A fluorescent activatable probe for imaging intracellular Mg<sup>2+</sup>

Treadwell, Ryan; Moliner, Fabio De; Subirós‐Funosas, Ramon; Hurd, Toby W.; Knox, Kirsten; Vendrell, Marc

doi:10.1039/c7ob02965a

Cited by 18 publications

(10 citation statements)

References 41 publications

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“…The BC- series of compounds have different numbers and positions of methyl groups on the BC , while the BP- series of compounds are modified by changing positions of acetamido groups on the phenyl ring. As the intramolecular rotation of the BODIPY rotors was found closely related to viscosity sensitivity, BODIPY derivatives applied in this study contained the 1,7-substituted core to inhibit the free rotation. − …”

Section: Resultsmentioning

confidence: 96%

Molecular Mechanism of Viscosity Sensitivity in BODIPY Rotors and Application to Motion-Based Fluorescent Sensors

et al. 2020

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Viscosity in the intracellular microenvironment shows a significant difference in various organelles and is closely related to cellular processes. Such microviscosity in live cells is often mapped and quantified with fluorescent molecular rotors. To enable the rational design of viscosity-sensitive molecular rotors, it is critical to understand their working mechanisms. Herein, we systematically synthesized and investigated two sets of BODIPY-based molecular rotors to study the relationship between intramolecular motions and viscosity sensitivity. Through experimental and computational studies, two conformations (i.e., the planar and butterfly conformations) are found to commonly exist in BODIPY rotors. We demonstrate that the transformation energy barrier from the planar conformation to the butterfly conformation is strongly affected by the molecular structures of BODIPY rotors and plays a critical role in viscosity sensitivity. These findings enable rational structure modifications of BODIPY molecular rotors for highly effective protein detection and recognition.

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Section: Resultsmentioning

confidence: 96%

Molecular Mechanism of Viscosity Sensitivity in BODIPY Rotors and Application to Motion-Based Fluorescent Sensors

et al. 2020

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“…Some APTRA-based probes developed in recent years also have higher affinity for Ca 2+ than Mg 2+ . − Although intracellular Ca 2+ concentration ([Ca 2+ ] i ) is estimated to be around 100 nM, it can reach levels of about 10 μM by various stimulation, and hence, fluorescence signals from those probes are often influenced by Ca 2+ . Therefore, our group has developed the highly selective Mg 2+ fluorescent probe KMG series based on the β-diketone moiety. , In recent years, some other groups also developed highly selective Mg 2+ ligands without interference from Ca 2+ , − which indicates that highly selective Mg 2+ probes are required for in detail investigation. However, the fluorescent dye moieties of these probes show green to red fluorescence emission, such as fluorescein (KMG-104: λ abs /λ em = 504/523), rhodamine (KMG-301: λ abs /λ em = 563/590), and styryl boron-dipyrromethene (MagQ-1: λ abs /λ em = 600/635) as summarized in Table .…”

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confidence: 99%

Near-Infrared Fluorescent Probes for Imaging of Intracellular Mg²⁺ and Application to Multi-Color Imaging of Mg²⁺, ATP, and Mitochondrial Membrane Potential

et al. 2019

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The magnesium ion (Mg2+) is an essential cation to maintain proper cellular activities. To visualize the dynamics and functions of Mg2+, there is a great need for the development of Mg2+-selective fluorescent probes. However, conventional Mg2+ fluorescent probes are falling behind in low selectivity and poor fluorescence color variation. In this report, to make available a distinct color window for multi-color imaging, we designed and synthesized highly Mg2+-selective and near-infrared (NIR) fluorescent probes, the KMG-500 series consisting of a charged β-diketone as a selective binding site for Mg2+ and a Si-rhodamine residue as the NIR fluorophore, which showed photoinduced electron transfer (PeT)-type OFF-ON response to the concentration of Mg2+. Two types of KMG-500 series probes, tetramethyl substituted Si-rhodamine KMG-501 and tetraethyl substituted Si-rhodamine KMG-502, were synthesized for the evaluation of cell permeability. For intracellular application, the membrane-permeable acetoxymethyl derivative KMG-501 (KMG-501AM) was synthesized and allowed to stably stain cultured rat hippocampal neurons during imaging of intracellular Mg2+. On the other hand, KMG-502 was cell membrane permeable without AM modification, preventing the probe from staying inside cells during imaging. KMG-501 distributed mainly in the cytoplasm and partially localized in lysosomes and mitochondria in cultured rat hippocampal neurons. Mg2+ increase in response to the FCCP uncoupler inducing depolarization of the mitochondrial inner membrane potential was detected in the KMG-501 stained neurons. For the first time, KMG-501 succeeded in imaging intracellular Mg2+ dynamics with NIR fluorescence. Moreover, it allows one to simultaneously visualize changes in Mg2+ and ATP concentration and also mitochondrial inner membrane potential and their interactions. This probe is expected to be a strong tool for multi-color imaging of intracellular Mg2+.

