1,8-Naphthalimide-based turn-on fluorescent chemosensor for Cu2+ and its application in bioimaging

Chen, Jiayi; Su, Wei; Wang, Enju; Yan-pin, Liu

doi:10.1016/j.jlumin.2016.08.040

Cited by 19 publications

(7 citation statements)

References 26 publications

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“…Effect of pH on the fluorescence property of ANT‐pen NPs was investigated by fluorescence titration using ANT‐pen NPs solution in an EtOH‐HEPES buffer (60:40) solution (pH 7.2) with regular addition of 1 M NaOH or 1 M HCl . It was observed that in absence of Cu II the fluorescence intensity of ANT‐pen NPs remained constant over a pH range of 3–12.…”

Section: Selective Detection Of Cuii By Ant‐pen Npsmentioning

confidence: 99%

Organic Nanoparticle-Based Fluorescent Chemosensor for Selective Switching ON and OFF of Photodynamic Therapy (PDT)

et al. 2016

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Photodynamic therapy (PDT) is a non‐invasive cancer treatment. For target‐specific PDT, targeting “overexpression” of some specific cellular markers will be highly beneficial. As CuII content is higher in cancer cells than in normal cells, selective binding with CuII can be the most effective mode for intracellular heterogeneity‐responsive targeted PDT. Thus, a photosensitizer showing competent PDT activity only after CuII chelation is important for tumor‐targeted PDT. Herein, we report a new ratiometric fluorescent chemosensor based on anthracene‐N‐phenylethylenediamine nanoparticles (ANT‐pen NPs), which showed fluorescence color change from green to red upon CuII chelation. Only the CuII‐bound state showed selective PDT activity; hence, this color change was used for real‐time monitoring of targeted PDT. Cellular images in cancerous HeLa and non‐cancerous NIH 3T3 cell lines showed the change in fluorescence of ANT‐pen NPs on selective binding with CuII in HeLa cells only. MTT assay in both cells suggested massive cell destruction by ANT‐pen‐CuII NPs only in HeLa cells upon visible light exposure, whereas NPs remained non‐toxic to NIH 3T3 cells.

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Section: Selective Detection Of Cuii By Ant‐pen Npsmentioning

confidence: 99%

Organic Nanoparticle-Based Fluorescent Chemosensor for Selective Switching ON and OFF of Photodynamic Therapy (PDT)

et al. 2016

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“…[3][4][5][6][7][8] During the course of our ongoing efforts to develop fluorescent probes for mental ions [9][10][11] , we have firstly found that some probes containing S-donor show turn on fluorescence responses to Cu 2+ , and so the S-donor may play an important role in protecting from Cu 2+ -induced fluorescence quenching. [12][13][14] Following this idea, a rationally designed fluorescent probe containing S-donor (1) was synthesized by incorporating 3-acetyl-7-hydroxycoumarin and 2-hydrazinylbenzo[d]thiazole for the fluorescence turn-on detection of cupric ion in the present work (Scheme 1). The binding mode between 1 and Cu 2+ was determined by ESI-MS.…”

Section: Introductionmentioning

confidence: 99%

Benzothiazolylhydrazone-Based Turn-on Fluorescent Probe for Detecting Cu2+: S-donor as a Cu2+-induced Fluorescence Quenching Inhibitor

Qiao¹,

Zhao²,

Wang³

2021

ACSi

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The fluorescent turn-on detection of metal ions is highly desirable for public health and environmental security. Herein, we report a rationally designed fluorescent probe (1) for the detection of Cu2+ synthesized by integrating 2-hydrazinylbenzothiazole with 3-acetyl-7-hydroxycoumarin. The probe alone is non-fluorescent due to the isomerization of C=N in the excited state. The addition of Cu2+ can cause a delayed fluorescence enhancement. A comparative study of 1 and its analogues indicated that the turn-on fluorescence response was thanks to the sulfur atom coordinating to Cu2+. The response delay of 1 in sensing Cu2+ was ascribed to the gradual transition from N-coordination to S-coordination (N and S in thiazole moiety). The proposed new function of S-donor would provide a new approach for the turn-on fluorescence sensation of Cu2+.

