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Design, Synthesis and Evaluation of Enzyme-Responsive Fluorogenic Probes Based on Pyridine-Flanked Diketopyrrolopyrrole Dyes

preprint
submitted on 25.09.2020 and posted on 28.09.2020 by Sébastien Jenni, Flavien Ponsot, Pierre Baroux, Lucille Collard, Takayuki Ikeno, Kenjiro Hanaoka, Valentin Quesneau, Kevin Renault, Anthony ROMIEU
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.

Funding

Butyrylcholinesterase-based fluorescent and/or colorimetric detection of organophosphorus nerve agents – DetectOP_BChE

Agence Nationale de la Recherche

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A luminogenic real-time detection system for monitoring enzymatic manufacturing of oligonucleotides – LuminoManufacOligo

Agence Nationale de la Recherche

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PROJET ISITE BFC BACTERIOBIOSENS (ANR-15-IDEX-0003)

PO FEDER-FSE BOURGOGNE 2014/2020

JSPS KAKENHI Grant Numbers JP19H05414, JP20H04767, and JP16H05099

History

Email Address of Submitting Author

anthony.romieu@u-bourgogne.fr

Institution

Univ. Bourgogne Franche-Comté

Country

France

ORCID For Submitting Author

0000-0002-2300-4499

Declaration of Conflict of Interest

No conflict of interest

Version Notes

Version 1 09-25-2020

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