An efficient two-step synthesis of pyrazoline ligand is described which is an effective "turn on" fluorescent sensor for Cd(2+) in MeCN. Oxidation to the corresponding pyrazole ligand creates a "turn on" fluorescent sensor now selective for Zn(2+) and able to distinguish it from Cd(2+).
The synthesis and antiproliferative activity of eleven 3-(pyrid-2-yl)-pyrazolines in two cancer cell lines are reported. X-ray crystallography was obtained of the lead compound 8i which was screened in the NCI 60 human tumour cell line and displayed sub-micromolar activity. Cell cycle analysis, in vitro tubulin assay and confocal microscopy are also reported and suggest that the lead compound disrupts microtubule formation.
Furocoumarin (furo[3,2-c]coumarin) derivatives have been synthesized from single step, high yielding (82-92%) chemistry involving a 4-hydroxycoumarin 4 + 1 cycloaddition reaction. They are characterized by FTIR, 1 H-NMR, and, for the first time, a comprehensive UV-Vis and fluorescence spectroscopy study has been carried out to determine if these compounds can serve as useful sensors. Based on the fluorescence data, the most promising furocoumarin derivative (2-(cyclohexylamino)-3-phenyl-4Hfuro[3,2-c]chromen-4-one, FH), exhibits strong fluorescence (ФF = 0.48) with long fluorescence lifetime (5.6 ns) and large Stokes' shift, suggesting FH could be used as a novel fluorescent chemosensor. FH exhibits a highly selective, sensitive and instant turn-off fluorescence response to Fe 3+ over other metal ions which was attributed to a charge transfer mechanism. Selectivity was demonstrated against 13 other competing metal ions
Inspired by biologically active natural products, a hybrid analogue that combines the N-Me urocanic side chain of the sarcodictyin family of compounds with the chalcone motif has been proposed, synthesised and examined for antiproliferative activity in three cancer cell lines and one normal primary cell line. The analogues are all synthesised in one or two steps from commercially available materials and, of the compounds examined, the proposed hybrid analogue displays the most active and selective inhibition of cell proliferation in human colon cancer cell line HT29 (IC 50 2.9 µM) and highly metastatic human breast carcinoma MDA-MB-231 (IC 50 4.8 µM).
The synthesis of a maltol-derived hydrazide is described which, once attached to a cell surface, induces rapid multicellular aggregation selectively in the presence of Fe(3+) ions. Heterocellular aggregates are also reported.
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