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“…1,8‐naphthalimides are a particularly privileged class of organic fluorophore because the photo‐physical properties can be fine‐tuned through careful structural design, as synthetic modifications are readily accommodated on either the aromatic naphthalene moiety (at the 3 or 4 position), or at the N ‐imide site . Such functionalised luminescent naphthalimides have been utilized in a wide range of applications such as hydrogen sulfide (H 2 S) detection, detection of mercury and methyl mercury ions or copper(II) ions, hypoxia responsiveness for imaging, and DNA binding …”

Section: Introductionmentioning

confidence: 99%

“…[3] For advanced sensing applications, fluorescencei savaluablep roperty due to its rapid response times and high sensitivity.1 ,8-naphthalimides are ap articularly privileged class of organic fluorophore because the photo-physical properties can be fine-tuned through careful structurald esign, as synthetic modifications are readily accommodated on either the aromatic naphthalene moiety (at the 3o r4position), or at the N-imide site. [3] Such functionalised luminescent naphthalimides have been utilized in aw ide range of applicationss uch as hydrogen sulfide (H 2 S) detec-tion, [4] detection of mercury and methyl mercury ions [5] or copper(II) ions, [6] hypoxiar esponsivenessf or imaging, [7] and DNA binding. [8] Many sensing applications are carried out in solution,h owever there is currently ap ush towards developing immobilised luminescent sensors where the responsive fluorophore is immobilised into am atrix, or onto as urface.…”

mentioning

confidence: 99%

Characterisation of N‐(Octadecyl)‐1,8‐naphthalimide Monolayer Compression Using Molecular Dynamics and Experimental Approaches

Welsh

Draper

Kim

et al. 2019

Chemistry An Asian Journal

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The development of luminescent surfaces is an active area of supramolecular chemistry, particularly for the development of new sensing platforms. One particularly useful surface deposition method is the Langmuir–Blodgett technique where organic amphiphilic fluorophores (e.g. 1,8‐naphthalimides) can form ordered monolayers at an air–water interface before being deposited onto solid supports. The ability to simulate monolayer formation and consequently develop predictability over film formation would allow for significant advances in the luminescent materials field where synthesis might be directed by simulation data. Here, we compare pressure‐area isotherms of N‐(octadecyl)‐1,8‐naphthalimide determined experimentally, using the Langmuir–Blodgett technique, and computationally, using three different simulation techniques. We find that all three simulation techniques are able to describe the liquid‐condensed/liquid‐expanded region of the isotherm, and that the isotherms are highly similar in this region, although the NγT ensemble performs best. Experimental isotherms showed film formation properties that align with the simulation data, suggesting that simulations are a viable means to direct synthesis. Investigation of the underlying structural details disclosed by the simulations reveals the compression‐induced ordering at atomic‐level detail, which will allow prediction of how functionalisation of the naphthalimides will alter the monolayer compression and mounting process.

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1,8-Naphthalimide-based turn-on fluorescent chemosensor for Cu2+ and its application in bioimaging

Cited by 19 publications

References 26 publications

Organic Nanoparticle-Based Fluorescent Chemosensor for Selective Switching ON and OFF of Photodynamic Therapy (PDT)

Organic Nanoparticle-Based Fluorescent Chemosensor for Selective Switching ON and OFF of Photodynamic Therapy (PDT)

Benzothiazolylhydrazone-Based Turn-on Fluorescent Probe for Detecting Cu2+: S-donor as a Cu2+-induced Fluorescence Quenching Inhibitor

Characterisation of N‐(Octadecyl)‐1,8‐naphthalimide Monolayer Compression Using Molecular Dynamics and Experimental Approaches

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