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

Karen Ka-Yan KungCai-Fung XuWa-Yi OQiong YuSai-Fung ChungSuet-Ying TamYun-Chung LeungMan-Kin Wong
Published in: RSC advances (2022)
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.
Keyphrases
  • living cells
  • quantum dots
  • fluorescent probe
  • visible light
  • single molecule
  • label free
  • amino acid
  • high throughput
  • single cell
  • molecularly imprinted