[12]aneN3-based BODIPY as a selective and sensitive off–on sensor for the sequential recognition of Cu2+ ions and ADP

Zhang, Ying; Gao, Yongguang; Shi, You‐Di; Tan, Lian-Qian; Yue, Jessica S.; Lu, Zhong‐Lin

doi:10.1016/j.cclet.2015.05.032

Cited by 23 publications

(6 citation statements)

References 36 publications

(42 reference statements)

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“…These results indicated that reducing steric hindrance or increasing the length of alkyl chain between naphthalimide unit and benzoic acid unit was beneficial to lower the detection limits of Cu 2þ . It should be noticed that the limits of detection toward Cu 2þ by these probes (except 1c) are lower than our previous reports, and far lower than the limit of Cu 2þ ions in drinking water (Zhong et al, 2013;Zhang et al, 2015).…”

Section: Spectroscopic Properties Of 1a-1econtrasting

confidence: 66%

“…In recent years, we have developed a series of small organic molecules containing rigid fluorescent moieties (naphthalimide, BODIPY, and coumarin) and [12]aneN 3 units (Yue et al, 2015;Zhang et al, 2015;Ding et al, 2017). It was found that [12]aneN 3 unite exhibited multiple functions such as good water solubility, strong coordination ability with metal ions and excellent DNA binding ability.…”

Section: Introductionmentioning

confidence: 99%

“…It was found that [12]aneN 3 unite exhibited multiple functions such as good water solubility, strong coordination ability with metal ions and excellent DNA binding ability. Therefore, some were used as non-viral vectors to deliver DNA into target cells (Yue et al, 2015;Ding et al, 2017) and some were applied in fluorescent probes for recognition of metal ions or small bioactive molecules (Zhang et al, 2015;. However, a functional molecule serving simultaneously as a gene vector as well as the fluorescence probe has not been investigated so far.…”

Section: Introductionmentioning

confidence: 99%

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[12]aneN ₃ -based multifunctional compounds as fluorescent probes and nucleic acids delivering agents

et al. 2019

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A series of multifunctional compounds (MFCs) 1a-1e based on 1,8-naphthalimide and [12]aneN 3 building blocks were designed and synthesized. They were used as not only fluorescent probes for recognition of Cu 2þ ions but also as non-viral gene vectors for DNA and RNA delivery. Furthermore, their complexes with Cu 2þ (1-Cu) could also selectively stain lysosome in HeLa cells. In order to achieve high performance multifunctional materials, structure-performance relationship of MFCs 1a-1e was studied. It was found that MFCs 1a-1e exhibited highly selective fluorescence turn-off for Cu 2þ , without interference by other metal ions in aqueous solution. The fluorescence emission of 1a-1e was quenched by a factor of 10-fold, 47-fold, 6-fold, 64-fold, and 15-fold respectively in the presence of Cu 2þ ions. Due to high sensitivity, good water solubility, and low cytotoxicity, MFCs 1a-1d were successfully applied in the recognition of Cu 2þ and selectively staining lysosome in HeLa cells. Most importantly, MFCs 1a and 1b had excellent HeLa cell selectivity in RNA delivery, and their performances were far better than lipofectamine 2000 and 25 kDa PEI.

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Section: Spectroscopic Properties Of 1a-1econtrasting

confidence: 66%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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[12]aneN ₃ -based multifunctional compounds as fluorescent probes and nucleic acids delivering agents

et al. 2019

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“…The mono-( O -propargyl)-modified, vicinal di( O -propargyl)-modified and tetra-( O -propargyl)-modified TPE compounds 5 , 6 , and 8 were prepared according to literature methods. , The geminal di( O -propargyl)-modified TPE 7 was prepared through a multistep synthesis involving titanium-catalyzed McMurry coupling, demethylation, and final propargation. The azide compound, 9 , an important building block for the preparation of multi-[12]aneN 3 compounds, was obtained following the literature procedure …”

Section: Resultsmentioning

confidence: 99%

[12]aneN₃ Modified Tetraphenylethene Molecules as High-Performance Sensing, Condensing, and Delivering Agents toward DNAs

