3-Hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one and 3-hydroxy-6H-benzo[c]chromen-6-one act as on-off selective fluorescent sensors for Iron (III) under in vitro and ex vivo conditions

• Published in: Turkish journal of chemistry Vol. 45; no. 3; pp. 858 - 867
• Main Authors: Shukur, Karar, Fallah, Amirhossein, Terali, Kerem, Kalkan, Rasime, Gazi, Mustafa, Gülcan, Hayrettin Ozan
• Format: Journal Article
• Language: English
• Published: Turkey The Scientific and Technological Research Council of Turkey 2021
• Subjects: Urolithin; Iron (III); on-off sensor; fluorescence probe
• ISSN: 1300-0527; 1303-6130; 1303-6130
• DOI: 10.3906/kim-2011-58

Regarding the abundant use of metals for different purposes, it becomes more critical from various scientific and technological perspectives to discover novel agents as selective probes for the detection of specific metals. In our previous studies, we have shown that aqueous solutions of natural urolithins (i.e., hydroxyl-substituted benzo[c]chromen-6-one derivatives) are selective Iron (III) sensors in fluorescence assays. In this study, we have extrapolated these findings to another coumarine compound (i.e., 3-Hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one) and compared the selective metal binding properties with Urolithin B (i.e., 3-Hydroxy-6H-benzo[c]chromen-6-one). Following the synthesis and structure identification studies, the fluorometric studies pointed out that the lactam group in the structure still persists to be the important scaffold for maintaining selective on-off sensor capacity that renders the compound a selective Iron (III) binding probe. Moreover, for the first time, fluorescence cellular imaging studies concomitant to cytotoxicity assays with the title compounds were also performed and the results displayed the cell-penetrative, safe, and fluorescent detectable characteristics of the compounds in neuroblastoma and glioblastoma cells through servings as intracellular Iron (III) on-off sensors.