A reaction-based, colorimetric and near-infrared fluorescent probe for Cu2+ and its applications

Gu, Biao; Huang, Long; Xu, Zhifeng; Tan, Zhimin; Meng, Hu; Yang, Zitun; Chen, Yanxia; Peng, Cheng; Xiao, Wenpei; Yu, Donghai; Li, Haitao

doi:10.1016/j.snb.2018.06.032

Cited by 60 publications

(20 citation statements)

References 62 publications

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“…Accordingly, this method offers high sensitivity for determination of low concentration of Cu 2+ , which is an ion of high biological impact. 17 On the other hand, values of LOD and LOQ for Co 2+ , Ni 2+ , and Hg 2+ also are somewhat low (Table 1, entries 2–4), which means that, in general, the designed ligands 6a – 6e are very efficient for these metals and they would form very stable chelates in each case. The measure was also obtained for the other photophysically studied ligands 6a and 6c , but the differences are negligible and the order of magnitude is the same in each experiment.…”

Section: Resultsmentioning

confidence: 99%

“…The unregulated Cu 2+ ions can cause oxidative stress, and their increase in the neuronal cytoplasm may contribute to the etiology of Alzheimer’s or Parkinson’s disease. 17 Cobalt is another vital trace element being part of cobalamin and a few metalloproteins. Co 2+ ions can be mildly toxic, and unregulated exposure may cause detrimental effects including heart disease, elevated red blood cells accompanied by increased cells in the bone marrow, vasodilation, and flushing.…”

Section: Introductionmentioning

confidence: 99%

“…Ligands 6a – 6e contain a fused tricyclic structure that is dialkyl- and triaryl-substituted and also have three pyridine nitrogen atoms (C=N:) suitably situated to achieve the formation of chelates. 14,17−20,22a,23 Thus, we have hypothesized that PBPs 6a – 6e have the necessary features for their use in the detection of metal ions through the fluorescence quenching process based on TICT mechanisms (Scheme 1b). 8−10,12 In this work, compounds 6a – 6e showed a high fluorescence emission in different solvents and large Stokes shifts due to the TICT process being favored.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Fluorescent 1,7-Dipyridyl-bis-pyrazolo[3,4-b:4′,3′-e]pyridines: Design of Reversible Chemosensors for Nanomolar Detection of Cu²⁺

2019

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An efficient access toward novel tridentate ligands based on 1,7-dipyridinyl-substituted bis-pyrazolo[3,4- b :4′,3′- e ]pyridines (BPs) and their usefulness as fluorescent probes for cation detection is reported. The synthesis proceeds by a three-step sequence starting from 2-chloropyridine ( 1 ), all reactions were performed using microwave radiation under solvent-free conditions, and an overall yield of up to 63% was obtained. Photophysical properties of three representative 1,7-dipyridinyl-BPs (PBPs, 6a – 6c ) substituted at position 4 with different donor (D) or acceptor (A) groups were investigated. Compounds exhibited large Stokes shift in different solvents and strong blue light emission in both solution and solid state, and quantum yields were as high as 88% for some of them; thus, a twisted intramolecular charge transfer (TICT) fluorescence mechanism characteristic of the 1,4,7-triaryl-BPs was confirmed. The 4-phenyl-substituted probe (Ph-PBP, 6b ) was used successfully in the detection of some metals (Cu 2+ , Co 2+ , Ni 2+ , and Hg 2+ ) by fluorescence quenching phenomena, which could be reversed in the presence of ethylenediamine. This probe showed a greater sensitivity toward Cu 2+ in concentrations as low as 26 nM, and in the process of “on–off–on” for this fluorescent molecular switch, only 1 equiv of the analyte was used.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Fluorescent 1,7-Dipyridyl-bis-pyrazolo[3,4-b:4′,3′-e]pyridines: Design of Reversible Chemosensors for Nanomolar Detection of Cu²⁺

