Pyrene appended bis-triazolylated 1,4-dihydropyridine as a selective fluorogenic sensor for Cu2+

Kumar, Rakesh; Bawa, Rashim; Gahlyan, Parveen; Dalela, Manu; Jindal, Kajal; Jha, Pradip K.; Tomar, Monika; Gupta, Vinay

doi:10.1016/j.dyepig.2018.09.049

Cited by 29 publications

(13 citation statements)

References 65 publications

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“…The synthesis was initiated by the preparation of substituted dihydropyridines ( 1 a – e ) by modified Hantzsch synthesis using literature procedure [33] . These synthesized dihydropyridines ( 1 a – e ) were further treated with a mild brominating agent N‐bromosuccinimide in DMF followed the addition of sodium azide to afford the corresponding azides ( 2 a – e ) [34] . This in situ conversion of dihydropyridines into their azides was also tried using several solvents such as acetonitrile, THF and methanol but the reaction was successfully driven in DMF only.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Evaluation and Molecular Docking Studies of Novel Triazole Linked 1,4‐Dihydropyridine‐isatin Scaffolds as Potent Anticancer Agents

et al. 2021

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A series of novel triazole linked isatin-dihydropyridine hybrids (N1-N15) have been synthesized and examined for their anti proliferative activity against human cancer cell lines viz. HeLa, Huh-7, PC-3, IMR-32 and MCF-7. All of the synthesized hybrids have shown moderate to potent cytotoxicity against all the tested cell lines except IMR-32. Compounds N1, N2 and N13 have displayed an enhanced inhibitory potency against Huh-7 cell line as compared to the standard drug, doxorubicin. Out of the three, N2 has shown the highest in vitro inhibitory action with IC 50 values of 6.73 � 0.33 μM and 17.94 � 0.23 μM against Huh-7 and MCF-7 cell lines, respectively. The docking studies of these most potent compounds have also been investigated which identified that N2 might be an excellent drug-like candidate worthy of further pursuit.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis, Evaluation and Molecular Docking Studies of Novel Triazole Linked 1,4‐Dihydropyridine‐isatin Scaffolds as Potent Anticancer Agents

et al. 2021

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“…Pyrene was demonstrated with special excimer fluorescent property and had been widely used for chem‐detection in reported works , . In order to achieve the detection of antimony by fluorescence, we first tested the fluorescent property of Py‐IPH in the mixture of THF and water, and explored its emission under different states.…”

Section: Resultsmentioning

confidence: 99%

“…The formation of pyrene excimers will be influenced by lots of factors, such as the concentration of pyrene molecules in the system, the interaction between the pyrene fluorogens, the steric configuration of the pyrene‐based molecules and so on , . Lots of pyrene‐based fluorescent probes have been reported to be used in the response to heavy metals, temperature and so on based on their excimer fluorescent property,, so it maybe a feasible way for combining antimony reactive functional group with pyrene core to design pyrene‐basd antimony probes, which can change the speed for the formation of pyrene excimers in the system, and achieve the fluorescent detection of antimony with high sensitivity.…”

Section: Introductionmentioning

confidence: 99%

A Pyrene‐based Probe for Antimony with Special Excimer Fluorescence

Wang

Huang

Wang

et al. 2020

Zeitschrift anorg allge chemie

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Py‐IPH, a pyrene‐based fluorogen with good thermal and mechanical stability was simply prepared by the Schiff base reaction and applied in the detection of antimony. Py‐IPH presented special excimer fluorescence in the mixture of THF and water with 80 % of water, and exhibited perfect fluorescent response to antimony. The mechanism was demonstrated to be the increasing speed of the formation of pyrene excimers in the system owing to the coordination between antimony and IPH group in Py‐IPH. Moreover, based on the special interaction between Py‐IPH and antimony, it could distinguish antimony with other cations well with high specificity and selectivity.

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“…In recent years, 1,4‐dihydropyridine‐based fluorescent molecules have received increasing attention because of their simple structures, easy syntheses, excellent photophysical properties, and extensive applications in fluorescent sensors . Importantly, some 1,4‐dihydropyridine derivatives reportedly exhibit outstanding AIE properties and emit good solid‐state fluorescence upon a simple structural modification.…”

Section: Introductionmentioning

confidence: 99%

“…In recent years, 1,4-dihydropyridine-based fluorescent molecules have received increasing attention because of their simple structures, easy syntheses, excellent photophysical properties, and extensive applications in fluorescent sensors. [12][13][14][15][16][17][18] Importantly,s ome1 ,4-dihydropyridined erivatives reportedly exhibit outstanding AIE properties and emit good solid-state fluorescenceu pon as imple structuralm odification. Specifically,anappropriate structuralunit introduced on the nitrogena tom of the 1,4-dihydropyridine ring can lead to twisted molecular conformations.…”

Section: Introductionmentioning

confidence: 99%

Aggregation‐Induced Emission‐Active 1,4‐Dihydropyridine‐Based Dual‐Phase Fluorescent Sensor with Multiple Functions

Zhou

Chen

Duan

et al. 2019

Chemistry An Asian Journal

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A N‐2‐phenylethyl‐substituted 1,4‐dihydropyridine derivative (NDHP) containing 5,5‐dimethylcyclohexane‐1,3‐dione and naphthylethylene was designed and synthesized. NDHP acts as a multifunctional fluorescent sensor in dual phases. The crystal structure analysis confirms that the NDHP molecules have highly twisted conformations. The twisted conformation results in aggregation‐induced emission properties and solid‐state emission, by restricting the intramolecular free rotation in the aggregated or solid state. In the solid state, NDHP exhibits reversible mechanochromic properties as a result of the transition between the amorphous and crystalline states. NDHP also exhibits a rare phenomenon of acid‐fumed solid‐state emission enhancement owing to the change in packing mode from a zigzag arrangement to J‐aggregation. The solid‐state stimuli‐responsive fluorescence switching is applied to realize a rewritable optical recording media and a multiple output combinational logic system. In solution, NDHP shows a selective fluorescence response for environmentally harmful Hg2+, with a limit of detection of 2.7 nm. This results from the “turn‐on” responsive behavior owing to the Hg2+‐triggered aggregation of the NDHP molecules. NDHP is also used in the imaging of intracellular Hg2+ in HeLa cells. These findings provide a feasible and attractive route for developing multifunctional fluorescent sensors for use in dual phases.

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Pyrene appended bis-triazolylated 1,4-dihydropyridine as a selective fluorogenic sensor for Cu2+

Cited by 29 publications

References 65 publications

Design, Synthesis, Evaluation and Molecular Docking Studies of Novel Triazole Linked 1,4‐Dihydropyridine‐isatin Scaffolds as Potent Anticancer Agents

Design, Synthesis, Evaluation and Molecular Docking Studies of Novel Triazole Linked 1,4‐Dihydropyridine‐isatin Scaffolds as Potent Anticancer Agents

A Pyrene‐based Probe for Antimony with Special Excimer Fluorescence

Aggregation‐Induced Emission‐Active 1,4‐Dihydropyridine‐Based Dual‐Phase Fluorescent Sensor with Multiple Functions

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