A single molecule that acts as a fluorescence sensor for zinc and cadmium and a colorimetric sensor for cobalt
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Abstract:
A new metal ion sensor that contains quinoline and pyridylaminophenol has been synthesized. In acetonitrile and in the presence of Zn2+, the sensor fluoresces. In contrast, in aqueous solutions the sensor fluoresces in the presence of Cd2+. The fluorescence of the molecule is selective for Zn2+ or Cd2+ and shows no fluorescence with other metal ions. The crystal structure of the Cd2+ complex shows coordination through the amide and phenol oxygens, as well as the amine nitrogen of the sensor. The sensor also acts as a colorimetric sensor for Co2+ by changing color from colorless to yellow. The color change is selective for Co2+ and is not observed with other metal ions. The unique combination of pyridine and phenol groups with quinoline results in the properties of this sensor.Keywords:
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Amide
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Two ω-mercaptoalkoxy quinoline compounds:6-(ω-mercaptodecoxy)-quinoline and 2-(ω-mercaptodecoxy)-4-methyl-quinoline were succesfully synthesized by reacting quinoline with 1,10- dibromodecane and thiourea in alkaline solution. The intermediates and products were characterized by IR, 1H NMR and MS.
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Benzo[f]quinoline and benzo[h]quinoline are widespread environmental pollutants which have been found to be mutagenic. The metabolism of benzo[f]quinoline and benzo[h]quinoline was investigated using a liver homogenate from Aroclor-pretreated rats. The metabolites of benzo[f]quinoline which were identified were 7,8-dihydroxy-7,8-dihydrobenzo[f]quinoline, 9,10-dihydroxy-9,10-dihydrobenzo[f]quinoline, 7-hydroxybenzo[f]quinoline, and benzo[f]quinoline-N-oxide. Metabolism studies on benzo[f]quinoline performed in the presence of the epoxide hydratase inhibitor, 3,3,3-trichloropropylene oxide, demonstrated that the formation of both of these dihydrodiols can be inhibited. The major metabolites of benzo[h]quinoline were identified as 5,6-dihydroxy-5,6-dihydrobenzo[h]quinoline and 7,8-dihydroxy-7,8-dihydrobenzo[h]quinoline. Benzo[h]quinoline-N-oxide was not detected as a metabolite. In the presence of an epoxide hydratase inhibitor, the major metabolites of benzo[h]quinoline were 5,6-epoxybenzo[h]quinoline and 7-hydroxybenzo[h]quinoline. The difference in the metabolism to N-oxides observed between benzo[h]quinoline and benzo[f]quinoline is consistent with previous observations in which sterically hindered aromatic ring nitrogen compounds such as benzo[h]quinoline are more resistant to N-oxide formation. The nitrogen atom of these aza-arenes with its lone pair of electrons has a significant influence on sites at which dihydrodiols are formed. The data suggest that the aromatic ring nitrogen of these azaphenanthrenes has an effect similar to that of a methyl substituent in directing their metabolic oxidation.
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Thirteen isomers of the p-dimethylaminophenylazoquinolines and their corresponding N-oxides were investigated for hepatic carcinogenic activity in Sprague-Dawley rats. The dyes were all fed at the 0.03 percent level, and the more active isomers were also examined at the 0.01 percent level. The isomers are listed in order of decreasing activity, with semiquantitative values based on p-dimethylaminoazobenzene as 6: 6- (p- dimethylaminophenylazo)quinoline, 200+ ; 5-(p-dimethylaminophenylazo)quinoline-1-oxide, 200+; 5-(p-dimethylaminophenylazo)quinoline, 150; 6-(p-dimethylaminophenylazo)quinoline-1-oxide, 100; 4-(p-dimethylaminophenylazo)quinoline-1-oxide, 22; 4-(p-dimethylaminophenylazo)quinoline, 15; 3- (p-dimethylaminophenylazo)quinoline-1-oxide, 3-(p-dimethylaminophenylazo)quinoline, 7-(p-dimethylaminophenylazo)quinoline-1-oxide, 7-(p-dimethylaminophenylazo)quinoline, 8-(p-dimethylaminophenylazo)quinoline-1-oxide, 8-(p-dimethylaminophenylazo)quinoline, and 2-(p-dimethylaminophenylazo)quinoline-1-oxide, with all the latter less than 2.
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Reactions of pyridine and quinoline N-oxides with N-methylformamide are described. N-Methylcarbamoylation occurred at the C-2 or C-4 position of pyridine and quinoline derivatives.
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