Pyridazino-1,3a,6a-Triazapentalenes as Versatile Fluorescent Probes: Impact of Their Post-Functionalization and Application for Cellular Imaging.

Doina Sirbu,Ivana Martinić,Nicolas Chopin,Marie-Aude Hiebel,Svetlana V Eliseeva,Stéphane Petoud,Moussa Ndiaye,Franck Suzenet

doi:10.3390/ijms22126645

Abstract

Pyridazino-1,3a,6a-triazapentalenes (PyTAP) are compact fused 6/5/5 tricyclic scaffolds which exhibit promising fluorescent properties. Chemically stable, they can be post-functionalized using standard Pd-catalyzed cross-coupling chemistry. Several original PyTAP bearing additional unsaturated substituents in positions 2 and 8 were synthetized and their spectroscopic properties analyzed. They have been successfully tested as fluorescent probes for cellular imaging.

Highlights

IntroductionImpact of Their Post-Small-organic fluorophores have become tools of major importance for biological, biochemical and biomedical research and for diagnosis [1,2,3]
Impact of Their Post-Small-organic fluorophores have become tools of major importance for biological, biochemical and biomedical research and for diagnosis [1,2,3]
Boc-protected amine and ester were well tolerated in position 2 and 8 on the PyTAP scaffold (4g, 3b and 4i)

Summary

Introduction

Impact of Their Post-Small-organic fluorophores have become tools of major importance for biological, biochemical and biomedical research and for diagnosis [1,2,3]. The development of a TAP system flanked with an additional fused heteroaromatic ring demonstrated a significant improvement in respect to the chemical stability while retaining promising spectroscopic properties [18,19]. This low molecular weight tricyclic framework is straightforwardly synthetized from either azides [18] or nitro derivatives [20,21] though a thermal activation or primary amines, ref. The most promising compounds were tested for their ability to be used as fluorescent probes for the imaging of living HeLa cancer cells

Methods

Results

Conclusion