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PreprintCC BY-NC-NDChemRxiv

Next-Generation Enzyme-Responsive "Covalent-Assembly" Fluorescent Probes Based on Dendritic Self-Immolative Molecular Amplification

  • Marek Chovanec1,2,3
  • Valentin Quesneau1,2
  • Kévin Renault1,2,4,5,6,7
  • Xavier Maes7
  • Mathieu Franck8
  • Anthony Romieu1,2,8
8 affiliations
  1. 1Institut de Chimie Moléculaire de l'Université de Bourgogne (ICMUB)
  2. 2Université Bourgogne Europe
  3. 3Department of Organic Chemistry, University of Chemistry and Technology, Technická 5, Prague, Czechia
  4. 4Institut Curie
  5. 5Université PSL
  6. 6Université Paris Saclay
  7. 7Research Unit of Organic Chemistry, Department of Chemistry, University of Namur, NARILIS (Namur Research Institute of Life Science, rue de Bruxelles 61, Namur, Belgium, 5000
  8. 8Institute of Chemistry of Nice (ICN), Université Côte d'Azur, 28, avenue Valrose, Nice, France, 06100
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Abstract

Activity-based fluorogenic sensing is now regarded as a powerful approach for the accurate and sensitive detection of a myriad of important analytes, in aqueous matrices of varying complexity. Among the different molecular strategies recently proposed to devise high-performance detection schemes based on the chemical reactivity of species to be detected, the "covalent-assembly" principle is particularly promising. In order to further improve detection performances of the probes designed using this approach, we have explored their combined use with a signal amplification strategy based on the integration of a dendritic self-immolative core whose degradation should lead to in situ synthesis of several fluorophore molecules. To establish and validate this sensing system, penicillin G acylase (PGA) from E. coli was chosen as model enzyme and Pinner cyclization for in situ formation of fluorescent 2-iminocoumarin was selected as an effective biocompatible reaction. Fluorogenic AB 2 and AB 3 dendritic self-immolative molecules have been successfully synthesized. The excellent performances of PGA-responsive AB 2 dendron in terms of signal amplification and aqueous stability have been highlighted through analytical validations involving fluorescence-based enzyme assays completed with RP-HPLC-fluorescence/MS investigations. This study is a further step towards even greater popularization of the "covalent-assembly" approach in the fields of fluorogenic sensing, and bioimaging.

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Cite

BibTeXRIS
BibTeX
@misc{chovanec2026nextgeneration,
  title = {{Next-Generation Enzyme-Responsive "Covalent-Assembly" Fluorescent Probes Based on Dendritic Self-Immolative Molecular Amplification}},
  author = {Marek Chovanec and Valentin Quesneau and Kévin Renault and Xavier Maes and Mathieu Franck and Anthony Romieu},
  howpublished = {ChemRxiv},
  year = {2026},
  month = sep,
  doi = {10.26434/chemrxiv.15008184/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008184/v1},
  note = {CC BY-NC-ND},
}
RIS
TY  - UNPB
TI  - Next-Generation Enzyme-Responsive "Covalent-Assembly" Fluorescent Probes Based on Dendritic Self-Immolative Molecular Amplification
AU  - Marek Chovanec
AU  - Valentin Quesneau
AU  - Kévin Renault
AU  - Xavier Maes
AU  - Mathieu Franck
AU  - Anthony Romieu
PY  - 2026
DA  - 2026/09/01
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15008184/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15008184/v1
AB  - Activity-based fluorogenic sensing is now regarded as a powerful approach for the accurate and sensitive detection of a myriad of important analytes, in aqueous matrices of varying complexity. Among the different molecular strategies recently proposed to devise high-performance detection schemes based on the chemical reactivity of species to be detected, the "covalent-assembly" principle is particularly promising. In order to further improve detection performances of the probes designed using this approach, we have explored their combined use with a signal amplification strategy based on the integration of a dendritic self-immolative core whose degradation should lead to in situ synthesis of several fluorophore molecules. To establish and validate this sensing system, penicillin G acylase (PGA) from E. coli was chosen as model enzyme and Pinner cyclization for in situ formation of fluorescent 2-iminocoumarin was selected as an effective biocompatible reaction. Fluorogenic AB 2 and AB 3 dendritic self-immolative molecules have been successfully synthesized. The excellent performances of PGA-responsive AB 2 dendron in terms of signal amplification and aqueous stability have been highlighted through analytical validations involving fluorescence-based enzyme assays completed with RP-HPLC-fluorescence/MS investigations. This study is a further step towards even greater popularization of the "covalent-assembly" approach in the fields of fluorogenic sensing, and bioimaging.
ER  -