Urolithin A and B Derivatives as ON-OFF Selective Fluorescent Sensors for Iron(III)

Fallah, Amirhossein; Noshadi, Bahareh; Gazi, Mustafa; Gülcan, Hayrettin Ozan

doi:10.1007/s10895-019-02475-0

Cited by 10 publications

(11 citation statements)

References 27 publications

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“…For THU-OH, the stoichiometry was found to be 3:2 (THU-OH:Iron (III)). These results pointed out that the interaction of THU-OH is the same as the urolithin compounds (i.e., Urolithin A and B) as we have found in our previous studies [11][12].…”

Section: The Stoichiometry Of Interaction With Iron (Iii)supporting

confidence: 86%

“…According to our previous findings, the lactone group in urolithin structure is the key group for the selective interaction with Iron (III), since the number of phenolic hydroxyls and their conversion to methyl ethers have been shown to be independent on this feature [12]. Based on this information, in the present study, 3-hydroxy-7,8,9,10tetrahydro-6H-benzo[c]chromen-6-one (i.e., THU-OH), a partially saturated analogue of Urolithin B (i.e., 3-hydroxy-6H-benzo[c]chromen-6-one, URO-B), was synthesized and its characteristics to interact with metals were aimed to be investigated concomitant to the comparison of the results obtained for Urolithin B under the same experimental conditions.…”

Section: Introductionmentioning

confidence: 93%

“…There have been many studies conducted on the discovery of small molecules or polymers acting as selective sensors to detect iron at different oxidation states. In our recent studies, we have demonstrated that urolithins (i.e., hydroxylated benzo[c]chromen -6-one derivatives) can act as fluorescent chemosensors for the selective detection of Iron (III) in aqueous solutions [11][12]. Urolithins are the bioavailable metabolites of an ellagitannin-rich diet including pomegranate, nuts, and berries.…”

Section: Introductionmentioning

confidence: 99%

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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

Shukur¹,

Fallah²,

Teralı³

et al. 2021

Turk J Chem

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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-6Hbenzo[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.

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Section: The Stoichiometry Of Interaction With Iron (Iii)supporting

confidence: 86%

Section: Introductionmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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

Shukur¹,

Fallah²,

Teralı³

et al. 2021

Turk J Chem

Self Cite

View full text Add to dashboard Cite

show abstract

“…On that account, our project aims to develop a novel analytical approach for the sensitive, selective and direct detection of urolithin through an optical homogeneous assay that allows fluorescence signals to be directly detected without the need for a heterogeneous phase and a separation of the labeled compound before analysis. Even though the intrinsic properties (e.g., optical, − electrochemical) of urolithin metabotypes and their derivatives have been extensively studied, as of now, there are no optical sensing strategies reported on the detection of urolithin. Being the two major metabolites produced from the metabolism of ellagic acid in the gut, urolithin A and B will be investigated in this study.…”

Section: Introductionmentioning

confidence: 99%

Portable Smartphone-Assisted Graphene Quantum Dots Sensing Platform for the Detection of Gut Microbial Metabolites

Lim,

Huang,

Ambrosi

et al. 2024

ACS Appl. Nano Mater.

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Metabolomics research is gaining traction lately as there is a growing interest in studying the global relationship between human diseases and the metabolite network. The presence and concentration of beneficial gut-derived metabolites depends on the individual's microbiota composition and diet, with direct metabolite-based supplementation being an appealing option for those unable to produce them. This work serves as an approach in the direct detection of gut-derived metabolites through a smartphone-based approach, as a faster and cheaper alternative to more traditional techniques such as chromatography or the study of gut bacteria culture. Urolithin, a beneficial gut microbial metabolite, was successfully detected with our developed smartphonebased optical assay with low limits of detection of 0.257−0.422 μM that were comparable to those measured with a fluorescence spectrophotometer or even better than some reported HPLC methods. On top of a good sensitive detection with a reduced analysis time, the proposed "turn off-to-on" fluorescence sensing strategy that employed graphene quantum dots coupled with copper(II) ions also distinguished urolithin metabotypes and exhibited good selectivity in the presence of other reducing compounds and phenolic analogues. Our developed approach has demonstrated its versatility in direct gut-derived metabolite detection in commercial dietary supplements, making it a user-friendly tool for food and pharmaceutical product analysis.

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“…For these reasons, there is great need to develop simpler, cheaper, and more stable FL probes and to construct FL probes with strong analytical performance. [ 15–18 ] It is well known that single intensity‐based sensors usually lack self‐calibration and exhibit background interference, and the effect of visualization analysis is undiversified. [ 19 ] Moreover, unlike traditional single channel‐based FL sensors, ratiometric FL probes possess two channels at two different wavelengths under the same excitation wavelength.…”

Section: Introductionmentioning

confidence: 99%

Ratiometric fluorescent probe for tetracycline detection based on waste printing paper

Liu

Wang

et al. 2021

Luminescence

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Tetracycline (TC) is a broad‐spectrum antibiotic used to treat bacterial infections. In this study, a ratiometric fluorescence (FL) probe was developed to detect TC in water samples using waste printing paper extract as a FL indicator. For this ratiometric probe, the emission of printing paper extract at 436 nm gradually decreased and the emission of a mixed solution at 538 nm significantly increased with the sequential addition of TC upon excitation at 390 nm, coupled with a marked FL colour change from bright blue to faint yellow. Therefore, a ratiometric F538/F436 FL probe was created for TC detection by simply mixing the printing paper extraction and TC. Under the optimized conditions, a linear range from 1 to 100 μM and a detection limit of 0.48 μM (S/N = 3) for TC were obtained. Importantly, the FL probe can be easily prepared with rapid response, high sensitivity, and good selectivity. The application of waste printing paper extract for detection of TC in environmental water samples was demonstrated.

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Urolithin A and B Derivatives as ON-OFF Selective Fluorescent Sensors for Iron(III)

Cited by 10 publications

References 27 publications

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

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

Portable Smartphone-Assisted Graphene Quantum Dots Sensing Platform for the Detection of Gut Microbial Metabolites

Ratiometric fluorescent probe for tetracycline detection based on waste printing paper

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