Cytostatics. 16. Antimicrobial and tumor-inhibiting properties of dithiourethane and studies on the mechanism of action

Abstract

Of 8 dithiourethanes and 4 dithiocarbamates tested for antimicrobial activity against 22 microorganisms, 6 had expressed fungistatic activity, 3-oxo-3-phenylpropyl N,N-dimethyldithiocarbamate (I) [30670-17-8] and Na N,N-dimethyldithiocarbamate [128-04-1] having the greatest effect. Only I and 3-oxobutyl N,N-dimethyldithiocarbamate [30538-01-3] had antibacterial activity, and none inhibited Yoshida sarcoma growth in rats or sarcoma 180 growth in mice. The corresponding dithiocarbamic acids, alpha ,beta -unsatd. ketones, and beta -ketones of the inactive dithiourethanes had increased fungistatic activity, whereas those derivs. of the active compds. were generally less effective. Cysteine-HCl [52-89-1], thioglycolic acid [68-11-1], and particularly bovine serum decreased the fungistatic effectiveness of the active compds. The antimicrobial properties of dithiourethanes depend on a complex interaction of different mechanisms, e.g. release of dithiocarbamic acid and alpha ,beta -unsatd. ketone, and acyl ethylation by dithiourethane.