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“…During the course of our studies, Vendrell and coworkers reported a related BODIPY compound, devoid of the water-solubilizing carboxypropyl groups, and demonstrated similar Mg 2+ sensing properties but only in aqueous/organic solvent mixtures. 33…”

Section: Resultsmentioning

confidence: 99%

Highly selective, red emitting BODIPY-based fluorescent indicators for intracellular Mg²⁺imaging

Lin

Buccella

2018

J. Mater. Chem. B

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Most fluorescent indicators for Mg2+ suffer from poor selectivity against other divalent cations, especially Ca2+, thus do not provide reliable information on cellular Mg2+ concentrations in processes in which such metals are involved. We report a new set of highly selective fluorescent indicators based on alkoxystyryl-functionalized BODIPY fluorophores decorated with a 4-oxo-4H-quinolizine-3-carboxylic acid metal binding moiety. The new sensors, MagQ1 and MagQ2, display absorption and emission maxima above 600 nm, with a 29-fold fluorescence enhancement and good quantum yields (Φ > 0.3) upon coordination of Mg2+ in aqueous buffer. Fluorescence response to Mg2+ is not affected by the presence of competing divalent cations typically present in the cellular milieu, and displays minimal pH dependence in the physiologically relevant range. The choice of alkoxy groups decorating the styryl BODIPY core does not influence the basic photophysical and metal binding properties of the compounds, but has a marked effect on their intracellular retention and thus in their applicability for detection of cellular Mg2+ by fluorescence imaging. In particular, we demonstrate the utility of a triethyleneglycol (TEG) functionalization tactic that endows MagQ2 with superior cellular retention in live cells by reducing active extrusion through organic anion transporters, which are thought to cause fast leakage of typical anionic dyes. With enhanced retention and excellent photophysical properties, MagQ2 can be applied in the detection of cellular Mg2+ influx without interference of high concentrations of Ca2+ akin to those involved in signaling.

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A fluorescent activatable probe for imaging intracellular Mg²⁺

Abstract: An BODIPY probe for detection and imaging of Mg2+ without interference from Ca2+ is described.

Cited by 18 publications

References 41 publications

Molecular Mechanism of Viscosity Sensitivity in BODIPY Rotors and Application to Motion-Based Fluorescent Sensors

Molecular Mechanism of Viscosity Sensitivity in BODIPY Rotors and Application to Motion-Based Fluorescent Sensors

Near-Infrared Fluorescent Probes for Imaging of Intracellular Mg²⁺ and Application to Multi-Color Imaging of Mg²⁺, ATP, and Mitochondrial Membrane Potential

Highly selective, red emitting BODIPY-based fluorescent indicators for intracellular Mg²⁺imaging

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A fluorescent activatable probe for imaging intracellular Mg2+

Abstract: An BODIPY probe for detection and imaging of Mg2+ without interference from Ca2+ is described.

Cited by 18 publications

References 41 publications

Molecular Mechanism of Viscosity Sensitivity in BODIPY Rotors and Application to Motion-Based Fluorescent Sensors

Molecular Mechanism of Viscosity Sensitivity in BODIPY Rotors and Application to Motion-Based Fluorescent Sensors

Near-Infrared Fluorescent Probes for Imaging of Intracellular Mg2+ and Application to Multi-Color Imaging of Mg2+, ATP, and Mitochondrial Membrane Potential

Highly selective, red emitting BODIPY-based fluorescent indicators for intracellular Mg2+imaging

Contact Info

Product

Resources

About

A fluorescent activatable probe for imaging intracellular Mg²⁺

Near-Infrared Fluorescent Probes for Imaging of Intracellular Mg²⁺ and Application to Multi-Color Imaging of Mg²⁺, ATP, and Mitochondrial Membrane Potential

Highly selective, red emitting BODIPY-based fluorescent indicators for intracellular Mg²⁺imaging