Mitomycin C is a natural methylazirinopyrroloindoledione antineoplastic antibiotic isolatedfrom Streptomycesspp that is able to inhibits bacterial DNA synthesis. Many structural variants of Mitomycin C have been isolated, and are called the Mitomycins. Mitomycin C has a unique and efficient mechanism of action of crosslinking DNA, and even a single crosslink per genome can cause death of a bacterial cell. It was discovered in the 1950s in Japan from fermentation cultures of S. caespitosus. Mitomycin C has anti-tumor properties.

CAS Number

50-07-7

Molecular Formula

C₁₅H₁₈N₄O₅

Molecular Weight

334.33

Mechanism of Action

Mitomycin C is activated by reductionin vivo, generating oxygen radicals which produce crosslinks in DNA by alkylation. The Mitomycin C itself does not react with DNA. Rather, upon reduction of the quinone, a transformation ensues, and the aziridine ring opens to product the unstable vinylogous quinone methide 2, which has high alkylating reactivity.

It has high efficiency and specificity for CpG sequences, and these sequences are very rare in the mammalian genome, thus mammalian DNA is crosslinked relatively poorly. This mechanism ultimately inhibits DNA synthesis. It can also cause mutagenesis and stimulate genetic recombination, chromosome breakage, and sister chromatid exchange.

Storage Conditions

2-8°C

Tariff Code

2941.90.1050

Spectrum

Mitomycin C is broad-spectrum, effective for Gram-negative and Gram-positive bacteria.