Carbazole–azine based fluorescence ‘<i>off–on</i>’ sensor for selective detection of Cu<sup>2+</sup> and its live cell imaging

Leslee, Denzil Britto Christopher; Sekar, Karuppannan; Vengaian, K. Muthu; Singaravadivel, Subramanian

doi:10.1002/bio.3332

Cited by 14 publications

(5 citation statements)

References 87 publications

(152 reference statements)

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“…It is therefore essential that one should design a molecule that has multifunctional usage in many different areas of technology [24]. Since carbazole is a relatively inexpensive material with unique properties such as high hole-transporting mobility [12,[25][26][27], pronounced thermal stability [2] and high fluorescent quantum yields [28,29] our attention was focused on carbazole derivatives. In addition to that, carbazole is a rigid ar-omatic molecule [30] with many different modification sites for multifunctionalisation [31].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

Altınölçek

Battal

Tavaslı

et al. 2020

Beilstein J. Org. Chem.

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Two novel carbazole-based compounds 7a and 7b were synthesised as potential candidates for application in organic electronics. The materials were fully characterised by NMR spectroscopy, mass spectrometry, FTIR, thermogravimetric analysis, differential scanning calorimetry, cyclic voltammetry, and absorption and emission spectroscopy. Compounds 7a and 7b, both of which were amorphous solids, were stable up to 291 °C and 307 °C, respectively. Compounds 7a and 7b show three distinctive absorption bands: high and mid energy bands due to locally excited (LE) transitions and low energy bands due to intramolecular charge transfer (ICT) transitions. In dichloromethane solutions compounds 7a and 7b gave emission maxima at 561 nm and 482 nm with quantum efficiencies of 5.4% and 97.4% ± 10%, respectively. At positive potential, compounds 7a and 7b gave two different oxidation peaks, respectively: quasi-reversible at 0.55 V and 0.71 V, and reversible at 0.84 V and 0.99 V. At negative potentials, compounds 7a and 7b only exhibited an irreversible reduction peak at −1.86 V and −1.93 V, respectively.

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Section: Introductionmentioning

confidence: 99%

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

Altınölçek

Battal

Tavaslı

et al. 2020

Beilstein J. Org. Chem.

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“…Dye CzA ( 238) is a dicarbazole-azine containing sensor, which binds to Cu(II) in a CuL 2 fashion, with a significant enhancement in green-yellow emission. 393 The authors attributed this to an alteration of ICT in the molecule and applied the probe in HeLa cells incubated with exogenous Cu(II). Probe BIDQ-1 (239) also operates by altered ICT, 394 while the fluorescence increase observed for 240 is likely due to altered ICT and alleviated PET quenching.…”

Section: Binding-based Turn-on Cu(ii) Probesmentioning

confidence: 99%

“…Dye CzA ( 238 ) is a dicarbazole-azine containing sensor, which binds to Cu(II) in a CuL 2 fashion, with a significant enhancement in green-yellow emission . The authors attributed this to an alteration of ICT in the molecule and applied the probe in HeLa cells incubated with exogenous Cu(II).…”

Section: Fluorescent Sensors For Coppermentioning

confidence: 99%

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Grover,

Koblova,

Pezacki

et al. 2024

Chem. Rev.

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Although transition metals constitute less than 0.1% of the total mass within a human body, they have a substantial impact on fundamental biological processes across all kingdoms of life. Indeed, these nutrients play crucial roles in the physiological functions of enzymes, with the redox properties of many of these metals being essential to their activity. At the same time, imbalances in transition metal pools can be detrimental to health. Modern analytical techniques are helping to illuminate the workings of metal homeostasis at a molecular and atomic level, their spatial localization in real time, and the implications of metal dysregulation in disease pathogenesis. Fluorescence microscopy has proven to be one of the most promising non-invasive methods for studying metal pools in biological samples. The accuracy and sensitivity of bioimaging experiments are predominantly determined by the fluorescent metal-responsive sensor, highlighting the importance of rational probe design for such measurements. This review covers activity-and binding-based fluorescent metal sensors that have been applied to cellular studies. We focus on the essential redox-active metals: iron, copper, manganese, cobalt, chromium, and nickel. We aim to encourage further targeted efforts in developing innovative approaches to understanding the biological chemistry of redox-active metals. CONTENTS5908 8.2. Activity-Based Fluorescent Sensors for Ni(II) 5911 9. Outlook 5911 Author Information 5912 Corresponding Authors 5912

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“…[35][36][37] Fluorescence based sensing is a widely accepted and powerful technique that is used for a variety of environmental, industrial, medical diagnostics, DNA sequencing, forensics, genetic analysis, and biotechnology applications. 38,39 Chromenylium cyanine, 40 styrylbenzothiazolium dye, 41 phenothiazine derivatives, 42,43 1-(1,3-dioxo-1H-inden-2(3H)ylidene)thiosemicarbazide, 44 carbazole-azine, 45 coumarin derivative, 46 oligothiophene-barbituric acid conjugate, 47 pyridine-Schiff base, 48 fluorescein, 49 cyanine dyes, 50,51 quinolone and pyridylaminophenol 52 are a few examples of the reported probes for detection of heavy metal ions like Cu 2+ , Hg 2+ , Co 2+ and Ni 2+ . Many quinoxaline-based probes have been developed recently, due to their excellent optical properties, for instance, indeno-quinoxaline-cyclo-2,4,7-trienol, 53 quinoxaline-ferrocene, 54 quinoxaline-nitrobenzohydrazide, 55 quinoxalinebenzimidazole-ferrocene, 56 and quinoxaline-hydroxybenzimine have been developed for detection of certain heavy metal ions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a quinoxaline–hydrazinobenzothiazole based probe—single point detection of Cu²⁺, Co²⁺, Ni²⁺ and Hg²⁺ ions in real water samples

et al. 2023

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Carbazole–azine based fluorescence ‘off–on’ sensor for selective detection of Cu²⁺ and its live cell imaging

Cited by 14 publications

References 87 publications

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Synthesis of a quinoxaline–hydrazinobenzothiazole based probe—single point detection of Cu²⁺, Co²⁺, Ni²⁺ and Hg²⁺ ions in real water samples

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Carbazole–azine based fluorescence ‘off–on’ sensor for selective detection of Cu2+ and its live cell imaging

Cited by 14 publications

References 87 publications

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Synthesis of a quinoxaline–hydrazinobenzothiazole based probe—single point detection of Cu2+, Co2+, Ni2+ and Hg2+ ions in real water samples

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Product

Resources

About

Carbazole–azine based fluorescence ‘off–on’ sensor for selective detection of Cu²⁺ and its live cell imaging

Synthesis of a quinoxaline–hydrazinobenzothiazole based probe—single point detection of Cu²⁺, Co²⁺, Ni²⁺ and Hg²⁺ ions in real water samples