Extremely selective “turn-on” fluorescence detection of hypochlorite confirmed by proof-of-principle neurological studies via esterase action in living cells

Singh, Atul Pratap; Tsay, Olga G.; Murale, Dhiraj P.; Jun, Taehong; Liew, Hyunjeong; Suh, Yoo‐Hun; Churchill, David G.

doi:10.1039/c3an00297g

Cited by 46 publications

(19 citation statements)

References 25 publications

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“…PET governed fluorescence quenching of BODIPY has also been investigated for the development of "OFF-ON" fluorescence probes for HOCl detection [164,165], in which the HOCl promoted oxidations of the chalcogenides, including S [166][167][168], Se [169,170] and Te chalcogenides, could be The annulated BODIPY-Te 61 (Fig. 9) was found to be reversible after further treatment with biothiols, suggesting the potential application in monitoring the HOCl generation in living systems.…”

Section: <Fig 8 Is Here>mentioning

confidence: 99%

Bioanalytical methods for hypochlorous acid detection: Recent advances and challenges

Zhang

Song

Yuan

2018

TrAC Trends in Analytical Chemistry

214

115

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Hypochlorous acid (HOCl), a well-known universal disinfectant in clinical practice, plays important roles in immune systems of animal and human bodies. For understanding the roles of HOCl in living systems, a number of approaches, including chemiluminescence, colorimetric, electrochemical and chromatographic methods have been explored. For the detection of HOCl in live organisms, cuttingedge techniques, such as fluorescence/phosphorescence molecular probes, responsive nanoprobes, Raman and activatable photoacoustic sensors, have also been developed recently. In this review, the recent advances in the development of bioanalytical methods for detection of HOCl in environmental and biological specimens were summarized. More specifically, traditional techniques for assay of HOCl in bulk solution were initially discussed, and then fluorescence molecular probes, phosphorescence probes, responsive nanoprobes and other methods for HOCl detection were reviewed, which gives an overview of the developments and applications in bioanalytical methods for HOCl detection.

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Section: <Fig 8 Is Here>mentioning

confidence: 99%

Bioanalytical methods for hypochlorous acid detection: Recent advances and challenges

Zhang

Song

Yuan

2018

TrAC Trends in Analytical Chemistry

214

115

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“…The group of Churchill pioneered the synthesis of meso ‐thienyl‐substituted corroles and their building blocks, and studied their characteristics . Through these investigations, it became clear that the presence of the meso ‐thienyl‐substituents in corroles (and dipyrrin‐based chromophores, such as boron‐dipyrromethene (BODIPY)) have a significant effect on the electronic structure and photophysical properties of the chromophores. However, we are not aware of a detailed description of the nature of the electronic interactions between the thienyl moieties and the central corrole chromophore.…”

Section: Introductionmentioning

confidence: 99%

A Spectroscopic and Theoretical Investigation of a Free‐Base meso‐Trithienylcorrole

Greco

Rossi

Birge

et al. 2013

Photochem & Photobiology

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The unique optical properties of free-base meso-trithienylcorrole were compared to those of the widely investigated meso-triphenyl-substituted analogue. A combination of spectroscopic and computational experiments were undertaken to elucidate the relationship between structural features of the neutral, mono-anionic, and mono-cationic forms of the corroles and their corresponding optical properties. A general bathochromic shift was measured for the thienyl-substituted corrole. The experimental spectra are supported by excited state calculations. A systematic series of ground state minimizations were performed to determine energy minima for the flexible and solvent-sensitive molecules. Trithienylcorrole was found to have a more non-planar macrocycle in conjunction with a high degree of π-overlap with the meso-substituents. Both structural features contribute to their bathochromically shifted optical spectra. The configurational character of the thienyl-substituted corrole is shown to have a larger degree of molecular orbital mixing and doubly excited character, which suggest a more complex electronic structure that does not fully adhere to the Gouterman four-orbital model. The reactivity of the thienyl groups, particularly with respect to their ability to be (electro)-polymerized, combined with the tight coupling of the meso-thienyl groups with the corrole chromophore elucidated in this work, recommends the meso-thienylcorroles as building blocks in, for instance, organic semiconductor devices.

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“…Esterification of the imaging agent is helpful to enter cells through the lipophilic membrane and activate in tumor cells, resulting in more accurate imaging. Some of the esterase-activating fluorescent probes have also the potential for tumor imaging in the future (Kamiya et al., 2007; Thompson et al., 2012; Singh et al., 2013).…”

Section: Application Of Esterase-responsive Nanoparticles In Tumor Trmentioning

confidence: 99%

Application and design of esterase-responsive nanoparticles for cancer therapy

et al. 2019

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Nanoparticles have been developed for tumor treatment due to the enhanced permeability and retention effects. However, lack of specific cancer cells selectivity results in low delivery efficiency and undesired side effects. In that case, the stimuli-responsive nanoparticles system designed for the specific structure and physicochemical properties of tumors have attracted more and more attention of researchers. Esterase-responsive nanoparticle system is widely used due to the overexpressed esterase in tumor cells. For a rational designed esterase-responsive nanoparticle, ester bonds and nanoparticle structures are the key characters. In this review, we overviewed the design of esterase-responsive nanoparticles, including ester bonds design and nano-structure design, and analyzed the fitness of each design for different application. In the end, the outlook of esterase-responsive nanoparticle is looking forward.

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Extremely selective “turn-on” fluorescence detection of hypochlorite confirmed by proof-of-principle neurological studies via esterase action in living cells

Cited by 46 publications

References 25 publications

Bioanalytical methods for hypochlorous acid detection: Recent advances and challenges

Bioanalytical methods for hypochlorous acid detection: Recent advances and challenges

A Spectroscopic and Theoretical Investigation of a Free‐Base meso‐Trithienylcorrole

Application and design of esterase-responsive nanoparticles for cancer therapy

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