2019

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“…As is known to all, copper ion (Cu 2+ ) occupies an important place in a variety of fundamental physiological processes in organisms ranging from bacteria to mammals (Huang et al, 2014 ; Arjmand et al, 2018 ; Wang P. et al, 2018 ; Wang Y. et al, 2018 ; Zeng et al, 2019 ; Aydin et al, 2020 ; Wang Z. G. et al, 2020 ). However, Cu 2+ can also lead to environmental pollution because it has been used widely in industrial and agricultural processes (Huang et al, 2014 ; Zhang et al, 2016 ; Gu et al, 2018 ; Wang et al, 2019 ; Zhu et al, 2020 ). So, it is urgent to develop some methods for recognition toward Cu 2+ .…”

Section: Introductionmentioning

confidence: 99%

A Coumarin-Based Fluorescent Probe for Ratiometric Detection of Cu2+ and Its Application in Bioimaging

Zhang

Chen

et al. 2020

Front. Chem.

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The fluorescent probe L , based on naphthalimide-modified coumarin, was designed, synthesized, and characterized, which could recognize Cu 2+ from other cations selectively and sensitively in HEPES buffer (10 mM, Ph = 7. 4)/CH 3 CN (1:4, V/V). When the probe L interacted with Cu 2+ , the color and the fluorescent intensity changed obviously and it provided the naked-eye detection for Cu 2+ . The recognition mode between them was achieved by Job's plot, IR, MS, SEM, and 1 HNMR. In addition, test strips made from L could still interact with Cu 2+ in tap water effectively. The limit of detection (LOD) of L was 3.5 × 10 −6 M. Additionally, the density functional theory (DFT) calculation method was used to analyze the action mechanism of L toward Cu 2+ . Importantly, the fluorescent probe L could demonstrate favorable selectivity toward Cu 2+ in Caenorhabditis elegans . Thus, L was considered to have some potential for application in bioimaging.

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“…For example, the pH value of lysosome lumen ranges from 4.0 to 6.0, while the cytoplasm is about 7.2. Therefore, many fluorescence probes for the recognition of lysosome or detection of Cu 2þ have been reported (Jeppe et al, 2013;Khan et al, 2015;Behnood et al, 2016;Gu et al, 2018;Li et al, 2018;Shi et al, 2018). However, the same compounds used for recognition of both Cu 2þ and lysosome are relatively rare.…”

Section: Introductionmentioning

confidence: 99%

[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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A reaction-based, colorimetric and near-infrared fluorescent probe for Cu2+ and its applications

Cited by 60 publications

References 62 publications

Synthesis of Fluorescent 1,7-Dipyridyl-bis-pyrazolo[3,4-b:4′,3′-e]pyridines: Design of Reversible Chemosensors for Nanomolar Detection of Cu²⁺

Synthesis of Fluorescent 1,7-Dipyridyl-bis-pyrazolo[3,4-b:4′,3′-e]pyridines: Design of Reversible Chemosensors for Nanomolar Detection of Cu²⁺

A Coumarin-Based Fluorescent Probe for Ratiometric Detection of Cu2+ and Its Application in Bioimaging

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

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A reaction-based, colorimetric and near-infrared fluorescent probe for Cu2+ and its applications

Cited by 60 publications

References 62 publications

Synthesis of Fluorescent 1,7-Dipyridyl-bis-pyrazolo[3,4-b:4′,3′-e]pyridines: Design of Reversible Chemosensors for Nanomolar Detection of Cu2+

Synthesis of Fluorescent 1,7-Dipyridyl-bis-pyrazolo[3,4-b:4′,3′-e]pyridines: Design of Reversible Chemosensors for Nanomolar Detection of Cu2+

A Coumarin-Based Fluorescent Probe for Ratiometric Detection of Cu2+ and Its Application in Bioimaging

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

Contact Info

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Synthesis of Fluorescent 1,7-Dipyridyl-bis-pyrazolo[3,4-b:4′,3′-e]pyridines: Design of Reversible Chemosensors for Nanomolar Detection of Cu²⁺

Synthesis of Fluorescent 1,7-Dipyridyl-bis-pyrazolo[3,4-b:4′,3′-e]pyridines: Design of Reversible Chemosensors for Nanomolar Detection of Cu²⁺

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