Native Chemical Ligation-Based Fluorescent Probes for Cysteine and Aminopeptidase N Using meso-thioester-BODIPY

Uisung Lee, Tae Il Kim, Sungjin Jeon, Yongyang Luo, Siyoung Cho, Jeehyeon Bae, Youngmi Kim

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

meso-Carboxyl-BODIPY responds to small electronic changes resulting from acyl substitution reactions with a marked change in fluorescence. Herein, the minute changes that accompany the thioester to amide conversion encountered in native chemical ligation (NCL) are exploited in the construction of fluorescent “turn-on” probes. Two fluorogenic probes, 1 a and 4, derived from a meso-thioester-BODIPY scaffold, were designed for the selective detection of cysteine (1 a) and aminopeptidase N (4), respectively. The aromatic (1 a) and aliphatic (4) thioesters of meso-carboxyl-BODIPY are nonfluorescent. However, specific analyte-induced conversion to the meso-amide derivative caused significant spectral changes and a dramatic fluorescence enhancement. Probe 1 a exhibited a large fluorescence “turn-on” response with high selectivity toward cysteine via a tandem NCL reaction. Probe 4 was successfully applied to the monitoring and imaging of endogenous aminopeptidase N in live cancer cells.

Original languageEnglish
Pages (from-to)12545-12551
Number of pages7
JournalChemistry - A European Journal
Volume27
Issue number49
DOIs
Publication statusPublished - 1 Sep 2021

Keywords

  • BODIPY
  • aminopeptidase N
  • biothiols
  • cysteine
  • fluorescent Probe

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