Coumarin based hydrazone as an ICT-based fluorescence chemosensor for the detection of Cu2+ ions and the application in HeLa cells

Mani, Kailasam Saravana; Rajamanikandan, Ramar; Murugesapandian, Balasubramanian; Shankar, Ravi; Sivaraman, Gandhi; Ilanchelian, Malaichamy; Rajendran, S. P.

doi:10.1016/j.saa.2019.02.020

Cited by 72 publications

(25 citation statements)

References 34 publications

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“…This probe resulted to be particularly selective for Cu 2+ even in the presence of several other ions [242]. Saravana Mani and colleagues designed in 2019 a coumarin hydrazine-based fluorescent probe for the detection of copper(II), called BENZEPYR (187, Figure 60), exploiting a reaction of condensation between 2-hydrazino benzothiazole and N,N -diethylamino-3-acetyl coumarin [243]. This particular fluorescent chemosensor could selectively detect Cu 2+ among other disturbing metal ions, resulting particularly specific and highly responsive, with a visible colorimetric change of the solution, which turned from yellow to wine red.…”

Section: Coumarins As Fluorescent Probesmentioning

confidence: 99%

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

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Dallavalle

et al. 2020

IJMS

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Privileged structures have been widely used as an effective template for the research and discovery of high value chemicals. Coumarin is a simple scaffold widespread in Nature and it can be found in a considerable number of plants as well as in some fungi and bacteria. In the last years, these natural compounds have been gaining an increasing attention from the scientific community for their wide range of biological activities, mainly due to their ability to interact with diverse enzymes and receptors in living organisms. In addition, coumarin nucleus has proved to be easily synthetized and decorated, giving the possibility of designing new coumarin-based compounds and investigating their potential in the treatment of various diseases. The versatility of coumarin scaffold finds applications not only in medicinal chemistry but also in the agrochemical field as well as in the cosmetic and fragrances industry. This review is intended to be a critical overview on coumarins, comprehensive of natural sources, metabolites, biological evaluations and synthetic approaches.

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Section: Coumarins As Fluorescent Probesmentioning

confidence: 99%

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Annunziata

Pinna

Dallavalle

et al. 2020

IJMS

249

156

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“…28,29 As a result, an increasing number of papers concerning coumarin derivatives uorescent chemosensors for copper(II) ion have emerged. [30][31][32][33] In 2009, Lee Jin Yong and coworkers developed a novel coumarin-based uorogenic probe, which can act as a uorescent chemosensor with high selectivity and suitable affinity in biological systems toward Cu 2+ (ref. 34).…”

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confidence: 99%

A coumarin-containing Schiff base fluorescent probe with AIE effect for the copper(ii) ion

et al. 2020

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“…The deprotonation of −OH groups occurs during the formation of LH 3 -Cu 2+ ensembles, which inhibit the ESIPT process and resulted in the gradual decrease in the emission intensity. 41 Further drastic decrease in the quantum yield was observed from 0.25 to 0.08% upon addition of Cu 2+ to the probe with a naked eye-detectable color change from fluorescent green to nonemissive under UV light (365 nm). It is interesting to note that the limit of detection value of LH 3 for Cu 2+ was calculated as 2.33 × 10 –7 M (23.3 ppm) (Figure S22), which is below the permissible value of Cu 2+ in drinking water according to WHO.…”

Section: Resultsmentioning

confidence: 95%

“…The quenching behavior of Cu 2+ might be due to the paramagnetic nature of Cu 2+ , inhibition of ESIPT, and chelation-enhanced quenching. 41,43…”

Section: Resultsmentioning

confidence: 99%

Star-Shaped ESIPT-Active Mechanoresponsive Luminescent AIEgen and Its On–Off–On Emissive Response to Cu²⁺/S^2–

et al. 2019

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Design and development of multifunctional materials have drawn incredible attraction in recent years. Herein, we report the design and construction of versatile star-shaped intramolecular charge transfer (ICT)-coupled excited-state intramolecular proton transfer (ESIPT)-active mechanoresponsive and aggregation-induced emissive (AIE) luminogen triaminoguanidine-diethylaminophenol ( LH 3 ) conjugate from simple precursors triaminoguanidine hydrochloride and 4-( N , N -diethylamino)salicylaldehyde. Solvent-dependent dual emission in nonpolar to polar protic solvents implies the presence of ICT-coupled ESIPT features in the excited state. Aggregation-enhanced emissive feature of LH 3 was established in the CH 3 CN/water mixture. Furthermore, this compound exhibits mechanochromic fluorescence behavior upon external grinding. Fluorescence microscopy images of pristine, crystal, and crushed crystals confirm the naked-eye mechanoresponsive characteristics of LH 3 . In addition, LH 3 selectively sensed a Cu 2+ ion through a colorimetric and fluorescence “turn-off” route, and subsequently, the LH 3 -Cu 2+ ensemble could act as a selective and sensitive sensor for S 2– in a “turn-on” fluorescence manner via a metal displacement approach. Reversible “turn-off–turn-on” features of LH 3 with Cu 2+ /S 2– ions were efficiently demonstrated to construct the IMPLICATION logic gate function. The Cu 2+ /S 2– -responsive sensing behavior of LH 3 was established in the paper strip experiment also, which can easily be characterized by the naked eye under daylight as well as a UV lamp (λ = 365 nm).

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Coumarin based hydrazone as an ICT-based fluorescence chemosensor for the detection of Cu2+ ions and the application in HeLa cells

Cited by 72 publications

References 34 publications

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

A coumarin-containing Schiff base fluorescent probe with AIE effect for the copper(ii) ion

Star-Shaped ESIPT-Active Mechanoresponsive Luminescent AIEgen and Its On–Off–On Emissive Response to Cu²⁺/S^2–

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Coumarin based hydrazone as an ICT-based fluorescence chemosensor for the detection of Cu2+ ions and the application in HeLa cells

Cited by 72 publications

References 34 publications

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

A coumarin-containing Schiff base fluorescent probe with AIE effect for the copper(ii) ion

Star-Shaped ESIPT-Active Mechanoresponsive Luminescent AIEgen and Its On–Off–On Emissive Response to Cu2+/S2–

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Product

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Star-Shaped ESIPT-Active Mechanoresponsive Luminescent AIEgen and Its On–Off–On Emissive Response to Cu²⁺/S^2–