Pyridine-pyrazole based Al(<scp>iii</scp>) ‘turn on’ sensor for MCF7 cancer cell imaging and detection of picric acid

Saha, Sayan; De, Avik; Ghosh, Arijit; Ghosh, Avik; Bera, Kaushik; Das, Kaustav; Akhtar, Sohel; Maiti, Nakul C.; Das, Abhijit K.; Das, Benu Brata; Mondal, Raju

doi:10.1039/d1ra00082a

Cited by 28 publications

(7 citation statements)

References 65 publications

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“…H 4 CPPC was synthesized with Schiff base condensation protocol. 2,6-Diacetylpyridine (1.63 g, 0.01 mol) and pyridine−pyrazole carbohydrazide 77 (4.06 g 0.02 mol) were taken in 250 mL of ethanol in a round-bottomed flask. A catalytic amount of acetic acid was mixed, and the mixture was refluxed for 24 h at 80 °C.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Synergistic Experimental and Theoretical Studies of Luminescent–Magnetic Ln₂Zn₆ Clusters

et al. 2022

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The present work is part of our ongoing quest for developing functional inorganic complexes using unorthodox pyridyl–pyrazolyl-based ligands. Accordingly, we report herein the synthesis, characterization, and luminescence and magnetic properties of four 3d–4f mixed-metal complexes with a general core of Ln2Zn6 (Ln = Dy, Gd, Tb, and Eu). In stark contrast to the popular wisdom of using a compartmental ligand with separate islands of hard and soft coordinating sites for selective coordination, we have vindicated our approach of using a ligand with overcrowded N-coordinating sites that show equal efficiency with both 4f and 3d metals toward multinuclear cage-cluster formation. The encouraging red and green photolumiscent features of noncytotoxic Eu2Zn6 and Tb2Zn6 complexes along with their existence in nanoscale dimension have been exploited with live-cell confocal microscopy imaging of human breast adenocarcinoma (MCF7) cells. The magnetic features of the Dy 2 Zn 6 complex confirm the single-molecule-magnet behavior with befitting frequency- and temperature-dependent out-of-phase signals along with an U eff value of ∼5 K and a relaxation time of 8.52 × 10–6 s. The Gd 2 Zn 6 complex, on the other hand, shows cryogenic magnetic refrigeration with an entropy change of 11.25 J kg–1 K–1 at a magnetic field of 7 T and at 2 K. Another important aspect of this work reflects the excellent agreement between the experimental results and theoretical calculations. The theoretical studies carried out using the broken-symmetry density functional theory, ORCA suite of programs, and MOLCAS calculations using the complete-active-space self-consistent-field method show an excellent synergism with the experimentally measured magnetic and spectroscopic data.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Synergistic Experimental and Theoretical Studies of Luminescent–Magnetic Ln₂Zn₆ Clusters

et al. 2022

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“…The quantum chemical calculations (discussed later in detail) show that HOMO‐LUMO energy gap of complex is lower ( NaL , 3.4289 eV) compared to that of the probe ( L , 4.6117 eV (for enol form)). Therefore, the overall electronic transition getting enhanced during the addition of Na + results in increased intensity of emission (λ em ) at 540 nm and decreased average life time for NaL complex [88] . The higher lifetime value and quantum yield (ϕ f =0.5330) of L suggests that the rate of non‐radiative decay (k nr =0.0702 ns −1 ) is lesser than that of radiative decay (k r =0.08 ns −1 ).…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, the overall electronic transition getting enhanced during the addition of Na + results in increased intensity of emission (λ em ) at 540 nm and decreased average life time for NaL complex. [88] The higher lifetime value and quantum yield (� f = 0.5330) of L suggests that the rate of non-radiative decay (k nr = 0.0702 ns À 1 ) is lesser than that of radiative decay (k r = 0.08 ns À 1 ). The large stokes shift, dual emission, biexponetial fits in fluorescence decay profile and effective ESIPT process collectively supported the high emission characteristic of probe (L).…”

Section: Excited State Lifetime Measurementmentioning

confidence: 99%

Small‐Molecule Fluorescent Probe: Ratiometric and Selective Detection of Sodium Ions for Imaging and Solid‐State Sensing Applications

Shankar¹,

Aravind

Ashokkumar

et al. 2022

ChemistrySelect

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A ratiometric highly fluorescent small molecular probe (L), 1,2,4-triazol-4-yliminomethyl-5-(hydroxymethyl)-2-methylpyridin-3-ol, was designed for detecting Na(I) ions in DMF:water (1 : 9, v/v) medium. The chemical structure of Na(I) complex of probe was confirmed by single crystal XRD. The fluorescence detection of Na + ion has been executed in both solid and solution medium. The observations suggest the same chemical structure in solution state as well. The detailed photochemical studies showed that highly selective sensing of Na + ions even in the presence of common interfering K + ions. The fluorescence decay studies showed that the lifetime of NaL is lesser than L. The excited state intramolecular proton transfer (ESIPT) mechanism and the nature of electronic transitions were examined by quantum chemical studies. The electrochemical behaviour was studied by cyclic voltammetry and impedance spectra. It has also been shown that the probe can be applied to paper based sensing and imaging of Na + ions in U87 cell lines.

