A naphthalimide–rhodamine two-photon fluorescent turn-on probe for hypochlorous acid by desulfurization-cyclization and fluorescence resonance energy transfer

Yao, Shankun; Qian, Ying

doi:10.1016/j.snb.2017.06.091

Cited by 62 publications

(14 citation statements)

References 59 publications

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“…After reaction with thiols, the electron-withdrawing DNBS is removed and the fluorescence of MT-1 recovered through a FRET process (as shown in Figure 2). As have been thoroughly studied, the emission spectra of naphthalimide moieties exhibit a broad emission range which overlaps with the absorption spectra of rhodamine B and forms an ideal FRET pair [53][54][55]. We observed nearly 200 nm large pseudo-Stokes shift after the treatment of MT-1 with GSH (λ ex = 395 nm, λ em = 589 nm).…”

Section: Design and Synthesis Of Mt-1mentioning

confidence: 94%

A FRET Based Two-Photon Fluorescent Probe for Visualizing Mitochondrial Thiols of Living Cells and Tissues

Liu

Wang

et al. 2020

Sensors

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Glutathione (GSH) is the main component of the mitochondrial thiol pool and plays key roles in the biological processes. Many evidences have suggested that cysteine and homocysteine also exist in mitochondria and are interrelated with GSH in biological systems. The fluctuation of the levels of mitochondrial thiols has been linked to many diseases and cells’ dysfunction. Therefore, the monitoring of mitochondrial thiol status is of great significance for clinical studies. We report here a novel fluorescence resonance energy transfer based two-photon probe MT-1 for mitochondrial thiols detection. MT-1 was constructed by integrating the naphthalimide moiety (donor) and rhodamine B (accepter and targeting group) through a newly designed linker. MT-1 shows a fast response, high selectivity, and sensitivity to thiols, as well as a low limit of detection. The two-photon property of MT-1 allows the direct visualization of thiols in live cells and tissues by two-photon microscopy. MT-1 can serve as an effective tool to unravel the diverse biological functions of mitochondrial thiols in living systems.

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Section: Design and Synthesis Of Mt-1mentioning

confidence: 94%

A FRET Based Two-Photon Fluorescent Probe for Visualizing Mitochondrial Thiols of Living Cells and Tissues

Liu

Wang

et al. 2020

Sensors

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“…The probe undergoes lactone ring opening to give ratiometric fluorescence at 600 nm due to the FRET effect. [143] Further study ion the liveA549 cells indicated that the probe can be used to detectH OClw ithin the live cells.…”

Section: Scheme84 Fluorescein Hydrazine Probe For Hocl Detectionmentioning

confidence: 99%

“…The probe is the combination between rhodamine‐thiosemicarbazide and pyridine‐naphthalimide in which connected by phenyl spacer (Scheme ). The probe undergoes lactone ring opening to give ratiometric fluorescence at 600 nm due to the FRET effect . Further study ion the live A549 cells indicated that the probe can be used to detect HOCl within the live cells.…”

Section: Introductionmentioning

confidence: 99%

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

Yudhistira

Mulay

Kim

et al. 2019

Chemistry An Asian Journal

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In recent decades, HOCl research has attracted a lot of scientists from around the world. This chemical species is well known as an important player in the biological systems of eukaryotic organisms including humans. In the human body, HOCl is produced by the myeloperoxidase enzyme from superoxide in very low concentrations (20 to 400 μm); this species is secreted by neutrophils and monocytes to help fight pathogens. However, in the condition called “oxidative stress”, HOCl has the capability to attack many important biomolecules such as amino acids, proteins, nucleotides, nucleic acids, carbohydrates, and lipids; these reactions could ultimately contribute to a number of diseases such as neurodegenerative diseases (AD, PD, and ALS), cardiovascular diseases, and diabetes. In this review, we discuss recent efforts by scientists to synthesize various fluorophores which are attached to receptors to detect HOCl such as: chalcogen‐based oxidation, oxidation of 4‐methoxyphenol, oxime/imine, lactone ring opening, and hydrazine. These synthetic molecules, involving rational synthetic pathways, allow us to chemoselectively target HOCl and to study the level of HOCl selectivity through emission responses. Virtually all the reports here deal with well‐defined and small synthetic molecular systems. A large number of published compounds have been reported over the past years; this growing field has given scientists new insights regarding the design of the chemosensors. Reversibility, for example is considered important from the stand point of chemosensor reuse within the biological system; facile regenerability using secondary analytes to obtain the initial probe is a very promising avenue. Another aspect which is also important is the energy of the emission wavelength of the sensor; near‐infrared (NIR) emission is favorable to prevent autofluorescence and harmful irradiation of tissue; thus, extended applicability of such sensors can be made to the mouse model or animal model to help image internal organs. In this review, we describe several well‐known types of receptors that are covalently attached to the fluorophore to detect HOCl. We also discuss the common fluorophores which are used by chemist to detect HOCl, Apart from the chemical aspects, we also discuss the capabilities of the compounds to detect HOCl in living cells as measured through confocal imaging. The growing insight from HOCl probing suggests that there is still much room for improvement regarding the available molecular designs, knowledge of interplay between analytes, biological applicability, biological targeting, and chemical switching, which can also serve to further sensor and theurapeutic agent development alike.

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“…In recent years, 1,8-naphthalimide derivatives have been widely applied as fluorescent dyes, metal sensors and organic light emitting materials because of their excellent fluorescence properties, high absorption coefficients, good fluorescence and quantum yields, large stokes shifts, good stability and easy modification. The considerable interest in 1,8-naphthalimide derivatives as the photoactive component of optical chemosensors is caused, on the one hand, by relative simplicity of their synthesis, on the other hand, by the great diversity of their photo-physical properties [ 7 , 8 , 9 ]. Naphthalimide-based probes have been developed to detect H + , Hg 2+ , Zn 2+ , Cu 2+ , Ag + , Cd 2+ , Pd 2+ , Cr 3+ , Al 3+ , Fe 3+ and F − via chromogenic and fluorometric analyses [ 10 , 11 , 12 , 13 , 14 , 15 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Fluorescent Property Study of Novel 1,8-Naphthalimide-Based Chemosensors

Pang

Wang

et al. 2018

Molecules

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A series of novel mono- and di-substituted N-n-butyl-1,8-naphthalimide derivatives were synthesized simultaneously via a three-step reaction. The single crystal structure of N-n-butyl-4-[N′,N′-bis(2′,4′-dichlorobenzoyl)ethylamino]-1,8-naphthalimide (3f) was determined. The UV-vis and fluorescence properties of compound 3f were investigated. The 3f showed highly selective and sensitive fluorescence changes response towards Pb2+. A titration of monomer with Pb2+ ion was performed. When Pb2+ ion concentration increased from 0 to 10 eq., the fluorescent intensity of 3f decreased from 199.97 to 48.21. The pH effect on 3f showed that it is stable in a wide range of pH. The results indicated that 3f might be a probe molecule for Pb2+.

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A naphthalimide–rhodamine two-photon fluorescent turn-on probe for hypochlorous acid by desulfurization-cyclization and fluorescence resonance energy transfer

Cited by 62 publications

References 59 publications

A FRET Based Two-Photon Fluorescent Probe for Visualizing Mitochondrial Thiols of Living Cells and Tissues

A FRET Based Two-Photon Fluorescent Probe for Visualizing Mitochondrial Thiols of Living Cells and Tissues

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

Synthesis and Fluorescent Property Study of Novel 1,8-Naphthalimide-Based Chemosensors

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