Design and Synthesis of a BODIPY‐Tetrazole Based “Off‐On” in‐Cell Fluorescence Reporter of Hydrogen Peroxide

An, Peng; Lewandowski, Tracey M.; Lin, Qing

doi:10.1002/cbic.201700656

Cited by 17 publications

(7 citation statements)

References 50 publications

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“…9−11 This might be due to the poor quantum efficiency of tetrazole-based probes in the aqueous medium. 12,13 Also, tetrazole-based probes often suffer from poor sensitivity and lack of selectivity, which limit their applicability in real-life sample analysis.…”

Section: Introductionmentioning

confidence: 99%

Fluorescent Nanoassembly of Tetrazole-Based Dyes with Amphoteric Surfactants: Investigation of Cyanide Sensing and Antitubercular Activity

Fernandes,

Kumari,

Sriram

et al. 2023

ACS Appl. Bio Mater.

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Tetrazole-based easily synthesizable fluorogenic probes have been developed that can form self-assembled nanostructures in the aqueous medium. Though the compounds could achieve detection of cyanide ions in apolar solvents, such as, THF, significant interference was observed from other basic anions, such as F–, AcO–, H2PO4 –, etc. On the other hand, a highly specific response was observed for CN– ions in the aqueous medium. However, the sensitivity was so poor that it could hardly be useful for real-life sample analysis. Interestingly, the co-assembly of such probe molecules with hydroxyethyl-anchored amphoteric surfactants could drastically improve the sensitivity toward CN– ions in water without dampening their excellent selectivity. Also, it was observed that the degree of fluorescence response for CN– ions depends on the nature of the polyaromatic scaffolds (naphthyl vs anthracenyl), the nature of the surfactant assembly (micelle vs vesicle), etc. The mechanistic investigation indicates the hydrogen bonding interaction between the tetrazole −NH group and cyanide ions in the aqueous medium, which can effectively change the electronics of the tetrazole unit, resulting in alteration in the extent of charge transfer interaction. Then, the biocompatible composite materials (dye-surfactant assemblies at different ratios) were tested for antituberculosis activity. Fortunately, in a few cases, the compositions were found to be as effective as the commercially available antituberculosis drug, ethambutol.

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Section: Introductionmentioning

confidence: 99%

Fluorescent Nanoassembly of Tetrazole-Based Dyes with Amphoteric Surfactants: Investigation of Cyanide Sensing and Antitubercular Activity

Fernandes,

Kumari,

Sriram

et al. 2023

ACS Appl. Bio Mater.

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“…[26] Furthermore, to the best of our knowledge, this emission efficiency is significantly higher than those reported recently for other pyrazolines exploited for biolabeling. [27,28] Therefore, our data suggest that it is unlikely for a photoreactive tetrazole to simultaneously achieve high cycloaddition vs hydration selectivity, yielding a pyrazoline with an excellent fluorescence emission. However, considering both these aspects, tetrazole T7 emerges as the best compromise, yielding the pyrazoline P7 with a high selectivity index (7.1 × 10 4 ) and a good fluorescence in water (Φ f = 42 %).…”

Section: Pyrazoline Spectroscopic Propertiesmentioning

confidence: 86%

The Quest for the Right Trade‐Off for an Efficient Photoclick Monitoring Reaction

et al. 2021

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Photoinduced cycloaddition of 2,5-diaryltetrazoles with alkenes, to produce 2,5-diarylpyrazolines, has been widely exploited as orthogonal ligation for bio-labeling and cross-linking. This reaction is particularly interesting and useful, as it combines mild activation conditions to the generation of a fluorescent product. However, it suffers from two major drawbacks, as under physiological conditions hydration by-products are formed and the fluorescent quantum yield of the emitting pyrazoline is often reduced in water. In this work, we have thoroughly investigated both the photoreactivity of a small library of water soluble tetrazoles and the optical properties of the resulting pyrazolines, to optimize both chemical selectivity (cycloaddition vs hydration) and photo-physical efficiency. Electron-withdrawing (A) and electron-donating (D) substituents tune pyrazoline reaction yields and their fluorescence quantum yields in opposite directions. The combination of two D-substituents on the tetrazoles ensures quantitative pyrazoline formation with low emission. On the contrary, two A-substituents afforded very emitting pyrazolines in low chemical yield. We have identified the water-soluble tetrazole T7 as the best compromise, able to afford a highly fluorescent pyrazoline, in high yields.

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“…98 Similarly, An et al developed a BODIPYlinked bithiophene-tetrazole 109 as an off-on fluorescence probe for the detection of hydrogen peroxide inside HeLa cells. 99 A drastic decrease of BODIPY fluorescence was observed for the meta-linked BODIPY-tetrazole after reaction with dimethyl fumarate. The BODIPY fluorescence was recovered after treatment with hydrogen peroxide (Scheme 25b).…”

Section: Chemosensorsmentioning

confidence: 98%

“…Owing to the efficient photochemical generation of nitriles imines, this approach provides improved sensitivity compared to the previously reported hydrazonyl chloride probes . Similarly, An et al developed a BODIPY-linked bithiophene-tetrazole 109 as an off-on fluorescence probe for the detection of hydrogen peroxide inside HeLa cells . A drastic decrease of BODIPY fluorescence was observed for the meta-linked BODIPY-tetrazole after reaction with dimethyl fumarate.…”

Section: Tetrazole Photoclick Chemistrymentioning

confidence: 99%

Light-Triggered Click Chemistry

2020

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The merging of click chemistry with discrete photochemical processes has led to the creation of a new class of click reactions, collectively known as photoclick chemistry. These light-triggered click reactions allow the synthesis of diverse organic structures in a rapid and precise manner under mild conditions. Because light offers unparalleled spatiotemporal control over the generation of the reactive intermediates, photoclick chemistry has become an indispensable tool for a wide range of spatially addressable applications including surface functionalization, polymer conjugation and cross-linking, and biomolecular labeling in the native cellular environment. Over the past decade, a growing number of photoclick reactions have been developed, especially those based on the 1,3-dipolar cycloadditions and Diels–Alder reactions owing to their excellent reaction kinetics, selectivity, and biocompatibility. This review summarizes the recent advances in the development of photoclick reactions and their applications in chemical biology and materials science. A particular emphasis is placed on the historical contexts and mechanistic insights into each of the selected reactions. The in-depth discussion presented here should stimulate further development of the field, including the design of new photoactivation modalities, the continuous expansion of λ-orthogonal tandem photoclick chemistry, and the innovative use of these unique tools in bioconjugation and nanomaterial synthesis.

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Design and Synthesis of a BODIPY‐Tetrazole Based “Off‐On” in‐Cell Fluorescence Reporter of Hydrogen Peroxide

Cited by 17 publications

References 50 publications

Fluorescent Nanoassembly of Tetrazole-Based Dyes with Amphoteric Surfactants: Investigation of Cyanide Sensing and Antitubercular Activity

Fluorescent Nanoassembly of Tetrazole-Based Dyes with Amphoteric Surfactants: Investigation of Cyanide Sensing and Antitubercular Activity

The Quest for the Right Trade‐Off for an Efficient Photoclick Monitoring Reaction

Light-Triggered Click Chemistry

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