Discovery of a size-record breaking green-emissive fluorophore: small, smaller, HINA

Kang, Rui; Talamini, Laura; D’Este, Elisa; Estevão, Bianca Martins; Cola, Luisa De; Klopper, Wim; Biedermann, Frank

doi:10.1039/d0sc05557c

Cited by 11 publications

(12 citation statements)

References 54 publications

(81 reference statements)

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“…For instance, our group has recently communicated the smallest green emissive fluorophore HINA (3-hydroxyisonicotinealdehyde) known so far (P2.55 in Figure 38) and found that its binding to a Pt IIcomplex results in its emission quenching in 900 μM CTAB in 25 mM carbonate buffer, pH 9.4. 169 Through subsequent addition of a thiol, e.g., cysteine, to the in situ formed probe P2.55, the HINA indicator is released within seconds, providing an emission turn-on response. The assay can be used for general thiol detection in buffered aqueous media with micromolar sensitivity.…”

Section: Molecular Probes For Amino Acids (And Proteins)mentioning

confidence: 99%

“…While most thiol-reactive probes exploit the nucleophilic or redox properties of thiols in organic reactions, it is also possible to develop thiol probes that capitalize on the strong, near-covalent bonding interactions of thiols with soft transition metal ions functional in aqueous media. For instance, our group has recently communicated the smallest green emissive fluorophore HINA (3-hydroxyisonicotinealdehyde) known so far ( P2.55 in Figure ) and found that its binding to a Pt II -complex results in its emission quenching in 900 μM CTAB in 25 mM carbonate buffer, pH 9.4 . Through subsequent addition of a thiol, e.g.…”

Section: Amino Acidsmentioning

confidence: 99%

Section: Amino Acidsmentioning

confidence: 99%

“…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%

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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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Section: Molecular Probes For Amino Acids (And Proteins)mentioning

confidence: 99%

Section: Amino Acidsmentioning

confidence: 99%

Section: Amino Acidsmentioning

confidence: 99%

Section: Lipids and Steroidsmentioning

confidence: 99%

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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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“…Damit hält dieses Molekül mit seinen 14 Atomen nun den Weltrekord für den kleinsten wasserlöslichen, grün fluoreszierenden Farbstoff. 39) Baeyer hatte im Jahr 1871 die Synthese von Fluorescein (44a) publiziert. Dennoch dauerte es 150 Jahre bis zur Synthese des Phosphonsäurederivats Phosphonofluorescein (44b) (Abbildung 13).…”

Section: Organische Materialien Und Nanostrukturenunclassified

Trendbericht Organische Chemie 2022

Andexer¹,

Beifuß²,

Brasholz³

et al. 2022

Nachr Chem

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Design of 2‐Pyridone Fluorophores for Brighter Emissions at Longer Wavelengths

Kim,

Lee

et al. 2024

Chemistry A European J

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The recent discovery of blue fluorophores with high quantum yields based on pyridone structures inspired the development of new low‐molecular‐weight fluorophores with bright emissions at tunable wavelengths, which are highly attractive for various applications. In this study, we propose a rational design strategy for 2‐pyridone‐based fluorophores with bright emissions at long wavelengths. With a detailed understanding of the positional substitution effects on each carbon atom of the 2‐pyridone core, we developed a bright blue fluorophore (λabs = 377 nm; λem = 433 nm; ε = 13,200 M−1 cm−1; ɸF = 88%) through C3‐aryl and C4‐ester substitutions followed by cyclization. Furthermore, by applying the intramolecular charge transfer (ICT) principle, we invented a bright green fluorophore through C3‐ and C4‐diester and C6‐aryl substitutions. The ICT fluorophore based on the pyridone structure shows large molar absorptivity (ε = 20,100 M−1 cm−1), longer emission wavelength (λem = 539 nm), high emission quantum yield (ɸF = 74%), and large Stokes shift (Δv = 5720 cm−1), which are comparable to those of practical fluorescent probes.

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Discovery of a size-record breaking green-emissive fluorophore: small, smaller, HINA

Abstract: Astonishingly, 3-hydroxyisonicotinealdehyde (HINA) is despite its small size a green-emitting push-pull fluorophore in water (QY of 15%) and shows ratiometric emission response to biological relevant pH differences (pKa2 ~7.1). Moreover,...

Cited by 11 publications

References 54 publications

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

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

Trendbericht Organische Chemie 2022

Design of 2‐Pyridone Fluorophores for Brighter Emissions at Longer Wavelengths

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