Meta-Fluors—A Unique Way To Create a 200 Da Ultrasmall Fluorophore Emitting in Red with Intense Stokes/Solvatochromic Shift: Imaging Subcellular Nanopolarity in Live Stem Cells

Mandal, Mrinal; Chatterjee, Tanmay; Das, Ananya; Mandal, Saptarshi; Sen, Ankita; Ta, Malancha; Mandal, Prasun K.

doi:10.1021/acs.jpcc.9b08524

Cited by 18 publications

(39 citation statements)

References 50 publications

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“…Advancing live cell imaging in cancerous cells, , mesenchymal stem cells with a clinical role in the maintenance and repair of tissues are coming up as emerging candidates. Moreover, measuring subcellular polarity has been a subject of significant topical interest. , Our group has been actively involved in bioimaging research in these directions. − Small red-emitting MBRF s (say MBRF s 7 and 8) with intense Stokes and solvatochromic shifts will be much less perturbative than large-sized red-emitting fluorophores toward bioimaging. , MBRF 7 goes inside live stem cells and gets localized in the perinuclear region (Figure a–c) (for MBRF 8, see Figure S16). Cytotoxicities of these MBRF s are quite low (cell viability ∼70% up to 12 h; Figures d and S17).…”

Section: Resultsmentioning

confidence: 99%

Innovative Strategy Toward Red Emission: Single-Benzenic, Ultrasmallmeta-Fluorophores

et al. 2020

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Contrary to the belief of the chemistry community, intense charge transfer is observed between meta-oriented donor–acceptor moieties in ultrasmall single-benzenic fluorophores. Red emission in any solvent has so far been reported with molecular fluorophores having the lowest molecular weight (MW) of 252.5 Da; however, we have achieved the same with a meta-fluorophore having an MW of only 203.1 Da. Red emission in a nonpolar solvent has so far been reported with a fluorophore having a minimum MW of 464.5 Da, but we have achieved the same with a meta-fluorophore having an MW of only 255.3 Da. Intense Stokes (260 nm) and solvatochromic (160 nm) shifts, high magnitudes of fluorescence quantum yield (>0.4), and excited-state lifetime (>16 ns) have been obtained in these single-benzenic meta-fluorophores, and these values are comparatively much higher in comparison to corresponding o-/p-fluorophores. These extraordinary meta-fluorophores have been employed to measure subcellular nanopolarity in live stem cells toward cost-effective white fluorescent ink and white light-emitting diodes (LEDs) in solid state.

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Section: Resultsmentioning

confidence: 99%

Innovative Strategy Toward Red Emission: Single-Benzenic, Ultrasmallmeta-Fluorophores

et al. 2020

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“…Environmentally sensitive fluorescent probes, such as compounds that show largely different emission spectra in apolar and polar solvents, have long been known, although compounds with extraordinary structural and photophysical properties continue to emerge. −, It is therefore not surprising that tailor-made probes can be designed for lipid droplet (LD) recognition but exciting to see that probes can readily distinguish cancerous from normal cells because the properties of LDs differ in terms of polarity, fluidity, and composition ( P8.1 in Figure ). …”

Section: Lipids and Steroidsmentioning

confidence: 99%

Molecular Probes, Chemosensors, and Nanosensors for Optical Detection of Biorelevant Molecules and Ions in Aqueous Media and Biofluids

et al. 2022

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Synthetic molecular probes, chemosensors, and nanosensors used in combination with innovative assay protocols hold great potential for the development of robust, low-cost, and fast-responding sensors that are applicable in biofluids (urine, blood, and saliva). Particularly, the development of sensors for metabolites, neurotransmitters, drugs, and inorganic ions is highly desirable due to a lack of suitable biosensors. In addition, the monitoring and analysis of metabolic and signaling networks in cells and organisms by optical probes and chemosensors is becoming increasingly important in molecular biology and medicine. Thus, new perspectives for personalized diagnostics, theranostics, and biochemical/ medical research will be unlocked when standing limitations of artificial binders and receptors are overcome. In this review, we survey synthetic sensing systems that have promising (future) application potential for the detection of small molecules, cations, and anions in aqueous media and biofluids. Special attention was given to sensing systems that provide a readily measurable optical signal through dynamic covalent chemistry, supramolecular host− guest interactions, or nanoparticles featuring plasmonic effects. This review shall also enable the reader to evaluate the current performance of molecular probes, chemosensors, and nanosensors in terms of sensitivity and selectivity with respect to practical requirement, and thereby inspiring new ideas for the development of further advanced systems.

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“…Mandal et al have developed a class of meta-fluors, having molecular weights of < 200 Da, as ultra-small solvatochromic fluorophores. [90] Using these probes, namely DEAB and DEAMB (74), the micropolarity of the perinuclear membrane was found to be like tetrahydrofuran or ethyl acetate.…”

Section: Polaritymentioning

confidence: 99%

Intracellular Physical Properties with Small Organic Fluorescent Probes: Recent Advances and Future Perspectives

Dutta

Pal

Koner

2022

The Chemical Record

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The intracellular physical parameters i. e., polarity, viscosity, fluidity, tension, potential, and temperature of a live cell are the hallmark of cellular health and have garnered immense interest over the past decade. In this context, small molecule organic fluorophores exhibit prominent useful properties including easy functionalizability, environmental sensitivity, biocompatibility, and fast yet efficient cellular uptakability which has made them a popular tool to understand intra‐cellular micro‐environmental properties. Throughout this discussion, we have outlined the basic design strategies of small molecules for specific organelle targeting and quantification of physical properties. The values of these parameters are indicative of cellular homeostasis and subtle alteration may be considered as the onset of disease. We believe this comprehensive review will facilitate the development of potential future probes for superior insight into the physical parameters that are yet to be quantified.

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Meta-Fluors—A Unique Way To Create a 200 Da Ultrasmall Fluorophore Emitting in Red with Intense Stokes/Solvatochromic Shift: Imaging Subcellular Nanopolarity in Live Stem Cells

Cited by 18 publications

References 50 publications

Innovative Strategy Toward Red Emission: Single-Benzenic, Ultrasmallmeta-Fluorophores

Innovative Strategy Toward Red Emission: Single-Benzenic, Ultrasmallmeta-Fluorophores

Molecular Probes, Chemosensors, and Nanosensors for Optical Detection of Biorelevant Molecules and Ions in Aqueous Media and Biofluids

Intracellular Physical Properties with Small Organic Fluorescent Probes: Recent Advances and Future Perspectives

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