A mitochondria/lysosome-targeting fluorescence probe based on azonia-cyanine dye and its application in nitroreductase detection

Sha, Xin-Long; Yang, Xiu-Zhi; Wei, Xue-Rui; Sun, Rong; Xu, Yu-Jie; Ge, Jian‐Feng

doi:10.1016/j.snb.2019.127653

Cited by 36 publications

(13 citation statements)

References 48 publications

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“…12,13 Importantly, N5 may be subject to alkylation reactions to generate pyrimidinium salts, a key group of compounds in organocatalysis 56 and biochemical applications. 57 While the C7-C8 distances remain virtually unchanged with the different aryl substituents (1.470 AE 0.007 A), the dihedrals are disturbed to a larger amplitude (from 34 to 64 ), causing the resonance breaking between the aryl group and the pyrazolo [1,5-a]pyrimidine core to different extents. The HOMO-LUMO gap also changes as there are variations in the substituents.…”

Section: Computational Calculationsmentioning

confidence: 99%

Pyrazolo[1,5-a]pyrimidines-based fluorophores: a comprehensive theoretical-experimental study

et al. 2020

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Section: Computational Calculationsmentioning

confidence: 99%

Pyrazolo[1,5-a]pyrimidines-based fluorophores: a comprehensive theoretical-experimental study

et al. 2020

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“…Moreover, diverse research shows that iminium salts represent an attractive scaffold as a CN – acceptor . In this context, pyrimidinium salts are electrophilic species that have numerous applications in chemistry and related areas. − These applications are from surfactants to catalysis and bioimaging to biomolecule detection; in general, several exciting uses have been reported for this organic salt. The chemical reactivity of pyrimidinium salts toward nucleophilic species has been well studied, and the carbon atoms in the pyrimidinium core are able to react with bisulfite, azide, morpholine, methoxide, and even water …”

Section: Introductionmentioning

confidence: 99%

Pyrazolo[1,5-a]pyrimidinium Salts for Cyanide Sensing: A Performance and Sustainability Study of the Probes

Tigreros

Zapata-Rivera

Portilla

2021

ACS Sustainable Chem. Eng.

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Herein, we report an efficient synthesis of two novel probes for cyanide sensing based on 7-arylpyrazolo[1,5-a]pyrimidinium salts PS (aryl = p-MeOPh) and T-PS (aryl = p-Ph 2 NPh). According to theoretical analyses, T-PS was found to be an ideal probe with improved absorption and emission properties due to a better intramolecular charge transfer (ICT) process. The experimental results, such as limit of detection (LOD; PS, 0.30 and 0.34 μmol/L → T-PS, 0.15, 0.15, and 0.25 μmol/L) and outstanding selectivity demonstrated the predicted properties. DFT calculations, HRMS analysis, and 1 H NMR titration experiments were carried out to confirm the mechanism, regioselectivity, and reversibility of the CN − addition reaction in detecting the probes. These findings are especially attractive in the cyanide-sensing field. However, important repercussions on the sustainability performance, such as raw material costs and waste generation, were observed when comparing PS with T-PS. Satisfyingly, test strips fabricated using T-PS also demonstrated its practical applicability; in addition, emission in solid-state measurements of T-PS supported on silica showed its capability to detect cyanide ions in the solid state and in bitter almonds after 50 ppm. Ultimately, small amounts of CN − (0.5 μmol/L) in tap water detected by using the probe T-PS. Therefore, this work provides a sustainable and applicable approach in cyanide chemosensor preparation.

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“…1,2 Besides decomposition of nucleic acids, cell fragments, and microorganisms and other waste, 3 the lysosome is also involved in various cell processes, including cell growth, differentiation, and cell signaling 4,5 and apoptosis. 6 It has been found that lysosomes with abnormal behaviors are closely related to the pathology of Alzheimer's disease, 7 cancer, 8 and some lung diseases. 9 As a result, achieving precise localization of lysosomes is helpful to understand the dynamic process of lysosomes, and further study the pathological mechanisms related to diseases.…”

mentioning

confidence: 99%

A novel lysosome‐localized fluorescent probe with aggregation‐induced emission without alkalinizing effect

et al. 2021

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Herein, a novel small molecule probe, tetraphenylethylene-cystein (TPE-Cys), was rationally designed and developed for the intracellular lysosome localization. The combination of tetraphenylethylene and cysteine serve as a novel strategy for lysosome-targeting, with significant aggregation-induced emission increases with the proportion of water by as high as 25-folds. Biofluorescence imaging experiments show that the probe TPE-Cys has a good colocalization effect with the commercially available lysotracker red, with a Pearson correlation coefficient of 0.91. In addition, we also demonstrate that TPE-Cys has good light stability. TPE-Cys, as a neutral compound, is free of alkalinizing effect when applied in lysosome localization. Moreover, molecular dynamics simulations and density function theories are employed to explore the detailed aggregation process and the mechanism of TPE-Cys aggregation in water solution. The mechanism of lysosome localization of probe TPE-Cys was explained by cellular endocytosis process and the formation of larger particle in the more acidic environment of lysosomes. This work not only demonstrates an efficient strategy for the construction of fluorescent probes for lysosome localization, but also indicates that they are promising as live cell imaging tools.

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A mitochondria/lysosome-targeting fluorescence probe based on azonia-cyanine dye and its application in nitroreductase detection

Cited by 36 publications

References 48 publications

Pyrazolo[1,5-a]pyrimidines-based fluorophores: a comprehensive theoretical-experimental study

Pyrazolo[1,5-a]pyrimidines-based fluorophores: a comprehensive theoretical-experimental study

Pyrazolo[1,5-a]pyrimidinium Salts for Cyanide Sensing: A Performance and Sustainability Study of the Probes

A novel lysosome‐localized fluorescent probe with aggregation‐induced emission without alkalinizing effect

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