Imidazo[1,5-a]pyridine-Based Fluorescent Probes: A Photophysical Investigation in Liposome Models

Molecules

Claudia Barolo¹  Giorgio Volpi¹  Giacomo Renno¹  Francesca Cardano¹  Guido Viscardi¹  Andrea Fin² 

[1] Department of Chemistry, University of Torino, Via P. Giuria 7, 10125 Torino, Italy;Department of Drug Science and Technology, University of Torino, Via P. Giuria 9, 10125 Torino, Italy;

关键词: imidazo[1,5-a]pyridine;    fluorescence;    large Stokes shift;    liposome;    membrane probes;   

DOI  :  10.3390/molecules27123856

来源: DOAJ

【 摘 要 】

Imidazo[1,5-a]pyridine is a stable scaffold, widely used for the development of emissive compounds in many application fields (e.g., optoelectronics, coordination chemistry, sensors, chemical biology). Their compact shape along with remarkable photophysical properties make them suitable candidates as cell membrane probes. The study of the membrane dynamics, hydration, and fluidity is of importance to monitor the cellular health and to explore crucial biochemical pathways. In this context, five imidazo[1,5-a]pyridine-based fluorophores were synthesized according to a one-pot cyclization between an aromatic ketone and benzaldehyde in the presence of ammonium acetate and acetic acid. The photophysical features of prepared compounds were investigated in several organic solvents and probes 2–4 exhibited the greatest solvatochromic behavior, resulting in a higher suitability as membrane probes. Their interaction with liposomes as artificial membrane model was tested showing a successful intercalation of the probes in the lipid bilayer. Kinetic experiments were carried out and the lipidic phase influence on the photophysical features was evaluated through temperature-dependent experiments. The results herein reported encourage further investigations on the use of imidazo[1,5-a]pyridine scaffold as fluorescent membrane probes.

【 授权许可】

Unknown