A new Fe3+-selective, sensitive, and dual-channel turn-on probe based on rhodamine carrying thiophenecarboxaldehyde: Smartphone application and imaging in living cells

Aribuga, Hulya; Ertugral, Utku; Alçay, Yusuf; Yavuz, Ozgur; Yildirim, Mustafa Semih; Ozdemir, Emre; Kaya, Kerem; Sert, Ayşe Buse Özdabak; Kok, Fatma Nese; Tüzün, Nurcan Ş.; Yılmaz, İsmail

doi:10.1016/j.saa.2022.122060

Cited by 19 publications

(3 citation statements)

References 90 publications

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“…The limit of detection (LOD) was found to be 1.80 × 10 –7 M (12.13 ppb) by using the formula (LOD = 3 × SD/ S , SD stands for the standard deviation of five blank measurements (0.0012) and S indicates the slope of calibration curve). , Based on the observed isosbestic points at 426 and 534 nm shown in Figure , the complex most likely underwent an initial 1:1 formation before transitioning to the 2:2 complex formation, as evidenced by the crystal structure. Furthermore, the association constant ( K a ) of the complex occurred between AQNQ and Cu 2+ was calculated as 2.24 × 10 4 M –1 according to the Benesi–Hildebrand equation , (Figure S11). Based on the results of the Benesi–Hildebrand equation graph, the linear calibration curve illustrates a 1:1 ratio of the resulting complex.…”

Section: Resultsmentioning

confidence: 99%

Architecture of Easy-to-Synthesize and Superior Probe Based on Aminoquinoline Appended Naphthoquinone: Instant and On-Site Cu²⁺ Ion Quantification in Real Samples and Unusual Crystal Structure and Logic Gate Operations

Kaplan,

Yavuz,

Ozdemir

et al. 2024

Inorg. Chem.

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Easy-to-synthesize aminoquinoline (AQ) appended naphthoquinone (NQ)-based colorimetric and ratiometric probe (AQNQ) was successfully synthesized in one step with high yield and low cost, and was utilized to supply an effective solution to critical shortcomings encountered in Cu 2+ analysis. The structure of AQNQ and its interaction with Cu 2+ forming an unusual AQNQ−Cu complex were enlightened with single-crystal X-ray diffraction analysis and different spectroscopic methods. AQNQ− Cu complex is the first Cu 2+ containing dinuclear crystal where the octahedral coordination sphere is fulfilled through the coordination of a NQ oxygen atom. AQNQ exhibited long-term stability (more than 1 month), superior probe ability toward Cu 2+ with quite fast response (30 s), high selectivity among many ions, and limit of detection of 12.13 ppb that is significantly below the highest amount of Cu 2+ allowed in drinking water established by both WHO and EPA. Ratiometric determination of Cu 2+ using AQNQ was performed with high recovery and low RSD values for drinking water, tap water, lake water, cherry, and watermelon samples. Colorimetric on-site determination including smartphone and paper strip applications, IMPLICATION, and INHIBIT logic gate applications were successfully carried out. The reversibility and reusability of the response to Cu 2+ ions with the paper strip application were examined for the first time.

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Section: Resultsmentioning

confidence: 99%

Architecture of Easy-to-Synthesize and Superior Probe Based on Aminoquinoline Appended Naphthoquinone: Instant and On-Site Cu²⁺ Ion Quantification in Real Samples and Unusual Crystal Structure and Logic Gate Operations

Kaplan,

Yavuz,

Ozdemir

et al. 2024

Inorg. Chem.

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“…Dye 99 was capable of detecting exogenously added Fe(III) in DL tumor cells. In the following years, the same strategy was used with different chelating groups to develop Fe(III)-selective probes ( 100 – 104 ), which were then employed in live cell imaging experiments. − Kumar’s group modified the known bis-rhodamine B derivative by introducing a rigid 1,10-phenanthroline moiety between two units, to produce 105 , which enhanced its affinity toward Fe(III) ions . This probe successfully tracked both endogenous and exogenously added Fe(III) ions localized in mitochondria and lysosomes of C6 glial cells with bright red response in fluorescence imaging, which is diminished in the presence of iron chelator DFO.…”

Section: Fluorescent Sensors For Ironmentioning

confidence: 99%

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Grover,

Koblova,

Pezacki

et al. 2024

Chem. Rev.

