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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.
Turkish journal of chemistry Pub Date : 2021-06-30 , DOI: 10.3906/kim-2011-58
Karar Shukur 1, 2 , Amirhossein Fallah 1 , Kerem Terali 3 , Rasime Kalkan 4 , Mustafa Gazi 2 , Hayrettin Ozan Gülcan 1
Affiliation  

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.

中文翻译:


3-羟基-7,8,9,10-四氢-6H-苯并[c]色满-6-酮和3-羟基-6H-苯并[c]色满-6-酮作为开关选择性荧光传感器体外和离体条件下的铁 (III)。



鉴于金属在不同用途中的大量使用,从各种科学和技术角度来看,发现新的试剂作为选择性探针来检测特定金属变得更加重要。在我们之前的研究中,我们已经证明天然尿石素(即羟基取代的苯并[c]色烯-6-酮衍生物)的水溶液是荧光测定中的选择性铁(III)传感器。在本研究中,我们将这些发现外推到另一种香豆素化合物(即 3-Hydroxy-7,8,9,10-tetrahydro-6H-Benz[c]chromen-6-one),并将选择性金属结合特性与尿石素B(即3-羟基-6H-苯并[c]色满-6-酮)。在合成和结构鉴定研究之后,荧光研究指出,结构中的内酰胺基团仍然是维持选择性开关传感器能力的重要支架,使该化合物成为选择性铁(III)结合探针。此外,还首次对标题化合物进行了与细胞毒性测定同时进行的荧光细胞成像研究,结果显示了该化合物通过作为细胞内铁在神经母细胞瘤和胶质母细胞瘤细胞中的细胞穿透性、安全性和荧光可检测特性。 (III)开关传感器。
更新日期:2021-06-30
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