Ding

Tang

Gao

et al. 2016

ACS Appl. Mater. Interfaces

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Four [12]aneN3 modified tetraphenylethene (TPE) compounds with different numbers of polyamine units and structure configurations, namely 1, 2, 3, and 4, were designed and synthesized. All compounds showed strong aggregation-induced emission (AIE) features. Compounds 2 and 4 showed significant emission enhancement after the addition of ssDNAs and dsDNAs of different lengths as well as calf thymus DNA (ctDNA). Compounds 1 and 3 showed very poor fluorescent responses toward DNAs. Gel electrophoresis demonstrated the abilities of 1-4 to condense DNA effectively. Complete retardation of plasmid DNA can be achieved at a concentration of 25 μM (1), 8 μM (for 2 and 3) and 4 μM (4). Experiments including fluorescent contrastive titrations, scanning electron microscopy, dynamic laser scattering, EB displacement, and gel electrophoresis demonstrated that the four compounds were able to integrate with DNA through electrostatic interactions and supramolecular stacking. A vicinal configuration around TPE (2) and more triazole-[12]aneN3 recognition sites (4) evidently enhanced the sensing capability toward oligonucleotides, and the TPE unit played an important role in the plasmid DNA condensation process because of its strong binding. With the advantages of low cytotoxicity, effective DNA sensing, and DNA condensing properties, compound 4 was successfully applied as a nonviral DNA vector and fluorescent tracer for label-free gene delivery, which is the first example of a nonviral gene vector with AIE activity.

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“…During the interaction of metal ions with dyes, bathochromic or hypsochromic shifts occur which depend upon the structure of dye chromophore and metals. Numerous chemosensors have been synthesized for the detection of Ag + , Hg +2 , Pb +2 , Fe +2 , Cu +2 , Cr +3 , and Fe +3 ions [12,13]. The chelation of azo dye with different solvents due to its structural modifications is discussed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Optical Study of Sensitive and Selective Detection of Fe (III) ions Based on Solvents

et al. 2020

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This study accentuates the synthesis and characterization of vanillin azo dye conjugate based on naked-eye colored chemodosimeters. Vanillin azo dye conjugate exhibited high selectivity and sensitivity in absorbance for detection of Fe(III) ions in all solvents which can be observed simply by naked eye. Mostly the variation occurs in hypochromic shift of different metals with ligand but Fe(III) ions show hypsochromic in all solvents. It was found that the selectivity is more prominent in non-polar or less polar solvents like Chloroform, diethyl ether etc but less protruding in more polar solvents such as DMSO. The detection limit of the synthesized ligand with Fe(III) ions probe was shown by dilution method up to 0.39 ppm. The formation of complexes with azo dye was also affected by dielectric constant of the solvents

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[12]aneN3-based BODIPY as a selective and sensitive off–on sensor for the sequential recognition of Cu2+ ions and ADP

Cited by 23 publications

References 36 publications

[12]aneN ₃ -based multifunctional compounds as fluorescent probes and nucleic acids delivering agents

[12]aneN ₃ -based multifunctional compounds as fluorescent probes and nucleic acids delivering agents

[12]aneN₃ Modified Tetraphenylethene Molecules as High-Performance Sensing, Condensing, and Delivering Agents toward DNAs

Synthesis and Optical Study of Sensitive and Selective Detection of Fe (III) ions Based on Solvents

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[12]aneN3-based BODIPY as a selective and sensitive off–on sensor for the sequential recognition of Cu2+ ions and ADP

Cited by 23 publications

References 36 publications

[12]aneN 3 -based multifunctional compounds as fluorescent probes and nucleic acids delivering agents

[12]aneN 3 -based multifunctional compounds as fluorescent probes and nucleic acids delivering agents

[12]aneN3 Modified Tetraphenylethene Molecules as High-Performance Sensing, Condensing, and Delivering Agents toward DNAs

Synthesis and Optical Study of Sensitive and Selective Detection of Fe (III) ions Based on Solvents

Contact Info

Product

Resources

About

[12]aneN ₃ -based multifunctional compounds as fluorescent probes and nucleic acids delivering agents

[12]aneN ₃ -based multifunctional compounds as fluorescent probes and nucleic acids delivering agents

[12]aneN₃ Modified Tetraphenylethene Molecules as High-Performance Sensing, Condensing, and Delivering Agents toward DNAs