A Comparison of the Photophysical, Electrochemical and Cytotoxic Properties of meso -(2-, 3- and 4-Pyridyl)-BODIPYs and Their Derivatives.
Caroline Ndung'uDaniel J LaMasterSimran DhingraNathan H MitchellPetia Bobadova-ParvanovaFrank R FronczekNoémie ElgrishiMaria da Graça Henriques VicentePublished in: Sensors (Basel, Switzerland) (2022)
Boron dipyrromethene (BODIPY) dyes bearing a pyridyl moiety have been used as metal ion sensors, pH sensors, fluorescence probes, and as sensitizers for phototherapy. A comparative study of the properties of the three structural isomers of meso -pyridyl-BODIPYs, their 2,6-dichloro derivatives, and their corresponding methylated cationic pyridinium-BODIPYs was conducted using spectroscopic and electrochemical methods, X-ray analyses, and TD-DFT calculations. Among the neutral derivatives, the 3Py and 4Py isomers showed the highest relative fluorescence quantum yields in organic solvents, which were further enhanced 2-4-fold via the introduction of two chlorines at the 2,6-positions. Among the cationic derivatives, the 2catPy showed the highest relative fluorescence quantum yield in organic solvents, which was further enhanced by the use of a bulky counter anion (PF 6 - ). In water, the quantum yields were greatly reduced for all three isomers but were shown to be enhanced upon introduction of 2,6-dichloro groups. Our results indicate that 2,6-dichloro- meso -(2- and 3-pyridinium)-BODIPYs are the most promising for sensing applications. Furthermore, all pyridinium BODIPYs are highly water-soluble and display low cytotoxicity towards human HEp2 cells.
Keyphrases
- water soluble
- energy transfer
- ionic liquid
- molecular dynamics
- single molecule
- gold nanoparticles
- density functional theory
- structure activity relationship
- molecular docking
- endothelial cells
- living cells
- monte carlo
- induced apoptosis
- small molecule
- molecularly imprinted
- molecular dynamics simulations
- quantum dots
- signaling pathway
- low cost
- cell cycle arrest
- fluorescent probe
- induced pluripotent stem cells
- magnetic resonance
- nucleic acid
- electron transfer
- photodynamic therapy