A novel solvent-dependently bifunctional NIR absorptive and fluorescent ratiometric probe for detecting Fe3+/Cu2+ and its application in bioimaging

Near-infrared (NIR) fluorescence imaging is a noninvasive technique that provides numerous advantages for the realtime in vivo monitoring of biological information in living subjects without the use of ionizing radiation. Near-infrared fluorescent (NIRF) dyes are widely used as fluorescent imaging probes. These fluorescent dyes remarkably decrease the interference caused by the self-absorption of substances and autofluorescence, increase detection selectivity and sensitivity, and reduce damage to the human body. Thus, they are beneficial for bioassays. Indole heptamethine cyanine dyes are widely investigated in the field of near-infrared fluorescence imaging. They are mainly composed of indole heterocyclics, heptamethine chains, and N-substituent side chains. With indole heptamethine cyanine dyes as the parent, introducing reactive groups to the parent compounds or changing their structures can make fluorescent probes have different functions like labeling protein and tumor, detecting intracellular metal cations, which has become the hotspot in the field of fluorescence imaging of biological research. Therefore, this study reviewed the applications of indole heptamethine cyanine fluorescent probes to metal cation detection, pH, molecules, tumor imaging, and protein in vivo. The distribution, imaging results, and metabolism of the probes in vivo and in vitro were described. The biological application trends and existing problems of fluorescent probes were discussed.

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“…Li et al [42] reported the probe 29 ( Fig. 16) that was used to detect Fe 3+ and Cu 2+ in MeOH/H 2 O and MeCN/ H 2 O solvents, respectively.…”

Section: Application Of Metal Ion Selective Nir Fluorescence Probesmentioning

confidence: 99%

Research progress of near-infrared fluorescence probes based on indole heptamethine cyanine dyes in vivo and in vitro

Sun

Wang

et al. 2020

BMC Chemistry

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“…Moreover, few recent studies show that the coumarin derivatives are capable of fluorescence chemosensory applications too . At the same time, coumarin molecules functionalized with a hydroxy group at the 7‐position are efficient fluorophores since the presence of an electron donating group at the 7‐position are known to enhance the fluorescence of such probes …”

Section: Introductionmentioning

confidence: 99%

ICT‐Based Blue‐Emitting Dual‐Functional Probe (Ugi EML BLUE) for Bio‐Imaging and Cytotoxic Activities on HeLa Cells

Puthumana

Bahulayan

2019

ChemistrySelect

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An Intramolecular Charge Transfer (ICT) based blue emitting fluorescent probe (Ugi EML BLUE) has been developed and its binding properties against human CDK2 protein have been studied via docking methods. The docking studies showed that, Ugi EML BLUE can effectively interact with the ATP binding sites of CDK2. The positive results obtained from the docking studies have been extended to the bio‐imaging as well as antineoplastic applications in HeLa cells. The in vitro biological activity studies revealed the remarkable potential of Ugi EML BLUE as a dual‐functional molecule that can be used not only as a CDK2‐targeted fluorescent probe for bio‐imaging (λabs 338 nm, λems 443 nm) but also as a CDK2 targeted inhibitor for HeLa cells (IC 50: 0.5 μg/mL). At the sub cellular level, Ugi EML BLUE can selectively interact with the ATP binding sites of the activated CDK 2 to arrest the transfer of phosphate groups from its bound ATP to the serine and threonine residues of the target substrates involved in DNA transcription and replication initiated at the G1 cell cycle phase and which will lead to the inhibition of tumor growth.

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“…[1][2][3][4][5] Especially, fluorescent methods have been regarded as effective tools over other optical chemosensors because of their low cost, accurate analysis and high selectivity. [10][11][12][13][14][15][16] Copper, as one of the most abundant metals in the earth, is not only an essential trace metal ion for many enzymatic processes but also a pollutant because of its wide usage in modern life. [10][11][12][13][14][15][16] Copper, as one of the most abundant metals in the earth, is not only an essential trace metal ion for many enzymatic processes but also a pollutant because of its wide usage in modern life.…”

Section: Introductionmentioning

confidence: 99%

“…Especially, fluorescent methods have been regarded as effective tools over other optical chemosensors because of their low cost, accurate analysis and high selectivity . In this regard, much effort was paid to design of fluorescent chemosensors targeted at a specific transition metal ion . Copper, as one of the most abundant metals in the earth, is not only an essential trace metal ion for many enzymatic processes but also a pollutant because of its wide usage in modern life .…”

Section: Introductionmentioning

confidence: 99%

A Phenanthroimidazole‐based Fluorescent Turn‐Off Chemosensor for the Selective Detection of Cu²⁺ in Aqueous Media

Hwang

Chae

Kim

2018

Bulletin Korean Chem Soc

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A new phenanthroline-based chemosensor 3-(1H-phenanthro[9,10-d]imidazol-2-yl)benzene-1,2-diol (1) was synthesized for the recognition of Cu 2+ . Sensor 1 showed selective fluorescence quenching for Cu 2+ in aqueous media. Detection limit (0.87 μM) for Cu 2+ was much lower than WHO guideline (31.5 μM). Sensing property of 1 toward Cu 2+ was studied by fluorescence and UV-Vis titrations, and Job plot and ESI-MS analyses. Moreover, turn-off fluorescence mechanism of 1 toward Cu 2+ induced by intramolecular charge-transfer (ICT) and ligand-to-metal charge-transfer (LMCT) was well demonstrated by theoretical calculations.

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A novel solvent-dependently bifunctional NIR absorptive and fluorescent ratiometric probe for detecting Fe3+/Cu2+ and its application in bioimaging

Cited by 87 publications

References 49 publications

Research progress of near-infrared fluorescence probes based on indole heptamethine cyanine dyes in vivo and in vitro

Research progress of near-infrared fluorescence probes based on indole heptamethine cyanine dyes in vivo and in vitro

ICT‐Based Blue‐Emitting Dual‐Functional Probe (Ugi EML BLUE) for Bio‐Imaging and Cytotoxic Activities on HeLa Cells

A Phenanthroimidazole‐based Fluorescent Turn‐Off Chemosensor for the Selective Detection of Cu²⁺ in Aqueous Media

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A novel solvent-dependently bifunctional NIR absorptive and fluorescent ratiometric probe for detecting Fe3+/Cu2+ and its application in bioimaging

Cited by 87 publications

References 49 publications

Research progress of near-infrared fluorescence probes based on indole heptamethine cyanine dyes in vivo and in vitro

Research progress of near-infrared fluorescence probes based on indole heptamethine cyanine dyes in vivo and in vitro

ICT‐Based Blue‐Emitting Dual‐Functional Probe (Ugi EML BLUE) for Bio‐Imaging and Cytotoxic Activities on HeLa Cells

A Phenanthroimidazole‐based Fluorescent Turn‐Off Chemosensor for the Selective Detection of Cu2+ in Aqueous Media

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A Phenanthroimidazole‐based Fluorescent Turn‐Off Chemosensor for the Selective Detection of Cu²⁺ in Aqueous Media