Novel sulphur-rich BODIPY systems that enable stepwise fluorescent O-atom turn-on and H2O2 neuronal system probing

Singh, Atul Pratap; Lee, Kang-Mun; Murale, Dhiraj P.; Jun, Taehong; Liew, Hyunjeong; Suh, Yoo‐Hun; Churchill, David G.

doi:10.1039/c2cc33076h

Cited by 39 publications

(12 citation statements)

References 23 publications

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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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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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“…Fluorescein dialdehyde was synthesized using reported literature . In the second step, bromination of fluorescein dialdehyde was carried out with NBS and product was obtained in good yield (95%) . Fluorescein dialdehyde was highly fluorescent while the final dibrominated product F was very less fluorescent.…”

Section: Resultsmentioning

confidence: 99%

““Turn‐On” Sensing Behaviour of an In Situ Generated Fluorescein‐Based Probe and Its Preferential Selectivity of Sodium Hypochlorite over tert‐Butyl Hydroperoxide in Lung Adenocarcinoma Cells”

et al. 2020

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Reactive Oxygen species (ROS) are well known for their oxidizing behaviour but it differs in fluorescein derivatives chemistry. With t‐BuOOH, the probe F shows its unique turn‐off sensing (A), while with NaOCl probe shows turn‐on sensing property (B). In this study, it was observed that in situ generated species formed by the reaction of probe (F) with t‐BuOOH is a unique molecule, having high turn‐on behaviour in presence of sodium hypochlorite (≈500 times). Further, fluorescence microscopy imaging using adenocarcinoma cells, A549 cells revealed that in‐situ generated molecule, could be used as an efficient fluorescent probe for detecting NaOCl in living cells.

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“…Ah igh number of novel heterocycles bearings ingle or multiple oxygen, sulfur,s elenium, or tellurium sites have been investigated over the years to help mimic redoxt ransformations which have involved ROS and biothiols. [39][40][41][42][43][44] These rationally designed synthetic molecules, provide ac hemoselectively oxidized (or reduced) compound towards hypochlorousacid and correlation in their optical responses. All reports discussed herein deal with well-defined and small synthetic molecular systems.…”

Section: Oxidation Of Organochalogen To Their Tetravalent (E = O) Oxidesmentioning

confidence: 99%

“…In recent years, sulfur‐, selenium‐, and tellurium‐based compounds have appeared in reports dealing with highly selective chemosensing for the detection of reactive oxygen species (ROS) (Scheme ). A high number of novel heterocycles bearing single or multiple oxygen, sulfur, selenium, or tellurium sites have been investigated over the years to help mimic redox transformations which have involved ROS and biothiols . These rationally designed synthetic molecules, provide a chemoselectively oxidized (or reduced) compound towards hypochlorous acid and correlation in their optical responses.…”

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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Novel sulphur-rich BODIPY systems that enable stepwise fluorescent O-atom turn-on and H2O2 neuronal system probing

Cited by 39 publications

References 23 publications

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

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

““Turn‐On” Sensing Behaviour of an In Situ Generated Fluorescein‐Based Probe and Its Preferential Selectivity of Sodium Hypochlorite over tert‐Butyl Hydroperoxide in Lung Adenocarcinoma Cells”

Imaging of Hypochlorous Acid by Fluorescence and Applications in Biological Systems

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