A three-dimensional (time, wavelength and intensity) functioning fluorescent probe for the selective recognition/discrimination of Cu2+, Hg2+, Fe3+ and F− ions

Ruan, Qin; Mu, Lan; Zeng, Xi; Zhao, Jiang‐Lin; Zeng, Li; Chen, Zhenmin; Cai, Yanfei; Wei, Gang; Redshaw, Carl

doi:10.1039/c7dt04785a

Cited by 16 publications

(6 citation statements)

References 31 publications

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“…The observed ratiometric absorption changes revealed that sensor L can behave as a ratiometric sensor for Ca 2+ . It is recognized that ratiometric responsive probes are superior to other types of probe given their built-in correction for environmental effects and self-correcting capability . On the other hand, the fluorescence titration experiments revealed a fluorescent quenching phenomenon upon increasing the amount of Ca 2+ (Figure b).…”

Section: Resultsmentioning

confidence: 99%

Molecular Tweezers-like Calix[4]arene Based Alkaline Earth Metal Cation (Ca²⁺, Sr²⁺, and Ba²⁺) Chemosensor and Its Imaging in Living Cells and Zebrafish

Fang

Zhao

et al. 2019

Inorg. Chem.

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Although alkaline earth metal cations play an important role in our daily life, little attention has been paid to the field of fast quantitative analysis of their content due to a lack of satisfactory precision, and a fast and convenient means of detection. In this study, we have designed a set of molecular tweezers based on the calix[4]arene chemosensor L, which was found to exhibit high selectivity and sensitivity towards Ca 2+ , Sr 2+ and Ba 2+ (by UV-vis and fluorescence methods) with low detection limits of the order of 10 -7 to 10 -8 M and high association constants (of the order of 10 6 ). More significantly, sensor L not only can recognize Ca 2+ , Sr 2+ and Ba 2+ , but can also further discriminate between these three cations via the differing red shifts in their UVvis spectra (560 nm for L•Ca 2+ , 570 nm for L•Sr 2+ and 580 nm for L•Ba 2+ complex) which is attributed to their different atomic radii. A rare synergistic effect for the recognition mechanism has been demonstrated by 1 H NMR spectroscopic titration. Sensor L constructed a high shielding field by the cooperation of Tris with alkaline earth metal ion after complex. Additionally, the presence of acetoxymethyl group in sensor L results in enhancement of cell permeability and as a consequence, sensor L exhibited excellent sensing and imaging (in vivo) in living cells and in Zebrafish. ASSOCIATED CONTENTSupporting Information. Detailed characterization, spectra and 1 H NMR titration data (PDF). This material is available free of charge via the Internet at http://pubs.acs.org.

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Section: Resultsmentioning

confidence: 99%

Molecular Tweezers-like Calix[4]arene Based Alkaline Earth Metal Cation (Ca²⁺, Sr²⁺, and Ba²⁺) Chemosensor and Its Imaging in Living Cells and Zebrafish

Fang

Zhao

et al. 2019

Inorg. Chem.

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“…The detection limit of probe TRN for Zn 2+ , Cu 2+ , Al 3+ and Hg 2+ was calculated based on the fluorescence titration data according to a reported method [47] . Under optimal conditions, calibration graphs for the determination of Zn 2+ , Cu 2+ , Al 3+ and Hg 2+ were constructed.…”

Section: 1mentioning

confidence: 99%

“…The association constants are estimated to be 1.88 × 10 4 M -1 ( TRN• Zn 2+ ), 2.73 × 10 4 M -1 ( TRN• Zn 2+ •Cu 2+ ), and 1.54 × 10 4 M -1 ( TRN •Hg 2+ ) by using a Benesi-Hildebrand plot assuming a 1:1 stoichiometry, respectively ( Fig.S5~S7). The association constants of T RN• Al 3+ are estimated to be 8.60 × 10 8 M -2 by using a Benesi-Hildebrand plot assuming a 1:2 stoichiometry ( Fig.S8)[46] .From the fluorescence titration, a linear relationship between the emission intensity of TRN and ions concentration was observed ( Fig.S9 ~ S13).The detection limit of probe TRN for Zn 2+ , Cu 2+ , Al 3+ and Hg 2+ was calculated based on the fluorescence titration data according to a reported method[47] . Under optimal conditions, calibration graphs for the determination of Zn 2+ , Cu 2+ , Al 3+ and Hg 2+ were constructed.…”

