A highly selective quinolizinium-based fluorescent probe for cysteine detection

Wa-Yi, O; Chan, Willy; Xu, Caifeng; Deng, Jie‐Ren; Ko, Ben C.B.; Wong, Man Leung

doi:10.1039/d1ra06104f

Cited by 16 publications

(2 citation statements)

References 64 publications

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“…Compared to common neutral fluorescent scaffolds, cationic heterocycles, such as quinolinium and quinolizinium, have attracted attention because they provide opportunities for solving the solubility problem. Nevertheless, studies on the use of quinolinium and quinolizinium as agents for imaging intracellular organelles, such as mitochondria, [28–30] endoplasmic reticula, and lysosomes, [31,32] are limited.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Intracellular Localization of 5,6‐Disubsutituted Pyrido[1′,2′;2,3]imidazo[5,1‐a]isoquinolinium Iodides

Kawakubo,

Inoh,

Inaguma

et al. 2023

ChemistrySelect

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Novel pyrido[1’,2’;2,3]imidazo[5,1‐a]isoquinolinium iodides independently substituted at their 5‐ and 6‐position were prepared from 5‐iodopyrido[1’,2’;2,3]imidazo[5,1‐a]isoquinolinium iodides using Suzuki‐Miyaura cross‐coupling reaction. The desired coupling products had cationic extended π‐conjugated skeletons and fluoresced strongly in the 420–460 nm region in methanol. In cell staining assay, the 5‐styryl‐substituted compounds, which showed lower fluorescence quantum yields in methanol, emitted high fluorescence in the intracellular environment and were specifically distributed to the endoplasmic reticulum.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Intracellular Localization of 5,6‐Disubsutituted Pyrido[1′,2′;2,3]imidazo[5,1‐a]isoquinolinium Iodides

Kawakubo,

Inoh,

Inaguma

et al. 2023

ChemistrySelect

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“…Most recently, our group has developed a new series of quinolizinium compounds as versatile cationic fluorescent heterocycles. 14 These quinoliziniums exhibit tunable photophysical properties in the visible light region and large Stokes shifts, enriching the applications of visible-light-induced photocatalysis, 14 a , b cellular imaging 14 a , c and molecular probes. 14 c As such, the design of functionalized quinolizinum compounds by incorporation of the electron-deficient alkynyl group delivers easily accessible reagents for cysteine modification of peptides and proteins ( Scheme 1 ).…”

Section: Introductionmentioning

confidence: 99%

Functionalized quinolizinium-based fluorescent reagents for modification of cysteine-containing peptides and proteins

Kung

Wa-Yi

et al. 2022

RSC Adv.

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Isoindolium‐Based Allenes: Reactivity Studies and Applications in Fluorescence Temperature Sensing and Cysteine Bioconjugation

Wa-Yi

Cui

et al. 2023

Angewandte Chemie

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The reaction of a series of electron‐deficient isoindolium‐based allenes with sulfhydryl compounds has been studied, leading to the formation of isoindolium‐based vinyl sulfides. The vinyl sulfides generated could be readily converted into the corresponding indanones and amines upon heating at 30–70 °C with good yields up to 61 %. The thermal cleavage reaction of vinyl sulfides was further studied for developing temperature‐sensitive systems. Notably, a novel FRET‐based fluorescent temperature sensor was designed and synthesized for temperature sensing at 50 °C, giving a 6.5‐fold blue fluorescence enhancement. Moreover, chemoselective bioconjugation of cysteine‐containing peptides with the isoindolium‐based allenes for the construction of multifunctional peptide bioconjugates was investigated. Thermal cleavage of isoindoliums on the modified peptides at 35–70 °C gave indanone bioconjugates with up to >99 % conversion. These results indicated the biocompatibility of this novel temperature‐sensitive reaction.

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A highly selective quinolizinium-based fluorescent probe for cysteine detection

Abstract: A novel fluorescent quinolizinium-based turn-off probe for selective detection of cysteine has been developed.

Cited by 16 publications

References 64 publications

Synthesis and Intracellular Localization of 5,6‐Disubsutituted Pyrido[1′,2′;2,3]imidazo[5,1‐a]isoquinolinium Iodides

Synthesis and Intracellular Localization of 5,6‐Disubsutituted Pyrido[1′,2′;2,3]imidazo[5,1‐a]isoquinolinium Iodides

Functionalized quinolizinium-based fluorescent reagents for modification of cysteine-containing peptides and proteins

Isoindolium‐Based Allenes: Reactivity Studies and Applications in Fluorescence Temperature Sensing and Cysteine Bioconjugation

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