- A Tetrakisquinoline Analog of Calcium Indicator Quin2 for Fluorescence Detection of Cd2+
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Quin2 (2-{2-[bis(carboxymethyl)amino-5-methylphenoxy]methyl}-6-methoxy-8-[bis(carboxymethyl)amino]quinoline) is a well-known fluorescent Ca2+ indicator. In this study, we replaced its four carboxy groups with quinolines and deleted a methyl group on the benzene ring to afford TQquin2 [N,N,N',N'-tetrakis(2-quinolylmethyl)-8-amino-2-(2-aminophenoxy)methyl-6-methoxyquinoline]. In methanol solution, TQquin2 exhibited fluorescence enhancement toward Cd2+ with excellent selectivity.
- Iwatsuki, Satoshi,Kaneda, Minori,Konno, Hideo,Matsumoto, Arimasa,Mikata, Yuji,Tanaka, Marin
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- Synthesis and characterization of 8-aminoquinolines, substituted by electron donating groups, as high-affinity copper chelators for the treatment of Alzheimer's disease
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The deregulation of copper homeostasis generates copper–amyloid aggregation and strongly participates in neuron damage in the brains of patients with Alzheimer's disease. Therefore, copper chelators able to regulate copper homeostasis should be considered
- Huang, Ju,Nguyen, Michel,Liu, Yan,Robert, Anne,Meunier, Bernard
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p. 419 - 427
(2019/06/13)
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- Novel quinolinequinone antitumor agents: Structure-metabolism studies with NAD(P)H:quinone oxidoreductase (NQO1)
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A series of quinolinequinones bearing various substituents has been synthesized, and the effects of substituents on the metabolism of the quinones by recombinant human NAD(P)H:quinone oxidoreductase (hNQO1) was studied. A range of quinolinequinones were selected for study, and were specifically designed to probe the effects of aryl substituents at C-2. A range of 28 quinolinequinones 2-29 was prepared using three general strategies: the palladium(0) catalyzed coupling of 2-chloroquinolines, the classical Friedlaender synthesis and the double-Vilsmeier reaction of acetanilides. One example of an isoquinolinequinone 30 was also prepared, and the reduction potentials of the quinones were measured by cyclic voltammetry. For simple substituents R2 at the quinoline 2-position, the rates of quinone metabolism by hNQO1 decrease for R2=Cl>H~Me>Ph. For aromatic substituents, the rate of reduction decreases dramatically for R 2=Ph>1-naphthyl>2-naphthyl>4-biphenyl. Compounds containing a pyridine substituent are the best substrates, and the rates decrease as R 2=4-pyridyl>3-pyridyl>2-pyridyl>4-methyl-2-pyridyl>5- methyl-2-pyridyl. The toxicity toward human colon carcinoma cells with either no detectable activity (H596 or BE-WT) or high NQO1 activity (H460 or BE-NQ) was also studied in representative quinones. Quinones that are good substrates for hNQO1 are more toxic to the NQO1 containing or expressing cell lines (H460 and BE-NQ) than the NQO1 deficient cell lines (H596 and BE-WT).
- Fryatt, Tara,Pettersson, Hanna I.,Gardipee, Walter T.,Bray, Kurtis C.,Green, Stephen J.,Slawin, Alexandra M. Z.,Beall, Howard D.,Moody, Christopher J.
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p. 1667 - 1687
(2007/10/03)
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