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Although transition metals constitute less than 0.1% of the total mass within a human body, they have a substantial impact on fundamental biological processes across all kingdoms of life. Indeed, these nutrients play crucial roles in the physiological functions of enzymes, with the redox properties of many of these metals being essential to their activity. At the same time, imbalances in transition metal pools can be detrimental to health. Modern analytical techniques are helping to illuminate the workings of metal homeostasis at a molecular and atomic level, their spatial localization in real time, and the implications of metal dysregulation in disease pathogenesis. Fluorescence microscopy has proven to be one of the most promising non-invasive methods for studying metal pools in biological samples. The accuracy and sensitivity of bioimaging experiments are predominantly determined by the fluorescent metal-responsive sensor, highlighting the importance of rational probe design for such measurements. This review covers activity-and binding-based fluorescent metal sensors that have been applied to cellular studies. We focus on the essential redox-active metals: iron, copper, manganese, cobalt, chromium, and nickel. We aim to encourage further targeted efforts in developing innovative approaches to understanding the biological chemistry of redox-active metals. CONTENTS5908 8.2. Activity-Based Fluorescent Sensors for Ni(II) 5911 9. Outlook 5911 Author Information 5912 Corresponding Authors 5912

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“…A very recent report described a rhodamine based chemosensor ( 44 ) (Scheme 6) which was derived from a reaction between 2,5-thiophenedicarboxaldehyde and rhodamine B hydrazide in ethanol. 61 It was used for the identification of Fe 3+ with no interference by other metal ions, as evidenced by the increase in fluorescence intensity at 580 nm and absorbance at 559 nm. The cation formed complex with the ring opened species through amide O, imine N, thiophene S and carbonyl O atoms.…”

Section: Introductionmentioning

confidence: 99%

Structure–metal ion selectivity of rhodamine-based chemosensors

Ghosh

Roy

2023

Chem. Commun.

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A new Fe3+-selective, sensitive, and dual-channel turn-on probe based on rhodamine carrying thiophenecarboxaldehyde: Smartphone application and imaging in living cells

Cited by 19 publications

References 90 publications

Architecture of Easy-to-Synthesize and Superior Probe Based on Aminoquinoline Appended Naphthoquinone: Instant and On-Site Cu²⁺ Ion Quantification in Real Samples and Unusual Crystal Structure and Logic Gate Operations

Architecture of Easy-to-Synthesize and Superior Probe Based on Aminoquinoline Appended Naphthoquinone: Instant and On-Site Cu²⁺ Ion Quantification in Real Samples and Unusual Crystal Structure and Logic Gate Operations

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Structure–metal ion selectivity of rhodamine-based chemosensors

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A new Fe3+-selective, sensitive, and dual-channel turn-on probe based on rhodamine carrying thiophenecarboxaldehyde: Smartphone application and imaging in living cells

Cited by 19 publications

References 90 publications

Architecture of Easy-to-Synthesize and Superior Probe Based on Aminoquinoline Appended Naphthoquinone: Instant and On-Site Cu2+ Ion Quantification in Real Samples and Unusual Crystal Structure and Logic Gate Operations

Architecture of Easy-to-Synthesize and Superior Probe Based on Aminoquinoline Appended Naphthoquinone: Instant and On-Site Cu2+ Ion Quantification in Real Samples and Unusual Crystal Structure and Logic Gate Operations

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Structure–metal ion selectivity of rhodamine-based chemosensors

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Product

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Architecture of Easy-to-Synthesize and Superior Probe Based on Aminoquinoline Appended Naphthoquinone: Instant and On-Site Cu²⁺ Ion Quantification in Real Samples and Unusual Crystal Structure and Logic Gate Operations

Architecture of Easy-to-Synthesize and Superior Probe Based on Aminoquinoline Appended Naphthoquinone: Instant and On-Site Cu²⁺ Ion Quantification in Real Samples and Unusual Crystal Structure and Logic Gate Operations