Design, synthesis and evaluation of enzyme-responsive fluorogenic probes based on pyridine-flanked diketopyrrolopyrrole dyes

Sébastien Jenni, Flavien Ponsot, Pierre Baroux, Lucile Collard, Takayuki Ikeno, Kenjiro Hanaoka, Valentin Quesneau, Kévin Renault, Anthony Romieu

Research output: Contribution to journalArticlepeer-review

Abstract

The ever-growing demand for fluorogenic dyes usable in the rapid construction of analyte-responsive fluorescent probes, has recently contributed to a revival of interest in the chemistry of diketopyrrolopyrrole (DPP) pigments. In this context, we have explored the potential of symmetrical and unsymmetrical DPP derivatives bearing two or one 4-pyridyl substituents acting as optically tunable group(s). The unique fluorogenic behavior of these molecules, closely linked to N-substitution/charge state of their pyridine unit (i.e., neutral pyridine or cationic pyridinium), has been used to design DPP-based fluorescent probes for detection of hypoxia-related redox enzymes and penicillin G acylase (PGA). In this paper, we describe synthesis, spectral characterization and bioanalytical validations of these probes. Dramatic differences in terms of aqueous stability and enzymatic fluorescence activation were observed. This systematic study enables to delineate the scope of application of pyridine-flanked DPP fluorophores in the field of enzyme biosensing.

Original languageEnglish
Article number119179
JournalSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
Volume248
DOIs
Publication statusPublished - 2021 Mar 5
Externally publishedYes

Keywords

  • Diketopyrrolopyrrole
  • Enzyme detection
  • Fluorogenic probe
  • Hypoxia
  • Penicillin G acylase
  • Reductase

ASJC Scopus subject areas

  • Analytical Chemistry
  • Atomic and Molecular Physics, and Optics
  • Instrumentation
  • Spectroscopy

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