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confidence: 99%

A flexible tripod fluorescent probe for multiple cations detection and its application in living cells

Yang

Ran

Zeng

et al. 2020

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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To the flexible tripod platform tren (tris(2-aminoethyl)amine), a Rhodamine and two naphthalene fluorophores were introduced. The resulting fluorescence probe named TRN was fully characterized and employed in cell imaging. Probe TRN exhibited high selectivity and excellent sensitivity for the simultaneous fluorescence detection of Zn 2+ / Hg 2+ / Al 3+ / Cu 2+ . The significant changes in the fluorescence color make naked-eye detection possible. Furthermore, fluorescence imaging experiments of Zn 2+ / Hg 2+ / Al 3+ / Cu 2+ in living PC3 cells demonstrated its value for practical applications in biological systems.Key words: flexible tripod probe, Zn 2+ / Hg 2+ / Al 3+ / Cu 2+ ions detection, cells imaging increasing demands for sensors in these fields. Among these, the metal ion s of mercury, zinc, aluminium and copper are synonymous with various prominent neurological conditions and biological processes. For instance, mercury is a well-known human toxin, capable of serious harm to the skin, nervous and renal systems even at very low levels [1][2][3][4] . Zinc is the second most abundant transition-metal ion and plays important roles in a variety of physiological and pathological processes [5][6][7] , and disorder associated with zinc metabolism in biological systems may lead to a variety of diseases such as Alzheimer's disease, diabetes, epilepsy [8][9][10][11] . Moreover, Al 3+ has been associated with conditions such as neuro dementia, Parkinson's disease, Alzheimer's disease and dialysis encephalopathy. Copper ions, as the third most abundant essential trace element after iron and zinc in the human body, also play an important role in various physiological and enzymatic processes [12][13][14] , such as in transforming melanin in skin pigments, assisting cross-linking in collagen, as well as tissue maintenance and repair [15][16][17] . Excessive copper is also toxic and a major cause for oxidative stress and disorders associated with neurodegenerative diseases including Alzheimer's, Parkinson's, Menkes, Wilson's and prion diseases [18][19][20] . Thus, there is an urgent need to develop sensors capable of detecting low concentrations of Hg 2+ , Al 3+ , Zn 2+ and Cu 2+ ions in biological samples.Fluorescent probes are ideal candidates for both the detection and monitoring of metal ions in a wide variety of samples. This is due to their high sensitivity, fast response, and ability to provide in situ and real-time information with high spatial-temporal resolution, and non-destructive detection. During the past two decades, many fluorescent probes have been developed for a variety of biological ly and environment ally related targets. However, most of the fluorescent probes that have been reported are of two-or three-ion sensor types that detect for example Fe 3+ / Cu 2+ [21] , Ba 2+ / Hg 2+ [22] , Zn 2+ / Cd 2+ [23] , Cu 2+ / Hg 2+ [24, 25] , Pb 2+ / Hg 2+ [26] , Zn 2+ / Hg 2+ / Cu 2+ [27] , Cu 2+ / Cysteine [28] , Zn 2+ / Cd 2+ / Hg 2+ [29] , Cr 3+ / Al 3+ / Fe 3+ [30, 31] . However, it remains a great ch...

