A New Ratiometric Fluorescent Probe for Detection of Fe<sup>2+</sup> with High Sensitivity and Its Intracellular Imaging Applications

Li, Ping; Fang, Libo; Zhou, Hui; Zhang, Wen; Wang, Xu; Li, Na; Zhong, Hongbo; Tang, Bo

doi:10.1002/chem.201101327

Cited by 107 publications

(44 citation statements)

References 25 publications

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“…Proposed reaction mechanism for the formation of meso-aminoBODIPYs. Sequence S N Ar-Sonogashira:I nitial experimentsw ith brominated amino-BODIPY 25 led to very sluggish reactions;t herefore, we turned our attention to the iodinated analogues.F or this process, two starting materials were chosen,o ne with ap rimary amino group at the meso-position (23), and another with as econdary amino group (22). These substrates were selected in order to explore whether the extent of the conjugation of the nitrogen lone pair of the BODIPY [17k] core would significantly modify the outcome of the Sonogashira reaction.…”

Section: Resultsmentioning

confidence: 99%

“…Chem.E ur.J. 2016,22,[1048][1049][1050][1051][1052][1053][1054][1055][1056][1057][1058][1059][1060][1061] www.chemeurj.org for selected functionalization of the BODIPY core, the usually avoidedb romine atoms are also adequate to attain bright-redemitting dyes, probablyb ecause the spin-orbit coupling in a p-extended chromophore is less efficient. To gain ad eeper insight into such behaviour,w ea lso considered the corresponding derivative 20 without aromatic chains at the 3-and 5-positions.…”

Section: Photophysical Propertiesmentioning

confidence: 98%

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Near‐IR BODIPY Dyes à la Carte—Programmed Orthogonal Functionalization of Rationally Designed Building Blocks

Gómez‐Durán

Esnal

Valois‐Escamilla

et al. 2015

Chemistry A European J

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Herein, we report the synthesis of polyfunctional BODIPY building blocks suitable to be subjected to several reaction sequences with complete chemoselectivity, thereby allowing the preparation of complex BODIPY derivatives in a versatile and programmable manner. The reactions included the Liebeskind-Srogl cross-coupling reaction (LSCC), nucleophilic aromatic substitution (SN Ar), Suzuki, Sonogashira, and Stille couplings, and a desulfitative reduction of the MeS group. This novel synthetic protocol is a powerful route to design a library of compounds with tailored photophysical properties for advanced applications. In this context, it is noteworthy that it offers a straightforward and cost-effective strategy to shift the BODIPY emission deep into the near-infrared spectral region while retaining high fluorescence quantum yields as well as highly efficient and stable laser action. These new dyes outperform the lasing behaviour of dyes considered as benchmarks over the red spectral region, overcoming the important drawbacks associated with these commercial laser dyes, namely low absorption at the standard pump wavelengths (355 and 532 nm) and/or poor photostability.

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Section: Resultsmentioning

confidence: 99%

Section: Photophysical Propertiesmentioning

confidence: 98%

Near‐IR BODIPY Dyes à la Carte—Programmed Orthogonal Functionalization of Rationally Designed Building Blocks

Gómez‐Durán

Esnal

Valois‐Escamilla

et al. 2015

Chemistry A European J

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“…The success of this approach is heavily dependent on the design and development of highly sensitive and selective Fe 2ϩ and Fe 3ϩ fluorescent probes that can be synthesized more efficiently. In particular, the Fe 2ϩ fluorescent probe design is still a great challenge, and due to the difficult chemical synthesis, only a few probes have been reported so far (85,86). However, dual-functional iron fluorescent probes, which can be used for Fe 2ϩ and Fe 3ϩ in combination with chemical agents such as H 2 O 2 (87), or depending on pH, have been successfully applied in biological sample imaging (51).…”

Section: Discussionmentioning

confidence: 99%

Mapping of Heavy Metal Ion Sorption to Cell-Extracellular Polymeric Substance-Mineral Aggregates by Using Metal-Selective Fluorescent Probes and Confocal Laser Scanning Microscopy

