Exploring the potential of anthracene derivatives as fluorescence emitters for biomedical applications

• Published in: Journal of materials chemistry. B, Materials for biology and medicine Materials for biology and medicine, 2023-05, Vol.11 (19), p.4287-4295
• Main Authors: Aydemir, Murat, Haykir, Gulcin, Selvitopi, Harun, Yildirim, Ozge Caglar, Arslan, Mehmet Enes, Abay, Bahattin, Turksoy, Figen
• Format: Article
• Language: English
• Subjects: Acrylonitrile; Anthracene; Anthracenes - chemistry; Biocompatibility; Biomedical materials; Cell culture; Cell Survival; Cell viability; Cellular structure; Charge transfer; Chemical synthesis; Conjugation; Cytotoxicity; Density functional theory; Electron affinity; Emitters; Energy levels; Ethidium bromide; Fluorescence; Fluorescent dyes; Fluorescent Dyes - chemistry; Fluorescent Dyes - pharmacology; Fluorescent indicators; Humans; Imaging; Mathematical analysis; Molecular docking; Molecular Docking Simulation; Photoluminescence; Photons; Physical properties; Spectroscopy; Staining; Staphylococcus aureus; Steric hindrance; Toxicity
• ISSN: 2050-750X; 2050-7518
• DOI: 10.1039/d3tb00449j

Two novel anthracene derivatives were synthesized, and detailed photo-physical and biological investigations were carried out using a variety of spectroscopy techniques. The effect of cyano (-CN) substitution was found to be effective to alter the charge population and frontier orbital energy levels via Density Functional Theory (DFT) calculations. Particularly, the introduction of styryl and triphenylamine groups attached to the anthracene core helped to increase the conjugation relative to the anthracene moiety. The results revealed that the molecules have intramolecular charge transfer (ICT) properties, occurring from the electron donating triphenylamine to the electron accepting anthracene moiety in solutions. In addition, the photo-physical properties are strongly cyano-dependent, where the cyano-substituted ( E / Z )-(2-anthracen-9-yl)-3-(4′-(diphenylamino)biphenyl-4yl)acrylonitrile molecule showed stronger electron affinity due to the enhanced internal steric hindrance compared to the ( E )-4′-(2-(anthracen-9-yl)vinyl)- N , N -diphenylbiphenyl-4-amine molecule, which resulted in a lower photoluminescence quantum yield (PLQY) value and a shorter lifetime in the molecule. Besides, the Molecular Docking approach was used to investigate possible cellular staining targets to confirm cellular imaging potential of the compounds. Moreover, cell viability analyses put forth that synthesized molecules do not exhibit significant cytotoxicity under 125 μg mL −1 concentration on the human dermal fibroblast cell line (HDFa). Moreover, both of the compounds showed great potential in cellular imaging of HDFa cells. Compared to Hoechst 33258, a common fluorescent dye used for nuclear staining, the compounds showed higher magnification of cellular structure imaging capacity by staining the whole cellular compartment. On the other hand, bacterial staining showed that ethidium bromide has higher resolution in monitoring Staphylococcus aureus ( S. aureus ) cell culture. We have discovered new anthracene derivatives with strong fluorescence properties in the visible region. They exhibit high binding affinities to microtubule proteins with the potential to be used as fluorescent probes for imaging applications.