• Mitomycin C packaged and labeled.

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Description

Mitomycin C is a natural methylazirinopyrroloindoledione antineoplastic antibiotic isolated from Streptomyces spp 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 reduction in 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.

Applications

    Application

    Mitomycin C can be used as an inhibitor for cell-free protein biosynthesis research. In addition, Mitomycin C is an efficient crosslinking machine, and it could be used to imagine new synthetic or semisynthetic compounds that imitate this function.

    Cancer Applications

    The antiproliferative effects of Mitomycin C may have a role in treating cancer as it was shown to inhibit the progression of dermal Kaposi's sarcoma post renal transplantation.

    Since only 5% of all guanines in the mammalian genome are present in CpG islands, it isn’t optimally designed for killing tumor cells. However, retaining this cross-linking ability but altering the sequence specificity could allow the design of more efficacious anti-tumor properties (Tomasz, 1995).

Specifications

    Form

    Powder

    Appearance

    Violet blue crystal

    Source

    Streptomyces caespitosus

    Water Content (Karl Fischer)

    ≤2.5%

    Potency (on a dry basis)

    ≥970 µg/mg

    pH

    6.0-7.5

    Melting Point

    360°C

References

    References

    Renault J,  Baron M; Mailliet P (1981).  Heterocyclic quinones.2.Quinoxaline-5,6-(and 5-8)-diones - Potential antitumoral agents. Eur. J. Med. Chem. 16(6):545–550

    Mao Y, Varoglu M and Sherman DH (1999)  Molecular characterization and analysis of the biosynthetic gene cluster for the antitumor antibiotic mitomycin C from Streptomyces Iavendulae NRRL 2564. Chem. and Biology 6(4): 251–263

    Szybalski, W and lyer VN (1964)  Crosslinking of DNA by enzymatic or activated mitomycins and porfiromycins, bifunctionally ‘alkylating’ antibiotics. Feder. Proc. 23:946-957 

    Tomasz M  (1995)  Mitomycin C: Small, fast and deadly (but very selective).  Chem. Biol. 2(9):575-579  PMID 9383461

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