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“…Thanks to the facile preparation and numerous possibilities for the functionalization of compound 1, there are many possible avenues to explore. 11,16 In view of the high importance of anion recognition and the interesting properties of azobenzene compounds, 17 we have introduced the (E)-2-hydroxy-5-((4-nitrophenyl)diazenyl)benzaldehyde group to compound 1 and constructed a tripodal structure. Schiff base groups can be unstable for certain applications, so.…”

Section: Synthesismentioning

confidence: 99%

“…Compound 1 was prepared by following the reported procedures. 11,16 UV-Vis absorption spectra were conducted on a UV-1800 spectrophotometer (Shimadzu) in a 1 cm quartz cell. 1 H and 13 C NMR spectra were measured on a JEOL JNM-ECZ400S 400 MHz NMR spectrometer (JEOL) at room temperature using TMS as an internal standard.…”

Section: Materials and Equipmentmentioning

confidence: 99%

An efficient ICT-based ratio/colorimetric tripodal azobenzene probe for the recognition/discrimination of F−, AcO− and H2PO4− anions

Fang

Zhao

et al. 2019

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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The tripodal probe L was readily prepared via introducing rhodamine and azobenzene groups in a two-step procedure. Studies of the recognition properties indicated that probe L exhibited high sensitivity and selectivity towards F -, AcOand H2PO4through a ratiometric colorimetric response with low detection limits of the order of 10 -7 M. The complexation behaviour was fully investigated by spectral titration, 1 H NMR spectroscopic titration and mass spectrometry. Probe L not only recognizes F -, AcOand H2PO4 -, but can also distinguish between these three anions via the different ratiometric behaviour in their UV-vis spectra (387/505 nm for L-H2PO4 -, 387/530 nm for L-AcOand 387/575 nm for L-Fcomplex) or via different colour changes (light coral for L-H2PO4 -, light pink for L-AcOand violet for the L-Fcomplex). Additionally, given the presence of NH and OH groups in probe L, which can be protonated and deprotonated, probe L further exhibited an excellent pH response over a wide pH range (pH 3 to pH 12).

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A three-dimensional (time, wavelength and intensity) functioning fluorescent probe for the selective recognition/discrimination of Cu²⁺, Hg²⁺, Fe³⁺ and F⁻ ions

Cited by 16 publications

References 31 publications

Molecular Tweezers-like Calix[4]arene Based Alkaline Earth Metal Cation (Ca²⁺, Sr²⁺, and Ba²⁺) Chemosensor and Its Imaging in Living Cells and Zebrafish

Molecular Tweezers-like Calix[4]arene Based Alkaline Earth Metal Cation (Ca²⁺, Sr²⁺, and Ba²⁺) Chemosensor and Its Imaging in Living Cells and Zebrafish

A flexible tripod fluorescent probe for multiple cations detection and its application in living cells

An efficient ICT-based ratio/colorimetric tripodal azobenzene probe for the recognition/discrimination of F−, AcO− and H2PO4− anions

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A three-dimensional (time, wavelength and intensity) functioning fluorescent probe for the selective recognition/discrimination of Cu2+, Hg2+, Fe3+ and F− ions

Cited by 16 publications

References 31 publications

Molecular Tweezers-like Calix[4]arene Based Alkaline Earth Metal Cation (Ca2+, Sr2+, and Ba2+) Chemosensor and Its Imaging in Living Cells and Zebrafish

Molecular Tweezers-like Calix[4]arene Based Alkaline Earth Metal Cation (Ca2+, Sr2+, and Ba2+) Chemosensor and Its Imaging in Living Cells and Zebrafish

A flexible tripod fluorescent probe for multiple cations detection and its application in living cells

An efficient ICT-based ratio/colorimetric tripodal azobenzene probe for the recognition/discrimination of F−, AcO− and H2PO4− anions

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Product

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A three-dimensional (time, wavelength and intensity) functioning fluorescent probe for the selective recognition/discrimination of Cu²⁺, Hg²⁺, Fe³⁺ and F⁻ ions

Molecular Tweezers-like Calix[4]arene Based Alkaline Earth Metal Cation (Ca²⁺, Sr²⁺, and Ba²⁺) Chemosensor and Its Imaging in Living Cells and Zebrafish

Molecular Tweezers-like Calix[4]arene Based Alkaline Earth Metal Cation (Ca²⁺, Sr²⁺, and Ba²⁺) Chemosensor and Its Imaging in Living Cells and Zebrafish