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

Kung, Karen Ka‐Yan; Xu, Cai-fung; Wa-Yi, O; Yu, Qiong; Chung, Sai-Fung; Tam, Suet-Ying; Leung, Yun-Chung; Wong, Man Leung

doi:10.1039/d1ra08329e

RSC Adv.

2022

DOI: 10.1039/d1ra08329e

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

Karen Ka‐Yan Kung

Cai-fung Xu

O Wa-Yi

et al.

Abstract: New quinolizinium-based fluorescent reagents were made by visible light-mediated gold-catalyzed cis-difunctionalization of quinolinium diazonium salts and trimethylsilyl alkyne derivatives.

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Cited by 3 publications

References 70 publications

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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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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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show abstract

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

Wa-Yi

Cui

et al. 2023

Angew Chem Int Ed

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Modular synthesis of pentacyclic-fused pyranoquinoliziniums as organelle-selective fluorescent probes

Tantipanjaporn,

Kung,

Deng

et al. 2024

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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

Abstract: New quinolizinium-based fluorescent reagents were made by visible light-mediated gold-catalyzed cis-difunctionalization of quinolinium diazonium salts and trimethylsilyl alkyne derivatives.

Cited by 3 publications

References 70 publications

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

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

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

Modular synthesis of pentacyclic-fused pyranoquinoliziniums as organelle-selective fluorescent probes

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