Picoline based fluorescence ‘turn-on’ chemosensor for zinc(II) ion recognition, cell imaging and cytotoxicity study: Synthesis, crystal structure, spectroscopy and DFT
A picoline based ‘turn-on’ chemosensor (L) and it’s zinc(II) complex, Zn(L)2 (1) have been synthesized and structurally characterized. The detection limit (0.36 µM) and association constant (log Kapp = 13.25) are evaluated by the fluorescence experiment. The probe shows reversibility in addition of...
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Published in | Polyhedron Vol. 192; pp. 114815 - 114827 |
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Main Authors | , , , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
01.12.2020
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | A picoline based ‘turn-on’ chemosensor (L) and it’s zinc(II) complex, Zn(L)2 (1) have been synthesized and structurally characterized. The detection limit (0.36 µM) and association constant (log Kapp = 13.25) are evaluated by the fluorescence experiment. The probe shows reversibility in addition of dihydrogen phosphate (H2PO4−) ion to the 1. The probe has sufficient cell permeability and intracellular Zn(II) imaging property. Both L and 1 are innocuous against PBMC (peripheral blood mononuclear cells) but effective antitumor agents against U-937 cancer cells.
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•Synthesis and structure of a highly selective and sensitive picoline based small molecule (Mol. Wt. 254).•A ‘turn on’ fluorescent probe with Zn(II) in HEPES buffer.•Excellent bleaching of fluorescence in H2PO4− to the Zn-complex.•Ligand has sufficient cell permeability and intracellular Zn(II) sensing property.•Compounds are innocuous against PBMC but effective antiproliferative against U-937 cancer cells.
A new picoline based ligand, namely 2-hydroxy-5-methyl-3-[{(6-methylpyridin-2-yl)imino}methyl]benzaldehyde (L) and it’s zinc(II) complex, Zn(L)2 (1) have been synthesized and structurally characterized. The ligand (L) selectively interacts with Zn2+ ion in presence of series of cations in CH3CN-H2O (v/v 1:1) in 1 mM HEPES buffer (pH 7.2). The fluorescence intensity of L is significantly enhanced, and it is increased to 52 times on coordination with Zn(II) ion. The fluorescence intensity value of the L does not show any significant change in the pH range 5 to 9, while the extent of emission phenomenon with Zn(II) ions is observed in the said pH range. The detection limit (0.36 µM) and association constant (log Kapp = 13.25) are evaluated by the fluorescence emission experiment. The probe shows reversibility in addition of dihydrogen phosphate (H2PO4−) ion to the 1. Additionally, the ‘turn-on’ fluorescence probe has sufficient cell permeability and intracellular Zn(II) sensing property as envisaged from the microscopic imaging in HEK293T cells. Both L and ZnL2 (1) are innocuous against PBMC (peripheral blood mononuclear cells) but effective antitumor agents against U-937 cancer cells. |
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ISSN: | 0277-5387 |
DOI: | 10.1016/j.poly.2020.114815 |