Mitomycin C: Chemical and Biological Studies on Alkylation

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Science  29 Nov 1963:
Vol. 142, Issue 3596, pp. 1181-1183
DOI: 10.1126/science.142.3596.1181


The presence of an aziridine ring in mitomycin C suggests that the mechanism of action of the antibiotic is like that of the antitumor alkylating agents. However the compound is unexpectedly stable during aerobic incubation with rat liver homogenates although rapidly metabolized anaerobically. Mitomycin is not reactive with γ-(4-nitrobenzyl) pyridine and reacts only slowly at acid pH with thiosulfate. It is proposed that mitomycin is activated in vivo, possibly by a reduction which "unmasks" the potential activity of the fused aziridine ring.