Synthesis and evaluation of fluorescence properties of Cu2+selective azocalix[4]arenes and their application in living cell imaging

Elçin, Serkan; Deligöz, Hasalettin; Bhatti, Asif Ali; Oğuz, Mehmet; Karakurt, Serdar

doi:10.1016/j.snb.2016.04.155

Cited by 15 publications

(7 citation statements)

References 25 publications

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“…3a). From the concentration analysis, the detection limits of the probe toward the sensing of Fe 3+ ions was estimated to be 7.0 x 10 − 8 M, which is inferior and comparable to those of reported sensors [38][39][40][41][42]. The binding constant of 8-HQC-NH with Fe 3+ was found to be 3.6x10 − 3 M − 1 using the uorescence titration data (Fig.…”

Section: 2fluorescence Spectral Studies Of 8-hqc-nhmentioning

confidence: 51%

Sensitivity and Selectivity of Fluorescent Chemosensor for the Detection of Fe 3+ and its Cell Images

Marimuthu

Ramu

2022

Preprint

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A simple probe (Z)-N'-((8-hydroxyquinolin-2-yl) methylene)nicotine hydrazide (8-HQC-NH) has been synthesized and realized as a “turn-off” fluorescent chemosensor for the detection for Fe3+ ion over the competitive metal ions in ethanol medium. The fluorescent intensity of the 8-HQC-NH probe intensely illustrated that the “turn-off” selective quenching upon the addition of Fe3+ owing to the chelation-enhanced fluorescence quenching (CHEQ) effect. The probe of 8-HQC-NH exhibited an ample linear response towards Fe3+ concentration rangingbetween 0 to 75 µM with satisfactory lower detection limits of 7x10− 8 M. Furthermore, the developed 8-HQC-NH probe offers many advantages like good biocompatibility, negligible cytotoxicity, being promising efficient fluorescent probe to recognize Fe3+ions in living cells. These features explore the way for the design of simple and efficient fluorescent method for the bio-sensing applications.

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Section: 2fluorescence Spectral Studies Of 8-hqc-nhmentioning

confidence: 51%

Sensitivity and Selectivity of Fluorescent Chemosensor for the Detection of Fe 3+ and its Cell Images

Marimuthu

Ramu

2022

Preprint

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“…To visualize the localization of compounds in DLD-1 cells, 1x10 5 of the cells were seeded into glass bottom-high quality imaging cell culture micro-Dishes and incubated for 24 h at 37°C with 5% CO 2 (20).…”

Section: Bio-imaging Studiesmentioning

confidence: 99%

Synthesized Two New Water-soluble Fluorescents Calix[4]arene 4-sulfo-1,8-naphthalimide Derivatives Inhibit Proliferation of Human Colorectal Carcinoma Cells

Yildirim

Karakurt

2021

Preprint

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Synthesis of 1,8-naphthalimide derivatives and biochemical studies using them as anti-cancer and cellular imaging agents have attracted significant attention in recent years. This study aimed to synthesize two new fluorescent lower rim-functionalized 4-sulfo-1,8-naphthalimide derivatives of calix[4]arenes [4 and 7] and examination of their cytotoxic properties for cancerous cells. For this purpose, p-tert-butylcalix[4]arene bearing dihydrazide [3] or diaminopropyl [6] units on its lower rim were reacted with 4-sulfo-1,8-naphthalic anhydrate. The structure of these synthesized compounds has been characterized using 1H-NMR, 13C-NMR, and FT-IR techniques. To investigate the anti-cancer properties, compounds 4, 7, and N,N-dimethylaminoethyl-1,8-naphthalimide [8] were tested on the human colorectal cancer cell line (DLD-1) as well as healthy colon epithelial cell line (CCD-18Co). The IC50 values of 4 and 7 were determined as 12.95 µM and 16.13 µM, respectively, on DLD-1 cells. Furthermore, following the treatment of CCD-18Co cells with 4 and 7, the IC50 values were determined as 508 µM and 269 µM, respectively. However, it was observed that compound 8 had no cytotoxic effect on both DLD-1 cells and CCD-18Co cells. Furthermore, the fluorescence imaging of human colorectal cancer cells treated with the synthesized compounds [4, 7, and 8] was performed on living cells.

