Bioscience, Biotechnology, and Biochemistry
Online ISSN : 1347-6947
Print ISSN : 0916-8451
Organic Chemistry Regular Papers
Structure-Activity Relationship of S-Benzylisothiourea Derivatives to Induce Spherical Cells in Escherichia coli
Noritaka IWAITakuma EBATAHirokatsu NAGURATomoya KITAZUMEKazuo NAGAIMasaaki WACHI
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2004 年 68 巻 11 号 p. 2265-2269

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We have previously reported that a novel S-benzylisothiourea derivative, S-(3,4-dichlorobenzyl)isothiourea, tentatively named A22, induced spherical cells in Escherichia coli. To elucidate the structural element(s) required for inducing these spherical cells, the biological activity of S-benzylisothiourea derivatives and related compounds toward E. coli cells was investigated. S-(4-Chlorobenzyl)isothiourea revealed spherical cell-inducing activity, although being slightly less potent than A22, and S-benzylisothiourea itself showed much less activity. S-Cyclohexylmethylisothiourea did not show antibacterial activity and had little effect on the cell shape. S-Heptylisothiourea showed antibacterial activity and induced elongated cells rather than spherical cells. Benzylisothiocyanate inhibited cell growth but did not induce spherical cells. S-Ethylisothiourea, benzylthiocyanate, benzylisocyanate, and N-phenylthiourea did not show any activity under the present experimental conditions. These results indicate that the S-benzylisothiourea structure was necessary and sufficient for inducing spherical cells and that 3- and/or 4-chloro-substitution of the S-benzyl group enhanced this activity.
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© 2004 by Japan Society for Bioscience, Biotechnology, and Agrochemistry
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