Hao

Kappler

et al. 2013

Appl Environ Microbiol

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b Biofilms, organic matter, iron/aluminum oxides, and clay minerals bind toxic heavy metal ions and control their fate and bioavailability in the environment. The spatial relationship of metal ions to biomacromolecules such as extracellular polymeric substances (EPS) in biofilms with microbial cells and biogenic minerals is complex and occurs at the micro-and submicrometer scale. Here, we review the application of highly selective and sensitive metal fluorescent probes for confocal laser scanning microscopy (CLSM) that were originally developed for use in life sciences and propose their suitability as a powerful tool for mapping heavy metals in environmental biofilms and cell-EPS-mineral aggregates (CEMAs). The benefit of using metal fluorescent dyes in combination with CLSM imaging over other techniques such as electron microscopy is that environmental samples can be analyzed in their natural hydrated state, avoiding artifacts such as aggregation from drying that is necessary for analytical electron microscopy. In this minireview, we present data for a group of sensitive fluorescent probes highly specific for Fe 3؉ , Cu 2؉ , Zn 2؉ , and Hg 2؉ , illustrating the potential of their application in environmental science. We evaluate their application in combination with other fluorescent probes that label constituents of CEMAs such as DNA or polysaccharides and provide selection guidelines for potential combinations of fluorescent probes. Correlation analysis of spatially resolved heavy metal distributions with EPS and biogenic minerals in their natural, hydrated state will further our understanding of the behavior of metals in environmental systems since it allows for identifying bonding sites in complex, heterogeneous systems. Biofilms are the dominant form of microbial life on Earth (1), and the organic material that is present in biofilms significantly impacts the cycling and sequestration of toxic heavy metals in the environment (2, 3). The underlying sorption and complexation mechanisms are difficult to evaluate (4), since biofilms are highly dynamic and complex structures that consist of diverse biomacromolecules (5) and the in situ heavy metal distributions are readily influenced by common invasive analysis approaches such as sequential extractions for the determination of different metal fractions. Here, we introduce a promising approach for studying the distribution and sorption of heavy metals in biofilms and cell-extracellular polymeric substance (EPS)-mineral aggregates (CEMAs) under close-to-natural conditions using confocal laser scanning microscopy (CLSM) in combination with highly selective metal ion-sensitive fluorescence probes. This approach is frequently used for metal detection in cell biology but was rarely applied in environmental and geomicrobiology research due to a former lack of highly selective fluorescence probes and due to the complexity of environmental biofilms and CEMAs.Biofilms are mainly composed of water, microorganisms, and an EPS matrix (6) that consists of mostly polysacchari...

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“…Tris (bipyridine) ruthenium (II)‐functionalized MOFs showed several advantages: very high sensitivity and excellent selectivity as well as convenient visual detection . In addition, the hole size of MOFs is different, which offers desirable selectivity in detection ,. Therefore, dye molecules@MOFs nanocomposites provide a novel way for the developments of fluorescent probe to detect ClO − .…”

Section: Introductionmentioning

confidence: 99%

Ratiometric Fluorescent Detection of ClO⁻ Based on Dual‐Emission F1‐Rubpy@Nanoscale Metal‐Organic Frameworks

et al. 2019

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Herein, a facile one‐pot strategy was developed to synthesize novel dual‐emission nanoscale ZnMOF74 encapsulating with fluorescein o‐acrylate (F1) and tris(2,2’‐bipyridyl)‐dichroruthenium(II) hexahydrate (Rubpy) (F1‐Rubpy@ZnMOF74). The as‐prepared dual‐emission F1‐Rubpy@ ZnMOF74 nanocomposites were characterized by scanning electron microscopy, X‐ray powder diffraction, N2 adsorption/desorption isotherms and fluorescence techniques. The results showed F1‐Rubpy@ZnMOF74 nanocomposites were spherical with diameter of 100–300 nm, and exhibited good water dispersion. F1 and Rubpy were uniformly encapsulated in the pores of ZnMOF74. The nanosensor displayed strong emission peaks of F1 at 512 nm and Rubpy at 600 nm. The I512nm/I600nm decreased with increasing concentration of ClO− in the range of 3.6 nM‐100 μM with low detection limit of 1.2 nM. The nanocomposites also showed high sensitivity, selectivity and stability, which was expected to apply in quality testing of industrial goods and further biological cell experiments. The work also provides a good method to construct ratiometric fluorescent sensors based on MOFs.

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A New Ratiometric Fluorescent Probe for Detection of Fe²⁺ with High Sensitivity and Its Intracellular Imaging Applications

Cited by 107 publications

References 25 publications

Near‐IR BODIPY Dyes à la Carte—Programmed Orthogonal Functionalization of Rationally Designed Building Blocks

Near‐IR BODIPY Dyes à la Carte—Programmed Orthogonal Functionalization of Rationally Designed Building Blocks

Mapping of Heavy Metal Ion Sorption to Cell-Extracellular Polymeric Substance-Mineral Aggregates by Using Metal-Selective Fluorescent Probes and Confocal Laser Scanning Microscopy

Ratiometric Fluorescent Detection of ClO⁻ Based on Dual‐Emission F1‐Rubpy@Nanoscale Metal‐Organic Frameworks

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A New Ratiometric Fluorescent Probe for Detection of Fe2+ with High Sensitivity and Its Intracellular Imaging Applications

Cited by 107 publications

References 25 publications

Near‐IR BODIPY Dyes à la Carte—Programmed Orthogonal Functionalization of Rationally Designed Building Blocks

Near‐IR BODIPY Dyes à la Carte—Programmed Orthogonal Functionalization of Rationally Designed Building Blocks

Mapping of Heavy Metal Ion Sorption to Cell-Extracellular Polymeric Substance-Mineral Aggregates by Using Metal-Selective Fluorescent Probes and Confocal Laser Scanning Microscopy

Ratiometric Fluorescent Detection of ClO− Based on Dual‐Emission F1‐Rubpy@Nanoscale Metal‐Organic Frameworks

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A New Ratiometric Fluorescent Probe for Detection of Fe²⁺ with High Sensitivity and Its Intracellular Imaging Applications

Ratiometric Fluorescent Detection of ClO⁻ Based on Dual‐Emission F1‐Rubpy@Nanoscale Metal‐Organic Frameworks