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“…16,17 Additionally, as an essential trace element in the human body, Cu 2+ plays a crucial role in cellular oxygen transportation/activation, energy generation, and signal transduction. 18,19 However, excessive or deficient intake of Cu 2+ is harmful to human health and results in serious neurodegenerative diseases including Menkes syndrome, Wilson’s disease, and Alzheimer’s. 20−22 Moreover, Cu 2+ and Fe 3+ ions are considered as important water pollution and toxic species because of their widespread application in industry and in our daily life.…”

Section: Introductionmentioning

confidence: 99%

“…As one of the most essential trace elements, Fe 3+ ions play critical roles in numerous physiological and pathological processes, such as oxygen metabolism, enzymatic catalysis, oxygen uptake, electron transfer, and regulation of body temperature. , However, the imbalance of the Fe 3+ ion within the body could cause several diseases including various cancers, heart failure, hepatitis diabetes, and Parkinson’s disease. , Additionally, as an essential trace element in the human body, Cu 2+ plays a crucial role in cellular oxygen transportation/activation, energy generation, and signal transduction. , However, excessive or deficient intake of Cu 2+ is harmful to human health and results in serious neurodegenerative diseases including Menkes syndrome, Wilson’s disease, and Alzheimer’s. − Moreover, Cu 2+ and Fe 3+ ions are considered as important water pollution and toxic species because of their widespread application in industry and in our daily life. According to the U.S. Environmental Protection Agency (EPA) reports, the upper limits of Cu 2+ and Fe 3+ in drinking water or food were 1.3 ppm (∼20 μM) and 0.3 ppm (∼5.4 μM), respectively. , Therefore, it is crucial to detect Cu 2+ and Fe 3+ in various biological and environmental systems.…”

Section: Introductionmentioning

confidence: 99%

Bifunctional Cu²⁺/Fe³⁺ Probe with Independent Signal Outputs Based on a Photochromic Diarylethene with a Dansylhydrazine Unit

Liang

Wang

et al. 2019

ACS Omega

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A novel dual-response fluorescent sensor based on a diarylethene photoswitching unit and a dansylhydrazine functional group has been synthesized. The compound exhibited high selectivity for Fe 3+ and Cu 2+ with independent fluorescence signal outputs. In the presence of Fe 3+ , the sensor formed a 1:1 metal complex, resulting in a remarkable “turn-off” fluorescence signal. On the other hand, its fluorescence intensity was notably enhanced (turn-on) and a color change from bright yellow to bright blue was observed when the sensor interacted with Cu 2+ , which was due to the hydrolysis reaction of the dansyl acid dye, as confirmed by high-resolution mass spectrometry–electrospray ionization and infrared spectrum. The detection limits were 9.73 × 10 –8 mol L –1 for Fe 3+ and 3.49 × 10 –7 mol L –1 for Cu 2+ , respectively. From the unimolecular platform, two molecular logic circuits were constructed using the fluorescence emission intensity at 557/494 nm (Fe 3+ /Cu 2+ ) as the outputs and the combined stimuli of Fe 3+ /ethylenediaminetetraacetic acid, Cu 2+ , and UV/vis as the inputs. In addition, the sensor was successfully used to determine Fe 3+ in water samples from Ganjiang River and soil samples from Nanchang fields.

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Synthesis and evaluation of fluorescence properties of Cu2+selective azocalix[4]arenes and their application in living cell imaging

Cited by 15 publications

References 25 publications

Sensitivity and Selectivity of Fluorescent Chemosensor for the Detection of Fe 3+ and its Cell Images

Sensitivity and Selectivity of Fluorescent Chemosensor for the Detection of Fe 3+ and its Cell Images

Synthesized Two New Water-soluble Fluorescents Calix[4]arene 4-sulfo-1,8-naphthalimide Derivatives Inhibit Proliferation of Human Colorectal Carcinoma Cells

Bifunctional Cu²⁺/Fe³⁺ Probe with Independent Signal Outputs Based on a Photochromic Diarylethene with a Dansylhydrazine Unit

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Synthesis and evaluation of fluorescence properties of Cu2+selective azocalix[4]arenes and their application in living cell imaging

Cited by 15 publications

References 25 publications

Sensitivity and Selectivity of Fluorescent Chemosensor for the Detection of Fe 3+ and its Cell Images

Sensitivity and Selectivity of Fluorescent Chemosensor for the Detection of Fe 3+ and its Cell Images

Synthesized Two New Water-soluble Fluorescents Calix[4]arene 4-sulfo-1,8-naphthalimide Derivatives Inhibit Proliferation of Human Colorectal Carcinoma Cells

Bifunctional Cu2+/Fe3+ Probe with Independent Signal Outputs Based on a Photochromic Diarylethene with a Dansylhydrazine Unit

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Bifunctional Cu²⁺/Fe³⁺ Probe with Independent Signal Outputs Based on a Photochromic Diarylethene with a Dansylhydrazine Unit