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

A series of quinolizinium-based fluorescent reagents were prepared by visible light-mediated gold-catalyzed cis -difunctionalization between quinolinium diazonium salts and electron-deficient alkyne-linked phenylethynyl trimethylsilanes. The electron-deficient alkynyl group of the quinolizinium-base...

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Bibliographic Details
Published in:RSC advances 2022-02, Vol.12 (1), p.6248-6254
Main Authors: Kung, Karen Ka-Yan, Xu, Cai-fung, O, Wa-Yi, Yu, Qiong, Chung, Sai-Fung, Tam, Suet-Ying, Leung, Yun-Chung, Wong, Man-Kin
Format: Article
Language:English
Subjects:
Alkynes
Chemistry
Cysteine
Fluorescence
Peptides
Proteins
Reagents
Toxicity
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Summary:A series of quinolizinium-based fluorescent reagents were prepared by visible light-mediated gold-catalyzed cis -difunctionalization between quinolinium diazonium salts and electron-deficient alkyne-linked phenylethynyl trimethylsilanes. The electron-deficient alkynyl group of the quinolizinium-based fluorescent reagents underwent nucleophilic addition reaction with the sulfhydryl group on cysteine-containing peptides and proteins. The quinolizinium-based fluorescent reagents were found to function as highly selective reagents for the modification of cysteine-containing peptides and proteins with good to excellent conversions (up to 99%). Moreover, the modified BCArg mutants bearing cationic quinolizinium compounds 1b , 1d , 1e and 1h exhibit comparable activity in enzymatic and cytotoxicity assays to the unmodified one. New quinolizinium-based fluorescent reagents were made by visible light-mediated gold-catalyzed cis -difunctionalization of quinolinium diazonium salts and trimethylsilyl alkyne derivatives.
ISSN:2046-2069
2046-2069
DOI:10.1039/d1ra08329e