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

研究成果: Article査読

抄録

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.

本文言語English
論文番号119179
ジャーナルSpectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy
248
DOI
出版ステータスPublished - 2021 3 5
外部発表はい

ASJC Scopus subject areas

  • 分析化学
  • 原子分子物理学および光学
  • 器械工学
  • 分光学

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