increasing fluorescence (FL) intensity. In this minireview, we describe recently developed FMRs including push-pull type π-conjugated chromophores, meso-phenyl (borondipyrromethene) (BODIPY) derivatives, dioxaborine derivatives, cyanine derivatives, and porphyrin derivatives whose FL mechanism is viscosity-responsive. In addition, FMR design strategies for addressing various issues (e.g., obtaining high FL contrast, internal FL references, and FL intensity-contrast trade-off) and their biological and microfluidic applications are also discussed.

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Section: Remarkable Issuesmentioning

confidence: 99%

“…Dual‐emissive porphyrin‐based FMRs (Figure ) are another representative ratiometric viscosity sensors . FMRs based on porphyrin dimers that can rotate around a linear diyne linker, show two emission bands at different wavelengths.…”

Section: Remarkable Issuesmentioning

confidence: 99%

Fluorescent Molecular Rotors for Viscosity Sensors

Lee

Heo

Woo

et al. 2018

Chemistry A European J

216

117

View full text Add to dashboard Cite

show abstract

“…One approach, technically challenging, is to use homo-FRET signal of mechanosensitive ion channels16. Among different mechanisms explored, Photoinduced electron Transfer (PeT) is better for voltage sensitivity26, whereas solvatochromism21, 28 and excited-state deplanarization in molecular rotors23, 24, 28, 29, 30, 31 are most promising for imaging membrane order.…”

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confidence: 99%

A fluorescent membrane tension probe

Colom¹,

Derivery²,

et al. 2018

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Cells and organelles are delimited by lipid bilayers in which high deformability is essential to many cell processes, including motility, endocytosis and cell division. Membrane tension is therefore a major regulator of the cell processes that remodel membranes, albeit one that is very hard to measure in vivo. Here we show that a planarizable push-pull fluorescent probe called FliptR (fluorescent lipid tension reporter) can monitor changes in membrane tension by changing its fluorescence lifetime as a function of the twist between its fluorescent groups. The fluorescence lifetime depends linearly on membrane tension within cells, enabling an easy quantification of membrane tension by fluorescence lifetime imaging microscopy. We further show, using model membranes, that this linear dependency between lifetime of the probe and membrane tension relies on a membrane-tension-dependent lipid phase separation. We also provide calibration curves that enable accurate measurement of membrane tension using fluorescence lifetime imaging microscopy.

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“…Time‐resolved fluorescence traces were recorded with time‐correlated single‐photon counting (TCSPC) by using either an IBH 5000F TCSPC device (Jobin–Ybon, Horiba) equipped with a 404 nm NanoLED as an excitation source (pulse width <200 ps, HORIBA) ( BDATA‐M2 ) or using a home‐built TCSPC setup previously described [55] with a pulsed diode laser at 477 nm (Becker & Hickl GmbH, 20 MHz) ( CDATA‐M2 ).…”

Section: Methodsmentioning

confidence: 99%

Assessing The Key Photophysical Properties of Triangulenium Dyes for DNA Binding by Alteration of the Fluorescent Core

Lewis

Bisballe

Santella

et al. 2020

Chemistry A European J

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Four‐stranded G‐quadruplex (G4) DNA is a non‐canonical DNA topology that has been proposed to form in cells and play key roles in how the genome is read and used by the cellular machinery. Previously, a fluorescent triangulenium probe (DAOTA‐M2) was used to visualise G4s in cellulo, thanks to its distinct fluorescence lifetimes when bound to different DNA topologies. Herein, the library of available triangulenium probes is expanded to explore how modifications to the fluorescent core of the molecule affect its photophysical characteristics, interaction with DNA and cellular localisation. The benzo‐bridged and isopropyl‐bridged diazatriangulenium dyes, BDATA‐M2 and CDATA‐M2 respectively, featuring ethyl‐morpholino substituents, were synthesised and characterised. The interactions of these molecules with different DNA topologies were studied to determine their binding affinity, fluorescence enhancement and fluorescence lifetime response. Finally, the cellular uptake and localisation of these optical probes were investigated. Whilst structural modifications to the triangulenium core only slightly alter the binding affinity to DNA, BDATA‐M2 and CDATA‐M2 cannot distinguish between DNA topologies through their fluorescence lifetime. It is argued theoretically and experimentally that this is due to reduced effectiveness of photoinduced electron transfer (PET) quenching. This work presents valuable new evidence into the critical role of PET quenching when using the fluorescence lifetime of triangulenium dyes to discriminate G4 DNA from duplex DNA, highlighting the importance of fine tuning redox and spectral properties when developing new triangulenium‐based G4 probes.

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Tuning the Sensitivity of Fluorescent Porphyrin Dimers to Viscosity and Temperature

Cited by 37 publications

References 40 publications

Fluorescent Molecular Rotors for Viscosity Sensors

Fluorescent Molecular Rotors for Viscosity Sensors

A fluorescent membrane tension probe

Assessing The Key Photophysical Properties of Triangulenium Dyes for DNA Binding by Alteration of the Fluorescent Core

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