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“…The binding stoichiometry was such that one molecule of the complex could bind to 3–4 base pairs of CT DNA. The reason could be attributed to the presence of the aromatic pyrazole and pyridine groups inducing planarity in all the complexes causing π–π stacking interactions making them to slide in and penetrate deep in between the DNA base pairs [ 50 , 51 ]. Among them, complex 1 exhibited the highest K b value followed by 2 and 3 .…”

Section: Resultsmentioning

confidence: 99%

Tris-(2-pyridyl)-pyrazolyl Borate Zinc(II) Complexes: Synthesis, DNA/Protein Binding and In Vitro Cytotoxicity Studies

et al. 2021

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Zn(II) complexes bearing tris[3-(2-pyridyl)-pyrazolyl] borate (Tppy) ligand (1–3) was synthesized and examined by spectroscopic and analytical tools. Mononuclear [TppyZnCl] (1) has a Zn(II) centre with one arm (pyrazolyl-pyridyl) dangling outside the coordination sphere which is a novel finding in TppyZn(II) chemistry. In complex [TppyZn(H2O)][BF4] (2) hydrogen bonding interaction of aqua moiety stabilizes the dangling arm. In addition, solution state behaviour of complex 1 confirms the tridentate binding mode and reactivity studies show the exogenous axial substituents used to form the [TppyZnN3] (3). The complexes (1–3) were tested for their ability to bind with Calf thymus (CT) DNA and Bovine serum albumin (BSA) wherein they revealed to exhibit good binding constant values with both the biomolecules in the order of 104–105 M−1. The intercalative binding mode with CT DNA was confirmed from the UV-Visible absorption, viscosity, and ethidium bromide (EB) DNA displacement studies. Further, the complexes were tested for in vitro cytotoxic ability on four triple-negative breast cancer (TNBC) cell lines (MDA-MB-231, MDA-MB-468, HCC1937, and Hs 578T). All three complexes (1–3) exhibited good IC50 values (6.81 to 16.87 μM for 24 h as seen from the MTS assay) results which indicated that these complexes were found to be potential anticancer agents against the TNBC cells.

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Pyridine-pyrazole based Al(iii) ‘turn on’ sensor for MCF7 cancer cell imaging and detection of picric acid

Abstract: We report herein the development of a new pyridine-pyrazole based bis-bidentate asymmetric chemosensor that shows excellent turn-on chelation-enhanced Al3+-responsive fluorescence.

Cited by 28 publications

References 65 publications

Synergistic Experimental and Theoretical Studies of Luminescent–Magnetic Ln₂Zn₆ Clusters

Synergistic Experimental and Theoretical Studies of Luminescent–Magnetic Ln₂Zn₆ Clusters

Small‐Molecule Fluorescent Probe: Ratiometric and Selective Detection of Sodium Ions for Imaging and Solid‐State Sensing Applications

Tris-(2-pyridyl)-pyrazolyl Borate Zinc(II) Complexes: Synthesis, DNA/Protein Binding and In Vitro Cytotoxicity Studies

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Pyridine-pyrazole based Al(iii) ‘turn on’ sensor for MCF7 cancer cell imaging and detection of picric acid

Abstract: We report herein the development of a new pyridine-pyrazole based bis-bidentate asymmetric chemosensor that shows excellent turn-on chelation-enhanced Al3+-responsive fluorescence.

Cited by 28 publications

References 65 publications

Synergistic Experimental and Theoretical Studies of Luminescent–Magnetic Ln2Zn6 Clusters

Synergistic Experimental and Theoretical Studies of Luminescent–Magnetic Ln2Zn6 Clusters

Small‐Molecule Fluorescent Probe: Ratiometric and Selective Detection of Sodium Ions for Imaging and Solid‐State Sensing Applications

Tris-(2-pyridyl)-pyrazolyl Borate Zinc(II) Complexes: Synthesis, DNA/Protein Binding and In Vitro Cytotoxicity Studies

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Synergistic Experimental and Theoretical Studies of Luminescent–Magnetic Ln₂Zn₆ Clusters

Synergistic Experimental and Theoretical Studies of Luminescent–Magnetic Ln₂Zn₆ Clusters