• Toxicological Research
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• v.26 no.2
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• pp.101-108
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• 2010

Halogenated organic compounds, such as 1-bromobutane (1-BB), have been used as cleaning agents, agents for chemical syntheses or extraction solvents in workplace. In the present study, immunotoxic effects of 1-BB and its conjugation with glutathione (GSH) were investigated in female BALB/c mice. Animals were treated orally with 1-BB at 375, 750 and 1500 mg/kg in corn oil once for dose response or treated orally with 1-BB at 1500 mg/kg for 6, 12, 24 and 48 hr for time course. S-Butyl GSH was identified in spleen by liquid chromatography-electrospray ionization tandem mass spectrometry. Splenic GSH levels were significantly reduced by single treatment with 1-BB. S-Butyl GSH conjugates were detected in spleen from 6 hr after treatment. Oral 1-BB significantly suppressed the antibody response to a T-dependent antigen and the production of splenic intracellular interlukin-2 in response to Con A. Our present results suggest that 1-BB could cause immunotoxicity as well as reduction of splenic GSH content, due to the formation of GSH conjugates in mice. The present results would be useful to understand molecular toxic mechanism of low molecular weight haloalkanes and to develop biological markers for exposure to haloalkanes.

• Journal of the Korean Chemical Society
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• v.34 no.2
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• pp.179-183
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• 1990

New synthesis and electroanthennogram (EAG) responses of the pheromones of the diamond back moth Plutella xylostella L. are described. Lithium dianion of propargyl alcohol was alkylated with 1-bromononane to give 2-dodecyn-1-ol, which was converted to 11-dodecyn-1-ol by acetylene-zipper reaction. Dianion of 11-dodecyn-1-ol was alkylated with 1-bromobutane to provide 11-hexadecyn-1-ol, which was in turn reduced over Pd/BaSO4 to afford (Z)-11-hexadecen-1-ol (3). (Z)-11-Hexadecen-1-ol was oxidized and acetylated to (Z)-11-hexadecen-1-al (1) and (Z)-11-hexadecen-1-yl acetate (2), respectively. The electroantennogram (EAG) responses of the diamond back moth to the pheromone compouds thus synthesized were measured.